Facile synthesis of triterpenoid saponins bearing β-Glu/Gal-(1→3)-β-GluA methyl ester and their cytotoxic activities

Abstract Two new 27-nor-triterpene glycosides, pyrocincholic acid 3β -O-β -D-glucopyranosyl-(1→4)- β -D-quinovopyranosyl-28-O-β -D-glucopyranoside (Metatrichoside A, 1), pyrocincholic acid 3β -O-β -D-glucopyranosyl-(1→4)-β -D-quinovopyranosyl-28-O-β -D-glucopyranosyl-(1→6)-β -Dglucopyranoside (Metatrichoside B, 2), together with pyrocincholic acid 3β -O-β -D-quinovopyranosyl- 28-O-β -D-glucopyranoside (3), pyrocincholic acid 3β -O-β -D-quinovopyranosyl-28-O-β -Dglucopyranosyl-( 1→6)-β -D-glucopyranoside (4), quinovic acid 3β -O-β -D-quinovopyranoside (5), quinovic acid 3β -O-β -D-quinovopyranosyl-28-O-β -D-glucopyranoside (6), quinovic acid 3β -O- β -D-glucopyranoside (7) and quinovic acid 3β -O-β -D-glucopyranosyl-28-O-β -D-glucopyranoside (8) were isolated from the barks of Metadina trichotoma. Their structures were mainly determined by mass spectrometric and 1D and 2D NMR spectroscopic methods. Compound 5 and 6 showed cytotoxic activities towards the A549 non-small-cell lung cancer cell line (IC50 = 8.43 and 6.06 μm), and the methanol extract inhibited the activity of cathepsin B with an IC50 value of 0.77 μg mL−1.

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Two New Triterpenoid Saponins from the Structural Modification of Pseudoginsenoside-F11 and their Cytotoxic Activities

Natural Product Communications ◽

10.1177/1934578x1601100510 ◽

2016 ◽

Vol 11 (5) ◽

pp. 1934578X1601100

Author(s):

Manman Li ◽

Zhicai Wang ◽

Pengfei Zhang ◽

Yan Xu ◽

Hongda Ding ◽

...

Keyword(s):

Acid Hydrolysis ◽

Tumor Cells ◽

Structural Modification ◽

Human Tumor ◽

2D Nmr ◽

Cytotoxic Activities ◽

Human Tumor Cells ◽

Triterpenoid Saponins ◽

Spectroscopic Analyses ◽

Hydrolysis Products

Two ginsenoside derivatives (1, 2) along with 2 known ginsenosides (3, 4) were isolated from the acid hydrolysis products of pseudoginsenoside-F11. Their structures were elucidated on the basis of spectroscopic analyses, including 1D, 2D NMR and HR-ESI-MS. Among them, (12 R, 20 S, 24 S)-20, 24; 12, 24-diepoxy-dammarane-3β, 6α-diol (1) and (20 R, 24 R)-dammar-20, 24-epoxy-3β, 6α, 12β, 25-tetraol (2) were identified as new triterpenoid saponins. They were subjected to assay for cytotoxic activities against six human tumor cells lines.

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Total synthesis and cytotoxic activities of longamide B, longamide B methyl ester, hanishin, and their analogues

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/j.bmcl.2015.11.069 ◽

2016 ◽

Vol 26 (1) ◽

pp. 6-8 ◽

Cited By ~ 10

Author(s):

Deng-Gao Zhao ◽

Yan-Yan Ma ◽

Wei Peng ◽

Ai-Yu Zhou ◽

Yu Zhang ◽

...

Keyword(s):

Methyl Ester ◽

Total Synthesis ◽

Cytotoxic Activities

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ChemInform Abstract: Facile Synthesis of Several Oleanane-Type Triterpenoid Saponins

ChemInform ◽

10.1002/chin.201137197 ◽

2011 ◽

Vol 42 (37) ◽

pp. no-no

Author(s):

Qingchao Liu ◽

Zheng Fan ◽

Dong Li ◽

Wenhong Li ◽

Tiantian Guo

Keyword(s):

Facile Synthesis ◽

Triterpenoid Saponins

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Two new glycosidal metabolites of endophytic fungus Penicillium sp. (NO.4) from Tapiscia sinensis

Zeitschrift für Naturforschung B ◽

10.1515/znb-2015-0184 ◽

2016 ◽

Vol 71 (4) ◽

pp. 283-286 ◽

Cited By ~ 5

Author(s):

Qiao Wan ◽

Ziwei Feng ◽

Xueshuang Li ◽

Mengmeng Lv ◽

Zhiyong Guo ◽

...

Keyword(s):

Methyl Ester ◽

Cell Lines ◽

Cancer Cell ◽

Endophytic Fungus ◽

Cancer Cell Line ◽

2D Nmr ◽

Cancer Cell Lines ◽

Antimicrobial Activities ◽

Cytotoxic Activities ◽

A549 Cancer Cell Line

AbstractTwo new glycosides, 8-O-β-d-glucopyranosyl-6-methyl-1-carboxylate methyl ester xanthone (1) and 4′-O-β-d-galactopyranosyl djalonensone (2), together with four known compounds, 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate methyl ester (3), cassionllin (4), djalonensone (5) and alternariol (6), were isolated from the endophytic fungus Penicillium sp. (NO.4) of Tapiscia sinensis Oliv. The structures of compounds 1–6 were elucidated by the analysis of 1D and 2D NMR and HRMS. The cytotoxic activities of these compounds were evaluated against four cancer cell lines, as well as antimicrobial activities against two plant-pathogenic microbes. Compounds 1–6 showed moderate cytotoxicity against the A549 cancer cell line with IC50 values ranging from 6.8 to 35.8 μg mL−1 and were found to be inactive against three other cancer cell lines MCF-7, Caski and Hep G-2.

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