C18 dibenzocyclooctadiene lignans from Kadsura philippinensis.
Four new C18 dibenzocyclooctadiene lignans, kadsuphilins A (1) and B (3), 6-epi-gomisin (2), and 1-demethylkadsuphilin A (4), along with eight known related metabolites, were isolated from an EtOAc fraction of an alcoholic extract of the aerial parts of Kadsura philippinensis growing in Taiwan. The structures of 1-4 were elucidated on the basis of spectroscopic analyses, including 2D NMR (HMQC, HMBC, and NOESY) experiments, and by comparison of their spectroscopic data with those of related metabolites. The configurations of the biphenyl and cyclooctadiene moieties were deduced from circular dichroism (CD) and NOESY NMR spectra, respectively. Some of the compounds showed radical-scavenging activity in a DPPH-HPLC method.
Shen
Ya-Ching
YC
Department of Marine Resources, National Sun Yat-Sen University, Kaohsiung 804, Taiwan, Republic of China. ycshen@mail.nsysu.edu.tw
Liaw
Chia-Ching
CC
Cheng
Yuan-Bin
YB
Ahmed
Atallah F
AF
Lai
Mei-Chou
MC
Liou
Shorong-Shii
SS
Wu
Tian-Shung
TS
Kuo
Yao-Haur
YH
Lin
Yu-Chi
YC
D001713:Biphenyl Compounds; D034242:Cyclooctanes / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D032135:Kadsura / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010851:Picrates / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D013624:Taiwan
D001713:Biphenyl Compounds; D034242:Cyclooctanes; D016166:Free Radical Scavengers; D017705:Lignans; D010851:Picrates; C511097:dibenzocyclooctadiene; C004931:1,1-diphenyl-2-picrylhydrazyl