Stereo and regioselective microbial reduction of the clerodane diterpene 3,12-dioxo-15,16-epoxy-4-hydroxycleroda-13(16),14-diene

Jair Mafezoli, Maria C.F. Oliveira, José R. Paiva, Antônio H. Sousa, Mary A.S. Lima, José N. Silva, Francisco G. Barbosa, E. M.Kithsiri Wijeratne, A. A.Leslie Gunatilaka

Research output: Contribution to journalArticle

2 Scopus citations

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 (3R,4S,5S,8S,9R,10S)-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.

Original languageEnglish (US)
Pages (from-to)759-762
Number of pages4
JournalNatural Product Communications
Volume9
Issue number6
StatePublished - 2014

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Keywords

  • 3α,4α-Dihydroxy-15,16-epoxy-12-oxo- cleroda-13(16),14-diene
  • Biotransformation
  • Cunninghamella echinulata
  • Rhizopus stolonifer
  • ent-neo-Clerodane diterpene

ASJC Scopus subject areas

  • Pharmacology
  • Plant Science
  • Drug Discovery
  • Complementary and alternative medicine

Cite this

Mafezoli, J., Oliveira, M. C. F., Paiva, J. R., Sousa, A. H., Lima, M. A. S., Silva, J. N., Barbosa, F. G., Wijeratne, E. M. K., & Gunatilaka, A. A. L. (2014). Stereo and regioselective microbial reduction of the clerodane diterpene 3,12-dioxo-15,16-epoxy-4-hydroxycleroda-13(16),14-diene. Natural Product Communications, 9(6), 759-762.