Molecules

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15 pages, 4524 KiB

Open AccessArticle

Mulinane and Azorellane Diterpenoid Biomarkers by GC-MS from a Representative Apiaceae (Umbelliferae) Species of the Andes

by Bernd R.T. Simoneit, Daniel R. Oros, Rudolf Jaffé, Alexandra Didyk-Peña, Carlos Areche, Beatriz Sepúlveda and Borys M. Didyk

Molecules 2019, 24(4), 684; https://doi.org/10.3390/molecules24040684 - 14 Feb 2019

Cited by 4 | Viewed by 4220

Abstract

Extracts of bled resin from Azorella compacta, of the Azorelloideae family from the Andes (>4000 m), were analyzed by gas chromatography-mass spectrometry. The mass spectra of the dominant compounds of the resin and its hydrogenation products were documented. The most abundant compounds [...] Read more.

Extracts of bled resin from Azorella compacta, of the Azorelloideae family from the Andes (>4000 m), were analyzed by gas chromatography-mass spectrometry. The mass spectra of the dominant compounds of the resin and its hydrogenation products were documented. The most abundant compounds were oxygenated diterpenoids, namely mulinadien-20-oic (Δ^11,13 and Δ^11,14) acids, azorell-13-en-20-oic acid, 13α,14β-dihydroxymulin-11-en-20-oic acid, and azorellanol, with a group of azorellenes and mulinadienes. The mass spectra of the novel diterpenoid hydrocarbons with the azorellane and mulinane skeletons were also presented. This study documents the molecular diversity of these diterpenoid classes, and could be of great utility for future organic geochemical, environmental, archeological, pharmaceutical, and forensic chemistry studies. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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13 pages, 2645 KiB

Open AccessFeature PaperArticle

Terpenoid Compositions of Resins from Callitris Species (Cupressaceae)

by Bernd R. T. Simoneit, Robert E. Cox, Daniel R. Oros and Angelika Otto

Molecules 2018, 23(12), 3384; https://doi.org/10.3390/molecules23123384 - 19 Dec 2018

Cited by 21 | Viewed by 5507

Abstract

The environmental fate of conifer resins and their natural product compounds as mixtures is of importance for source, alteration, and transport studies. The compound compositions of resins of the common Callitris species (Cupressaceae) based on gas chromatography-mass spectrometry have not been [...] Read more.

The environmental fate of conifer resins and their natural product compounds as mixtures is of importance for source, alteration, and transport studies. The compound compositions of resins of the common Callitris species (Cupressaceae) based on gas chromatography-mass spectrometry have not been reported. Results show that diterpenoids were the most abundant components and callitrisic acid was present in the resin extracts of all Callitris species analyzed. Significant amounts of 4-epi-pimaric and sandaracopimaric acids, with lesser communic, ozic, and lambertianic acids, were also in the mixtures. Phenolic diterpenoids, for example, ferruginol, hinokiol, were found in trace quantities in some samples. Thus, callitrisic acid and 4-epi-pimaric acid are the characteristic diterpenoids of Callitris species that are amenable to molecular biomarker analyses in geological or environmental applications. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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12 pages, 3784 KiB

Open AccessArticle

Friedelin in Maytenus ilicifolia Is Produced by Friedelin Synthase Isoforms

by Thaís B. Alves, Tatiana M. Souza-Moreira, Sandro R. Valentini, Cleslei F. Zanelli and Maysa Furlan

Molecules 2018, 23(3), 700; https://doi.org/10.3390/molecules23030700 - 20 Mar 2018

Cited by 16 | Viewed by 6620

Abstract

Triterpenes are interesting compounds because they play an important role in cell homeostasis and a wide variety exhibiting defense functions is produced by plant secondary metabolism. Those same plant secondary metabolites also exhibit biological properties with promising therapeutic potential as anti-inflammatory and antitumor [...] Read more.

Triterpenes are interesting compounds because they play an important role in cell homeostasis and a wide variety exhibiting defense functions is produced by plant secondary metabolism. Those same plant secondary metabolites also exhibit biological properties with promising therapeutic potential as anti-inflammatory and antitumor agents. Friedelin is a triterpene ketone with anti-inflammatory and gastroprotective activities and it is a precursor of relevant antitumor quinonemethides. Although many triterpene synthases have been described, only two friedelin synthases were characterized and there is no information about their genomic features and alleles. In the present work, we aimed to identify the gene and new isoforms of friedelin synthase in Maytenus ilicifolia leaves to be functionally characterized in Saccharomyces cerevisiae. The gene sequence analysis elucidated the exon/intron structure and confirmed the presence of single nucleotide polymorphisms with four non-synonymous mutations outside the active site of the enzyme. Therefore, two new isoforms were observed and the heterologous production of the enzymes in yeast showed similar production of friedelin. This first description of different alleles of the gene of friedelin synthase in M. ilicifolia can guide their validation as markers for friedelin-producer specimens. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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11 pages, 538 KiB

Open AccessArticle

Nigella damascena L. Essential Oil—A Valuable Source of β-Elemene for Antimicrobial Testing

by Elwira Sieniawska, Rafal Sawicki, Joanna Golus, Marta Swatko-Ossor, Grazyna Ginalska and Krystyna Skalicka-Wozniak

Molecules 2018, 23(2), 256; https://doi.org/10.3390/molecules23020256 - 28 Jan 2018

Cited by 33 | Viewed by 6066

Abstract

The most commonly used plant source of β-elemene is Curcuma wenyujin Y. H. Chen & C. Ling (syn. of Curcuma aromatic Salisb.) with its content in supercritical CO₂ extract up to 27.83%. However, the other rich source of this compound is Nigella [...] Read more.

The most commonly used plant source of β-elemene is Curcuma wenyujin Y. H. Chen & C. Ling (syn. of Curcuma aromatic Salisb.) with its content in supercritical CO₂ extract up to 27.83%. However, the other rich source of this compound is Nigella damascena L. essential oil, in which β-elemene accounts for 47%. In this work, the effective protocol for preparative isolation of β-elemene from a new source—N. damascena essential oil—using high performance counter-current chromatography HPCCC was elaborated. Furthermore, since sesquiterpens are known as potent antimicrobials, the need for finding new agents designed to combat multi-drug resistant strains was addressed and the purified target compound and the essential oil were tested for its activity against a panel of Gram-positive and Gram-negative bacteria, fungi, and mycobacterial strains. The application of the mixture of petroleum ether, acetonitrile, and acetone in the ratio 2:1.5:0.5 (v/v) in the reversed phase mode yielded β-elemene with high purity in 70 min. The results obtained for antimicrobial assay clearly indicated that N. damascena essential oil and isolated β-elemene exert action against Mycobacterium tuberculosis strain H37Ra. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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12 pages, 3446 KiB

Open AccessArticle

GC-MS Analysis of the Volatile Constituents in the Leaves of 14 Compositae Plants

by Yiguang Wang, Xiran Li, Qinjie Jiang, Hainan Sun, Jiafu Jiang, Sumei Chen, Zhiyong Guan, Weimin Fang and Fadi Chen

Molecules 2018, 23(1), 166; https://doi.org/10.3390/molecules23010166 - 18 Jan 2018

Cited by 55 | Viewed by 9998

Abstract

The green organs, especially the leaves, of many Compositae plants possess characteristic aromas. To exploit the utility value of these germplasm resources, the constituents, mainly volatile compounds, in the leaves of 14 scented plant materials were qualitatively and quantitatively compared via gas chromatography-mass [...] Read more.

The green organs, especially the leaves, of many Compositae plants possess characteristic aromas. To exploit the utility value of these germplasm resources, the constituents, mainly volatile compounds, in the leaves of 14 scented plant materials were qualitatively and quantitatively compared via gas chromatography-mass spectrometry (GC-MS). A total of 213 constituents were detected and tentatively identified in the leaf extracts, and terpenoids (especially monoterpene and sesquiterpene derivatives), accounting for 40.45–90.38% of the total compounds, were the main components. The quantitative results revealed diverse concentrations and compositions of the chemical constituents between species. Principal component analysis (PCA) showed that different groups of these Compositae plants were characterized by main components of α-thujone, germacrene D, eucalyptol, β-caryophyllene, and camphor, for example. On the other hand, cluster memberships corresponding to the molecular phylogenetic framework, were found by hierarchical cluster analysis (HCA) based on the terpenoid composition of the tested species. These results provide a phytochemical foundation for the use of these scented Compositae plants, and for the further study of the chemotaxonomy and differential metabolism of Compositae species. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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2313 KiB

Open AccessArticle

Exploring the Chemical Diversity of Algerian Plants: Three New Pentacyclic Triterpenoids from Launaea acanthoclada Roots

by Nabila Zergainoh, Maria Letizia Ciavatta, Marianna Carbone, Fatma Bitam, Mohamed Cherif Aberkane and Margherita Gavagnin

Molecules 2018, 23(1), 80; https://doi.org/10.3390/molecules23010080 - 30 Dec 2017

Cited by 8 | Viewed by 4120

Abstract

The chemical study of Launaea acanthoclada from South-East Algeria led to the isolation of twelve oxygenated terpenoid compounds, including three new pentacyclic triterpenoids 1–3 with either lupane or ursane rearranged skeletons. The structure and the stereochemistry of these compounds were established [...] Read more.

The chemical study of Launaea acanthoclada from South-East Algeria led to the isolation of twelve oxygenated terpenoid compounds, including three new pentacyclic triterpenoids 1–3 with either lupane or ursane rearranged skeletons. The structure and the stereochemistry of these compounds were established by spectroscopic methods, including NMR techniques. The chemical pattern of L. acanthoclada is in accordance with the triterpenoid scenario of the genus Launaea embracing to date lupane, oleane, ursane and taraxastane skeletons. However, the carbon frameworks exhibited by new compounds 1–3 have never been reported from Launaea species. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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1996 KiB

Open AccessArticle

Labdane-Type Diterpenes, Galangalditerpenes A–C, with Melanogenesis Inhibitory Activity from the Fruit of Alpinia galanga

by Yoshiaki Manse, Kiyofumi Ninomiya, Ryosuke Nishi, Yoshinori Hashimoto, Saowanee Chaipech, Osamu Muraoka and Toshio Morikawa

Molecules 2017, 22(12), 2279; https://doi.org/10.3390/molecules22122279 - 20 Dec 2017

Cited by 22 | Viewed by 5979

Abstract

In our continuing study of biologically active natural products from the fruit of Alpinia galanga (Zingiberaceae), we newly isolated three new labdane-type diterpenes, termed galangalditerpenes A–C (1–3), along with four known sesquiterpenes (4–7) and two [...] Read more.

In our continuing study of biologically active natural products from the fruit of Alpinia galanga (Zingiberaceae), we newly isolated three new labdane-type diterpenes, termed galangalditerpenes A–C (1–3), along with four known sesquiterpenes (4–7) and two diterpenes (8 and 9). The stereostructures of 1–3 were elucidated on the basis of their spectroscopic properties. The melanogenesis inhibitory activities in theophylline-stimulated murine B16 melanoma 4A5 cells of these isolates, including the new diterpenes (1–3, IC₅₀ = 4.4, 8.6, and 4.6 μM, respectively), were found to be more than 6–87-fold higher than that of arbutin (174 μM), a commercially available positive control. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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2496 KiB

Open AccessArticle

Acid-Induced Rearrangement of Epoxygermacranolides: Synthesis of Furanoheliangolides and Cadinanes from Nobilin

by Maria De Mieri, Martin Smieško, Isidor Ismajili, Marcel Kaiser and Matthias Hamburger

Molecules 2017, 22(12), 2252; https://doi.org/10.3390/molecules22122252 - 18 Dec 2017

Viewed by 4550

Abstract

The acid-induced rearrangement of three epoxyderivatives of nobilin 1, the most abundant sesquiterpene lactone in Anthemis nobilis flowers, was investigated. From the 1,10-epoxyderivative 2, furanoheliangolide 5 was obtained, while the 4,5-epoxy group of 3 did not react. Conversely, when the 3-hydroxy [...] Read more.

The acid-induced rearrangement of three epoxyderivatives of nobilin 1, the most abundant sesquiterpene lactone in Anthemis nobilis flowers, was investigated. From the 1,10-epoxyderivative 2, furanoheliangolide 5 was obtained, while the 4,5-epoxy group of 3 did not react. Conversely, when the 3-hydroxy function of nobilin was acetylated (12), the 4,5-epoxy derivative did cyclize into cadinanes (15 and 16) under Lewis acid catalysis. The reactivity of the 4,5- and 1,10-epoxy derivatives of nobilin (2 and 3) was compared with that of parthenolide, and rationalized on the basis of quantum chemical calculations. All isolated reaction products were fully characterized by spectroscopic and computational methods, and their in vitro anti-protozoal activity was evaluated. The paper could provide new insights into the biosynthesis of this class of natural products. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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1540 KiB

Open AccessArticle

Anti-Proliferative Activity of Triterpenoids and Sterols Isolated from Alstonia scholaris against Non-Small-Cell Lung Carcinoma Cells

by Chao-Min Wang, Shang-Jie Tsai, Yun-Lian Jhan, Kuei-Lin Yeh and Chang-Hung Chou

Molecules 2017, 22(12), 2119; https://doi.org/10.3390/molecules22122119 - 1 Dec 2017

Cited by 36 | Viewed by 5486

Abstract

(1) Background: In China and South Asia, Alstonia scholaris (Apocynaceae) is an important medicinal plant that has been historically used in traditional ethnopharmacy to treat infectious diseases. Although various pharmacological activities have been reported, the anti-lung cancer components of A. scholaris have not [...] Read more.

(1) Background: In China and South Asia, Alstonia scholaris (Apocynaceae) is an important medicinal plant that has been historically used in traditional ethnopharmacy to treat infectious diseases. Although various pharmacological activities have been reported, the anti-lung cancer components of A. scholaris have not yet been identified. The objective of this study is to evaluate the active components of the leaf extract of A. scholaris, and assess the anti-proliferation effects of isolated compounds against non-small-cell lung carcinoma cells; (2) Methods: NMR was used to identify the chemical constitutes isolated from the leaf extract of A. scholaris. The anti-proliferative activity of compounds against non-small-cell lung carcinoma cells was assessed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay; (3) Results: Eight triterpenoids and five sterols were isolated from the hexane portion of A. scholaris, and structurally identified as: (1) ursolic acid, (2) oleanolic acid, (3) betulinic acid, (4) betulin, (5) 2β,3β,28-lup-20(29)-ene-triol, (6) lupeol, (7) β-amyrin, (8) α-amyrin, (9) poriferasterol, (10) epicampesterol, (11) β-sitosterol, (12) 6β-hydroxy-4-stigmasten-3-one, and (13) ergosta-7,22-diene-3β,5α,6β-triol. Compound 5 was isolated from a plant source for the first time. In addition, compounds 9, 10, 12, and 13 were also isolated from A. scholaris for the first time. Ursolic acid, betulinic acid, betulin, and 2β,3β,28-lup-20(29)-ene-triol showed anti-proliferative activity against NSCLC, with IC₅₀ of 39.8, 40.1, 240.5 and 172.6 μM, respectively.; (4) Conclusion: These findings reflect that pentacyclic triterpenoids are the anti-lung cancer chemicals in A. scholaris. The ability of ursolic acid, betulinic acid, betulin, and 2β,3β,28-lup-20(29)-ene-triol to inhibit the proliferative activity of NSCLC can constitute a valuable group of therapeutic agents in the future. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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1932 KiB

Open AccessArticle

Terpenoids and Phenylpropanoids in Ligularia duciformis, L. kongkalingensis, L. nelumbifolia, and L. limprichtii

by Chiaki Kuroda, Ryohei Kobayashi, Ayumi Nagata, Yumi Nakadozono, Taketo Itoh, Yasuko Okamoto, Motoo Tori, Ryo Hanai and Xun Gong

Molecules 2017, 22(12), 2062; https://doi.org/10.3390/molecules22122062 - 25 Nov 2017

Cited by 3 | Viewed by 4321

Abstract

The diversity in root chemicals and evolutionally neutral DNA regions in the complex of Ligularia duciformis, L. kongkalingensis, and L. nelumbifolia (the d/k/n complex) was studied using eight samples collected in central and northern Sichuan Province of China. Cacalol (14 [...] Read more.

The diversity in root chemicals and evolutionally neutral DNA regions in the complex of Ligularia duciformis, L. kongkalingensis, and L. nelumbifolia (the d/k/n complex) was studied using eight samples collected in central and northern Sichuan Province of China. Cacalol (14) and epicacalone (15), rearranged eremophilanes, were isolated from the complex for the first time. Two new phenylpropanoids were also obtained. Seven of the eight samples produced phenylpropanoids and the other produced lupeol alone. Two of the seven samples also produced furanoeremophilanes or their derivatives and one produced oplopanes. The geographical distribution of the sesquiterpene-producing populations suggests that the production of sesquiterpenes evolved independently in separate regions. L. limprichtii collected in northern Sichuan was also analyzed and its chemical composition and the sequence of internal transcribed spacers (ITSs) in the ribosomal RNA gene cluster were found to be similar to that in the d/k/n complex and L. yunnanensis, which are morphologically similar. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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232 KiB

Open AccessCommunication

Headspace Solid-Phase Microextraction and Ultrasonic Extraction with the Solvent Sequences in Chemical Profiling of Allium ursinum L. Honey

by Igor Jerković and Piotr M. Kuś

Molecules 2017, 22(11), 1909; https://doi.org/10.3390/molecules22111909 - 6 Nov 2017

Cited by 3 | Viewed by 4102

Abstract

A volatile profile of ramson (wild garlic, Allium ursinum L.) honey was investigated by headspace solid-phase microextraction (HS-SPME) and ultrasonic solvent extraction (USE) followed by gas chromatography and mass spectrometry (GC-FID/GC-MS) analyses. The headspace was dominated by linalool derivatives: cis- and trans [...] Read more.

A volatile profile of ramson (wild garlic, Allium ursinum L.) honey was investigated by headspace solid-phase microextraction (HS-SPME) and ultrasonic solvent extraction (USE) followed by gas chromatography and mass spectrometry (GC-FID/GC-MS) analyses. The headspace was dominated by linalool derivatives: cis- and trans-linalool oxides (25.3%; 9.2%), hotrienol (12.7%), and linalool (5.8%). Besides direct extraction with dichloromethane and pentane/diethyl ether mixture (1:2, v/v), two solvent sequences (I: pentane → diethyl ether; II: pentane → pentane/diethyl ether (1:2, v/v) → dichloromethane) were applied. Striking differences were noted among the obtained chemical profiles. The extracts with diethyl ether contained hydroquinone (25.8–36.8%) and 4-hydroxybenzoic acid (11.6–16.6%) as the major compounds, while (E)-4-(r-1′,t-2′,c-4′-trihydroxy-2′,6′,6′-trimethylcyclohexyl)but-3-en-2-one predominated in dichloromethane extracts (18.3–49.1%). Therefore, combination of different solvents was crucial for the comprehensive investigation of volatile organic compounds in this honey type. This particular magastigmane was previously reported only in thymus honey and hydroquinone in vipers bugloss honey, while a combination of the mentioned predominant compounds is unique for A. ursinum honey. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

3496 KiB

Open AccessArticle

Characterization, Function, and Transcriptional Profiling Analysis of 3-Hydroxy-3-methylglutaryl-CoA Synthase Gene (GbHMGS1) towards Stresses and Exogenous Hormone Treatments in Ginkgo biloba

by Xiangxiang Meng, Qiling Song, Jiabao Ye, Lanlan Wang and Feng Xu

Molecules 2017, 22(10), 1706; https://doi.org/10.3390/molecules22101706 - 12 Oct 2017

Cited by 29 | Viewed by 5697

Abstract

3-Hydroxy-3-methylglutaryl-CoA synthase (HMGS) is one of the rate-limiting enzymes in the mevalonate pathway as it catalyzes the condensation of acetoacetyl-CoA to form 3-hydroxy-3-methylglutaryl-CoA. In this study, A HMGS gene (designated as GbHMGS1) was cloned from Ginkgo biloba for the first time. GbHMGS1 [...] Read more.

3-Hydroxy-3-methylglutaryl-CoA synthase (HMGS) is one of the rate-limiting enzymes in the mevalonate pathway as it catalyzes the condensation of acetoacetyl-CoA to form 3-hydroxy-3-methylglutaryl-CoA. In this study, A HMGS gene (designated as GbHMGS1) was cloned from Ginkgo biloba for the first time. GbHMGS1 contained a 1422-bp open-reading frame encoding 474 amino acids. Comparative and bioinformatics analysis revealed that GbHMGS1 was extensively homologous to HMGSs from other plant species. Phylogenetic analysis indicated that the GbHMGS1 belonged to the plant HMGS superfamily, sharing a common evolutionary ancestor with other HMGSs, and had a further relationship with other gymnosperm species. The yeast complement assay of GbHMGS1 in HMGS-deficient Saccharomyces cerevisiae strain YSC6274 demonstrated that GbHMGS1 gene encodes a functional HMGS enzyme. The recombinant protein of GbHMGS1 was successfully expressed in E. coli. The in vitro enzyme activity assay showed that the k_cat and K_m values of GbHMGS1 were 195.4 min⁻¹ and 689 μM, respectively. GbHMGS1 was constitutively expressed in all tested tissues, including the roots, stems, leaves, female flowers, male flowers and fruits. The transcript accumulation for GbHMGS1 was highest in the leaves. Expression profiling analyses revealed that GbHMGS1 expression was induced by abiotic stresses (ultraviolet B and cold) and hormone treatments (salicylic acid, methyl jasmonate, and ethephon) in G. biloba, indicating that GbHMGS1 gene was involved in the response to environmental stresses and plant hormones. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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1228 KiB

Open AccessArticle

Gypmacrophin A, a Rare Pentacyclic Sesterterpenoid, Together with Three Depsides, Functioned as New Chemical Evidence for Gypsoplaca macrophylla (Zahlbr.) Timdal Identification

by Yuan-Fei Zhou, Hai-Xia Shi, Kun Hu, Jian-Wei Tang, Xing-Ren Li, Xue Du, Han-Dong Sun, Li-Song Wang and Jian-Xin Pu

Molecules 2017, 22(10), 1675; https://doi.org/10.3390/molecules22101675 - 9 Oct 2017

Cited by 5 | Viewed by 9824

Abstract

The phytochemical investigation on 1 g of materials from Gypsoplaca macrophylla (Zahlbr.) Timdal resulted in the discovery of gypmacrophin A, a rare pentacyclic sesterterpenoid; brialmontin III, a new polysubstituted depside and two known ones, brialmontins I and II. The structure and absolute configurations [...] Read more.

The phytochemical investigation on 1 g of materials from Gypsoplaca macrophylla (Zahlbr.) Timdal resulted in the discovery of gypmacrophin A, a rare pentacyclic sesterterpenoid; brialmontin III, a new polysubstituted depside and two known ones, brialmontins I and II. The structure and absolute configurations of gypmacrophin A were elucidated by spectroscopic analyses and computational methods. Gypmacrophin A showed weak inhibition of AchE with an IC₅₀ value of 32.03 μM. The four compounds provided new chemical evidence for G. macrophylla identification. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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517 KiB

Open AccessArticle

Three New Sesquiterpene Glycosides from the Rhizomes of Trillium tschonoskii

by Jie Yang, Yin-Jun Yang, Xin-Guang Sun, Jie Zhang, Yang Zhao, Bei Wang, Qian-Zhi Ding, Bao-Lin Guo and Bai-Ping Ma

Molecules 2017, 22(8), 1283; https://doi.org/10.3390/molecules22081283 - 2 Aug 2017

Viewed by 3797

Abstract

Three new sesquiterpene glycosides, possessing a rare aglycone with a sulfonyl between C-1 and C-15 positions, named 3-(3′E-7′R,8′-dihydroxy-4′,8′-dimethyl-3′-nonenyl)-2,5-dihydro-1,1-dioxo-thiophen 7′-O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranoside (1), 3-(3′E-7′R,8′-dihydroxy-4′,8′-dimethyl-3′-nonenyl)-2,5-dihydro-1,1-dioxo-thiophen [...] Read more.

Three new sesquiterpene glycosides, possessing a rare aglycone with a sulfonyl between C-1 and C-15 positions, named 3-(3′E-7′R,8′-dihydroxy-4′,8′-dimethyl-3′-nonenyl)-2,5-dihydro-1,1-dioxo-thiophen 7′-O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranoside (1), 3-(3′E-7′R,8′-dihydroxy-4′,8′-dimethyl-3′-nonenyl)-2,5-dihydro-1,1-dioxo-thiophen 7′-O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranoside (2), and 3-(3′E-7′R,8′-dihydroxy-4′,8′-dimethyl-3′-nonenyl)-2,5-dihydro-1,1-dioxo-thiophen 7′-O-β-d-glucopyranosyl-6′-O-acetyl-(1→4)-O-β-d-glucopyranosyl-(1→4)-O-β-d-glucopyranoside (3), respectively, were isolated from the rhizomes of Trillium tschonoskii. Their structures were established on the basis of spectroscopic data, including HR-ESI-MS, IR, 1D and 2D NMR. The cytotoxic properties of the three compounds were investigated using human hepatic L02 cells. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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1303 KiB

Open AccessArticle

Antifungal and Ichthyotoxic Sesquiterpenoids from Santalum album Heartwood

by Tae Hoon Kim, Tsutomu Hatano, Keinosuke Okamoto, Takashi Yoshida, Hiroshi Kanzaki, Michiko Arita and Hideyuki Ito

Molecules 2017, 22(7), 1139; https://doi.org/10.3390/molecules22071139 - 8 Jul 2017

Cited by 19 | Viewed by 6500

Abstract

In our continuing study on a survey of biologically active natural products from heartwood of Santalum album (Southwest Indian origin), we newly found potent fish toxic activity of an n-hexane soluble extract upon primary screening using killifish (medaka) and characterized α-santalol and [...] Read more.

In our continuing study on a survey of biologically active natural products from heartwood of Santalum album (Southwest Indian origin), we newly found potent fish toxic activity of an n-hexane soluble extract upon primary screening using killifish (medaka) and characterized α-santalol and β-santalol as the active components. The toxicity (median tolerance limit (TLm) after 24 h at 1.9 ppm) of α-santalol was comparable with that of a positive control, inulavosin (TLm after 24 h at 1.3 ppm). These fish toxic compounds including inulavosin were also found to show a significant antifungal effect against a dermatophytic fungus, Trichophyton rubrum. Based on a similarity of the morphological change of the immobilized Trichophyton hyphae in scanning electron micrographs between treatments with α-santalol and griseofulvin (used as the positive control), inhibitory effect of α-santalol on mitosis (the antifungal mechanism proposed for griseofulvin) was assessed using sea urchin embryos. As a result, α-santalol was revealed to be a potent antimitotic agent induced by interference with microtubule assembly. These data suggested that α-santalol or sandalwood oil would be promising to further practically investigate as therapeutic agent for cancers as well as fungal skin infections. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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1568 KiB

Open AccessArticle

Comparative Analysis of Saponins from Different Phytolaccaceae Species and Their Antiproliferative Activities

by Flora Didii Saleri, Guilin Chen, Xun Li and Mingquan Guo

Molecules 2017, 22(7), 1077; https://doi.org/10.3390/molecules22071077 - 29 Jun 2017

Cited by 18 | Viewed by 6811

Abstract

The quality and the efficacy of herbal medicine are of great concern especially with the increase in their global use. Medicinal plants of different species or collected from different geographical regions have shown variations in both their contents and pharmacological activities due to [...] Read more.

The quality and the efficacy of herbal medicine are of great concern especially with the increase in their global use. Medicinal plants of different species or collected from different geographical regions have shown variations in both their contents and pharmacological activities due to the differences in the environmental conditions of the collected sites. In this study, roots of Phytolacca acinosa found in different provinces in south China (Sichuan and Shandong) and a species of Phytolacca americana were investigated. To ensure a maximum yield of the major compounds, the extraction method and conditions were optimized. The preeminent method of extraction in this analysis was determined to be the ultrasound-assisted method with specific conditions as follows: ethanol-H₂O (1:1, v/v), with a solvent: sample ratio of 1:8, and extraction was performed 3 times, each for 30 min. Under these conditions, samples from the different regions varied both in quantity and quality via the LC-MS analysis. A total of 60 triterpenoid saponins were detected within the three samples, among which 22 were identified as common in the three samples. The amounts of these common triterpenoid saponin identified varied across the samples. Moreover, the analysis led to the detection of some novel compounds that have not yet been reported in this family, while other compounds differ in their fragmentation pathways compared to previous literature. To further divulge the correlations between the bioactivities in these three samples and the quantity and quality of their bioactive components, a cytotoxic analysis was thus carried out with two cancer cell lines, and SGC-7901 and Hep G2, which evidently showed remarkable differences in their anti-proliferative activities with respect to the IC₅₀ value. Samples of P. acinosa from Sichuan showed higher values in both cell lines (27.20 ± 1.60 and 25.59 ± 1.63 µg/mL) compared to those of Shandong and P. americana. For the first time, analysis and comparison of both interspecies and of different species in this family were carried out. This study will significantly contribute to the quality insurance of herbal medicine, especially in the Phytolaccaceae family. Full article

(This article belongs to the Special Issue Diversity of Terpenoids)

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