Enhancing Structural Diversity of Lathyrane Derivatives through Biotransformation by the Marine-Derived Actinomycete Streptomyces puniceus BC-5GB.11

Felipe Escobar-Montaño; Victoria E. González-Rodríguez; Antonio J. Macías-Sánchez; José M. Botubol-Ares; Rosa Durán-Patrón; Rosario Hernández-Galán

doi:10.20944/preprints202401.1881.v1

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preprints.org > chemistry and materials science > organic chemistry > doi: 10.20944/preprints202401.1881.v1

Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Enhancing Structural Diversity of Lathyrane Derivatives through Biotransformation by the Marine-Derived Actinomycete Streptomyces puniceus BC-5GB.11

Felipe Escobar-Montaño

Victoria E. González-Rodríguez

Antonio J. Macías-Sánchez

José M. Botubol-Ares

^* ,

Rosa Durán-Patrón

^* ,

Rosario Hernández-Galán

Version 1 : Received: 25 January 2024 / Approved: 26 January 2024 / Online: 26 January 2024 (07:51:07 CET)

A peer-reviewed article of this Preprint also exists.

Escobar-Montaño, F., González-Rodríguez, V. E., Macías-Sánchez, A. J., Botubol-Ares, J. M., Durán-Patrón, R., & Hernández-Galán, R. (2024). Enhancing Structural Diversity of Lathyrane Derivatives through Biotransformation by the Marine-Derived Actinomycete Streptomyces puniceus BC-5GB. 11. Escobar-Montaño, F., González-Rodríguez, V. E., Macías-Sánchez, A. J., Botubol-Ares, J. M., Durán-Patrón, R., & Hernández-Galán, R. (2024). Enhancing Structural Diversity of Lathyrane Derivatives through Biotransformation by the Marine-Derived Actinomycete Streptomyces puniceus BC-5GB. 11.

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 lathyranes to explore their 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 them reported here for the first time. The main biotransformation pathways involved regioselective oxidation at non-activated carbons (3-5) and isomerization of the D^12,13 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.

Keywords

marine-derived actynomicete; Streptomyces; diterpenoids; lathyranes; biotransformation

Subject

Chemistry and Materials Science, Organic Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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