2008Planta MedicaRequires access

Biotransformation of onopordopicrin, a sesquiterpene lactone, by Aspergillus niger

Akbar Esmaeili, A Rustaiyan, Nader Moazami

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Abstract

The biotransformation of sesquiterpene lactones from Aspergillus niger was studied previously [1]. In the course of our work related to compounds extracted from the aerial parts of Onopordon leptolopis, Asteraceae [2], we studied the biotransformation of onopordopicrin by Aspergillus niger which afforded 11α,13-dihydro-onopordopicrin ( 1 ), 11β,13-dihydro-onopordopicrin ( 2 ) and 3-hydroxy-11α,13-dihydro onopordopicrin ( 3 ). The last compound ( 3 ) again submitted to biotransformation by Aspergillus niger gave 3,14-dihydroxy –11α,13-dihydro-onopordopicrin ( 4 ). Onopordopicrin and related compounds were identified by 1 H NMR, 13 C NMR, mass spectroscopy and IR spectroscopy. References: 1. Hoshimoto, T. et al. (2001) Heterocycles 54: 529–559. 2. Rustaiyan, A., et al. (1979) Phytochemistry 18: 883–884.

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What this paper is about

The biotransformation of sesquiterpene lactones from Aspergillus niger was studied previously [1]. In the course of our work related to compounds extracted from the aerial parts of Onopordon leptolopis, Asteraceae [2], we studied the biotransformation of onopordopicrin by Aspergillus niger which afforded 11α,13-dihydro-onopordopicrin ( 1 ), 11β,13-dihydro-onopordopicrin ( 2 ) and 3-hydroxy-11α,13-dihydro onopordopicrin ( 3 ). The last compound ( 3 ) again submitted to biotransformation by Aspergillus niger gave 3,14-dihydroxy –11α,13-dihydro-onopordopicrin ( 4 ). Onopordopicrin and related compounds were identified by 1 H NMR, 13 C NMR, mass spectroscopy and IR spectroscopy. References: 1. Hoshimoto, T. et al. (2001) Heterocycles 54: 529–559. 2. Rustaiyan, A., et al. (1979) Phytochemistry 18: 883–884.

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Available abstract

The biotransformation of sesquiterpene lactones from Aspergillus niger was studied previously [1]. In the course of our work related to compounds extracted from the aerial parts of Onopordon leptolopis, Asteraceae [2], we studied the biotransformation of onopordopicrin by Aspergillus niger which afforded 11α,13-dihydro-onopordopicrin ( 1 ), 11β,13-dihydro-onopordopicrin ( 2 ) and 3-hydroxy-11α,13-dihydro onopordopicrin ( 3 ). The last compound ( 3 ) again submitted to biotransformation by Aspergillus niger gave 3,14-dihydroxy –11α,13-dihydro-onopordopicrin ( 4 ). Onopordopicrin and related compounds were identified by 1 H NMR, 13 C NMR, mass spectroscopy and IR spectroscopy. References: 1. Hoshimoto, T. et al. (2001) Heterocycles 54: 529–559. 2. Rustaiyan, A., et al. (1979) Phytochemistry 18: 883–884.

Key concepts: Aspergillus niger, Biotransformation, Sesquiterpene, Lactone, Sesquiterpene lactone, Asteraceae, Aspergillus, Chemistry

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