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Enhancing Structural Diversity of Lathyrane Derivatives through Biotransformation by the Marine-Derived Actinomycete Streptomyces puniceus BC-5GB.11.
- Source :
-
International journal of molecular sciences [Int J Mol Sci] 2024 Feb 14; Vol. 25 (4). Date of Electronic Publication: 2024 Feb 14. - Publication Year :
- 2024
-
Abstract
- Lathyrane-type diterpenes have a wide range of biological activities. Among them, euphoboetirane A ( 1 ) exerts neurogenesis-promoting activity. In order to increase the structural diversity of this type of lathyrane and explore its potential use in neurodegenerative disorders, the biotransformation of 1 by Streptomyces puniceus BC-5GB.11 has been investigated. The strain BC-5GB.11, isolated from surface sediments collected from the intertidal zone of the inner Bay of Cadiz, was identified as Streptomyces puniceus , as determined by phylogenetic analysis using 16S rRNA gene sequence. Biotransformation of 1 by BC-5GB.11 afforded five products ( 3 - 7 ), all of which were reported here for the first time. The main biotransformation pathways involved regioselective oxidation at non-activated carbons ( 3 - 5 ) and isomerization of the ∆ <superscript>12,13</superscript> double bond ( 6 ). In addition, a cyclopropane-rearranged compound was found ( 7 ). The structures of all compounds were elucidated on the basis of extensive NMR and HRESIMS spectroscopic studies.
Details
- Language :
- English
- ISSN :
- 1422-0067
- Volume :
- 25
- Issue :
- 4
- Database :
- MEDLINE
- Journal :
- International journal of molecular sciences
- Publication Type :
- Academic Journal
- Accession number :
- 38396965
- Full Text :
- https://doi.org/10.3390/ijms25042289