Limonoids from the seeds of a Godavari mangrove, Xylocarpus moluccensis.
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 3β-acetoxy-1-oxomeliaca-8(30),14-dienoate (17), and methyl 3β-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 C₇-C₂₈ ester-linked δ-lactone ring, while godavarins D-G are further additions to the small group of limonoids with a C₁-C₂₉ 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.
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ABSTRACT: A new andirobin, thaimoluccensin A (1), and two new phragmalin-type limonoids, thaimoluccensins B (2) and C (3), were isolated from seeds of a Thai mangrove plant, Xylocarpus moluccensis, together with eight known compounds. The structures of these compounds were elucidated on the basis of spectroscopic data. Only 7-deacetylgedunin (7), a gedunin-type limonoid, exhibited significant inhibitory activity against nitric oxide production from activated macrophages with IC(50) value less than 10 μM, suggesting that the compound has anti-inflammatory activity.Bioorganic & medicinal chemistry letters 08/2011; 21(15):4485-9. DOI:10.1016/j.bmcl.2011.06.010 · 2.33 Impact Factor
Article: Marine natural products[Show abstract] [Hide abstract]
ABSTRACT: Covering: 2010. Previous review: Nat. Prod. Rep., 2011, 28, 196. This review covers the literature published in 2010 for marine natural products, with 895 citations (590 for the period January to December 2010) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1003 for 2010), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.Natural Product Reports 02/2012; 29(2):144-222. DOI:10.1039/c2np00090c · 10.72 Impact Factor
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ABSTRACT: Five new limonoids, including andhraxylocarpins A and B (1 and 2) which contain a 9-oxa-tricyclo[220.127.116.11(7, 10) ]undecane-2-ene motif, andhraxylocarpins C and D (3 and 4), which contain a (Z)-bicyclo[5.2.1]dec-3-en-8-one substructure, and andhraxylocarpin E (5), which contains a tricyclo[18.104.22.168(3, 6) ]decane-9-one scaffold, were isolated from the seeds of two true mangroves, Xylocarpus granatum and Xylocarpus moluccensis, that were collected in the estuaries of Andhra Pradesh, India. The absolute configurations of these compounds were determined by extensive NMR investigations, single-crystal X-ray diffraction analysis, and by circular dichroism and optical rotatory dispersion spectroscopy, in combination with quantum-chemical calculations. The pronounced structural diversity of limonoids from these mangroves might originate from environmental factors.Chemistry - A European Journal 11/2012; 18(45):14342-51. DOI:10.1002/chem.201202356 · 5.70 Impact Factor