Labdane diterpenoids and highly methoxylated bibenzyls from the liverwort Frullania inouei.

Abstract

Four undescribed labdane diterpenoids, 1,2-dehydro-3,7-dioxo-manoyl oxide (1), 1,2-dehydro-7 beta-hydroxy-3-oxo-manoyl oxide (2), 3,7-dioxo-manoyl oxide (3), and 3beta-hydroxy-7-oxo-manoyl oxide (4) together with three known diterpenoids (5-7) and four highly methoxylated bibenzyls (8-11) were isolated from the liverwort Frullania inouei. The absolute structures of 1-4 were established by combined analysis of NMR data, CD data coupled with TDDFT CD calculations, and single-crystal X-ray diffraction measurement. Cytotoxicity tests to human tumor KB, KB/VCR, K562 or K562/A02 cells showed bibenzyls 8-11 inhibited cell proliferation with ID(50) values ranging from 11.3 to 49.6 microM and overcame the multidrug resistance (MDR) with the reversal fold (RF) values ranging from 3.19 to 10.91 (5 microM) for vincristine-resistant KB/VCR and RF values from 4.40 to 8.26 (5 microM) for adriamycin-resistant K562/A02 cells, respectively. However, none of the diterpenoids were found to be active (ID(50)>50 microM).

• Authors: Dong-Xiao Guo, Feng Xiang, Xiao-Ning Wang, Hui-Qing Yuan, Guang-Min Xi, Yan-Yan Wang, Wen-Tao Yu, Hong-Xiang Lou
• Journal: Phytochemistry (Phytochemistry) Vol. 71 Issue 13 Pg. 1573-8 (Sep 2010) ISSN: 1873-3700 [Electronic] England
• PMID: 20561654 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: (c) 2010 Elsevier Ltd. All rights reserved.

Chemical References

• Antineoplastic Agents
• Bibenzyls
• Diterpenes

Topics

• Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
• Bibenzyls (chemistry, isolation & purification, pharmacology)
• Cell Line, Tumor
• Circular Dichroism
• Diterpenes (chemistry, isolation & purification, pharmacology)
• Drug Resistance, Multiple (drug effects)
• Frullania (chemistry)
• Humans
• Inhibitory Concentration 50
• Magnetic Resonance Spectroscopy
• Models, Molecular
• Molecular Conformation
• X-Ray Diffraction