Cytotoxic serratane triterpenes from Diphasiastrum complanatum with a hydroxy group at C-27.
Four serratane-type triterpenes ( 1- 4) were isolated from D. COMPLANATUM. Their chemical structures were elucidated as 14alpha,15alpha,20beta,21beta,24,27alpha,29-heptahydroxyserrat-3-one ( 1), 3beta,14alpha,15alpha,20beta,21beta,24,27alpha,29-octahydroxyserratane ( 2), 3alpha,14alpha,20beta,21beta,24,27alpha,29-heptahydroxyserratane ( 3) and 3beta,14alpha,21beta,24,27alpha-pentahydroxyl-serratane-29-yl ( E)- P-coumarate ( 4) by spectroscopic methods (MS, 1D and 2D NMR) and X-ray crystallography. Interestingly, the most characteristic methylene (C-27) of the serratane ring C was oxidized to a methine. Compound 4 showed significant cytotoxic activity against the human leukemia K562/S and the doxorubicin-resistant K562/R cell lines, but the other compounds were inactive.
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, the Chinese Academy of Sciences, Kunming, People's Republic of China.
Jian
J
Yan
Lirong
L
Sun
Wei
W
Li
Lin
L
Zhou
Zhongrong
Z
Li
Xianmin
X
Zhang
Ling
L
Yang
Minghua
M
Qiu
D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*; D045744:Cell Line, Tumor; D004317:Doxorubicin; D019008:Drug Resistance, Neoplasm; D006801:Humans; D007938:Leukemia / Q000188:drug therapy*; D029542:Lycopodiaceae / Q000737:chemistry*; D015394:Molecular Structure; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use*; D014315:Triterpenes / Q000302:isolation & purification / Q000494:pharmacology / Q000627:therapeutic use*
C551643:3,14,21,24,27-pentahydroxyserratane-29-yl 4-coumarate; D000972:Antineoplastic Agents, Phytogenic; D010936:Plant Extracts; D014315:Triterpenes; D004317:Doxorubicin