Semisynthesis of Linariophyllenes A-C and Rumphellolide H, Structure Revisions and Proposed Biosynthesis Pathways
Journal of Natural Products 2023
Georgijs Stakanovs, Anastasija Blazevica, Sergey Belyakov, Dace Rasiņa, Aigars Jirgensons

The first semisynthetic routes toward terrestrial anti-inflammatory natural products linariophyllene A-C and the refined route toward marine natural product rumphellolide H are presented. Among the synthesized target compounds, the correct structure of linariophyllene A was determined to be the diastereomer of the originally proposed structure with an inverted stereocenter at the secondary alcohol. The proposed structures of linariophyllene B and rumphellolide H were confirmed. However, the correct structure of linariophyllene C was found to be the diastereomer of the originally proposed structure with an inverted stereocenter at the tertiary carbon of the epoxide moiety. The structures of linariophyllenes A-C and rumphellolide H were unequivocally confirmed by single-crystal X-ray diffractometry. The obtained results enabled the proposal of the biosynthetic origins of the aforementioned natural products and bolstered the diversity of available sesquiterpenoids. Linariophyllenes A-C and rumphellolide H were obtained in sufficient amounts to further expand their bioactivity profile and utility as reference standards in future studies of chemical constituents of terrestrial and marine organisms.


DOI
10.1021/acs.jnatprod.3c00574
Hipersaite
https://pubs.acs.org/doi/10.1021/acs.jnatprod.3c00574

Stakanovs, G., Blazevica, A., Belyakov, S., Rasiņa, D., Jirgensons, A. Semisynthesis of Linariophyllenes A-C and Rumphellolide H, Structure Revisions and Proposed Biosynthesis Pathways. Journal of Natural Products, 2023, Vol. 86, No. 10, 2368.-2378.lpp. ISSN 0163-3864. Pieejams: doi:10.1021/acs.jnatprod.3c00574

Publikācijas valoda
English (en)
RTU Zinātniskā bibliotēka.
E-pasts: uzzinas@rtu.lv; Tālr: +371 28399196