Bioactive Aromatic Compounds from Leaves and Stems of Vanilla fragrans

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• 作者：Rongqi Sun ; John N. Sacalis ; Chee-Kok Chin ; and Cecil C. Still
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2001
• 出版时间：November 2001
• 年：2001
• 卷：49
• 期：11
• 页码：5161 - 5164
• 全文大小：46K
• 年卷期：v.49,no.11(November 2001)
• ISSN：1520-5118

文摘

Alcoholic extracts of leaves and stems of Vanilla fragrans were fractionated with ethyl acetate andaqueous butanol. All three fractions of ethyl acetate, butanol, and water were screened for toxicbioactivity against mosquito larvae. The results of these experiments showed that the fractionsfrom the ethyl acetate and butanol phases were both active in the bioassay. Bioactivity of the ethylacetate fraction was found to be much greater than that from the butanol fraction in mosquitolarvae toxicity. The water phase appeared to contain no substances that impaired mosquito larvalgrowth. Repeated column chromatography of the ethyl acetate fraction on silica gel led to the isolationof 4-ethoxymethylphenol (1), 4-butoxymethylphenol (2), vanillin (3), 4-hydroxy-2-methoxycinnamaldehyde (4), and 3,4-dihydroxyphenylacetic acid (5). Compounds 4 and 5 were isolated from Vanillaspecies for the first time and 2 has not been reported to have been found in a natural form.4-Ethoxymethylphenol (1) was the predominant compound, but 4-butoxymethylphenol (2) showedthe strongest toxicity to mosquito larvae. The structures of the compounds were determined on thebasis of their mass spectra and ¹H or ¹³C NMR data.Keywords: Vanilla fragrans; bioactivity; insecticidal properties; 4-ethoxymethylphenol; 4-butoxymethylphenol; vanillin; toxicity