Cycloartane and Oleanane Glycosides from the Tubers of Eranthis cilicica

Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1–11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC50 14.8 μM) than 1a (IC50 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.

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Fusarins G–L with Inhibition of NO in RAW264.7 from Marine-Derived Fungus Fusarium solani 7227

Marine Drugs ◽

10.3390/md19060305 ◽

2021 ◽

Vol 19 (6) ◽

pp. 305

Author(s):

Guangyuan Luo ◽

Li Zheng ◽

Qilin Wu ◽

Senhua Chen ◽

Jing Li ◽

...

Keyword(s):

Fusarium Solani ◽

2D Nmr ◽

Inflammatory Activity ◽

Raw264.7 Cells ◽

Spectroscopic Methods ◽

X Ray ◽

X Ray Crystallography ◽

Structure Activity ◽

Ic50 Values ◽

New Compounds

Six new fusarin derivatives, fusarins G–L (1–6), together with five known compounds (5–11) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 5–11 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 μM. The structure–activity relationships of the fusarins are discussed herein.

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Structure and Cytotoxicity of Novel Lignans and Lignan Glycosides from the Aerial Parts of Larrea tridentata

Molecules ◽

10.3390/molecules26206186 ◽

2021 ◽

Vol 26 (20) ◽

pp. 6186

Author(s):

Akihito Yokosuka ◽

Tomoki Iguchi ◽

Maki Jitsuno ◽

Yoshihiro Mimaki

Keyword(s):

Cell Death ◽

Spectroscopic Analysis ◽

Apoptotic Cell ◽

Larrea Tridentata ◽

Promyelocytic Leukemia ◽

Leukemia Cells ◽

Aerial Parts ◽

Ic50 Values ◽

Lignan Glycosides ◽

New Compounds

Previously, the authors conducted phytochemical investigations of the aerial parts of Larrea tridentata and reported triterpene glycosides and lignan derivatives. In continuation of the preceding studies, 17 lignans and lignan glycosides (1–17) were isolated, including seven new compounds (1–7). Herein, the structure of the new compounds was determined based on spectroscopic analysis and enzymatic hydrolysis. The cytotoxicity of 1–17 against HL-60 human promyelocytic leukemia cells was examined. Compounds 4–11 and 14–16 were cytotoxic to HL-60 cells, with IC50 values in the range of 2.7–17 μM. Compound 6, which was the most cytotoxic among the unprecedented compounds, was shown to induce apoptotic cell death in HL-60 cells.

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Diketopiperazine and Diphenylether Derivatives from Marine Algae-Derived Aspergillus versicolor OUCMDZ-2738 by Epigenetic Activation

Marine Drugs ◽

10.3390/md17010006 ◽

2018 ◽

Vol 17 (1) ◽

pp. 6 ◽

Cited By ~ 7

Author(s):

Wen Liu ◽

Liping Wang ◽

Bin Wang ◽

Yanchao Xu ◽

Guoliang Zhu ◽

...

Keyword(s):

Spectroscopic Analysis ◽

Specific Rotation ◽

Crystallographic Analysis ◽

Aspergillus Versicolor ◽

X Ray ◽

Naturally Occurring ◽

Ic50 Values ◽

New Compounds ◽

First Time ◽

Optically Pure

A chemical-epigenetic method was used to enhance the chemodiversity of a marine algicolous fungus. Apart from thirteen known compounds, (+)-brevianamide R ((+)-3), (‒)-brevianamide R ((‒)-3), (+)-brevianamide Q ((+)-4), (‒)-brevianamide Q ((‒)-4), brevianamide V ((+)-5), brevianamide W ((‒)-5), brevianamide K (6), diorcinol B (7), diorcinol C (8), diorcinol E (9), diorcinol J (10), diorcinol (11), 4-methoxycarbonyldiorcinol (12), two new compounds, (+)- and (‒)-brevianamide X ((+)- and (‒)- 2)), as well as a new naturally occurring one, 3-[6-(2-methylpropyl)-2-oxo-1H-pyrazin-3-yl]propanamide (1), were isolated from chemical-epigenetic cultures of Aspergillus versicolor OUCMDZ-2738 with 10 µM vorinostat (SAHA). Compared to cultures in the same medium without SAHA, compounds 1–4, 8, 9, 11, and 12 were solely observed under SAHA condition. The structures of these compounds were elucidated based on spectroscopic analysis, specific rotation analysis, ECD, and X-ray crystallographic analysis. (±)-3, (±)-4, and (±)-5 were further resolved into the corresponding optically pure enantiomers and their absolute configurations were determined for the first time. Compounds 11 and 12 showed selective antibacterial against Pseudomonas aeruginosa with a minimum inhibitory concentration (MIC) of 17.4 and 13.9 μM, respectively. Compound 10 exhibited better α-glucosidase inhibitory activity than the assay control acarbose with IC50 values of 117.3 and 255.3 μM, respectively.

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Isolation of New Glycosides from Anemarrhena Asphodeloides Rhizome and Screening of their Anticancer Activity

Letters in Organic Chemistry ◽

10.2174/1570178615666181102125553 ◽

2019 ◽

Vol 16 (6) ◽

pp. 474-477 ◽

Cited By ~ 1

Author(s):

Pham Van Khang ◽

Nguyen Thi Hien Lan ◽

Le Quang Truong ◽

Mai Thi Minh Chau ◽

Mai Xuan Truong ◽

...

Keyword(s):

Anticancer Activity ◽

Spectral Data ◽

Cell Lines ◽

Cancer Cell ◽

Spectroscopic Analysis ◽

2D Nmr ◽

Ic50 Values ◽

Nmr Techniques ◽

Inhibitory Activities ◽

Anemarrhena Asphodeloides

In this report, two new steroidal glycosides were isolated and determined from n-butanol fraction of A.asphodeloides. The structures were confirmed in comparison with the spectral data of known compounds by using different spectroscopic analysis approaches including 1D & 2D-NMR techniques and HRMS. The anti-proliferation screening against cancer cell lines A549 and HeLa indicated that compound 1 exhibited good inhibitory activities with IC50 values of 0.79 and 0.55 µg/mL, respectively.

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Phytochemical Analysis of Anvillea garcinii Leaves: Identification of Garcinamines F–H and Their Antiproliferative Activities

Plants ◽

10.3390/plants10061130 ◽

2021 ◽

Vol 10 (6) ◽

pp. 1130

Author(s):

Hanan Y. Aati ◽

Shagufta Perveen ◽

Raha Orfali ◽

Areej M. Al-Taweel ◽

Jiangnan Peng ◽

...

Keyword(s):

Cell Lines ◽

Liver Diseases ◽

Mcf7 Cell ◽

Sesquiterpene Lactones ◽

2D Nmr ◽

Phytochemical Analysis ◽

Antidiabetic Agent ◽

Arab Region ◽

New Compounds ◽

Acid Unit

Anvillea garcinii is a medicinal plant used in the Arab region for intestinal diseases, lung and liver diseases, digestive problems, and as an antidiabetic agent. Repeated chromatographic purifications of A. garcinii leaves led to the isolation of three undescribed guaiane sesquiterpene derivatives, named garcinamines F–H, characterized by the presence of an amino acid unit, along with five known sesquiterpene lactones (garcinamines B–E and 9β-hydroxyparthenolide). The structures of the new compounds were established using spectroscopic (1D and 2D NMR) and spectrometric methods (ESIMS). Garcinamine H possesses a double bond at the Δ1,10 position, a structural feature rarely reported in guaianolide-type sesquiterpenes. The antiproliferative activity of the isolated sesquiterpenes was screened against three different cancer cell lines, and 9β-hydroxyparthenolide and garcinamines C and D displayed significant effects against lung carcinoma (A549), colon carcinoma (LoVo), and breast carcinoma (MCF7) cell lines.

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Secondary Metabolites with Nitric Oxide Inhibition from Marine-Derived Fungus Alternaria sp. 5102

Marine Drugs ◽

10.3390/md18080426 ◽

2020 ◽

Vol 18 (8) ◽

pp. 426 ◽

Cited By ~ 1

Author(s):

Senhua Chen ◽

Yanlian Deng ◽

Chong Yan ◽

Zhenger Wu ◽

Heng Guo ◽

...

Keyword(s):

Secondary Metabolites ◽

2D Nmr ◽

X Ray ◽

X Ray Crystallography ◽

Spectroscopic Analyses ◽

Structure Activity ◽

Ic50 Values ◽

Alternaria Sp ◽

Modified Mosher’S Method ◽

Oxide Inhibition

Two new benzofurans, alternabenzofurans A and B (1 and 2) and two new sesquiterpenoids, alternaterpenoids A and B (3 and 4), along with 18 known polyketides (5−22), were isolated from the marine-derived fungus Alternaria sp. 5102. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HR-ESIMS, and ECD) and X-ray crystallography, as well as the modified Mosher’s method. Compounds 2, 3, 5, 7, 9–18, and 20–22 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50 values in the range from 1.3 to 41.1 μM. Structure-activity relationships of the secondary metabolites were discussed.

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Mono- and Dimeric Xanthones with Anti-Glioma and Anti-Inflammatory Activities from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722

Marine Drugs ◽

10.3390/md20010051 ◽

2022 ◽

Vol 20 (1) ◽

pp. 51

Author(s):

Senhua Chen ◽

Heng Guo ◽

Minghua Jiang ◽

Qilin Wu ◽

Jing Li ◽

...

Keyword(s):

High Resolution Mass Spectrometry ◽

2D Nmr ◽

Crystallographic Analysis ◽

Selective Cytotoxicity ◽

X Ray ◽

Planar Structures ◽

Spectroscopic Analyses ◽

Ic50 Values ◽

Anti Inflammatory ◽

Resolution Mass

Seven new xanthones, diaporthones A−G (1−7), together with 13 known analogues, including five mono- (8−14) and six dimeric xanthones (15−20), were obtained from the ascidian-derived fungus Diaporthe sp. SYSU-MS4722. Their planar structures were established by extensive spectroscopic analyses, including 1D and 2D NMR and high-resolution mass spectrometry (HR-ESIMS). The absolute configurations of 1−7 were clearly identified by X-ray crystallographic analysis and calculation of the ECD Spectra. Compounds 15−20 showed significant anti-inflammatory activity with IC50 values between 6.3 and 8.0 μM. In addition, dimeric xanthones (15−20) showed selective cytotoxicity against T98G cell lines with IC50 values ranging from 19.5 to 78.0 μM.

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Benzyl Furanones and Pyrones from the Marine-Derived Fungus Aspergillus terreus Induced by Chemical Epigenetic Modification

Molecules ◽

10.3390/molecules25173927 ◽

2020 ◽

Vol 25 (17) ◽

pp. 3927

Author(s):

Jing-Shuai Wu ◽

Xiao-Hui Shi ◽

Ya-Hui Zhang ◽

Chang-Lun Shao ◽

Xiu-Mei Fu ◽

...

Keyword(s):

Aspergillus Terreus ◽

Epigenetic Modification ◽

2D Nmr ◽

Etoac Extract ◽

One Dimensional ◽

X Ray ◽

Deacetylase Inhibitor ◽

Ic50 Values ◽

First Time ◽

Mic Value

Chemical epigenetic modification on a marine-derived fungus Aspergillus terreus RA2905 using a histone deacetylase inhibitor, suberoylanilide hydroxamic acid (SAHA), resulted in a significantly changed metabolic profile. A chemical investigation of its ethyl acetate (EtOAc) extract led to the isolation of a racemate of benzyl furanone racemate (±)-1, which further separated chirally as a pair of new enantiomers, (+)- and (−)-asperfuranone (1), together with two new benzyl pyrones, asperpyranones A (2) and B (3). Their structures were elucidated by analysis of the comprehensive spectroscopic data, including one-dimensional (1D) and two-dimensional (2D) NMR, and HRESIMS. The absolute configurations were determined by electronic circular dichroism (ECD) calculation and single-crystal X-ray crystallographic experiment. The structures with benzyl furanone or benzyl pyrone skeletons were discovered from natural products for the first time. Compounds (±)-1, (+)-1, (−)-1, and 2 displayed the antifungal activities against Candida albicans with MIC values of 32, 16, 64, and 64 μg/mL and PTP1B inhibitory activities with the IC50 values of 45.79, 17.32, 35.50, and 42.32 μM, respectively. Compound 2 exhibited antibacterial activity against Pseudomonas aeruginosa with the MIC value of 32 μg/mL.

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New Cyclopentyl Fatty Acid and Cyanohydrin Glycosides from Fruits of Hydnocarpus hainanensis

Natural Product Communications ◽

10.1177/1934578x1701200228 ◽

2017 ◽

Vol 12 (2) ◽

pp. 1934578X1701200

Author(s):

Thanh Tra Nguyen ◽

Bich Ngan Truong ◽

Huong Doan Thi Mai ◽

Marc Litaudon ◽

Van Hung Nguyen ◽

...

Keyword(s):

Fatty Acid ◽

Cytotoxic Activity ◽

Cell Line ◽

Spectroscopic Analysis ◽

2D Nmr ◽

New Compounds ◽

Line Compound

Three new compounds, hydnohainanic acid (1), and hydnohainanin A (2) and B (3) were isolated from the fruits of Hydnocarpus hainanensis (Achariaceae). Their structures were determined by spectroscopic analysis, including 2D NMR, and MS. Compounds 1-3 were evaluated for their cytotoxic activity against the KB cell line. Compound 1 had a moderate cytotoxicity with an IC50 value of 32.5 μg/mL, while the two remaining compounds did not exhibit inhibition, even at a concentration of 128 μg/mL.

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Highly Substituted Benzophenone Aldehydes and Eremophilane Derivatives from the Deep-Sea Derived Fungus Phomopsis lithocarpus FS508

Marine Drugs ◽

10.3390/md16090329 ◽

2018 ◽

Vol 16 (9) ◽

pp. 329 ◽

Cited By ~ 9

Author(s):

Jian-Lin Xu ◽

Hong-Xin Liu ◽

Yu-Chan Chen ◽

Hai-Bo Tan ◽

Heng Guo ◽

...

Keyword(s):

Cytotoxic Activity ◽

Cell Lines ◽

A549 Cell ◽

Marine Sediment ◽

Deep Sea ◽

Crystallographic Analysis ◽

X Ray ◽

Naturally Occurring ◽

Ic50 Values ◽

New Compounds

Five new benzophenone derivatives named tenellones D–H (1–5), sharing a rare naturally occurring aldehyde functionality in this family, and a new eremophilane derivative named lithocarin A (7), together with two known compounds (6 and 8), were isolated from the deep marine sediment-derived fungus Phomopsis lithocarpus FS508. All of the structures for these new compounds were fully characterized and established on the basis of extensive spectroscopic interpretation and X-ray crystallographic analysis. Compound 5 exhibited cytotoxic activity against HepG-2 and A549 cell lines with IC50 values of 16.0 and 17.6 μM, respectively.

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