Isolation and structure elucidation of kadlongilactones C-F from Kadsura longipedunculata by NMR spectroscopy and DFT computational methods.
Four new triterpenoids, kadlongilactones C-F (2-5), containing a consecutive hexacyclic [7,7,5,6,6,6] ring system, were isolated from the leaves and stems of Kadsura longipedunculata. In comparison with the NMR data of kadlongilactones A (1) and D (3), a significant phenomena was discovered that ring D of 3 inverted from a half-chair in 1 to a half-boat conformation when the HO-16 group changed from alpha- to beta-orientation. The structures of 2-5 were established on the basis of detailed spectroscopic analysis, and DFT computational methods were applied in the structural validation of compounds 3 and 5. Compounds 1-4 showed significant cytotoxicity against A549, HT-29, and K562 cell lines with IC50 values of 0.49-3.61 microM in vitro.
Pu
Jian-Xin
JX
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People's Republic of China.
Huang
Sheng-Xiong
SX
Ren
Jie
J
Xiao
Wei-Lie
WL
Li
Li-Mei
LM
Li
Rong-Tao
RT
Li
Liang-Bo
LB
Liao
Tou-Gen
TG
Lou
Li-Guang
LG
Zhu
Hua-Jie
HJ
Sun
Han-Dong
HD
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D032135:Kadsura / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000972:Antineoplastic Agents, Phytogenic; D004365:Drugs, Chinese Herbal; D014315:Triterpenes