Cytotoxic triterpenoid saponins from Vaccaria segetalis

Abstract

By the guidance of bioassay, one new cytotoxic triterpenoid saponin, 3-O-[beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl] quillaic acid 28-O-beta-D-glucopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-fucopyranosyl-(1-->4)]-beta-D-fucopyranoside (1), and five known cytotoxic triterpenoid saponins, vaccaroside E (2), vaccaroside G (3), vaccaroside B (4), segetoside H (5) and segetoside I (6), were isolated from Vaccaria segetalis. Their structures were established on the basis of ESI-MS, IR, extensive NMR ((1)H NMR, (13)C NMR, TOCSY, (1)H-(1)H COSY, DEPT, HMQC, HMBC and ROESY) analyses, chemical degradation, and by comparing with previously reported data. Compounds 1-6 showed moderate cytotoxic activities against LNcap, P-388 and A-549 cell lines with IC(50) values in the range 0.1-12.9 microM.

Phytochemistry and pharmacological activities of Vaccaria hispanica (Miller) Rauschert: a review

“…Cytotoxic activities against LNcap, A-549, and P-388 cell lines Seed Koike et al (1998), Ma et al (2008), Yun et al (1997b) 20 Vaccaroside C Seed Koike et al (1998) Ma et al (2008) 27 Dianoside G Seed Sang et al (1999) Phytochem Rev presumably involved in the biosynthesis of vaccaroside A-D (18-21) (Meesapyodsuk et al 2007). A number of these saponins have been documented to have cytotoxic activities and growth inhibition of luteal cell (Table 1).…”

Vaccaria segetalis: A Review of Ethnomedicinal, Phytochemical, Pharmacological, and Toxicological Findings

“…V. segetalis is composed of several chemical components. Saponins (Ma et al, 2008 ), flavonoids (Wang et al, 2011 ), polysaccharides (Qing et al, 2014 ), and cyclic peptides (Sang et al, 2002 ) are believed to be the principal active constituents of V. segetalis . The seeds also contain components such as coumarins, lipids, fatty acids, and metallic elements (Jin-Ling et al, 2014 ).…”

In vivo metabolism study of vaccarin in rat using HPLC‐LTQ‐MSn

“…Our research group has focused on Vaccaria segetalis for several years (Ma et al, 2008), and has completed part of the isolation of this plant. It contains good quality flavonoids, cyclic peptides (Zhang et al, 1998) and triterpene saponins (Kazuo et al, 1998;Ma et al, 2001).…”

“…The seed of this plant, well‐known as Wang‐Bu‐Liu‐Xing, is traditionally used to invigorate blood circulation, regulate menstrual disturbance and dispel edema, promote diuresis and milk secretion, activate blood and relieve carbuncles (Sang et al ., ; Li and Liang, ). Our research group has focused on Vaccaria segetalis for several years (Ma et al ., ), and has completed part of the isolation of this plant. It contains good quality flavonoids, cyclic peptides (Zhang et al ., ) and triterpene saponins (Kazuo et al ., ; Ma et al ., ).…”