Ent-kaurane diterpenoids and other constituents from the stem of Xylopia laevigata (Annonaceae)

Phytochemical investigation of the hexane extract from the stem of Xylopia laevigata led to the isolation of the ent-kaurane diterpenoids, ent-kaur-16-en-19-oic acid, 4-epi-kaurenic acid, ent-16β-hydroxy-17-acetoxy-kauran-19-al, ent-3β-hydroxy-kaur-16-en-19-oic acid, and ent-16β,17-dihydroxy-kauran-...

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Bibliographic Details
Published in:	Química Nova Vol. 35; no. 8; pp. 1570 - 1576
Main Authors:	Silva, Dayanne Meneses, Costa, Emmanoel Vilaça, Nogueira, Paulo Cesar de Lima, Moraes, Valéria Regina de Souza, Cavalcanti, Sócrates Cabral de Holanda, Salvador, Marcos José, Ribeiro, Luis Henrique Gonzaga, Gadelha, Fernanda Ramos, Barison, Andersson, Ferreira, Antonio Gilberto
Format:	Journal Article
Language:	English
Published:	Sociedade Brasileira de Química 2012
Subjects:	ent-kaurane-diterpenes larvicidal and antifungal properties Xylopia laevigata
Online Access:	Get full text
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Summary:	Phytochemical investigation of the hexane extract from the stem of Xylopia laevigata led to the isolation of the ent-kaurane diterpenoids, ent-kaur-16-en-19-oic acid, 4-epi-kaurenic acid, ent-16β-hydroxy-17-acetoxy-kauran-19-al, ent-3β-hydroxy-kaur-16-en-19-oic acid, and ent-16β,17-dihydroxy-kauran-19-oic acid, as well as spathulenol and a mixture of β-sitosterol, stigmasterol and campesterol. The identification of the compounds was performed on the basis of spectrometric methods including GC-MS, IR, and 1D and 2D NMR. Potent larvicidal activity against Aedes aegypti larvae with LC50 of 62.7 µg mL-1 was found for ent-3β-hydroxy-kaur-16-en-19-oic acid. This compound also showed significant antifungal activity against Candida glabrata and Candida dubliniensis with MIC values of 62.5 µg mL-1.
ISSN:	0100-4042 1678-7064
DOI:	10.1590/S0100-40422012000800015