Labdane diterpenoids and highly methoxylated bibenzyls from the liverwort Frullania inouei.
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).
Guo
Dong-Xiao
DX
Department of Natural Products Chemistry, School of Pharmaceutical Sciences, Shandong University, No. 44 West Wenhua Road, Jinan 250012, People's Republic of China.
Xiang
Feng
F
Wang
Xiao-Ning
XN
Yuan
Hui-Qing
HQ
Xi
Guang-Min
GM
Wang
Yan-Yan
YY
Yu
Wen-Tao
WT
Lou
Hong-Xiang
HX
D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D001632:Bibenzyls / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002942:Circular Dichroism; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D018432:Drug Resistance, Multiple / Q000187:drug effects; D037961:Frullania / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D014961:X-Ray Diffraction
D000970:Antineoplastic Agents; D001632:Bibenzyls; D004224:Diterpenes