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ABSTRACT: Eight limonoids, named moluccensins R-Y (1, 2, 5-10), and six known compounds, including 6-hydroxymexicanolide (3), were isolated from the seeds of an Indian mangrove, Xylocarpus moluccensis, collected in the estuaries of Andhra Pradesh. The absolute configuration of moluccensin V (7) was confirmed by means of single-crystal X-ray diffraction analysis. The (1)H and (13)C NMR data for 6-hydroxymexicanolide (3) was assigned for the first time, and the 6R absolute configuration established by single-crystal X-ray diffraction analysis. Moluccensin R (1), 6R-hydroxymexicanolide (3), and 2-hydroxyfissinolide (4) exhibited marked antifeedant activity against the third-instar larvae of Brontispa longissima at a concentration of 1 mg/mL. The most potent compound tested was 2-hydroxyfissinolide (4), with an AFC(50) (concentration for 50% antifeedant activity) value of 94 μg/mL at 24 h.
Journal of Natural Products 06/2012; 75(7):1277-83. · 3.13 Impact Factor
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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.
Phytochemistry 11/2010; 71(16):1917-24. · 3.35 Impact Factor
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ABSTRACT: Six new phragmalins, moluccensins H-M (1-6), two new andirobin-type limonoids, moluccensins N and O (7, 8), and two new tirucallane derivatives, moluccensins P and Q (9, 10), were isolated from seeds of an Indian mangrove, Xylocarpus moluccensis, together with the known compound 3beta,22S-dihydroxytirucalla-7,24-dien-23-one. The structures of these compounds were established on the basis of spectroscopic data. Moluccensins H-L were phragmalins with a C-30 carbonyl group, and moluccensin M was a unique ring-D-opened 16-norphragmalin. Moluccensins H-J possess conjugated Delta(8,9) and Delta(14,15) double bonds, moluccensins K and L contain a Delta(8,14) double bond, and moluccensin M has a characteristic C(15)-C(30) linked five-membered lactone ring. Moluccensins H and I showed moderate insecticidal activity against the fifth instar larvae of Brontispa longissima (Gestro) at a concentration of 100 mg/L.
Journal of Natural Products 02/2010; 73(4):644-9. · 3.13 Impact Factor
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ABSTRACT: Seven new limonoids (1-7), named granatumins A-G, were isolated from seeds of an Indian mangrove (Xylocarpus granatum) collected from the wetlands of Krishna estuary, Andhra Pradesh. The known compounds khayasin T, tigloylseneganolide A, 6-deoxyswietenine, swietemahonolide, febrifugin A, gedunin, xylogranatinin, phaseic acid, (2R,3R)-3,4',5,7-tetrahydroxyflavanone, and (E)-4-hydroxycinnamic acid were also isolated. The structures were established on the basis of spectroscopic data. Granatumins A and B are mexicanolides with endo-conjugated Delta(8,30) and Delta(14,15) double bonds, and granatumins F and G are polyhydroxylated phragmalins found previously in plants of the Meliaceae. Khayasin T exhibited moderate insecticidal activity against fifth instar larvae of Brontispa longissima (Gestro) at a concentration of 20 mg/L.
Journal of Natural Products 11/2009; 72(12):2110-4. · 3.13 Impact Factor
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Natural Product Reports 10/2009; 26(10):1251-92. · 9.79 Impact Factor
