Triterpenoid saponins and phenylpropanoid glycoside from the roots of Ardisia crenata 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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Five new triterpenoid saponins from the Roots of Camellia oleifera C. Abel with cytotoxic activities

Phytochemistry Letters ◽

10.1016/j.phytol.2015.08.005 ◽

2015 ◽

Vol 13 ◽

pp. 379-385 ◽

Cited By ~ 12

Author(s):

Jiangping Wu ◽

Jianping Zhao ◽

Yanli Liu ◽

Xiaoran Li ◽

Qiongming Xu ◽

...

Keyword(s):

Cytotoxic Activities ◽

Camellia Oleifera ◽

Triterpenoid Saponins

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

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/j.bmcl.2012.02.032 ◽

2012 ◽

Vol 22 (7) ◽

pp. 2396-2400 ◽

Cited By ~ 5

Author(s):

Jian Gao ◽

Xia Li ◽

Guofeng Gu ◽

Shanshan Liu ◽

Min Cui ◽

...

Keyword(s):

Methyl Ester ◽

Cytotoxic Activities ◽

Facile Synthesis ◽

Triterpenoid Saponins

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Two New Oleanane-type Triterpenoids from Methanolyzed Saponins of Momordica cochinchinensis

Natural Product Communications ◽

10.1177/1934578x1601100607 ◽

2016 ◽

Vol 11 (6) ◽

pp. 1934578X1601100

Author(s):

Rong Fan ◽

Rong-Rong Cheng ◽

Hong-Tao Zhu ◽

Dong Wang ◽

Chong-Ren Yang ◽

...

Keyword(s):

Glucose Uptake ◽

Cell Lines ◽

Human Cancer ◽

Glucose Consumption ◽

2D Nmr ◽

Cytotoxic Activities ◽

Triterpenoid Saponins ◽

Human Cancer Cell Lines ◽

Momordica Cochinchinensis ◽

Uptake Activity

Two new oleanane-type triterpenoid saponins (1 and 2) were isolated from the methanolyzed total saponins of the seeds of Momordica cochinchinensis (Lour.) Spreng, together with 16 known compounds (3—18). Their structures were elucidated on the basis of detailed spectroscopic, including ID and 2D NMR, mass spectrometric, methanolysis and LC-MS analysis. All the isolates were tested for their cytotoxic activities against five human cancer cell lines (HL-60, SMMC-7721, PANC-1, A-549, and SW-480) and the glucose uptake activity. The known compound 6 exhibited toxic effects against HL-60 with an IC50 value of 18.1 μM, while 10 showed cytotoxicity against SMMC-7721 and A-549 cell lines, with IC50 values of 34.4 and 32.8 μM, respectively. In addition, the new compound 2 showed glucose uptake activity with a glucose consumption value of 0.29 μM at 10 μM concentration.

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