Xylogranatins A-D: novel tetranortriterpenoids with an unusual 9,10-seco scaffold from marine mangrove Xylocarpus granatum.
[reaction: see text] Four novel tetranortriterpenoids, xylogranatins A-D (1-4), with an unusual 9,10-seco skeleton were isolated from the seeds of a Chinese marine mangrove Xylocarpus granatum. Their structures were determined by spectroscopic and chemical means. Xylogranatin A (1) featured by a unique 1,9-oxygen bridge was confirmed by single-crystal X-ray diffraction, and xylogranatin D (4) with an unprecedented skeleton of C-30-C-9 linkage was postulated biogenetically from 3 via an alpha-hydroxyl ketone rearrangement and was chemically mimicked.
Yin
Sheng
S
State Key Laboratory of Drug Research, Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 555 Zuchongzhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, PRC.
Fan
Cheng-Qi
CQ
Wang
Xiao-Ning
XN
Lin
Li-Ping
LP
Ding
Jian
J
Yue
Jian-Min
JM
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D007941:Leukemia P388; D036701:Limonins / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D029582:Meliaceae / Q000737:chemistry*; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*
D000972:Antineoplastic Agents, Phytogenic; D036701:Limonins