New triterpenoid saponins from Glochidion eriocarpum and their cytotoxic activity.

Abstract

Combined chromatographic methods led to the isolation of two new triterpenoid saponins, glochieriosides A and B (1, 2), from the aerial parts of Glochidion eriocarpum, along with three known triterpenes, glochidone (3), lup-20(29)-en-3beta,23-diol (4), and lup-20(29)-en-1beta,3beta-diol (5). The structures of the new saponins were determined to be 22beta-benzoyloxy-3beta,16beta,28-trihydroxyolean-12-ene 3-O-[beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranoside] (1) and 22beta-benzoyloxy-3beta,16beta,28-trihydroxyolean-12-ene 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-xylopyranoside] (2). The structural elucidation was accomplished by using a combination of the 1D-NMR (1H-, 13C-NMR, distortionless enhancement by polarization transfer (DEPT) 90 degrees , and DEPT 135 degrees ), 2D-NMR (1H-1H correlation spectroscopy, heteronuclear multiple quantum correlation, heteronuclear multiple bond correlation, and rotating frame Overhouser effect spectroscopy), ESI-MS, and HR-FAB-MS experiments. Glochieriosides A and B exhibited significant cytotoxic activity against HL-60, HT-29, MCF-7 and SK-OV-3 human cancer cell lines with the IC50 values of 5.5, 6.8, 29.1, and 22.7 microM for glochierioside A, respectively, and 6.6, 18.6, 36.1, and 16.0 microM for glochierioside B. Glochidone was less active with IC50 values greater than 100 microM while lup-20(29)-en-1beta,3beta-diol was moderately active with IC50 values of 43.3, 67.0, 66.1, and 48.0 microM, respectively.

• Authors: Phan Van Kiem, Vu Kim Thu, Pham Hai Yen, Nguyen Xuan Nhiem, Nguyen Huu Tung, Nguyen Xuan Cuong, Chau Van Minh, Hoang Thanh Huong, Jae-Hee Hyun, Hee-Kyoung Kang, Young Ho Kim
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 57 Issue 1 Pg. 102-5 (Jan 2009) ISSN: 0009-2363 [Print] Japan
• PMID: 19122328 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Plant Extracts
• Saponins
• Sesquiterpenes
• Triterpenes
• glochicoccinoside A
• glochicoccinoside B

Topics

• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Cells (drug effects)
• Drug Screening Assays, Antitumor
• Humans
• Inhibitory Concentration 50
• Magnetic Resonance Spectroscopy
• Molecular Structure
• Phyllanthus (chemistry)
• Plant Components, Aerial (chemistry)
• Plant Extracts (chemistry, pharmacology)
• Saponins (chemistry, pharmacology)
• Sesquiterpenes (chemistry, pharmacology)
• Triterpenes (chemistry, pharmacology)