Absolute stereostructure of Andirolides A-G from the flower of Carapa guianensis (Meliaceae) |
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Authors: | Yuji TanakaTakeshi Yamada Yasuko InOsamu Muraoka Tetsuya KajimotoReiko Tanaka |
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Affiliation: | a Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan b Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashiosaka, Osaka 577-8502, Japan |
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Abstract: | A new gedunin, three new mexicanolides and three new phragmalin-type limonoids named Andirolides A (1), B (2), C (3), D (4), E (5), F (6), and G (7) were isolated from oil of the flower of Carapa guianensis Aublet (Meliaceae). Their absolute stereostructures were determined by 2D NMR and CD spectra, and single-crystal X-ray analysis, and all compounds were confirmed to have the C-17βH configuration. Considering the similarity in CD spectra between Andirolide G (7) and the xyloccensins reported by Wu, we concluded that the structures of xyloccensins should be revised so as to have the absolute configuration of 17R. |
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Keywords: | Carapa guianensis Limonoid Andirolides A-G CD spectrum X-ray analysis |
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