Pseudolaridimers A and B, hetero-cycloartane-labdane Diels-Alder adducts from the cone of Pseudolarix amabilis.
Pseudolaridimers A (1) and B (2), two unprecedented heterodimers formed via a [4 + 2] Diels-Alder cycloaddition between a cycloartane triterpenoid unit and a labdane diterpenoid unit, were isolated from the cones of Pseudolarix amabilis. Their structures were established by extensive analysis of HRESIMS and NMR spectra. The absolute configuration of 1 was determined by single crystal X-ray diffraction (CuK(α)) of its methyl esterified derivative. Pseudolaridimer A (1) showed strong cytotoxicity against HCT116, ZR-75-30, and HL-60 human tumor cell lines, with IC(50) values 9.62, 7.84, 8.29 μg/mL, respectively. Pseudolaridimer B (2) only exhibited potent inhibition against the HL-60 cell line with an IC(50) value of 7.50 μg/mL.
Department of Phytochemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, P. R. China.
Bo
B
Li
De-Yun
DY
Kong
Yun-Heng
YH
Shen
Hu
H
Yuan
Rong-Cai
RC
Yue
Yi-Ren
YR
He
Lu
L
Lu
Lei
L
Shan
Hui-Liang
HL
Li
Ji
J
Ye
Xian-Wen
XW
Yang
Juan
J
Su
Run-Hui
RH
Liu
Wei-Dong
WD
Zhang
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D045325:HCT116 Cells; D018922:HL-60 Cells; D006801:Humans; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D028201:Pinaceae / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology
D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes; D014315:Triterpenes; C578106:pseudolaridimer A; C578107:pseudolaridimer B; C085352:cycloartane