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19 pages, 888 KiB

Open AccessArticle

Basic Chemical Composition, Antioxidant Activity and Selected Polyphenolic Compounds Profile in Garlic Leaves and Bulbs Collected at Various Stages of Development

by Joanna Skoczylas, Elżbieta Jędrszczyk, Kinga Dziadek, Ewa Dacewicz and Aneta Kopeć

Molecules 2023, 28(18), 6653; https://doi.org/10.3390/molecules28186653 - 16 Sep 2023

Cited by 8 | Viewed by 1855

Abstract

Garlic is commonly used as vegetable or spice and as a herb in folklore as well as traditional medicine in many countries. The current study aimed to compare the chemical composition, antioxidant activity, and the content of selected polyphenolic compounds in cloves as [...] Read more.

Garlic is commonly used as vegetable or spice and as a herb in folklore as well as traditional medicine in many countries. The current study aimed to compare the chemical composition, antioxidant activity, and the content of selected polyphenolic compounds in cloves as well as leaves of winter garlic plants of the Harnaś and Ornak cultivars, which are of Polish origin. Garlic was grown from cloves for three years (2018–2020) in the experimental field of the University of Agriculture in Krakow, Poland. The research material was harvested on three dates: May; June, unripe garlic plants; and in July, the plant at full maturity. The content of vitamin C in the fresh material was determined. The proximate analysis was determined in the freeze-dried plants of garlic, and the total carbohydrate content was calculated. The antioxidant activity and the content of selected polyphenolic compounds were also determined. Garlic cloves showed a higher content of dry matter, and total carbohydrates than the leaves of garlic plants. On the other hand, in the leaves, a significantly higher content of protein, total fat and ash were observed. Additionally, garlic leaves were characterised by a higher content of vitamin C, total polyphenols, and a higher antioxidant activity than garlic cloves. The leaves of young garlic plants from the May harvest were distinguished by a higher content of these compounds. The dominant phenolic compounds were catechin and epicatechin. The leaves of young plants can be a valuable source of bioactive substances, especially in early spring. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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21 pages, 5073 KiB

Open AccessArticle

Ginsentide-like Coffeetides Isolated from Coffee Waste Are Cell-Penetrating and Metal-Binding Microproteins

by James P. Tam, Jiayi Huang, Shining Loo, Yimeng Li and Antony Kam

Molecules 2023, 28(18), 6556; https://doi.org/10.3390/molecules28186556 - 10 Sep 2023

Cited by 2 | Viewed by 2167

Abstract

Coffee processing generates a huge amount of waste that contains many natural products. Here, we report the discovery of a panel of novel cell-penetrating and metal ion-binding microproteins designated coffeetide cC1a–c and cL1–6 from the husk of two popular coffee plants, Coffea canephora [...] Read more.

Coffee processing generates a huge amount of waste that contains many natural products. Here, we report the discovery of a panel of novel cell-penetrating and metal ion-binding microproteins designated coffeetide cC1a–c and cL1–6 from the husk of two popular coffee plants, Coffea canephora and Coffea liberica, respectively. Combining sequence determination and a database search, we show that the prototypic coffeetide cC1a is a 37-residue, eight-cysteine microprotein with a hevein-like cysteine motif, but without a chitin-binding domain. NMR determination of cC1a reveals a compact structure that confers its resistance to heat and proteolytic degradation. Disulfide mapping together with chemical synthesis reveals that cC1a has a ginsentide-like, and not a hevein-like, disulfide connectivity. In addition, transcriptomic analysis showed that the 98-residue micrcoproten-like coffeetide precursor contains a three-domain arrangement, like ginsentide precursors. Molecular modeling, together with experimental validation, revealed a Mg²⁺ and Fe³⁺ binding pocket at the N-terminus formed by three glutamic acids. Importantly, cC1a is amphipathic with a continuous stretch of 19 apolar amino acids, which enables its cell penetration to target intracellular proteins, despite being highly negatively charged. Our findings suggest that coffee by-products could provide a source of ginsentide-like bioactive peptides that have the potential to target intracellular proteins. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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25 pages, 5125 KiB

Open AccessArticle

Exploration of Baicalein-Core Derivatives as Potent Antifungal Agents: SAR and Mechanism Insights

by Heyang Zhou, Niao Yang, Wei Li, Xuemi Peng, Jiaxiao Dong, Yuanying Jiang, Lan Yan, Dazhi Zhang and Yongsheng Jin

Molecules 2023, 28(17), 6340; https://doi.org/10.3390/molecules28176340 - 30 Aug 2023

Cited by 1 | Viewed by 1468

Abstract

Baicalein (BE), the major component of Scutellaria Baicalensis, exhibited potently antifungal activity against drug-resistant Candida albicans, and strong inhibition on biofilm formation. Therefore, a series of baicalein-core derivatives were designed and synthesized to find more potent compounds and investigate [...] Read more.

Baicalein (BE), the major component of Scutellaria Baicalensis, exhibited potently antifungal activity against drug-resistant Candida albicans, and strong inhibition on biofilm formation. Therefore, a series of baicalein-core derivatives were designed and synthesized to find more potent compounds and investigate structure–activity relationship (SAR) and mode of action (MoA). Results demonstrate that A4 and B5 exert a more potent antifungal effect (MIC₈₀ = 0.125 μg/mL) than BE (MIC₈₀ = 4 μg/mL) when used in combination with fluconazole (FLC), while the MIC₈₀ of FLC dropped from 128 μg/mL to 1 μg/mL. SAR analysis indicates that the presence of 5-OH is crucial for synergistic antifungal activities, while o-dihydroxyls and vic-trihydroxyls are an essential pharmacophore, whether they are located on the A ring or the B ring of flavonoids. The MoA demonstrated that these compounds exhibited potent antifungal effects by inhibiting hypha formation of C. albicans. However, sterol composition assay and enzymatic assay conducted in vitro indicated minimal impact of these compounds on sterol biosynthesis and Eno1. These findings were further confirmed by the results of the in-silico assay, which assessed the stability of the complexes. Moreover, the inhibition of hypha of this kind of compound could be attributed to their effect on the catalytic subunit of 1,3-β-d-glucan synthase, 1,3-β-d-glucan-UDP glucosyltransferase and glycosyl-phosphatidylinositol protein, rather than inhibiting ergosterol biosynthesis and Eno1 activity by Induced-Fit Docking and Molecular Dynamics Simulations. This study presents potential antifungal agents with synergistic effects that can effectively inhibit hypha formation. It also provides new insights into the MoA. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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23 pages, 7986 KiB

Open AccessArticle

A New Diterpenoid of Indonesian Scoparia dulcis Linn: Isolation and Cytotoxic Activity against MCF-7 and T47D Cell Lines

by Hasnawati Hasnawati, Subagus Wahyuono, Ratna Asmah Susidarti, Djoko Santosa and Arfan Arfan

Molecules 2023, 28(16), 5960; https://doi.org/10.3390/molecules28165960 - 9 Aug 2023

Viewed by 1559

Abstract

Scoparia dulcis Linn plays an important role in treatment because it contains active compounds that are proven to have a variety of activities, including cytotoxicity on various cancer cells. The objective of this study is to isolate and identify the cytotoxic compounds in [...] Read more.

Scoparia dulcis Linn plays an important role in treatment because it contains active compounds that are proven to have a variety of activities, including cytotoxicity on various cancer cells. The objective of this study is to isolate and identify the cytotoxic compounds in the ethyl acetate fraction of Scoparia dulcis, observe cell cycle inhibition and induction of apoptosis in vitro, and carry out molecular studies using in silico studies. A new diterpene compound was isolated from the ethyl acetate fraction of Scoparia dulcis L. of Indonesian origin. Chromatographic methods were used to isolate the compound, spectroscopic methods were used to elucidate its structure, and these data were compared with those reported in the literature. The compound was tested for its cytotoxic activity against two breast cancer cells (MCF-7 and T47D). The results of the isolated compound showed a cytotoxic effect on MCF-7 and T47D breast cancer cells at IC₅₀ 70.56 ± 1.54 and <3.125 ± 0.43 µg/mL, respectively. The compound inhibited the growth of MCF-7 and T47D breast cancer cells and the accumulation of cells in the G1 phases, and it induced apoptosis. Based on a spectroscopic analysis, the isolated compound was identified as 2α-hydroxyscopadiol, which is a new diterpenoid. A docking study revealed that the isolate’s hydroxyl groups are essential for interacting with crucial residues on the active sites of the ER and PR and caspase-9. The isolate inhibits ER and PR activity with binding energies of −8.2 kcal/mol and −7.3 kcal/mol, respectively. In addition, the isolate was also able to induce apoptosis through the activation of the caspase-9 pathway with an affinity of −9.0 kcal/mol. In conclusion, the isolated compound from S. dulcis demonstrated anticancer activity based on in vitro and in silico studies. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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17 pages, 4750 KiB

Open AccessArticle

Phytochemicals from Anneslea fragrans Wall. and Their Hepatoprotective and Anti-Inflammatory Activities

by Yan Wang, Changshu Cheng, Tianrui Zhao, Jianxin Cao, Yaping Liu, Yudan Wang, Wenbing Zhou and Guiguang Cheng

Molecules 2023, 28(14), 5480; https://doi.org/10.3390/molecules28145480 - 18 Jul 2023

Cited by 1 | Viewed by 1451

Abstract

Anneslea fragrans Wall., popularly known as “Pangpo tea”, is an edible, medicinal, and ornamental plant of the Family Theaceae. The leaves of A. fragrans were historically applied for the treatment of liver and intestinal inflammatory diseases in China. This study aimed to explore [...] Read more.

Anneslea fragrans Wall., popularly known as “Pangpo tea”, is an edible, medicinal, and ornamental plant of the Family Theaceae. The leaves of A. fragrans were historically applied for the treatment of liver and intestinal inflammatory diseases in China. This study aimed to explore the hepatoprotective agents from A. fragrans leaves through hepatoprotective and anti-inflammatory assessment. The phytochemical investigation of the leaves of A. fragrans resulted in the isolation and identification of a total of 18 chemical compounds, including triterpenoids, aliphatic alcohol, dihydrochalcones, chalcones, flavanols, phenolic glycoside, and lignans. Compounds 1–2, 4–6, 11–12, and 16–18 were identified from A. fragrans for the first time. Compounds 7 and 14 could significantly alleviate hepatocellular damage by decreasing the contents of aspartate aminotransferase (AST) and alanine aminotransferase (ALT) and inhibit the hepatocellular apoptosis in the HepG2 cells induced by N-acetyl-p-aminophenol (APAP). In addition, compounds 7 and 14 inhibited reactive oxygen species (ROS) and malondialdehyde (MDA) contents and increased the catalase (CAT) superoxide dismutase (SOD), and glutathione (GSH) levels for suppressing APAP-induced oxidative stress. Additionally, compounds 7, 13, and 14 also had significant anti-inflammatory effects by inhibiting interleukin-6 (IL-6), interleukin-1β (IL-1β), and tumor necrosis factor-α (TNF-α) productions on LPS-induced RAW246.7 cells. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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20 pages, 1713 KiB

Open AccessArticle

Microfluidizing Technique Application for Algerian Cymbopogon citratus (DC.) Stapf Effects Enhanced Volatile Content, Antimicrobial, and Anti-Mycotoxigenic Properties

by Amel Boudechicha, Abdelhakim Aouf, Amr Farouk, Hatem S. Ali, Manal F. Elkhadragy, Hany M. Yehia and Ahmed Noah Badr

Molecules 2023, 28(14), 5367; https://doi.org/10.3390/molecules28145367 - 12 Jul 2023

Cited by 7 | Viewed by 2010

Abstract

Medicinal plant extracts are a promising source of bioactive minor contents. The present study aimed to evaluate the distinguished volatile content of Algerian Cymbopogon citratus (DC.) Stapf before and after the microfluidization process and their related antimicrobial and anti-mycotoxigenic impacts and changes. The [...] Read more.

Medicinal plant extracts are a promising source of bioactive minor contents. The present study aimed to evaluate the distinguished volatile content of Algerian Cymbopogon citratus (DC.) Stapf before and after the microfluidization process and their related antimicrobial and anti-mycotoxigenic impacts and changes. The GC-MS apparatus was utilized for a comparative examination of Algerian lemongrass essential oil (LGEO) with its microfluidization nanoemulsion (MF-LGEO) volatile content. The MF-LGEO was characterized using Zetasizer and an electron microscope. Cytotoxicity, antibacterial, and antifungal activities were determined for the LGEO and MF-LGEO. The result reflected changes in the content of volatiles for the MF-LGEO. The microfluidizing process enhanced the presence of compounds known for their exceptional antifungal and antibacterial properties in MF-LGEO, namely, neral, geranial, and carvacrol. However, certain terpenes, such as camphor and citronellal, were absent, while decanal, not found in the raw LGEO, was detected. The droplet diameter was 20.76 ± 0.36 nm, and the polydispersity index (PDI) was 0.179 ± 0.03. In cytotoxicity studies, LGEO showed higher activity against the HepG2 cell line than MF-LGEO. Antibacterial LGEO activity against Gram-positive bacteria recorded an inhibitory zone from 41.82 ± 2.84 mm to 58.74 ± 2.64 mm, while the zone ranged from 12.71 ± 1.38 mm to 16.54 ± 1.42 mm for Gram-negative bacteria. Antibacterial activity was enhanced to be up to 71.43 ± 2.54 nm and 31.54 ± 1.01 nm for MF-LGEO impact against Gram-positive and Gram-negative pathogens. The antifungal effect was considerable, particularly against Fusarium fungi. It reached 17.56 ± 1.01 mm and 13.04 ± 1.37 mm for LGEO and MF-LGEO application of a well-diffusion assay, respectively. The MF-LGEO was more promising in reducing mycotoxin production in simulated fungal growth media due to the changes linked to essential compounds content. The reduction ratio was 54.3% and 74.57% for total aflatoxins (AFs) and ochratoxin A (OCA) contents, respectively. These results reflect the microfluidizing improvement impact regarding the LGEO antibacterial, antifungal and anti-mycotoxigenic properties. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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16 pages, 2955 KiB

Open AccessArticle

Identification of Anti-Inflammatory Compounds from Peucedanum praeruptorum Roots by Using Nitric Oxide-Producing Rat Hepatocytes Stimulated by Interleukin 1β

by Hiromu Ozaki, Yuto Nishidono, Airi Fujii, Tetsuya Okuyama, Kaito Nakamura, Takanori Maesako, Saki Shirako, Richi Nakatake, Ken Tanaka, Yukinobu Ikeya and Mikio Nishizawa

Molecules 2023, 28(13), 5076; https://doi.org/10.3390/molecules28135076 - 28 Jun 2023

Cited by 4 | Viewed by 1646

Abstract

The roots of Peucedanum praeruptorum Dunn and Angelica decursiva Franchet et Savatier are designated Zenko, which is a crude drug defined by the Japanese Pharmacopoeia. This crude drug is used as an antitussive and an expectorant and is included in the Kampo [...] Read more.

The roots of Peucedanum praeruptorum Dunn and Angelica decursiva Franchet et Savatier are designated Zenko, which is a crude drug defined by the Japanese Pharmacopoeia. This crude drug is used as an antitussive and an expectorant and is included in the Kampo formula Jinsoin, which improves cough, fever, and headache. Although the anti-inflammatory effects of this crude drug have been determined, the constituents responsible for this effect remain unknown. To investigate biologically active compounds, rat hepatocytes were used, which produce proinflammatory mediator nitric oxide (NO) in response to proinflammatory cytokine interleukin 1β (IL-1β). A methanol extract of P. praeruptorum roots, which suppressed IL-1β-induced NO production, was fractionated into three crude fractions (ethyl acetate (EtOAc)-soluble, n-butanol-soluble, and water-soluble fractions) based on hydrophobicity. The EtOAc-soluble fraction markedly inhibited NO production. After this fraction was purified, three biologically active compounds were identified as praeruptorins A, B, and E, the contents of which were high. A comparison of their activities indicated that praeruptorin B exhibited the highest potency to inhibit NO production by decreasing inducible NO synthase expression and suppressed the expression of mRNAs encoding proinflammatory cytokines. Collectively, the three praeruptorins may primarily contribute to the anti-inflammatory effects of P. praeruptorum roots. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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9 pages, 1415 KiB

Open AccessArticle

New Phenolic Dimers from Plant Paeonia suffruticosa and Their Cytotoxicity and NO Production Inhibition

by Qianqian Meng, Shunyao Tong, Yuqing Zhao, Xingrong Peng, Zhenghui Li, Tao Feng and Jikai Liu

Molecules 2023, 28(12), 4590; https://doi.org/10.3390/molecules28124590 - 6 Jun 2023

Cited by 1 | Viewed by 1270

Abstract

The Paeonia suffruticosa, known as ‘Feng Dan’, has been used for thousands of years in traditional Chinese medicine. In our chemical investigation on the root bark of the plant, five new phenolic dimers, namely, paeobenzofuranones A–E (1–5), were [...] Read more.

The Paeonia suffruticosa, known as ‘Feng Dan’, has been used for thousands of years in traditional Chinese medicine. In our chemical investigation on the root bark of the plant, five new phenolic dimers, namely, paeobenzofuranones A–E (1–5), were characterized. Their structures were determined using spectroscopic analysis including 1D and 2D NMR, HRESIMS, UV, and IR, as well as ECD calculations. Compounds 2, 4, and 5 showed cytotoxicity against three human cancer cell lines, with IC₅₀ values ranging from 6.7 to 25.1 μM. Compounds 1 and 2 showed certain inhibitory activity on NO production. To the best of our knowledge, the benzofuranone dimers and their cytotoxicity of P. suffruticosa are reported for the first time in this paper. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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11 pages, 531 KiB

Open AccessArticle

Identification and Bioaccessibility of Maillard Reaction Products and Phenolic Compounds in Buckwheat Biscuits Formulated from Flour Fermented by Rhizopus oligosporus 2710

by Małgorzata Wronkowska, Wiesław Wiczkowski, Joanna Topolska, Dorota Szawara-Nowak, Mariusz Konrad Piskuła and Henryk Zieliński

Molecules 2023, 28(6), 2746; https://doi.org/10.3390/molecules28062746 - 18 Mar 2023

Cited by 1 | Viewed by 1584

Abstract

The identification and potential bioaccessibility of phenolic compounds using the highly sensitive micro-HPLC-QTRAP/MS/MS technique and Maillard reaction products (MRPs) in buckwheat biscuits formulated from flours, raw and roasted, fermented by Rhizopus oligosporus 2710 was addressed in this study after in vitro digestion. The [...] Read more.

The identification and potential bioaccessibility of phenolic compounds using the highly sensitive micro-HPLC-QTRAP/MS/MS technique and Maillard reaction products (MRPs) in buckwheat biscuits formulated from flours, raw and roasted, fermented by Rhizopus oligosporus 2710 was addressed in this study after in vitro digestion. The content of the analyzed MRPs such as furosine, FAST index, and the level of melanoidins defined by the browning index was increased in the biscuits prepared from fermented flours as compared to the control biscuits prepared from non-fermented ones. After in vitro digestion higher content of furosine was observed in control and tested biscuits providing its high potential bioaccessibility. The fermented buckwheat flours used for baking affected the nutritional value of biscuits in comparison to the control biscuits in the context of the twice-increased FAST index. More than three times higher value of the browning index was noted in control and tested biscuits after digestion in vitro indicating the high bioaccessibility of melanoidins. Our results showed the presence of ten phenolic acids and eight flavonoids in the investigated biscuits. Among phenolic acids, vanillic, syringic, and protocatechuic were predominant while in the group of flavonoids, rutin, epicatechin, and vitexin were the main compounds in analyzed biscuits. Generally, the lower potential bioaccessibility of phenolic acids and higher potential bioaccessibility of flavonoids was found for biscuits obtained from buckwheat flours fermented by fungi compared to control biscuits obtained from non-fermented flours. Fermentation of buckwheat flour with the fungus R. oligosporus 2710 seems to be a good way to obtain high-quality biscuits; however, further research on their functional properties is needed. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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13 pages, 2165 KiB

Open AccessArticle

Chemical Constituents of Thesium chinense Turcz and Their In Vitro Antioxidant, Anti-Inflammatory and Cytotoxic Activities

by Zhen-Zhen Liu, Jun-Cheng Ma, Peng Deng, Fu-Cai Ren and Ning Li

Molecules 2023, 28(6), 2685; https://doi.org/10.3390/molecules28062685 - 16 Mar 2023

Cited by 6 | Viewed by 1827

Abstract

Three novel compounds (1–3) along with twenty-six known compounds, two known steroids (4–5) and twenty-four known phenylpropanoids (6–29) were isolated from the whole plant of Thesium chinense Turcz. The structures of the three new compounds were elucidated [...] Read more.

Three novel compounds (1–3) along with twenty-six known compounds, two known steroids (4–5) and twenty-four known phenylpropanoids (6–29) were isolated from the whole plant of Thesium chinense Turcz. The structures of the three new compounds were elucidated on the basis of ESI-MS, HR-ESIMS, 1D and 2D NMR, IR, UV spectroscopic data. The absolute stereochemistry of compound 1 was determined by the Gauge-Including Atomic Orbitals (GIAO) method. The in vitro antioxidant, anti-inflammatory and cytotoxic activities of the isolated compounds were evaluated by DPPH radical-scavenging assay, LPS-activated RAW 264.7 cells model and CCK-8 kit, respectively. Compound 11 showed high antioxidant activity with an SC₅₀ value of 16.2 ± 1.6 μM. Compound 21 showed considerable anti-inflammatory activity with an IC₅₀ value of 28.6 ± 3.0 μM. Compounds 4 and 5 displayed potent cytotoxic activity against human NCI-H292, SiHa, A549, and MKN45 cell lines, with the compound 4 having IC₅₀ values of 17.4 ± 2.4, 22.2 ± 1.1, 9.7 ± 0.9, 9.5 ±0.7 μM, and the compound 5 having all IC₅₀ values less than 0.1 μM in vitro. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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9 pages, 4483 KiB

Open AccessCommunication

Structural Elucidation and Cytotoxic Activity of New Monoterpenoid Indoles from Gelsemium elegans

by Da Song, Jia-Jun Liang, Shi-Biao Pu, Pan-Pan Zhang, Yun-Lin Peng, Xia Liu, Ting-Ting Feng, Xiang Pu, Ying Zhou, Xiong-Wei Liu and Xin Wei

Molecules 2023, 28(6), 2531; https://doi.org/10.3390/molecules28062531 - 10 Mar 2023

Cited by 2 | Viewed by 1796

Abstract

Two new monoterpenoid indole alkaloids, gelselegandines F (1) and G (2), were isolated from the aerial parts of Gelsemium elegans. Their structures were elucidated by means of spectroscopic techniques and quantum chemical calculations. The ECD calculations were conducted [...] Read more.

Two new monoterpenoid indole alkaloids, gelselegandines F (1) and G (2), were isolated from the aerial parts of Gelsemium elegans. Their structures were elucidated by means of spectroscopic techniques and quantum chemical calculations. The ECD calculations were conducted at the B3LYP/6-311G(d,p) level and NMR calculations were carried out using the Gauge-Including Atomic Orbitals (GIAO) method. Structurally, the two new compounds possessed rare, cage-like, monoterpenoid indole skeletons. All isolated compounds and the total alkaloids extract were tested for cytotoxicity against four different tumor cell lines. The total alkaloids extract of G. elegans exhibited significant antitumor activity with IC₅₀ values ranging from 32.63 to 82.24 ug/mL. In order to discover anticancer leads from the active extraction, both new indole compounds (1–2) were then screened for cytotoxicity. Interestingly, compound 2 showed moderate cytotoxicity against K562 leukemia cells with an IC₅₀ value of 57.02 uM. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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16 pages, 12735 KiB

Open AccessArticle

Confusoside from Anneslea fragrans Alleviates Acetaminophen-Induced Liver Injury in HepG2 via PI3K-CASP3 Signaling Pathway

by Jing-Hao Zhao, Jing Li, Xiao-Yu Zhang, Shang Shi, Lin Wang, Ming-Long Yuan, Ya-Ping Liu and Yu-Dan Wang

Molecules 2023, 28(4), 1932; https://doi.org/10.3390/molecules28041932 - 17 Feb 2023

Cited by 3 | Viewed by 2395

Abstract

Confusoside (CF), a major chemical compound in the leaves of Anneslea fragrans Wall., is a dihydrochalcone glycoside with excellent antioxidant and anti-inflammatory effects. However, the hepatoprotective effect of CF has not been described. This study aimed to explore the hepatoprotective effect of CF [...] Read more.

Confusoside (CF), a major chemical compound in the leaves of Anneslea fragrans Wall., is a dihydrochalcone glycoside with excellent antioxidant and anti-inflammatory effects. However, the hepatoprotective effect of CF has not been described. This study aimed to explore the hepatoprotective effect of CF against acetaminophen (APAP)-induced hepatic injury in HepG2 cells. First, the potential hepatoprotective effect mechanisms of CF were predicted by network pharmacology and were thought to involve reducing inflammation and inhibiting apoptosis. Target proteins (phosphatidylinositol3-kinase (PI3K) and caspase-3 (CASP3)) were found via molecular docking analysis. To verify the predicted results, an analysis of biological indicators was performed using commercial kits and Western blotting. The results showed that CF significantly decreased the levels of liver injury biomarkers (ALT, AST, and LDH), strongly inhibited the production of inflammatory cytokines (IL-1β, IL-6, and TNF-α) and the NO level via inhibiting the activation of the NF-κB signaling pathway, and markedly regulated the expression levels of Bcl2, Bax, and cleaved-CASP3/9 proteins by activating the PI3K-CASP3 apoptosis pathway. The results demonstrated that CF has a therapeutic effect on APAP-induced liver injury by inhibiting intracellular inflammation and cell apoptosis, indicating that CF may be used as a potential reagent for the prevention and treatment of APAP-induced liver injury. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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14 pages, 4494 KiB

Open AccessArticle

Interaction of Camptothecin Anticancer Drugs with Ribosomal Proteins L15 and L11: A Molecular Docking Study

by Christian Bailly and Gérard Vergoten

Molecules 2023, 28(4), 1828; https://doi.org/10.3390/molecules28041828 - 15 Feb 2023

Cited by 3 | Viewed by 2594

Abstract

The antitumor drug topotecan (TPT) is a potent inhibitor of topoisomerase I, triggering DNA breaks lethal for proliferating cancer cells. The mechanism is common to camptothecins SN38 (the active metabolite of irinotecan) and belotecan (BLT). Recently, TPT was shown to bind the ribosomal [...] Read more.

The antitumor drug topotecan (TPT) is a potent inhibitor of topoisomerase I, triggering DNA breaks lethal for proliferating cancer cells. The mechanism is common to camptothecins SN38 (the active metabolite of irinotecan) and belotecan (BLT). Recently, TPT was shown to bind the ribosomal protein L15, inducing an antitumor immune activation independent of topoisomerase I. We have modeled the interaction of four camptothecins with RPL15 derived from the 80S human ribosome. Two potential drug-binding sites were identified at Ile135 and Phe129. SN38 can form robust RPL15 complexes at both sites, whereas BLT essentially gave stable complexes with site Ile135. The empirical energy of interaction (ΔE) for SN38 binding to RPL15 is similar to that determined for TPT binding to the topoisomerase I-DNA complex. Molecular models with the ribosomal protein L11 sensitive to topoisomerase inhibitors show that SN38 can form a robust complex at a single site (Cys25), much more stable than those with TPT and BLT. The main camptothecin structural elements implicated in the ribosomal protein interaction are the lactone moiety, the aromatic system and the 10-hydroxyl group. The study provides guidance to the design of modulators of ribosomal proteins L11 and L15, both considered anticancer targets. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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12 pages, 1329 KiB

Open AccessArticle

Meroterpenoids with Immunosuppressive Activity from Edible Fungus Craterellus odoratus

by Quan Dai, Li-Ting Pang, Fa-Lei Zhang, Gang-Qiang Wang, Xue-Mei Li, Ji-Kai Liu and Tao Feng

Molecules 2023, 28(4), 1564; https://doi.org/10.3390/molecules28041564 - 6 Feb 2023

Viewed by 1443

Abstract

Two unusual polyketide–sesquiterpene metabolites, craterodoratins T (1) and U (2), along with the known compound craterellin A (3), were isolated from the higher fungus Craterellus odoratus. The structures of isolated compounds were characterized based on nuclear [...] Read more.

Two unusual polyketide–sesquiterpene metabolites, craterodoratins T (1) and U (2), along with the known compound craterellin A (3), were isolated from the higher fungus Craterellus odoratus. The structures of isolated compounds were characterized based on nuclear magnetic resonance (NMR) and mass spectrum (MS) spectroscopic analysis, while the absolute configuration of the compounds was determined by theoretical NMR and electronic circular dichroism (ECD) calculations. Compound 1 possessed a rare structure with two aromatic groups. Compounds 1 and 3 showed immunosuppressive activity with IC₅₀ values ranging from 5.516 to 19.953 μM. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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11 pages, 2646 KiB

Open AccessArticle

Sesquiterpene Lactones with Anti-Inflammatory Activity from the Halophyte Sonchus brachyotus DC

by Young-Kyung Lee, Hangy Lee, Yun Na Kim, Jun Kang, Eun Ju Jeong and Jung-Rae Rho

Molecules 2023, 28(4), 1518; https://doi.org/10.3390/molecules28041518 - 4 Feb 2023

Cited by 1 | Viewed by 1866

Abstract

There were five sesquiterpene lactones, belonging to the eudesmanolide class, isolated from the halophyte Sonchus brachyotus DC. The structures of the compounds were determined using spectroscopic methods, including 1D and 2D NMR spectra, MS data, and optical rotation values. Compounds 4 and 5 [...] Read more.

There were five sesquiterpene lactones, belonging to the eudesmanolide class, isolated from the halophyte Sonchus brachyotus DC. The structures of the compounds were determined using spectroscopic methods, including 1D and 2D NMR spectra, MS data, and optical rotation values. Compounds 4 and 5 were characterized by the position of p-hydroxyphenylacetyl group in the sugar moiety. In the evaluation of anti-inflammatory effects on LPS-activated RAW264.7 macrophages, compound 1, 5α,6βH-eudesma-3,11(13)-dien-12,6α-olide, potently suppressed the expression of iNOS and COS-2, as well as the production of TNF-α, IL-6, and IL-10. Treatment of 1 regulates the Nrf2/HO-1 pathway. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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15 pages, 1935 KiB

Open AccessArticle

Characterization and Comparison of Steroidal Glycosides from Polygonatum Species by High-Performance Liquid Chromatography–Electrospray Ionization Mass Spectrometry

by Danyang Liu, Takashi Kikuchi and Wei Li

Molecules 2023, 28(2), 705; https://doi.org/10.3390/molecules28020705 - 10 Jan 2023

Cited by 2 | Viewed by 2231

Abstract

Polygonatum species have been used as traditional medicines and functional foods in Asia and Europe since ancient times. In this study, a fast and simple method based on liquid chromatography coupled with electrospray ionization mass spectrometry (LC-ESI-MS) was developed to systematically analyze and [...] Read more.

Polygonatum species have been used as traditional medicines and functional foods in Asia and Europe since ancient times. In this study, a fast and simple method based on liquid chromatography coupled with electrospray ionization mass spectrometry (LC-ESI-MS) was developed to systematically analyze and identify the steroidal glycosides in four major Polygonatum species distributed in Japan, including P. odoratum, P. falcatum, P. macranthum, and P. sibiricum. As a result, 31 steroidal glycosides were tentatively identified, including 18 known and 13 previously unreported glycosides. Their structures were identified by the interpretation of chromatographic behavior and ESI-MS fragmentation patterns. The identification of 31 steroidal glycosides was indicative of a common biogenetic pathway in Polygonatum species. Our study disclosed the chemical profiling of steroidal glycosides in the plants of Polygonatum species, which will benefit better phytochemotaxonomical and phytochemical understanding and quality control for their medicinal usage. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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9 pages, 2064 KiB

Open AccessArticle

The Roots of Neorautanenia mitis (A. Rich) Verdcourt: Further Evidence of Its Antidiarrhoeal Activity

by Christiana J. Dawurung, Joy G. Usman, Jurbe G. Gotep and Stephen G. Pyne

Molecules 2023, 28(2), 673; https://doi.org/10.3390/molecules28020673 - 9 Jan 2023

Viewed by 2059

Abstract

Despite the current management options and therapeutics used in the treatment of diarrhoea, in Africa and Asia, diarrhoea remains a major concern, especially in children under the age of 5 years. Traditional knowledge of medicinal plants used in the management of diarrhoea symptoms [...] Read more.

Despite the current management options and therapeutics used in the treatment of diarrhoea, in Africa and Asia, diarrhoea remains a major concern, especially in children under the age of 5 years. Traditional knowledge of medicinal plants used in the management of diarrhoea symptoms can be explored for their efficacy. In Nigeria, the TMPs (Traditional Medicine Practitioners) have, over the years, employed medicinal plants in the management of diarrhoea symptoms. In our current and previous studies, we aimed at validating the effectiveness of Neorautanenia mitis in the management of diarrhoea as claimed by the TMPs. Out of the 20 compounds isolated from N. mitis, the compounds neodulin, pachyrrhizine, neotenone and dolineone were the most abundant, and in this study, neodulin showed a pronounced relaxation of the rhythmic contraction of the isolated rabbit jejunum in an organ bath in a concentration-dependent manner, with a complete relaxation at 60 µg/mL. Neotenone and dolineone showed a dose-dependent inhibition of defecation of 65.07%, and 50.01%, respectively, at 20 mg/kg in a castor-oil-induced diarrhoea model. This is a strong indication that compounds from N. mitis possess antidiarrhoeal properties, thereby giving credence to its traditional usage in diarrhoea therapy, and therefore validating its antidiarrhoeal activity and its being worthy of further investigation. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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13 pages, 1926 KiB

Open AccessArticle

High Yield Synthesis of Curcumin and Symmetric Curcuminoids: A “Click” and “Unclick” Chemistry Approach

by Marco A. Obregón-Mendoza, William Meza-Morales, Yair Alvarez-Ricardo, M. Mirian Estévez-Carmona and Raúl G. Enríquez

Molecules 2023, 28(1), 289; https://doi.org/10.3390/molecules28010289 - 30 Dec 2022

Cited by 6 | Viewed by 4002

Abstract

The worldwide known and employed spice of Asian origin, turmeric, receives significant attention due to its numerous purported medicinal properties. Herein, we report an optimized synthesis of curcumin and symmetric curcuminoids of aromatic (bisdemethoxycurcumin) and heterocyclic type, with yields going from good to [...] Read more.

The worldwide known and employed spice of Asian origin, turmeric, receives significant attention due to its numerous purported medicinal properties. Herein, we report an optimized synthesis of curcumin and symmetric curcuminoids of aromatic (bisdemethoxycurcumin) and heterocyclic type, with yields going from good to excellent using the cyclic difluoro-boronate derivative of acetylacetone prepared by reaction of 2,4-pentanedione with boron trifluoride in THF (ca. 95%). The subsequent cleavage of the BF₂ group is of significant importance for achieving a high overall yield in this two-step procedure. Such cleavage occurs by treatment with hydrated alumina (Al₂O₃) or silica (SiO₂) oxides, thus allowing the target heptanoids obtained in high yields as an amorphous powder to be filtered off directly from the reaction media. Furthermore, crystallization instead of chromatographic procedures provides a straightforward purification step. The ease and efficiency with which the present methodology can be applied to synthesizing the title compounds earns the terms “click” and “unclick” applied to describe particularly straightforward, efficient reactions. Furthermore, the methodology offers a simple, versatile, fast, and economical synthetic alternative for the obtention of curcumin (85% yield), bis-demethoxycurcumin (78% yield), and the symmetrical heterocyclic curcuminoids (80–92% yield), in pure form and excellent yields. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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18 pages, 2097 KiB

Open AccessArticle

Bioactive Profile of Distilled Solid By-Products of Rosemary, Greek Sage and Spearmint as Affected by Distillation Methods

by Stamatia Christaki, Elisavet Bouloumpasi, Eleni Lalidou, Paschalina Chatzopoulou and Maria Irakli

Molecules 2022, 27(24), 9058; https://doi.org/10.3390/molecules27249058 - 19 Dec 2022

Cited by 17 | Viewed by 2686

Abstract

By-products of essential oils (EOs) in the industry represent an exploitable material for natural and safe antioxidant production. One representative group of such by-products is distilled solid residues, whose composition is properly modulated by the distillation method applied for the recovery of EOs. [...] Read more.

By-products of essential oils (EOs) in the industry represent an exploitable material for natural and safe antioxidant production. One representative group of such by-products is distilled solid residues, whose composition is properly modulated by the distillation method applied for the recovery of EOs. Recently, in terms of Green Chemistry principles, conventional extraction and distillation processes are considered outdated and tend to be replaced by more environmentally friendly ones. In the present study, microwave-assisted hydro-distillation (MAHD) was employed as a novel and green method for the recovery of EOs from three aromatic plants (rosemary, Greek sage and spearmint). The method was compared to conventional ones, hydro-distillation (HD) and steam-distillation (SD), in terms of phytochemical composition of distilled solid residues, which was estimated by spectrophotometric and chromatographic methods. Total phenolic content (TPC), total flavonoid content (TFC) and antioxidant activity (ABTS, DPPH and FRAP) results highlighted the distilled solid residues as good sources of antioxidants. Moreover, higher antioxidant activity was achieved for MAHD extracts of solid residues in comparison to HD and SD extracts. A metabolomics approach was carried out on the methanolic extracts of solid residues obtained by different distillation methods using LC-MS analysis followed by multivariate data analysis. A total of 29 specialized metabolites were detected, and 26 of them were identified and quantified, presenting a similar phenolic profile among different treatments, whereas differences were observed among different species. Rosmarinic acid was the most abundant phenolic compound in all extracts, being higher in MAHD extracts. In rosemary and Greek sage extracts, carnosol and carnosic acid were quantified in significant amounts, while trimers and tetramers of caffeic acid (salvianolic acids isomers) were identified and quantified in spearmint extracts, being higher in MAHD extracts. The obtained results pointed out that MAHD extracts of distilled solid by-products could be a good source of bioactives with potential application in the food, pharmaceutical and cosmetic industries, contributing to the circular economy. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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17 pages, 3099 KiB

Open AccessArticle

Chemical Composition of Tobacco Seed Oils and Their Antioxidant, Anti-Inflammatory, and Whitening Activities

by Ji Gu, Xiaoyu Zhang, Biqing Song, Dongjie Zhou, Yongzhi Niu, Guiguang Cheng, Yunye Zheng and Yudan Wang

Molecules 2022, 27(23), 8516; https://doi.org/10.3390/molecules27238516 - 3 Dec 2022

Cited by 4 | Viewed by 2349

Abstract

Tobacco seeds are a valuable food oil resource, and tobacco seed oil is rich in nutrients, especially polyunsaturated fatty acids. The aim of this work was to perform a comprehensive study on the chemical constituents, and the antioxidant, anti-inflammatory, and whitening activities of [...] Read more.

Tobacco seeds are a valuable food oil resource, and tobacco seed oil is rich in nutrients, especially polyunsaturated fatty acids. The aim of this work was to perform a comprehensive study on the chemical constituents, and the antioxidant, anti-inflammatory, and whitening activities of tobacco seed oils (NC89 and BS4). A GC/MS analysis revealed that NC89 and BS4 had 11 and 6 volatile compounds, respectively. The PUFA contents in NC89 and BS4 were 74.98% and 72.84%, respectively. These two tobacco seed oils also presented good radical scavenging capacities with the neutralization of ABTS, OH⁻, and superoxide (O₂⁻) radicals in a concentration-dependent manner. Meanwhile, NC89 and BS4 inhibited reactive oxygen species (ROS) accumulation and cell apoptosis, enhanced SOD and CAT activities, and increased the GSH content in H₂O₂-induced HepG2 cells. In addition, NC89 and BS4 exhibited significant anti-inflammatory activities by inhibiting the expressions of NO, TNF-α, IL-1β, and IL-6 in LPS-induced RAW.264.7 cells through the regulation of the MAPK signaling pathway. Moreover, NC89 and BS4 expressed whitening activities by inhibiting tyrosinase activity and intracellular melanin production. Therefore, tobacco seed oils could be used as an important oil resource for the development of high value-added products. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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13 pages, 1334 KiB

Open AccessArticle

Phytochemistry and Antihyperglycemic Potential of Cistus salviifolius L., Cistaceae

by Maja Hitl, Katarina Bijelić, Nebojša Stilinović, Biljana Božin, Branislava Srđenović-Čonić, Ljilja Torović and Nebojša Kladar

Molecules 2022, 27(22), 8003; https://doi.org/10.3390/molecules27228003 - 18 Nov 2022

Cited by 3 | Viewed by 1924

Abstract

Cistus salviifolius has been previously reported as a traditional remedy for hyperglycemia. However, the plant has been scarcely investigated from scientific point of view. Thus, the aim was to examine the chemical composition and to evaluate its antioxidant and antihyperglycemic potential in vitro. [...] Read more.

Cistus salviifolius has been previously reported as a traditional remedy for hyperglycemia. However, the plant has been scarcely investigated from scientific point of view. Thus, the aim was to examine the chemical composition and to evaluate its antioxidant and antihyperglycemic potential in vitro. Aqueous and ethanolic extracts were evaluated for total phenolic, tannin, and flavonoid content using spectrophotometric methods. Detailed chemical characterization was performed by high-performance liquid chromatography (HPLC-DAD). The volatile organic compounds (VOCs) profile was assessed by gas chromatography technique. The potential in diabetes treatment was evaluated through tests of free radicals neutralization, inhibition of lipid peroxidation process, and test of ferric ion reduction; activity in tests of inhibition of α-amylase, α-glucosidase and dipeptidyl peptidase-4 was also evaluated. High content of phenolics (majority being tannins) was detected; detailed HPLC analysis revealed high content of gallic acid, followed by rutin, chlorogenic and caffeic acids. The VOCs analysis determined sesquiterpene hydrocarbons and oxygenated sesquiterpenes as the main groups of compounds. The assays classified extracts as potent neutralizers of 2,2-diphenyl-1-picrylhydrazil and nitroso radicals formation and potent inhibitors of α-amylase and α-glucosidase. In conclusion, Cistus salviifolius represents a rich source of phenolics and essential oil with sesquiterpenes. The established results suggested its promising antioxidant and antihyperglycemic activities. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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11 pages, 3553 KiB

Open AccessArticle

Phytotoxic Metabolites Isolated from Aspergillus sp., an Endophytic Fungus of Crassula arborescens

by Jingjing Ma, Chunhua Lu, Yajie Tang and Yuemao Shen

Molecules 2022, 27(22), 7710; https://doi.org/10.3390/molecules27227710 - 9 Nov 2022

Cited by 3 | Viewed by 1798

Abstract

Aspergillus sp., an endophytic fungus isolated from Crassula arborescens, displayed potent inhibitory activity against the seed germination of Arabidopsis thaliana. The bioactivity-guided fractionation of the culture extract of Aspergillus sp. MJ01 led to the isolation of nine compounds, including one previously [...] Read more.

Aspergillus sp., an endophytic fungus isolated from Crassula arborescens, displayed potent inhibitory activity against the seed germination of Arabidopsis thaliana. The bioactivity-guided fractionation of the culture extract of Aspergillus sp. MJ01 led to the isolation of nine compounds, including one previously undescribed furanone, namely aspertamarinoic acid (1), and eight known compounds, (−)-dihydrocanadensolide (2), kojic acid (3), citreoisocoumarin (4), astellolide A (5), astellolide B (6), astellolide G (7), cyclo-N-methylphenylalanyltryptophenyl (8) and (−)-ditryptophenaline (9). In the evaluation of the phytotoxic activities of compounds 1–9, the results suggested that 1 and 5 showed significant inhibitory activity on the seed germination of A. thaliana. This is the first report to disclose the phytotoxic activity of these compounds. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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11 pages, 2086 KiB

Open AccessArticle

Two New Phenolic Glycosides with Lactone Structural Units from Leaves of Ardisia crenata Sims with Antibacterial and Anti-Inflammatory Activities

by Huihui Tao, Yongqiang Zhou, Xin Yin, Xin Wei and Ying Zhou

Molecules 2022, 27(15), 4903; https://doi.org/10.3390/molecules27154903 - 31 Jul 2022

Cited by 6 | Viewed by 2298

Abstract

Two new lactones, named Ardisicreolides A–B (1–2), together with four known flavonoids, Quercetin (3), Myricetrin (4), Quercitrin (5), Tamarixetin 3-O-rhamnoside (6), were isolated from the ethyl acetate portion of 70% ethanol [...] Read more.

Two new lactones, named Ardisicreolides A–B (1–2), together with four known flavonoids, Quercetin (3), Myricetrin (4), Quercitrin (5), Tamarixetin 3-O-rhamnoside (6), were isolated from the ethyl acetate portion of 70% ethanol extracts of dried leaves from Ardisia crenata Sims. These compounds were identified from Ardisia crenata Sims for the first time. The structures of 1–6 were elucidated according to 1D and 2D-NMR methods and together with the published literature. All of the isolated compounds were evaluated for in vitro anti-microbial effect against Escherichia coli, Pseudomonas aeuroginosa, Enterococcus faecalis, Proteus vulgaris, Staphylococcus aureus, and Bacillus subtilis. In addition, compounds 1–2 were assessed for anti-inflammatory activity by acting on LPS-induced RAW 264.7 macrophage cells in vitro. The results showed that only compound 2 exhibited moderate antibacterial activity on Bacillus subtilis. Moreover, compounds 1 and 2 were found to significantly inhibit the production of nitric oxide (NO) and reduce the release of tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), interleukin-4 (IL-4), and interleukin-10 (IL-10) in LPS-induced RAW 264.7 macrophage cells. The present data suggest that lactones from the leaves of A. crenata Sims might be used as a potential source of natural anti-inflammatory agents. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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13 pages, 4048 KiB

Open AccessArticle

Therapeutic Effect of Renifolin F on Airway Allergy in an Ovalbumin-Induced Asthma Mouse Model In Vivo

by Zhuya Yang, Xiaohong Li, Rongbing Fu, Min Hu, Yijie Wei, Xuhong Hu, Wenhong Tan, Xiaoyun Tong and Feng Huang

Molecules 2022, 27(12), 3789; https://doi.org/10.3390/molecules27123789 - 12 Jun 2022

Cited by 8 | Viewed by 2966

Abstract

Renifolin F is a prenylated chalcone isolated from Shuteria involucrata, a traditional minority ethnic medicine used to treat the respiratory diseases and asthma. Based on the effects of the original medicine plant, we established an in vivo mouse model of allergic asthma [...] Read more.

Renifolin F is a prenylated chalcone isolated from Shuteria involucrata, a traditional minority ethnic medicine used to treat the respiratory diseases and asthma. Based on the effects of the original medicine plant, we established an in vivo mouse model of allergic asthma using ovalbumin (OVA) as an inducer to evaluate the therapeutic effects of Renifolin F. In the research, mice were sensitized and challenged with OVA to establish an allergic asthma model to evaluate the effects of Renifolin F on allergic asthma. The airway hyper-reactivity (AHR) to methacholine, cytokine levels, ILC2s quantity and mircoRNA-155 expression were assessed. We discovered that Renifolin F attenuated AHR and airway inflammation in the OVA-induced asthmatic mouse model by inhibiting the regulation of ILC2s in the lung, thereby, reducing the upstream inflammatory cytokines IL-25, IL-33 and TSLP; the downstream inflammatory cytokines IL-4, IL-5, IL-9 and IL-13 of ILC2s; and the co-stimulatory factors IL-2 and IL-7; as well as the expression of microRNA-155 in the lung. The findings suggest a therapeutic potential of Renifolin F on OVA-induced airway inflammation. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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15 pages, 3002 KiB

Open AccessArticle

Hepatoprotective Polysaccharides from Geranium wilfordii: Purification, Structural Characterization, and Their Mechanism

by Jia-Yi Feng, Yan-Qing Xie, Peng Zhang, Qian Zhou, Afsar Khan, Zhi-Hong Zhou, Xian-Song Xia and Lu Liu

Molecules 2022, 27(11), 3602; https://doi.org/10.3390/molecules27113602 - 3 Jun 2022

Viewed by 2409

Abstract

Traditional Chinese Medicine is generally used as a decoction to guard health. Many active ingredients in the decoction are chemical ingredients that are not usually paid attention to in phytochemical research, such as polysaccharides, etc. Based on research interest in Chinese herbal decoction, [...] Read more.

Traditional Chinese Medicine is generally used as a decoction to guard health. Many active ingredients in the decoction are chemical ingredients that are not usually paid attention to in phytochemical research, such as polysaccharides, etc. Based on research interest in Chinese herbal decoction, crude polysaccharides from G. wilfordii (GCP) were purified to obtain two relatively homogeneous polysaccharides, a neutral polysaccharide (GNP), and an acid polysaccharide (GAP) by various chromatographic separation methods, which were initially characterized by GC-MS, NMR, IR, and methylation analysis. Studies on the hepatoprotective activity of GCP in vivo showed that GCP might be a potential agent for the prevention and treatment of acute liver injury by inhibiting the secretion levels of ALT, AST, IL-6, IL-1β, TNF-α, and MDA expression levels, increasing SOD, and the GSH-Px activity value. Further, in vitro assays, GNP and GAP, decrease the inflammatory response by inhibiting the secretion of IL-6 and TNF-α, involved in the STAT1/T-bet signaling pathway. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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17 pages, 13086 KiB

Open AccessArticle

Phenolic Constituents, Antioxidant and Cytoprotective Activities, Enzyme Inhibition Abilities of Five Fractions from Vaccinium dunalianum Wight

by Chang-Shu Cheng, Qing-Hui Gu, Jin-Ke Zhang, Jun-Hong Tao, Tian-Rui Zhao, Jian-Xin Cao, Gui-Guang Cheng, Guo-Fang Lai and Ya-Ping Liu

Molecules 2022, 27(11), 3432; https://doi.org/10.3390/molecules27113432 - 26 May 2022

Cited by 7 | Viewed by 1920

Abstract

The bud of Vaccinium dunalianum Wight has been traditionally consumed as health herbal tea by “Yi” people in Yunnan Province, China, which was locally named “Que Zui tea”. This paper studied the chemical constituents of five fractions from Vaccinium dunalianum, and their [...] Read more.

The bud of Vaccinium dunalianum Wight has been traditionally consumed as health herbal tea by “Yi” people in Yunnan Province, China, which was locally named “Que Zui tea”. This paper studied the chemical constituents of five fractions from Vaccinium dunalianum, and their enzyme inhibitory effects of α-glucosidase and pancreatic lipase, antioxidant activity, and cytoprotective effects on H₂O₂-induced oxidative damage in HepG2 cells. The methanol extract of V. dunalianum was successively partitioned with petroleum ether (PF), chloroform (CF), ethyl acetate (EF), n-butanol (BF), and aqueous (WF) to obtain five fractions. The chemical profiling of the five fractions was analyzed by ultra-high-performance liquid chromatography coupled with a tandem mass spectrometry (UHPLC-MS/MS), and 18 compounds were tentatively identified. Compared to PF, CF, BF and WF, the EF revealed the highest total phenols (TPC) and total flavonoids (TFC), and displayed the strongest enzyme inhibition ability (α-glucosidase and pancreatic lipase) and antioxidant capacity (DPPH, ABTS and FRAP). Furthermore, these five fractions, especially EF, could effectively inhibit reactive oxygen species (ROS) production and cell apoptosis on H₂O₂-induced oxidative damage protection in HepG2 cells. This inhibitory effect might be caused by the up-regulation of intracellular antioxidant enzyme activity (CAT, SOD, and GSH). The flavonoids and phenolic acids of V. dunalianum might be the bioactive substances responsible for enzyme inhibitory, antioxidant, and cytoprotective activities. Full article

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8 pages, 566 KiB

Open AccessArticle

Four New Sesquiterpenoids from the Rice Fermentation of Antrodiella albocinnamomea

by Min Guo, Ying-Zhong Liang, Xiu-Ming Cui, Lin-Jiao Shao, Yin-Fei Li and Xiao-Yan Yang

Molecules 2022, 27(10), 3344; https://doi.org/10.3390/molecules27103344 - 23 May 2022

Viewed by 1828

Abstract

Albocimea B-E (1–4), four new sesquiterpenoids, and four known compounds, steperoxide A (5), dankasterone (6), 1H-indole-3-carboxylic acid (7), and (+)-formylanserinone B (8), were isolated from the rice fermentation of [...] Read more.

Albocimea B-E (1–4), four new sesquiterpenoids, and four known compounds, steperoxide A (5), dankasterone (6), 1H-indole-3-carboxylic acid (7), and (+)-formylanserinone B (8), were isolated from the rice fermentation of the fungus Antrodiella albocinnamomea. The structures of new compounds were elucidated by comprehensive spectroscopic techniques, the planar structures of new compounds were determined by comprehensive spectroscopic techniques, and their absolute configurations were confirmed via gauge-independent atomic orbital calculations (GIAO), calculation of the electronic circular dichroism (ECD), and optical rotation (OR). These were determined by spectroscopic data analysis. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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17 pages, 2990 KiB

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Ethanolic Extract from Pteris wallichiana Alleviates DSS-Induced Intestinal Inflammation and Intestinal Barrier Dysfunction by Inhibiting the TLR4/NF-κB Pathway and Regulating Tight Junction Proteins

by Junhong Tao, Zhihua Huang, Yudan Wang, Yaping Liu, Tianrui Zhao, Yifen Wang, Lei Tian and Guiguang Cheng

Molecules 2022, 27(10), 3093; https://doi.org/10.3390/molecules27103093 - 11 May 2022

Cited by 6 | Viewed by 2374

Abstract

The aim of the research was to determine the protective effect and mechanism of Pteris wallichiana J. Agardh extract (PWE) on DSS-induced ulcerative colitis (UC) in mice. In this research, PWE is rich in flavonoids and diterpenoids by UPLC-MS/MS analysis. In LPS-induced RAW264.7 [...] Read more.

The aim of the research was to determine the protective effect and mechanism of Pteris wallichiana J. Agardh extract (PWE) on DSS-induced ulcerative colitis (UC) in mice. In this research, PWE is rich in flavonoids and diterpenoids by UPLC-MS/MS analysis. In LPS-induced RAW264.7 cells, PWE reduced the productions of inflammatory factors (i.e., NO, TNF-α, IL-6, and IL-1β). In DSS-induced UC in mice, PWE improved disease activity index (DAI) score, attenuated oxidative stress by decreasing MPO and MDA activities and activating GSH and SOD levels, and inhibited TNF-α, IL-6, and IL-1β expressions in the colonic tissues. PWE also improved the intestinal barrier by upregulating the expressions of tight junction proteins, including occludin and ZO-1. Moreover, PWE extract alleviated intestinal inflammation by suppressing the TLR4/MyD88/NF-κB signaling pathway. Conclusion: PWE can alleviate DSS-induced UC in mice by increasing the expressions of intestinal tight junction proteins and inhibiting the TLR4/NF-κB inflammatory pathway. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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23 pages, 923 KiB

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Characteristics, Isolation Methods, and Biological Properties of Aucubin

by Kartini Kartini, Michelle Abigail Irawan, Finna Setiawan and Nikmatul Ikhrom Eka Jayani

Molecules 2023, 28(10), 4154; https://doi.org/10.3390/molecules28104154 - 17 May 2023

Cited by 8 | Viewed by 3067

Abstract

Aucubin is an iridoid glycoside widely spread in the families Cornaceae, Garryaceae, Orobanchaceae, Globulariaceae, Eucommiaceae, Scrophulariaceae, Plantaginaceae, and Rubiaceae. This review is intended to provide data on the physicochemical characteristics, isolation methods, and biological activities [...] Read more.

Aucubin is an iridoid glycoside widely spread in the families Cornaceae, Garryaceae, Orobanchaceae, Globulariaceae, Eucommiaceae, Scrophulariaceae, Plantaginaceae, and Rubiaceae. This review is intended to provide data on the physicochemical characteristics, isolation methods, and biological activities of aucubin and its producing plants. Aucubin is unstable and can be deglycosylated into its aglycone, aucubigenin. Various chromatographic methods (column chromatography, vacuum liquid chromatography, medium pressure liquid chromatography, and high-performance liquid chromatography) have been used together to isolate aucubin, mainly with the stationary phase C-18 and the mobile phase water–methanol solution made in gradients. In vitro and in vivo studies reveal that aucubin has a wide range of activities, including anti-inflammatory, antioxidant, anxiolytic and antidepressant, antidiabetic, antifibrotic, antimicrobial, anticancer, antihyperlipidemic, gastroprotective, cardioprotective, hepatoprotective, retinoprotective, neuroprotective, osteoprotective, and renoprotective. Even though aucubin has been extensively investigated, further research in humans is urgently needed primarily to substantiate the clinical evidence. Moreover, extensive studies on its drug delivery systems will help maximize efficacy and minimize side effects. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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34 pages, 6083 KiB

Open AccessReview

Biological Activities and Secondary Metabolites from Sophora tonkinensis and Its Endophytic Fungi

by Jia-Jun Liang, Pan-Pan Zhang, Wei Zhang, Da Song, Xin Wei, Xin Yin, Yong-Qiang Zhou, Xiang Pu and Ying Zhou

Molecules 2022, 27(17), 5562; https://doi.org/10.3390/molecules27175562 - 29 Aug 2022

Cited by 6 | Viewed by 2521

Abstract

The roots of Sophora tonkinensis Gagnep., a traditional Chinese medicine, is known as Shan Dou Gen in the Miao ethnopharmacy. A large number of previous studies have suggested the usage of S. tonkinensis in the folk treatment of lung, stomach, and throat diseases, [...] Read more.

The roots of Sophora tonkinensis Gagnep., a traditional Chinese medicine, is known as Shan Dou Gen in the Miao ethnopharmacy. A large number of previous studies have suggested the usage of S. tonkinensis in the folk treatment of lung, stomach, and throat diseases, and the roots of S. tonkinensis have been produced as Chinese patent medicines to treat related diseases. Existing phytochemical works reported more than 300 compounds from different parts and the endophytic fungi of S. tonkinensis. Some of the isolated extracts and monomer compounds from S. tonkinensis have been proved to exhibit diverse biological activities, including anti-tumor, anti-inflammatory, antibacterial, antiviral, and so on. The research progress on the phytochemistry and pharmacological activities of S. tonkinensis have been systematically summarized, which may be useful for its further research. Full article

(This article belongs to the Special Issue Isolation, Identification and Application of Biologically Active Natural Products)

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