A1 Refereed original research article in a scientific journal
Limonoids from the seeds of a Godavari mangrove, Xylocarpus moluccensis
Authors: Li J, Li MY, Feng G, Xiao QA, Sinkkonen J, Satyanandamurty T, Wu J
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Publication year: 2010
Journal:Phytochemistry
Journal name in sourcePHYTOCHEMISTRY
Journal acronym: PHYTOCHEMISTRY
Number in series: 16
Volume: 71
Issue: 16
First page : 1917
Last page: 1924
Number of pages: 8
ISSN: 0031-9422
DOI: https://doi.org/10.1016/j.phytochem.2010.07.015
Abstract
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.
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.