Stereo and Regioselective Microbial Reduction of the Clerodane Diterpene 3,12-Dioxo-15,16-epoxy-4-hydroxycleroda-13(16),14-diene-Reference-Cited by-同舟云学术

Stereo and Regioselective Microbial Reduction of the Clerodane Diterpene 3,12-Dioxo-15,16-epoxy-4-hydroxycleroda-13(16),14-diene

Published:2014-06 Issue:6 Volume:9 Page:1934578X1400900
ISSN:1934-578X
Container-title:Natural Product Communications
language:en
Short-container-title:Natural Product Communications

Author:

Mafezoli Jair¹²,Oliveira Maria C. F.¹²,Paiva José R.¹,Sousa Antônio H.¹,Lima Mary A. S.¹,Júnior José N. Silva¹,Barbosa Francisco G.¹,Wijeratne E. M. Kithsiri²,Gunatilaka A. A. Leslie²

Affiliation:

1. Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, Campus do Pici, Caixa Postal 6044, Fortaleza-CE, 60455–970, Brazil

2. SW Center for Natural Products Research and Commercialization, School of Natural Resources and the Environment, College of Agriculture and Life Sciences, University of Arizona, 250 E. Valencia Road, Tucson, Arizona 85706–6800, USA

Abstract

The biotransformation of the clerodane diterpene, 3,12-dioxo-15,16-epoxy-4-hydroxy-cleroda-13(16),14-diene (1), obtained from Croton micans var. argyroglossum (Baill.) Müll., was investigated for the first time. Whole cells of Cunninghamella echinulata and Rhizopus stolonifer were used as enzymatic systems, and with both fungi the only biotransformation product obtained was the new ent-neo-clerodane diterpene (3 R,4 S,5 S,8 S,9 R,10 S)-3,4-dihydroxy-15,16-epoxy-12-oxo-cleroda-13(16),14-diene (2a). The absolute stereochemistry of 2a was inferred by comparison of its optical rotation with those of the chemical reduction product of 1 and its quasienantiomer 2c.

Publisher

SAGE Publications

Subject

Complementary and alternative medicine,Plant Science,Drug Discovery,Pharmacology,General Medicine

Link

http://journals.sagepub.com/doi/pdf/10.1177/1934578X1400900607

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4. Microbial Transformations of Aryltetralone and Aryltetralin Lignans by Cunninghamella echinulata and Beauveria bassiana

5. Biotransformation of clerodane diterpenoids by Rhizopus stolonifer and antibacterial activity of resulting metabolites

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2. New Clerodane Diterpenes from Fungal Biotransformation of the 3,12-Dioxo-15,16-Epoxy-4-Hydroxycleroda-13(16),14-Diene;MOJ Bioorganic & Organic Chemistry;2017-11-29