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.
Yan
Jian
J
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.
Sun
Lirong
L
Li
Wei
W
Zhou
Lin
L
Li
Zhongrong
Z
Zhang
Xianmin
X
Yang
Ling
L
Qiu
Minghua
M
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