Limonoids from the seeds of a Godavari mangrove, Xylocarpus moluccensis

: Li J, Li MY, Feng G, Xiao QA, Sinkkonen J, Satyanandamurty T, Wu J

Publisher: PERGAMON-ELSEVIER SCIENCE LTD

: 2010

Phytochemistry

PHYTOCHEMISTRY

: PHYTOCHEMISTRY

: 16

: 71

: 16

: 1917

: 1924

: 8

: 0031-9422

DOI: https://doi.org/10.1016/j.phytochem.2010.07.015

Ten limonoids, named godavarins A-J (1-7, 9-11), were isolated from seeds of an Indian mangrove (Xylocarpus moluccensis) collected in the mangrove wetlands of Godavari estuary, Andhra Pradesh. Eight known limonoids, viz xyloccensins L (8), P (12), Q (13). mexicanolide (14), 6-deoxy-3-detigloyl-swietenine acetate (15), fissinolide (16), methyl 3 beta-acetoxy-1-oxomeliaca-8(30),14-dienoate (17), and methyl 3 beta-acetoxy-1-oxomeliaca-8(9),14-dienoate (18), were also obtained. The structures of these compounds were established on the basis of spectroscopic data or comparison with data in the literature (known compounds). The stereostructure of godavarin D was confirmed by means of single-crystal X-ray analysis. Godavarins A-C are the first mexicanolide derivatives with a C(7)-C(28) ester-linked delta-lactone ring, while godavarins D-G are further additions to the small group of limonoids with a C(1)-C(29) oxygen bridge. Godavarin H is a phragmalin with five acetoxy groups. Two limonoids, mexicanolide and fissinolide, were found to exhibit marked antifeedant activity against the third-instar larvae of Brontispa longissima (Gestro) at a concentration of 0.5 mg/mL. The most potent compound was mexicanolide. It also showed moderate insecticidal activity. (C) 2010 Elsevier Ltd. All rights reserved.