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379 KiB

Open AccessArticle

Enhancement of Cunninghamella elegans UCP/WFCC 0542 Biomass and Chitosan with Amino Acid Supply

by Ednaldo Ramos Dos Santos, Marta Cristina Freitas Da Silva, Patrícia Mendes De Souza, Antonio Cardoso Da Silva, Sergio Carvalho De Paiva, Clarissa D. C. Albuquerque, Aline E. Nascimento, Kaoru Okada and Galba M. Campos-Takaki

Molecules 2013, 18(9), 10095-10107; https://doi.org/10.3390/molecules180910095 - 22 Aug 2013

Cited by 7 | Viewed by 7281

Abstract

Studies were carried out with Cunninghamella elegans UCP/WFCC 0542 to evaluate the effects of an abundant supply of amino acids, asparagine and corn steep liquor associated with sucrose on the production of biomass and chitosan by submerged fermentation. The concentrations of the components [...] Read more.

Studies were carried out with Cunninghamella elegans UCP/WFCC 0542 to evaluate the effects of an abundant supply of amino acids, asparagine and corn steep liquor associated with sucrose on the production of biomass and chitosan by submerged fermentation. The concentrations of the components of the culture medium which were determined by a 2³ full factorial design evaluated the interactions and effects of the independent variables of the sucrose, asparagine and corn steep liquor in relation to carbon and nitrogen sources, on the production of chitosan regarding biomass. The best results were observed at the central point [asparagine 0.025%, sucrose 0.15% and 0.45% of corn steep liquor, ratio C:N=2:6], and produced maximum yields of 16.95 g/L biomass and 2.14 g/L chitosan, after 96 h of submerged fermentation. However, the lowest level of sucrose, asparagine and corn steep liquor produced a low amount of biomass (10.83 g/L) and chitosan (0.60g/L). The infrared spectrum absorption of the chitosan produced by C. elegans showed bands regarding OH-axial stretching between 3406 and 3432 cm⁻¹, superimposed on the NH stretching band with axial deformation of the amide C=O group at about 1639 cm⁻¹, NH angular deformation at approximately 1560 cm⁻¹; axial deformation of amide-CN at around 1421 cm⁻¹, symmetrical angular deformation in CH₃ at 1379 cm⁻¹, -CN axial deformation of amino groups from 1125 to 1250 cm⁻¹ and polysaccharide structure bands in the range of between 890–1150 cm⁻¹. The crystallinity index of chitosan was 60.92%, and its degree of deacetylation was 75.25%. A low percentage of a supply of sucrose and asparagine with corn steep liquor offered higher yields of biomass and chitosan production at low cost. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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939 KiB

Open AccessArticle

Intravenous and Subcutaneous Toxicity and Absorption Kinetics in Mice and Dogs of the Antileishmanial Triterpene Saponin PX-6518

by Louis Maes

Molecules 2013, 18(4), 4803-4815; https://doi.org/10.3390/molecules18044803 - 22 Apr 2013

Cited by 2 | Viewed by 7277

Abstract

The intravenous (IV) and subcutaneous (SC) toxicity and absorption kinetics of the antileishmanial triterpene saponin PX-6518 and its active constituents maesabalide-III and -IV were studied in mice and dogs. A high-dose wash-out study of PX-6518 at 20 mg/kg SC for 5 days and [...] Read more.

The intravenous (IV) and subcutaneous (SC) toxicity and absorption kinetics of the antileishmanial triterpene saponin PX-6518 and its active constituents maesabalide-III and -IV were studied in mice and dogs. A high-dose wash-out study of PX-6518 at 20 mg/kg SC for 5 days and a single low-dose wash-out study at 1, 2.5 or 5 mg/kg SC and IV with follow-up until day 35 after treatment were performed in mice. Beagle dogs received three escalating doses of maesabalide-III and -IV at weekly intervals (0.01, 0.1 and 0.5 mg/kg IV and maesabalide-III was also dosed SC at 0.1, 0.2 and 0.4 mg/kg). Endpoint measurements included clinical, hematological and serum biochemical parameters. Pathology and toxicokinetic studies were performed on the dogs. Whereas the neutrophils and aspartate aminotransferase and alanine aminotransferase levels were increased in the high-dose wash-out mouse study, these parameters did not change in the low-dose wash-out study. The dogs were far more susceptible than mice to liver toxicity (hepatocellular necrosis and elevated liver enzymes) and developed a painful inflammatory reaction at the SC injection site. Toxicokinetic analysis revealed a non dose-linear systemic availability with plasma concentrations above the antileishmanial IC₅₀ after only a single dose at 0.01 mg/kg IV or 0.1 mg/kg SC. Related to the long half-life (T_1/2 71–91 h after SC dosing), repeated dosing at weekly intervals may result in drug accumulation and enhanced toxicity. It was decided not to pursue further drug development for PX-6518 because of the hepatotoxic risk. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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984 KiB

Open AccessArticle

Preparation, Purification and Regioselective Functionalization of Protoescigenin—The Main Aglycone of Escin Complex

by Mariusz M. Gruza, Kamil Jatczak, Bogdan Zagrodzki, Marta Łaszcz, Katarzyna Koziak, Maura Malińska, Piotr Cmoch, Tomasz Giller, Oliwia Zegrocka-Stendel, Krzysztof Woźniak and Grzegorz Grynkiewicz

Molecules 2013, 18(4), 4389-4402; https://doi.org/10.3390/molecules18044389 - 15 Apr 2013

Cited by 13 | Viewed by 8006

Abstract

A two-step chemical process for controlled degradation of escin, affording a mixture of olean-12-ene sapogenins, was elaborated and scaled up. The main component of the mixture—protoescigenin—was isolated and purified, in the form of its corresponding monohydrate, without resource to chromatographic methods. This material [...] Read more.

A two-step chemical process for controlled degradation of escin, affording a mixture of olean-12-ene sapogenins, was elaborated and scaled up. The main component of the mixture—protoescigenin—was isolated and purified, in the form of its corresponding monohydrate, without resource to chromatographic methods. This material was further converted into the high purity 3,24;16,22-di-O,O-isopropylidene derivative in a validated large scale laboratory process. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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245 KiB

Open AccessArticle

Metabolomic Analysis of Methyl Jasmonate-Induced Triterpenoid Production in the Medicinal Herb Centella asiatica (L.) Urban

by Jacinda T. James, Fidele Tugizimana, Paul A. Steenkamp and Ian A. Dubery

Molecules 2013, 18(4), 4267-4281; https://doi.org/10.3390/molecules18044267 - 11 Apr 2013

Cited by 54 | Viewed by 9835

Abstract

Centella asiatica is an important source of biologically active pentacyclic triterpenoids. The enhancement of the biosynthesis of the centellosides by manipulation of associated metabolic pathways is receiving much attention. Jasmonates play critical roles in plant metabolism by up-regulating the expression of genes related [...] Read more.

Centella asiatica is an important source of biologically active pentacyclic triterpenoids. The enhancement of the biosynthesis of the centellosides by manipulation of associated metabolic pathways is receiving much attention. Jasmonates play critical roles in plant metabolism by up-regulating the expression of genes related to secondary metabolites. Here, we investigated the effect of methyl jasmonate (MeJa) in C. asiatica through targeted metabolomic profiling of asiaticoside and madecassoside as well as their aglycones, asiatic acid and madecassic acid. Cell suspensions were treated with 0.2 mM MeJa for 2, 4 and 6 days. Liquid chromatography coupled to mass spectrometry (LC-MS) was used to explore induced changes in metabolite profiles, both qualitatively and quantitatively. Principal component analysis (PCA)-derived scores plots revealed clusters of sample replicates for control and treated samples at 2, 4 and 6 days while loading plots aided in identifying signatory biomarkers (asiatic acid and madecassic acid, as well as asiaticoside and madecassoside) that clearly demonstrate the variability between samples. In addition to increased biosynthesis of the targeted centelloids, other differential changes in the intracellular metabolite profiles reflected the response of the C. asiatica cells to the MeJa-treatment as a reprogramming of the metabolome. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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225 KiB

Open AccessArticle

Triterpene Esters: Natural Products from Dorstenia arifolia (Moraceae)

by Catharina E. Fingolo, Thabata De S. Santos, Marcelo D. M. Vianna Filho and Maria Auxiliadora C. Kaplan

Molecules 2013, 18(4), 4247-4256; https://doi.org/10.3390/molecules18044247 - 11 Apr 2013

Cited by 49 | Viewed by 8717

Abstract

The phytochemical study of Dorstenia arifolia Lam. (Moraceae) has led to the identification of 18 triterpenes esterified by fatty acids, five triterpenes without esterification, 12 triterpenes esterified by acetic acid, together with a known furanocoumarin: α-amyrin (1), β-amyrin (2) [...] Read more.

The phytochemical study of Dorstenia arifolia Lam. (Moraceae) has led to the identification of 18 triterpenes esterified by fatty acids, five triterpenes without esterification, 12 triterpenes esterified by acetic acid, together with a known furanocoumarin: α-amyrin (1), β-amyrin (2) α-amyrin acetate (3) β-amyrin acetate (4), α-amyrin octanoate (5), β-amyrin octanoate (6), α-amyrin decanoate (7), β-amyrin decanoate (8), α-amyrin dodecanoate (9), β-amyrin dodecanoate (10), α-amyrin tetradecanoate (11), β-amyrin tetradecanoate (12), α-amyrin hexadecanoate (13), β-amyrin hexadecanoate (14), glutinol (15), glutinyl acetate (16), 11-oxo-α-amyrin (17), 11-oxo-β-amyrin (18), 11-oxo-α-amyrin acetate (19), 11-oxo-β-amyrin acetate (20) 11-oxo-α-amyrin octanoate (21) 11-oxo-β-amyrin octanoate (22), 11-oxo-α-amyrin decanoate (23), 11-oxo-β-amyrin decanoate (24) 11-oxo-α-amyrin dodecanoate (25) 11-oxo-β-amyrin dodecanoate (26), ursa-9(11),12-dien-3-yl acetate (27), oleana-9(11),12-dien-3-yl acetate (28), ursa-9(11),12-dien-3-yl decanoate (29), oleana-9(11),12-dien-3-yl decanoate (30), 12,13-epoxyolean-3-yl acetate (31), 12,13-epoxyolean-9(11)en-3-yl acetate (32), taraxeryl acetate (33), lupenyl acetate (34), lanosta-8,24-dien-3-yl acetate (35) and psoralen (36). The identification of the triterpene compounds isolated as isomeric mixtures obtained from the hexane extract was based mainly in mass spectra and ¹³C-NMR data. The long-chain alkanoic acid esters of the triterpenes α- and β-amyrin; 11-oxo-α- and 11-oxo-β-amyrin; ursa- and olean-9(11),12-dien-3-yl; have not been reported before in the literature as constituents of the Dorstenia genus. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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297 KiB

Open AccessCommunication

Anti-Inflammatory Cycloartane-Type Saponins of Astragalus membranaceus

by Dae-Young Lee, Hyung-Jun Noh, Jehun Choi, Kyeong-Hee Lee, Min-Ho Lee, Ji-Hyun Lee, Yoonpyo Hong, Seung-Eun Lee, Seung-Yu Kim and Geum-Soog Kim

Molecules 2013, 18(4), 3725-3732; https://doi.org/10.3390/molecules18043725 - 25 Mar 2013

Cited by 64 | Viewed by 9977

Abstract

A new cycloartane-type triterpene glycoside, agroastragaloside V (1) was isolated from the roots of Astragalus membranaceus. The structure was identified as 3-O-β-(2'-O-acetyl)-D-xylopyranosyl-6-O-β-D-glucopyranosyl-(24S)-3β,6α,24α,25-tetrahydroxy- [...] Read more.

A new cycloartane-type triterpene glycoside, agroastragaloside V (1) was isolated from the roots of Astragalus membranaceus. The structure was identified as 3-O-β-(2'-O-acetyl)-D-xylopyranosyl-6-O-β-D-glucopyranosyl-(24S)-3β,6α,24α,25-tetrahydroxy- 9,19-cyclolanostane, by means of spectroscopic methods, including HR-FAB/MS, 1D NMR (¹H, ¹³C, DEPT), 2D NMR (gCOSY, gHSQC, gHMBC, NOESY), and IR spectroscopy. Four known cycloartane glycosides, namely, agroastragaloside I (2), agroastragaloside II (3), isoastragaloside II (4) and astragaloside IV (5) were also isolated. All isolated compounds were tested for the ability to inhibit LPS-induced nitric oxide production in RAW264.7 macrophages. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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225 KiB

Open AccessArticle

Efficient Synthesis and Anti-Fungal Activity of Oleanolic Acid Oxime Esters

by Hanqing Zhao, Minjie Zhou, Lifeng Duan, Wei Wang, Jianjun Zhang, Daoquan Wang and Xiaomei Liang

Molecules 2013, 18(3), 3615-3629; https://doi.org/10.3390/molecules18033615 - 21 Mar 2013

Cited by 52 | Viewed by 8218

Abstract

In order to develop potential glucosamine-6-phosphate synthase inhibitors and anti-fungal agents, twenty five oleanolic acid oxime esters were synthesized in an efficient way. The structures of the new compounds were confirmed by MS, HRMS, ¹H-NMR and ¹³C-NMR. Preliminary studies based on [...] Read more.

In order to develop potential glucosamine-6-phosphate synthase inhibitors and anti-fungal agents, twenty five oleanolic acid oxime esters were synthesized in an efficient way. The structures of the new compounds were confirmed by MS, HRMS, ¹H-NMR and ¹³C-NMR. Preliminary studies based on means of the Elson-Morgan method indicated that many compounds exhibited some inhibitory activity of glucosamine-6-phosphate synthase (GlmS), and the original fungicidal activities results showed that some of the compounds exhibited good fungicidal activities towards Sclerotinia sclerotiorum (Lib.) de Bary, Rhizoctonia solani Kuhn and Botrytis cinerea Pers at the concentration of 50 µg/mL. These compounds would thus merit further study and development as antifungal agents. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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980 KiB

Open AccessArticle

Inhibition of Telomerase Activity by Oleanane Triterpenoid CDDO-Me in Pancreatic Cancer Cells is ROS-Dependent

by Dorrah Deeb, Xiaohua Gao, Yongbo Liu, Nadimpalli R. S. Varma, Ali S. Arbab and Subhash C. Gautam

Molecules 2013, 18(3), 3250-3265; https://doi.org/10.3390/molecules18033250 - 13 Mar 2013

Cited by 43 | Viewed by 8148

Abstract

Methyl-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate (CDDO-Me) is a synthetic derivative of oleanolic acid, a triterpene, with apoptosis-inducing activity in a wide range of cancer cells. Induction of apoptosis by CDDO-Me is associated with the generation of reactive oxygen species (ROS) and inhibition of telomerase activity. In the [...] Read more.

Methyl-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate (CDDO-Me) is a synthetic derivative of oleanolic acid, a triterpene, with apoptosis-inducing activity in a wide range of cancer cells. Induction of apoptosis by CDDO-Me is associated with the generation of reactive oxygen species (ROS) and inhibition of telomerase activity. In the present study, we investigated the role of ROS in inhibition of telomerase by CDDO-me. Treatment of MiaPaCa-2 and Panc-1 pancreatic cancer cell lines with CDDO-Me induced the production of hydrogen peroxide and superoxide anions and inhibited the telomerase activity. Pretreatment of cells with N-acetylcycsteine, a general purpose antioxidant or overexpression of glutathione peroxidase (GPx) or superoxide dismutase-1 (SOD-1) blocked the telomerase inhibitory activity of CDDO-Me. Furthermore, blocking ROS generation also prevented the inhibition of hTERT gene expression, hTERT protein production and expression of a number of hTERT–regulatory proteins by CDDO-Me (e.g., c-Myc, Sp1, NF-κB and p-Akt). Data also showed that Akt plays an important role in the activation of telomerase activity. Together, these data suggest that inhibition of telomerase activity by CDDO-Me is mediated through a ROS-dependent mechanism; however, more work is needed to fully understand the role of ROS in down-regulation of hTERT gene and hTERT-regulatory proteins by CDDO-Me. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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660 KiB

Open AccessArticle

Repeated Oral Administration of Oleanolic Acid Produces Cholestatic Liver Injury in Mice

by Yuan-Fu Lu, Xiao-Li Wan, Yasha Xu and Jie Liu

Molecules 2013, 18(3), 3060-3071; https://doi.org/10.3390/molecules18033060 - 7 Mar 2013

Cited by 51 | Viewed by 8484

Abstract

Oleanolic acid (OA) is a triterpenoid and a fantastic molecule with many beneficial effects. However, high-doses and long-term use can produce adverse effects. This study aimed to characterize the hepatotoxic potential of OA. Mice were given OA at doses of 100–3,000 µmol/kg (45–1,350 [...] Read more.

Oleanolic acid (OA) is a triterpenoid and a fantastic molecule with many beneficial effects. However, high-doses and long-term use can produce adverse effects. This study aimed to characterize the hepatotoxic potential of OA. Mice were given OA at doses of 100–3,000 µmol/kg (45–1,350 mg/kg), po for 10 days, and the hepatotoxicity was determined by serum biochemistry, histopathology, and toxicity-related gene expression via real-time RT-PCR. Animal body weight loss was evident at OA doses of 1,000 µmol/kg and above. Serum alanine aminotransferase activities were increased in a dose-dependent manner, indicative of hepatotoxicity. Serum total bilirubin concentrations were increased, indicative of cholestasis. OA administration produced dose-dependent pathological lesions to the liver, including inflammation, hepatocellular apoptosis, necrosis, and feathery degeneration indicative of cholestasis. These lesions were evident at OA doses of 500 µmol/kg and above. Real-time RT-PCR revealed that OA produced dose-dependent increases in acute phase proteins (MT-1, Ho-1, Nrf2 and Nqo1), decreases in bile acid synthesis genes (Cyp7a1 and Cyp8b1), and decreases in liver bile acid transporters (Ntcp, Bsep, Oatp1a1, Oatp1b2, and Ostβ). Thus, the clinical use of OA and OA-type triterpenoids should balance the beneficial effects and toxicity potentials. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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279 KiB

Open AccessArticle

Simultaneous Determination of Flavonoids, Isochlorogenic Acids and Triterpenoids in Ilex hainanensis Using High Performance Liquid Chromatography Coupled with Diode Array and Evaporative Light Scattering Detection

by Bo Peng, Chun-Feng Qiao, Jing Zhao, Wei-Hua Huang, De-Jun Hu, Hua-Gang Liu and Shao-Ping Li

Molecules 2013, 18(3), 2934-2941; https://doi.org/10.3390/molecules18032934 - 4 Mar 2013

Cited by 10 | Viewed by 7588

Abstract

A high performance liquid chromatography coupled with diode array and evaporative light scattering detection (HPLC-DAD-ELSD) method for simultaneous determination of eight major bioactive compounds including two flavonoids (rutin and eriodictyol-7-O-β-D-glucopyranoside), two isochlorogenic acids (isochlorogenic acid A and isochlorogenic acid C) and [...] Read more.

A high performance liquid chromatography coupled with diode array and evaporative light scattering detection (HPLC-DAD-ELSD) method for simultaneous determination of eight major bioactive compounds including two flavonoids (rutin and eriodictyol-7-O-β-D-glucopyranoside), two isochlorogenic acids (isochlorogenic acid A and isochlorogenic acid C) and four triterpenoids (ilexhainanoside D, ilexsaponin A₁, ilexgenin A and ursolic acid) in Ilex hainanensis has been developed for the first time. The 283 nm wavelength was chosen for determination of two flavonoids and two isochlorogenic acids. ELSD was applied to determine four triterpenoids. The analysis was performed on an Agilent Zorbax SB-C₁₈ column (250 × 4.6 mm i.d., 5 µm) with gradient elution of 0.2% formic acid in water and acetonitrile. The method was validated for linearity, limit of detection, limit of quantification, precision, repeatability and accuracy. The proposed method has been successfully applied for simultaneous quantification of the analytes in four samples of Ilex hainanensis, which is helpful for quality control of this plant. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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1399 KiB

Open AccessArticle

Cell Suspension Culture of Eriobotrya japonica Regulates the Diabetic and Hyperlipidemic Signs of High-Fat-Fed Mice

by Chun-Ching Shih, Jiun-Lin Ciou, Cheng-Hsiu Lin, Jin-Bin Wu and Hui-Ya Ho

Molecules 2013, 18(3), 2726-2753; https://doi.org/10.3390/molecules18032726 - 1 Mar 2013

Cited by 39 | Viewed by 14709

Abstract

The present study investigates the anti-hyperlipidemic and antihyperglycemic effects and mechanism in high-fat (HF)-fed mice of cell suspension culture of Eriobotrya japonica (TA), which contains a great number of pentacyclic terpenoids. Firstly, C57BL/6J mice were randomly divided into two groups: the control (CON) [...] Read more.

The present study investigates the anti-hyperlipidemic and antihyperglycemic effects and mechanism in high-fat (HF)-fed mice of cell suspension culture of Eriobotrya japonica (TA), which contains a great number of pentacyclic terpenoids. Firstly, C57BL/6J mice were randomly divided into two groups: the control (CON) group was fed with a low-fat diet (n = 9), whereas the experimental group was fed a 45% HF diet for 8 weeks. Afterwards, the CON group was treated with vehicle, whereas the HF group was subdivided into five groups and was orally given TA or rosiglitazone or not for 4 weeks. Blood and visceral adipose tissue, liver tissue and skeletal muscle were examined. Treatment with TA reduced body weight gain, weights of white adipose tissue (WAT) (including epididymal, perirenal, mesenteric WAT and visceral fat), and hepatic triacylglycerol content significantly without affecting food intake in diet-induced diabetic mice. TA effectively prevented HF diet-induced increases in the levels of blood glucose, insulin, leptin and HOMA-IR index (p < 0.001, p < 0.05, p < 0.05, p < 0.01, respectively) and attenuated insulin resistance. Treatment with TA, adipocytes in the visceral depots showed a reduction in size. TA effectively significantly increased the protein contents of phosphorylation of AMPK-α (Thr172) both in liver and adipose tissue. It is shown that TA exhibits hypolipidemic effect in HF-fed mice by decreasing gene expressions of fatty acid synthesis, including acyl-coenzyme A: diacylglycerol acyltransferase (DGAT) 2, which catalyzes the final step in the synthesis of triglycerides, and antidiabetic properties occurred as a result of decreased hepatic glucose production via phosphenolpyruvate carboxykinase (PEPCK) down- regulation, improved insulin sensitization and TA (at 1.0 g/kg dose) decreased expression of hepatic and adipose 11-β-hydroxysteroid dehydroxygenase (11β-HSD1) gene, which contributed in attenuating diabetic state. Futhermore, TA at doses of 0.5 and 1.0 g/kg had serum lipid-lowering action characterized by the inhibition of DGAT 1 expression. Thus, amelioration of diabetic and dyslipidemic state by TA in HF-fed mice occurred by regulation of PEPCK, DGAT2 and AMPK phosphorylation. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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267 KiB

Open AccessArticle

Ulososides and Urabosides — Triterpenoid Saponins from the Caribbean Marine Sponge Ectyoplasia ferox

by Jhonny Colorado, Diana Muñoz, Diana Marquez, Maria Elena Marquez, Juan Lopez, Olivier P. Thomas and Alejandro Martinez

Molecules 2013, 18(3), 2598-2610; https://doi.org/10.3390/molecules18032598 - 27 Feb 2013

Cited by 14 | Viewed by 9186

Abstract

Three new triterpene glycosides, named ulososide F (1), urabosides A (2) and B (3), together with the previously reported ulososide A (4), were isolated from the Caribbean marine sponge Ectyoplasia ferox. Their structures were [...] Read more.

Three new triterpene glycosides, named ulososide F (1), urabosides A (2) and B (3), together with the previously reported ulososide A (4), were isolated from the Caribbean marine sponge Ectyoplasia ferox. Their structures were elucidated using extensive interpretation of 1D and 2D-NMR data, as well as HRESIMS. The aglycon of all compounds is a rare 30-norlonastane and the sugar residues were identified after acid hydrolysis and GC analyses. Cytotoxicities of the isolated compounds were evaluated against Jurkat and CHO cell lines by a MTT in vitro assay as well as a hemolysis assay. Unexpectedly, all these saponin derivatives showed very low activity in our bioassays. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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226 KiB

Open AccessArticle

Hirtinone, a Novel Cycloartane-Type Triterpene and Other Compounds from Trichilia hirta L. (Meliaceae)

by Ivo José Curcino Vieira, Otoniel De Aquino Azevedo, Jucimar Jorgeane De Souza, Raimundo Braz-Filho, Milena Dos Santos Gonçalves and Marcelo Francisco De Araújo

Molecules 2013, 18(3), 2589-2597; https://doi.org/10.3390/molecules18032589 - 26 Feb 2013

Cited by 18 | Viewed by 8095

Abstract

One novel triterpene cycloartane-type, named hirtinone (1), six protolimonoids – nilocitin (2), dihydronilocitin B (3), melianone epimers (4) and (5), piscidinol A (6) and melianone lactone (7), one tertranortriterpenoid, [...] Read more.

One novel triterpene cycloartane-type, named hirtinone (1), six protolimonoids – nilocitin (2), dihydronilocitin B (3), melianone epimers (4) and (5), piscidinol A (6) and melianone lactone (7), one tertranortriterpenoid, hirtin (8), and one sesquiterpene, spathulenol (9), were identified in the fruits of Trichilia hirta. The structures were established by 1D and 2D NMR (¹H and ¹³C-NMR, DEPTQ, ¹H-¹H-COSY, ¹H-¹H-NOESY, HSQC and HMBC), high resolution mass spectroscopy (HR-ESI-MS) and infrared (IR) spectral data. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessArticle

Methyl Antcinate A Suppresses the Population of Cancer Stem-Like Cells in MCF7 Human Breast Cancer Cell Line

by Chih-Yu Peng, Pin-Chung Fong, Cheng-Chia Yu, Wan-Chi Tsai, Yew-Min Tzeng and Wen-Wei Chang

Molecules 2013, 18(3), 2539-2548; https://doi.org/10.3390/molecules18032539 - 26 Feb 2013

Cited by 20 | Viewed by 9296

Abstract

Methyl antcinate A (MAA) is an ergostane-type triterpenoid extracted from the fruiting bodies of Antrodia camphorate that has been reported to be a cytotoxic agent towards some types of cancer cells, such as oral cancer and liver cancer. Cancer stem cells (CSCs) are [...] Read more.

Methyl antcinate A (MAA) is an ergostane-type triterpenoid extracted from the fruiting bodies of Antrodia camphorate that has been reported to be a cytotoxic agent towards some types of cancer cells, such as oral cancer and liver cancer. Cancer stem cells (CSCs) are a particular population within cancer cells which are responsible for tumor initiation, drug resistance and metastasis and targeting CSCs is an emerging area in cancer therapy. In this study, we examine the effect of MAA on cancer stem-like cells in the MCF7 human breast cancer cell line. Although MAA displayed very low cytotoxic effect towards MCF7 under normal culture conditions, it did show good inhibitory effects on the self-renewal capability which was examined by mammosphere culture including primary and secondary sphere. MAA also inhibited cell migration ability of MCF7 sphere cells. By western blot analysis, MAA was shown to suppress the expression of heat shock protein 27 and increase the expression of IkBα and p53. In conclusion, our data demonstrate that MAA has anti-CSC activity and is worthy of future development of potent anticancer agents. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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271 KiB

Open AccessArticle

Cytotoxic and Radical Scavenging Nor-Dammarane Triterpenoids from Viburnum mongolicum

by Xiaohua Wang and Wei Wang

Molecules 2013, 18(2), 1405-1417; https://doi.org/10.3390/molecules18021405 - 24 Jan 2013

Cited by 7 | Viewed by 4988

Abstract

The ethanol extract of the whole plants of Viburnum mongolicum afforded six new nor-dammarane triterpenoids: 3β,12β-dihydroxy-25,26,27-trinordammara-22-en -24,20-olide (1), 3β,12β-dihydroxy-24α-methoxy-25,26,27-trinordammara-20,24-epoxy (2), 3β-O-acetyl-12β-hydroxy-23,24,25,26,27-hexanordammarane-20-one (3 [...] Read more.

The ethanol extract of the whole plants of Viburnum mongolicum afforded six new nor-dammarane triterpenoids: 3β,12β-dihydroxy-25,26,27-trinordammara-22-en -24,20-olide (1), 3β,12β-dihydroxy-24α-methoxy-25,26,27-trinordammara-20,24-epoxy (2), 3β-O-acetyl-12β-hydroxy-23,24,25,26,27-hexanordammarane-20-one (3), 12β-O- acetyl-15α-hydroxy-17β-methoxy-3-oxo-20,21,22-23,24,25,26,27-octanordammanrane (4), 12β-O-acetyl-15α,17β-dihydroxy-3-oxo-20,21,22-23,24,25,26,27-octanordammanrane (5), and 12β,15α-dihydroxy-3-oxo-17-en-20,21,22-23,24,25,26,27-octanordammanrane (6), together with two known nor-dammarane triterpenoids, 12β-hydroxy-3-oxo-24α-methoxy- 25,26,27-trinordammara-20,24-epoxy (7) and 3β,12β-dihydroxy-23,24,25,26,27- hexanordammarane-20-one (8). The structures of the isolated compounds were established based on 1D and 2D (¹H-¹H COSY, HMQC, and HMBC) NMR spectroscopy, in addition to high resolution mass spectrometry. The isolated compounds were tested in vitro for cytotoxic potential against seven tumor cell lines and radical scavenging activities. Compounds 4–6 exhibited significant cytotoxic activities against all tested tumor cell lines and radical scavenging activities against ABTS^·+ radicals comparable with the standard drug Trolox. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessArticle

A New Triterpenoid from Teucrium viscidum

by Xincai Hao, Jinwen Zhang, Guangxin Xia, Yongbo Xue, Zengwei Luo, Yanyan Si, Guangmin Yao and Yonghui Zhang

Molecules 2013, 18(1), 1262-1269; https://doi.org/10.3390/molecules18011262 - 21 Jan 2013

Cited by 13 | Viewed by 6134

Abstract

A new ursane-type triterpenoid, 3β-hydroxy-urs-30-p-Z-hydroxycinnamoyloxy-12-en-28-oic-acid (1), together with three known triterpenoids, 3β-hydroxy-urs-30-p-E-hydroxycinnamoyloxy-12-en-28-oic-acid (2), 2α,3β,19α-trihydroxy-urs-12-en-28-oic-acid (3), and ursolic acid ( [...] Read more.

A new ursane-type triterpenoid, 3β-hydroxy-urs-30-p-Z-hydroxycinnamoyloxy-12-en-28-oic-acid (1), together with three known triterpenoids, 3β-hydroxy-urs-30-p-E-hydroxycinnamoyloxy-12-en-28-oic-acid (2), 2α,3β,19α-trihydroxy-urs-12-en-28-oic-acid (3), and ursolic acid (4), four known lignans, pinoresinol (5), 9α-hydroxypinoresinol (6), (+)-medioresinol (7), and (+)-kobusin (8), and two steroids, β-sitosterol (9), and daucosterol (10), were isolated from the whole parts of Teucrium viscidum. Their structures were established by a combination of spectroscopic data analysis, besides comparison with literature data. Compounds 1–4 were evaluated for their inhibitory activities against 11β-hydroxysteroid dehydrogenase 1 (11β-HSD1). Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessArticle

Antiprotozoal Activity of Quinonemethide Triterpenes from Maytenus ilicifolia (Celastraceae)

by Vania A. F. F. M. Dos Santos, Karoline M. Leite, Mariana Da Costa Siqueira, Luis O. Regasini, Isabel Martinez, Camila T. Nogueira, Mariana Kolos Galuppo, Beatriz S. Stolf, Ana Maria Soares Pereira, Regina M. B. Cicarelli, Maysa Furlan and Marcia A. S. Graminha

Molecules 2013, 18(1), 1053-1062; https://doi.org/10.3390/molecules18011053 - 15 Jan 2013

Cited by 52 | Viewed by 7888

Abstract

The present study describes the leishmanicidal and trypanocidal activities of two quinonemethide triterpenes, maytenin (1) and pristimerin (2), isolated from Maytenus ilicifolia root barks (Celastraceae). The compounds were effective against the Trypanosomatidae Leishmania amazonensis and Leishmania chagasi and Trypanosoma [...] Read more.

The present study describes the leishmanicidal and trypanocidal activities of two quinonemethide triterpenes, maytenin (1) and pristimerin (2), isolated from Maytenus ilicifolia root barks (Celastraceae). The compounds were effective against the Trypanosomatidae Leishmania amazonensis and Leishmania chagasi and Trypanosoma cruzi, etiologic agents of leishmaniasis and Chagas’ disease, respectively. The quinonemethide triterpenes 1 and 2 exhibited a marked in vitro leishmanicidal activity against promastigotes and amastigotes with 50% inhibitory concentration (IC₅₀) values of less than 0.88 nM. Both compounds showed IC₅₀ lower than 0.3 nM against Trypanosoma cruzi epimastigotes. The selectivity indexes (SI) based on BALB/c macrophages for L. amazonensis and L. chagasi were 243.65 and 46.61 for (1) and 193.63 and 23.85 for (2) indicating that both compounds presented high selectivity for Leishmania sp. The data here presented suggests that these compounds should be considered in the development of new and more potent drugs for the treatment of leishmaniasis and Chagas’ disease. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessArticle

Telomerase Reverse Transcriptase (TERT) is a Therapeutic Target of Oleanane Triterpenoid CDDO-Me in Prostate Cancer

by Yongbo Liu, Xiaohua Gao, Dorrah Deeb, Ali S. Arbab and Subhash C. Gautam

Molecules 2012, 17(12), 14795-14809; https://doi.org/10.3390/molecules171214795 - 11 Dec 2012

Cited by 20 | Viewed by 5587

Abstract

Methyl-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate (CDDO-Me) is an synthetic oleanane triterpenoid with strong antiprolifertive and proapoptotic activities in cancer cells. However, the effect of CDDO-Me on human telomerase reverse transcriptase (hTERT) and its telomerase activity in prostate cancer cells has not been studied. We investigated the role [...] Read more.

Methyl-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate (CDDO-Me) is an synthetic oleanane triterpenoid with strong antiprolifertive and proapoptotic activities in cancer cells. However, the effect of CDDO-Me on human telomerase reverse transcriptase (hTERT) and its telomerase activity in prostate cancer cells has not been studied. We investigated the role of hTERT in mediating the anticancer activity of CDDO-Me in prostate cancer cells in vitro and in vivo. The inhibition of cell proliferation and induction of apoptosis by CDDO-Me in LNCaP and PC-3 prostate cancer cell lines was associated with the inhibition of hTERT gene expression, hTERT telomerase activity and a number of proteins that regulate hTERT transcriptionally and post-translationally. Furthermore, ablation of hTERT protein increased the sensitivity of cancer cells to CDDO-Me, whereas its overexpression rendered them resistant to CDDO-Me. In addition, inhibition of progression of preneoplastic lesions (i.e., low and high-grade prostate intraepithelial neoplasms, PINs) to adenocarcinoma of the prostate by CDDO-Me in TRAMP mice was associated with significant decrease in TERT and its regulatory proteins in the prostate gland. These data provide evidence that telomerase is a potential target of CDDO-Me for the prevention and treatment of prostate cancer. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessArticle

New Triterpenes from Maytenus robusta: Structural Elucidation Based on NMR Experimental Data and Theoretical Calculations

by Grasiely F. Sousa, Lucienir P. Duarte, Antônio F. C. Alcântara, Grácia D. F. Silva, Sidney A. Vieira-Filho, Roqueline R. Silva, Djalma M. Oliveira and Jacqueline A. Takahashi

Molecules 2012, 17(11), 13439-13456; https://doi.org/10.3390/molecules171113439 - 12 Nov 2012

Cited by 74 | Viewed by 9259

Abstract

Leaves of Maytenus robusta (Celastraceae) were subjected to phytochemical investigation mainly directed at the isolation of pentacyclic triterpenes. The compounds friedelin (1), β-friedelinol (2), 3-oxo-21β-H-hop-22(29)-ene (7), 3,4-seco-friedelan-3,11β-olide ( [...] Read more.

Leaves of Maytenus robusta (Celastraceae) were subjected to phytochemical investigation mainly directed at the isolation of pentacyclic triterpenes. The compounds friedelin (1), β-friedelinol (2), 3-oxo-21β-H-hop-22(29)-ene (7), 3,4-seco-friedelan-3,11β-olide (8), 3β-hydroxy-21β-H-hop-22(29)-ene (9), 3,4-seco-21β-H-hop-22(29)-en-3-oic acid (10), 3,4-seco-friedelan-3-oic acid (11), and sitosterol were identified in the hexane extract of M. robusta leaves. Compounds 8 and 9 are described herein for the first time. The structure and stereochemistry of both compounds were experimentally established by IR, HRLC-MS, and 1D (¹H, ¹³C, and DEPT 135) and 2D (HSQC, HMBC and COSY) NMR data and supported by correlations with carbon chemical shifts calculated using the DFT method (BLYP/6-31G* level). Compounds 7 and 10 are also described for the first time, and their chemical structures were established by comparison with NMR data of similar structures described in the literature and correlations with BLYP/6-31G* calculated carbon chemical shifts. Compound 9, a mixture of 11 and sitosterol, and 3β,11β-dihydroxyfriedelane (4) were evaluated by the Ellman’s method and all these compounds showed acethylcholinesterase inhibitory properties. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessCommunication

Bioactive Oleanane, Lupane and Ursane Triterpene Acid Derivatives

by Maria De L. e Silva, Juceni P. David, Lidércia C. R. C. Silva, Rauldenis A. F. Santos, Jorge M. David, Luciano S. Lima, Pedro S. Reis and Renato Fontana

Molecules 2012, 17(10), 12197-12205; https://doi.org/10.3390/molecules171012197 - 17 Oct 2012

Cited by 53 | Viewed by 10493

Abstract

Betulinic, ursolic and oleanolic acids isolated from the aerial parts of Eriope blanchetii (Lamiaceae) were subjected to different esterification reactions, yielding 12 C-3 position ester derivatives. All compounds were identified using spectroscopic techniques, such as IR, ¹H-NMR and MS. The derivatives were [...] Read more.

Betulinic, ursolic and oleanolic acids isolated from the aerial parts of Eriope blanchetii (Lamiaceae) were subjected to different esterification reactions, yielding 12 C-3 position ester derivatives. All compounds were identified using spectroscopic techniques, such as IR, ¹H-NMR and MS. The derivatives were further investigated for their antioxidant level, Artemia salina lethality and antimicrobial activity. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessArticle

A New Saponin from Tea Seed Pomace (Camellia oleifera Abel) and Its Protective Effect on PC12 Cells

by Xin-Fu Zhang, Ying-Ying Han, Guan-Hu Bao, Tie-Jun Ling, Liang Zhang, Li-Ping Gao and Tao Xia

Molecules 2012, 17(10), 11721-11728; https://doi.org/10.3390/molecules171011721 - 1 Oct 2012

Cited by 45 | Viewed by 8869

Abstract

A new triterpenoid saponin, oleiferasaponin A₁, was isolated from tea seed pomace (Camellia oleifera Abel). The structure of oleiferasaponin A₁ was elucidated on the basis of chemical and physicochemical evidence and was found to be 22-O-cis [...] Read more.

A new triterpenoid saponin, oleiferasaponin A₁, was isolated from tea seed pomace (Camellia oleifera Abel). The structure of oleiferasaponin A₁ was elucidated on the basis of chemical and physicochemical evidence and was found to be 22-O-cis-2-hexenoyl-A₁-barrigenol 3-O-[β-D-galactopyranosyl(1→2)] [β-D-glucopyranosyl(1→2)-α-L-arabinopyranosyl(1→3)]-β-D-glucopyranosiduronic acid. PC12 cells injured with H₂O₂ were used as the model to test the protective effects of oleiferasaponin A₁. The results indicated that oleiferasaponin A₁ can potentially prevent the H₂O₂-induced cell death of PC12 cells. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessArticle

Phorbol Esters from Jatropha Meal Triggered Apoptosis, Activated PKC-δ, Caspase-3 Proteins and Down-Regulated the Proto-Oncogenes in MCF-7 and HeLa Cancer Cell Lines

by Ehsan Oskoueian, Norhani Abdullah and Syahida Ahmad

Molecules 2012, 17(9), 10816-10830; https://doi.org/10.3390/molecules170910816 - 10 Sep 2012

Cited by 26 | Viewed by 6940

Abstract

Jatropha meal produced from the kernel of Jatropha curcas Linn. grown in Malaysia contains phorbol esters (PEs). The potential benefits of PEs present in the meal as anticancer agent are still not well understood. Hence, this study was conducted to evaluate the cytotoxic [...] Read more.

Jatropha meal produced from the kernel of Jatropha curcas Linn. grown in Malaysia contains phorbol esters (PEs). The potential benefits of PEs present in the meal as anticancer agent are still not well understood. Hence, this study was conducted to evaluate the cytotoxic effects and mode of actions of PEs isolated from Jatropha meal against breast (MCF-7) and cervical (HeLa) cancer cell lines. Isolated PEs inhibited cells proliferation in a dose-dependent manner of both MCF-7 and HeLa cell lines with the IC₅₀ of 128.6 ± 2.51 and 133.0 ± 1.96 µg PMA equivalents/mL respectively, while the values for the phorbol 12-myristate 13-acetate (PMA) as positive control were 114.7 ± 1.73 and 119.6 ± 3.73 µg/mL, respectively. Microscopic examination showed significant morphological changes that resemble apoptosis in both cell lines when treated with PEs and PMA at IC₅₀ concentration after 24 h. Flow cytometry analysis and DNA fragmentation results confirmed the apoptosis induction of PEs and PMA in both cell lines. The PEs isolated from Jatropha meal activated the PKC-δ and down-regulated the proto-oncogenes (c-Myc, c-Fos and c-Jun). These changes probably led to the activation of Caspase-3 protein and apoptosis cell death occurred in MCF-7 and HeLa cell lines upon 24 h treatment with PEs and PMA. Phorbol esters of Jatropha meal were found to be promising as an alternative to replace the chemotherapeutic drugs for cancer therapy. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessArticle

Pentacyclic Triterpene Distribution in Various Plants – Rich Sources for a New Group of Multi-Potent Plant Extracts

by Sebastian Jäger, Holger Trojan, Thomas Kopp, Melanie N. Laszczyk and Armin Scheffler

Molecules 2009, 14(6), 2016-2031; https://doi.org/10.3390/molecules14062016 - 4 Jun 2009

Cited by 519 | Viewed by 31583

Abstract

Pentacyclic triterpenes are secondary plant metabolites widespread in fruit peel, leaves and stem bark. In particular the lupane-, oleanane-, and ursane triterpenes display various pharmacological effects while being devoid of prominent toxicity. Therefore, these triterpenes are promising leading compounds for the development of [...] Read more.

Pentacyclic triterpenes are secondary plant metabolites widespread in fruit peel, leaves and stem bark. In particular the lupane-, oleanane-, and ursane triterpenes display various pharmacological effects while being devoid of prominent toxicity. Therefore, these triterpenes are promising leading compounds for the development of new multi-targeting bioactive agents. Screening of 39 plant materials identified triterpene rich (> 0.1% dry matter) plant parts. Plant materials with high triterpene concentrations were then used to obtain dry extracts by accelerated solvent extraction resulting in a triterpene content of 50 - 90%. Depending on the plant material, betulin (birch bark), betulinic acid (plane bark), oleanolic acid (olive leaves, olive pomace, mistletoe sprouts, clove flowers), ursolic acid (apple pomace) or an equal mixture of the three triterpene acids (rosemary leaves) are the main components of these dry extracts. They are quantitatively characterised plant extracts supplying a high concentration of actives and therefore can be used for development of phytopharmaceutical formulations. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessArticle

Comparision of the Cytotoxic Effects of Birch Bark Extract, Betulin and Betulinic Acid Towards Human Gastric Carcinoma and Pancreatic Carcinoma Drug-sensitive and Drug-Resistant Cell Lines

by Marcin Drag, Pawel Surowiak, Malgorzata Drag-Zalesinska, Manfred Dietel, Hermann Lage and Józef Oleksyszyn

Molecules 2009, 14(4), 1639-1651; https://doi.org/10.3390/molecules14041639 - 24 Apr 2009

Cited by 73 | Viewed by 18566

Abstract

Betulin and betulinic acid are naturally occurring pentacyclic triterpenes showing cytotoxicity towards a number of cancer cell lines. These compounds can be found in the bark of the many plants. In this report we have compared the cytotoxic activity of crude birch bark [...] Read more.

Betulin and betulinic acid are naturally occurring pentacyclic triterpenes showing cytotoxicity towards a number of cancer cell lines. These compounds can be found in the bark of the many plants. In this report we have compared the cytotoxic activity of crude birch bark extract and purified betulin and betulinic acid towards human gastric carcinoma (EPG85-257) and human pancreatic carcinoma (EPP85-181) drug-sensitive and drug-resistant (daunorubicin and mitoxantrone) cell lines. Our results show significant differences in sensitivity between cell lines depending on the compound used, and suggest that both betulin and betulinic acid can be considered as a promising leads in the treatment of cancer. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessCommunication

Stereochemistry of 16a-Hydroxyfriedelin and 3-Oxo-16-methylfriedel-16-ene Established by 2D NMR Spectroscopy

by Lucienir Pains Duarte, Roqueline Rodrigues Silva de Miranda, Salomão Bento Vasconcelos Rodrigues Rodrigues, Grácia Divina De Fátima Silva, Sidney Augusto Vieira Filho and Vagner Fernandes Knupp

Molecules 2009, 14(2), 598-607; https://doi.org/10.3390/molecules14020598 - 4 Feb 2009

Cited by 11 | Viewed by 14273

Abstract

Friedelin (1), 3b-friedelinol (2), 28-hydroxyfriedelin (3), 16a-hydroxyfriedelin (4), 30-hydroxyfriedelin (5) and 16a,28-dihydroxyfriedelin (6) were isolated through fractionation of the hexane extract obtained from branches of Salacia elliptica. After a week in CDCl₃ solution, 16a-hydroxyfriedelin (4) reacted turning into 3-oxo-16-methylfriedel-16-ene (7). This is [...] Read more.

Friedelin (1), 3b-friedelinol (2), 28-hydroxyfriedelin (3), 16a-hydroxyfriedelin (4), 30-hydroxyfriedelin (5) and 16a,28-dihydroxyfriedelin (6) were isolated through fractionation of the hexane extract obtained from branches of Salacia elliptica. After a week in CDCl₃ solution, 16a-hydroxyfriedelin (4) reacted turning into 3-oxo-16-methylfriedel-16-ene (7). This is the first report of a dehydration followed by a Nametkin rearrangement of a pentacyclic triterpene in CDCl₃ solution occurring in the NMR tube. These seven pentacyclic triterpenes was identified through NMR spectroscopy and the stereochemistry of compound 4 and 7 was established by 2D NMR (NOESY) spectroscopy and mass spectrometry (GC-MS). It is also the first time that all the ¹³C-NMR and 2D NMR spectral data are reported for compounds 4 and 7. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessArticle

A Preliminary Pharmacokinetic Study of Betulin, the Main Pentacyclic Triterpene from Extract of Outer Bark of Birch (Betulae alba cortex)

by Sebastian Jäger, Melanie N. Laszczyk and Armin Scheffler

Molecules 2008, 13(12), 3224-3235; https://doi.org/10.3390/molecules13123224 - 18 Dec 2008

Cited by 124 | Viewed by 19074

Abstract

During the last two decades triterpenes have attracted attention because of their pharmacological potential. Triterpene extract (TE) from outer bark of birch consisting mainly of betulin is able to form an oleogel which was successfully tested in the treatment of actinic keratosis. Some [...] Read more.

During the last two decades triterpenes have attracted attention because of their pharmacological potential. Triterpene extract (TE) from outer bark of birch consisting mainly of betulin is able to form an oleogel which was successfully tested in the treatment of actinic keratosis. Some aspects of TE in vitro pharmacology are already known. Now we show preliminary pharmacokinetics of betulin and results of a subchronic toxicity study of TE in rats and dogs. Because of poor aqueous solubility of the TE-triterpenes (< 0.1 μg/mL respectively), for pharmacokinetic studies it was suspended in sesame oil (rats, i.p.) and PEG 400 / 0.9 % NaCl (dogs, s.c.). I.p. administered, betulin, the main component of TE, shows time dependency over a period of 4 h and reaches a dose-independent serum level of 0.13 μg/mL. Dose dependency was observed with s.c. administration. At 300 mg/kg a maximum plasma concentration of 0.33 μg/mL betulin was detected after 28 daily applications. The subchronic toxicity study showed no toxicity of TE in rats (i.p.) and dogs (s.c.). In conclusion, triterpene extract from birch bark is safe, its betulin is bioavailable and in addition to published triterpene biological activities TE provides high potential for further pharmaceutical and pharmacological research. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessArticle

Bioactive Pentacyclic Triterpenes from the Stems of Combretum laxum

by Eder Bisoli, Walmir Silva Garcez, Lidilhone Hamerski, Caroline Tieppo and Fernanda Rodrigues Garcez

Molecules 2008, 13(11), 2717-2728; https://doi.org/10.3390/molecules13112717 - 1 Nov 2008

Cited by 91 | Viewed by 16241

Abstract

Two new triterpene glucosides, β-D-glucopyranosyl 2α,3β,24-trihydroxyolean- 12-en-28-oate and β-D-glucopyranosyl 2α,3β,23,24-tetrahydroxyurs-12-en-28-oate, in addition to nine known compounds belonging to three different triterpene classes (oleanane-, ursane- and lupane-type) have been isolated from the stems of a specimen of Combretum laxum growing in the “Pantanal” of [...] Read more.

Two new triterpene glucosides, β-D-glucopyranosyl 2α,3β,24-trihydroxyolean- 12-en-28-oate and β-D-glucopyranosyl 2α,3β,23,24-tetrahydroxyurs-12-en-28-oate, in addition to nine known compounds belonging to three different triterpene classes (oleanane-, ursane- and lupane-type) have been isolated from the stems of a specimen of Combretum laxum growing in the “Pantanal” of the central-western region of Brazil. Among the known triterpenes, β-D-glucopyranosyl 2α,3β,6β-trihydroxyolean-12-en-28-oate is reported for the first time in the Combretaceae, while bellericoside and asiatic acid are described for the first time in the genus Combretum. The structures of the isolated compounds have been established on the basis of spectral techniques (1D-, 2D-NMR and MS). Their in vitro antifungal activities against standard strains of Candida albicans, C. krusei and Cryptococcus neoformans were also evaluated in this work. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Review

Jump to: Research

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Open AccessReview

Triterpenoids of Marine Origin as Anti-Cancer Agents

by Yong-Xin Li, S. W. A. Himaya and Se-Kwon Kim

Molecules 2013, 18(7), 7886-7909; https://doi.org/10.3390/molecules18077886 - 4 Jul 2013

Cited by 62 | Viewed by 10405

Abstract

Triterpenoids are the most abundant secondary metabolites present in marine organisms, such as marine sponges, sea cucumbers, marine algae and marine-derived fungi. A large number of triterpenoids are known to exhibit cytotoxicity against a variety of tumor cells, as well as anticancer efficacy [...] Read more.

Triterpenoids are the most abundant secondary metabolites present in marine organisms, such as marine sponges, sea cucumbers, marine algae and marine-derived fungi. A large number of triterpenoids are known to exhibit cytotoxicity against a variety of tumor cells, as well as anticancer efficacy in preclinical animal models. In this review efforts have been taken to review the structural features and the potential use of triterpenoids of marine origin to be used in the pharmaceutical industry as potential anti-cancer drug leads. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessReview

Protostane and Fusidane Triterpenes: A Mini-Review

by Ming Zhao, Tanja Gödecke, Jordan Gunn, Jin-Ao Duan and Chun-Tao Che

Molecules 2013, 18(4), 4054-4080; https://doi.org/10.3390/molecules18044054 - 5 Apr 2013

Cited by 70 | Viewed by 12035

Abstract

Protostane triterpenes belong to a group of tetracyclic triterpene that exhibit unique structural characteristics. Their natural distribution is primarily limited to the genus Alisma of the Alismataceae family, but they have also been occasionally found in other plant genera such as Lobelia, [...] Read more.

Protostane triterpenes belong to a group of tetracyclic triterpene that exhibit unique structural characteristics. Their natural distribution is primarily limited to the genus Alisma of the Alismataceae family, but they have also been occasionally found in other plant genera such as Lobelia, Garcinia, and Leucas. To date, there are 59 known protostane structures. Many of them have been reported to possess biological properties such as improving lipotropism, hepatoprotection, anti-viral activity against hepatitis B and HIV-I virus, anti-cancer activity, as well as reversal of multidrug resistance in cancer cells. On the other hand, fusidanes are fungal products characterized by 29-nor protostane structures. They possess antibiotic properties against staphylococci, including the methicillin-resistant Staphylococcus aureus (MRSA). Fusidic acid is a representative member which has found clinical applications. This review covers plant sources of the protostanes, their structure elucidation, characteristic structural and spectral properties, as well as biological activities. The fungal sources, structural features, biological activities of fusidanes are also covered in this review. Additionally, the biogenesis of these two types of triterpenes is discussed and a refined pathway is proposed. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessReview

Steroidal Triterpenes of Cholesterol Synthesis

by Jure Ačimovič and Damjana Rozman

Molecules 2013, 18(4), 4002-4017; https://doi.org/10.3390/molecules18044002 - 4 Apr 2013

Cited by 54 | Viewed by 11785

Abstract

Cholesterol synthesis is a ubiquitous and housekeeping metabolic pathway that leads to cholesterol, an essential structural component of mammalian cell membranes, required for proper membrane permeability and fluidity. The last part of the pathway involves steroidal triterpenes with cholestane ring structures. It starts [...] Read more.

Cholesterol synthesis is a ubiquitous and housekeeping metabolic pathway that leads to cholesterol, an essential structural component of mammalian cell membranes, required for proper membrane permeability and fluidity. The last part of the pathway involves steroidal triterpenes with cholestane ring structures. It starts by conversion of acyclic squalene into lanosterol, the first sterol intermediate of the pathway, followed by production of 20 structurally very similar steroidal triterpene molecules in over 11 complex enzyme reactions. Due to the structural similarities of sterol intermediates and the broad substrate specificity of the enzymes involved (especially sterol-Δ²⁴-reductase; DHCR24) the exact sequence of the reactions between lanosterol and cholesterol remains undefined. This article reviews all hitherto known structures of post-squalene steroidal triterpenes of cholesterol synthesis, their biological roles and the enzymes responsible for their synthesis. Furthermore, it summarises kinetic parameters of enzymes (V_max and K_m) and sterol intermediate concentrations from various tissues. Due to the complexity of the post-squalene cholesterol synthesis pathway, future studies will require a comprehensive meta-analysis of the pathway to elucidate the exact reaction sequence in different tissues, physiological or disease conditions. A major reason for the standstill of detailed late cholesterol synthesis research was the lack of several steroidal triterpene standards. We aid to this efforts by summarizing commercial and laboratory standards, referring also to chemical syntheses of meiosis-activating sterols. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Open AccessReview

Steroidal Triterpenes: Design of Substrate-Based Inhibitors of Ergosterol and Sitosterol Synthesis

by Jialin Liu and William David Nes

Molecules 2009, 14(11), 4690-4706; https://doi.org/10.3390/molecules14114690 - 18 Nov 2009

Cited by 27 | Viewed by 20017

Abstract

This article reviews the design and study, in our own laboratory and others, of new steroidal triterpenes with a modified lanosterol or cycloartenol frame. These compounds, along with a number of known analogs with the cholestane skeleton, have been evaluated as reversible or [...] Read more.

This article reviews the design and study, in our own laboratory and others, of new steroidal triterpenes with a modified lanosterol or cycloartenol frame. These compounds, along with a number of known analogs with the cholestane skeleton, have been evaluated as reversible or irreversible inhibitors of sterol C24-methyltransferase (SMT) from plants, fungi and protozoa. The SMT catalyzes the C24-methylation reaction involved with the introduction of the C24-methyl group of ergosterol and the C24-ethyl group of sitosterol, cholesterol surrogates that function as essential membrane inserts in many photosynthetic and non-photosynthetic eukaryotic organisms. Sterol side chains constructed with a nitrogen, sulfur, bromine or fluorine atom, altered to possess a methylene cyclopropane group, or elongated to include terminal double or triple bonds are shown to exhibit different in vitro activities toward the SMT which are mirrored in the inhibition potencies detected in the growth response of treated cultured human and plant cells or microbes. Several of the substrate-based analogs surveyed here appear to be taxaspecific compounds acting as mechanism-based inactivators of the SMT, a crucial enzyme not synthesized by animals. Possible mechanisms for the inactivation process and generation of novel products catalyzed by the variant SMTs are discussed. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Pentacyclic Triterpenoids from the Medicinal Herb, Centella asiatica (L.) Urban

by Jacinda T. James and Ian A. Dubery

Molecules 2009, 14(10), 3922-3941; https://doi.org/10.3390/molecules14103922 - 9 Oct 2009

Cited by 306 | Viewed by 34935

Abstract

Centella asiatica accumulates large quantities of pentacyclic triterpenoid saponins, collectively known as centelloids. These terpenoids include asiaticoside, centelloside, madecassoside, brahmoside, brahminoside, thankuniside, sceffoleoside, centellose, asiatic-, brahmic-, centellic- and madecassic acids. The triterpene saponins are common secondary plant metabolites and are synthesized via the [...] Read more.

Centella asiatica accumulates large quantities of pentacyclic triterpenoid saponins, collectively known as centelloids. These terpenoids include asiaticoside, centelloside, madecassoside, brahmoside, brahminoside, thankuniside, sceffoleoside, centellose, asiatic-, brahmic-, centellic- and madecassic acids. The triterpene saponins are common secondary plant metabolites and are synthesized via the isoprenoid pathway to produce a hydrophobic triterpenoid structure (aglycone) containing a hydrophilic sugar chain (glycone). The biological activity of saponins has been attributed to these characteristics. In planta, the Centella triterpenoids can be regarded as phytoanticipins due to their antimicrobial activities and protective role against attempted pathogen infections. Preparations of C. asiatica are used in traditional and alternative medicine due to the wide spectrum of pharmacological activities associated with these secondary metabolites. Here, the biosynthesis of the centelloid triterpenoids is reviewed; the range of metabolites found in C. asiatica, together with their known biological activities and the chemotype variation in the production of these metabolites due to growth conditions are summarized. These plant-derived pharmacologically active compounds have complex structures, making chemical synthesis an economically uncompetitive option. Production of secondary metabolites by cultured cells provides a particularly important benefit to manipulate and improve the production of desired compounds; thus biotechnological approaches to increase the concentrations of the metabolites are discussed. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Squalene Emulsions for Parenteral Vaccine and Drug Delivery

by Christopher B. Fox

Molecules 2009, 14(9), 3286-3312; https://doi.org/10.3390/molecules14093286 - 1 Sep 2009

Cited by 171 | Viewed by 23009

Abstract

Squalene is a linear triterpene that is extensively utilized as a principal component of parenteral emulsions for drug and vaccine delivery. In this review, the chemical structure and sources of squalene are presented. Moreover, the physicochemical and biological properties of squalene-containing emulsions are [...] Read more.

Squalene is a linear triterpene that is extensively utilized as a principal component of parenteral emulsions for drug and vaccine delivery. In this review, the chemical structure and sources of squalene are presented. Moreover, the physicochemical and biological properties of squalene-containing emulsions are evaluated in the context of parenteral formulations. Historical and current parenteral emulsion products containing squalene or squalane are discussed. The safety of squalene-based products is also addressed. Finally, analytica techniques for characterization of squalene emulsions are examined. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Chemical and Biological Characterization of Oleanane Triterpenoids from Soy

by Wei Zhang and David G. Popovich

Molecules 2009, 14(8), 2959-2975; https://doi.org/10.3390/molecules14082959 - 10 Aug 2009

Cited by 72 | Viewed by 20051

Abstract

Soyasaponins are a group of complex and structural diverse oleanane triterpenoids found in soy (Glycine max) and other legumes. They are primarily classified into two main groups − group A and B − based on the attachment of sugar moieties at [...] Read more.

Soyasaponins are a group of complex and structural diverse oleanane triterpenoids found in soy (Glycine max) and other legumes. They are primarily classified into two main groups − group A and B − based on the attachment of sugar moieties at positions C-3 and C-22 of the ring structures. Group A soyasaponins are bidesmosidic, while group B soyasaponins are monodesmosidic. Group B soyasaponins are further classified into two subcategories known as 2,3-dihydro-2,5-dihydroxy-6 -methyl-4H-pyran-4-one (DDMP) and non-DDMP conjugated molecules. The preparation and purification of soyasaponin molecules is complicated by the presence of bioactive soy isoflavones, which often overlap with soyasaponin in polarity and must removed from extracts before biological assessment. Soyasaponin extracts, aglycones of group A and B and individual group B soyasaponins such as soyasaponin I have been reported to posses specific bioactive properties, such as in vitro anti-cancer properties by modulating the cell cycle and inducing apoptosis. The isolation, chemical characterization and detection strategies by HPLC and HPLC-MS are reviewed, along with the reported bioactive effects of soyasaponin extracts and individual molecules in cultured cancer cell experiments. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Steroidal Lactones from Withania somnifera, an Ancient Plant for Novel Medicine

by Mohammad Hossein Mirjalili, Elisabeth Moyano, Mercedes Bonfill, Rosa M. Cusido and Javier Palazón

Molecules 2009, 14(7), 2373-2393; https://doi.org/10.3390/molecules14072373 - 3 Jul 2009

Cited by 457 | Viewed by 66359

Abstract

Withania somnifera, commonly known as Ashwagandha, is an important medicinal plant that has been used in Ayurvedic and indigenous medicine for over 3,000 years. In view of its varied therapeutic potential, it has also been the subject of considerable modern scientific attention. The [...] Read more.

Withania somnifera, commonly known as Ashwagandha, is an important medicinal plant that has been used in Ayurvedic and indigenous medicine for over 3,000 years. In view of its varied therapeutic potential, it has also been the subject of considerable modern scientific attention. The major chemical constituents of the Withania genus, the withanolides, are a group of naturally occurring C28-steroidal lactone triterpenoids built on an intact or rearranged ergostane framework, in which C-22 and C-26 are appropriately oxidized to form a six-membered lactone ring. In recent years, numerous pharmacological investigations have been carried out into the components of W. somnifera extracts. We present here an overview of the chemical structures of triterpenoid components and their biological activity, focusing on two novel activities, tumor inhibition and antiangiogenic properties of withaferin A and the effects of withanolide A on Alzheimer's disease. The most recent attempts in biotechnological production of withanolides are also discussed. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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Biological and Pharmacological Activities of Squalene and Related Compounds: Potential Uses in Cosmetic Dermatology

by Zih-Rou Huang, Yin-Ku Lin and Jia-You Fang

Molecules 2009, 14(1), 540-554; https://doi.org/10.3390/molecules14010540 - 23 Jan 2009

Cited by 358 | Viewed by 53921

Abstract

Squalene is a triterpene that is an intermediate in the cholesterol biosynthesis pathway. It was so named because of its occurrence in shark liver oil, which contains large quantities and is considered its richest source. However, it is widely distributed in nature, with [...] Read more.

Squalene is a triterpene that is an intermediate in the cholesterol biosynthesis pathway. It was so named because of its occurrence in shark liver oil, which contains large quantities and is considered its richest source. However, it is widely distributed in nature, with reasonable amounts found in olive oil, palm oil, wheat-germ oil, amaranth oil, and rice bran oil. Squalene, the main component of skin surface polyunsaturated lipids, shows some advantages for the skin as an emollient and antioxidant, and for hydration and its antitumor activities. It is also used as a material in topically applied vehicles such as lipid emulsions and nanostructured lipid carriers (NLCs). Substances related to squalene, including β-carotene, coenzyme Q10 (ubiquinone) and vitamins A, E, and K, are also included in this review article to introduce their benefits to skin physiology. We summarize investigations performed in previous reports from both in vitro and in vivo models. Full article

(This article belongs to the Special Issue Triterpenes and Triterpenoids 2013)

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