دورية أكاديمية
Unusual Sesquiterpenes from Streptomyces olindensis DAUFPE 5622.
| العنوان: | Unusual Sesquiterpenes from Streptomyces olindensis DAUFPE 5622. |
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| المؤلفون: | Chagas FO; Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP 05508-070, Brazil.; Instituto de Pesquisas de Produtos Naturais Walter Mors, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ 21941-617, Brazil., Garrido LM; Instituto de Ciências Biomédicas, Universidade de São Paulo, São Paulo, SP 05508-070, Brazil., Conti R; Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP 05508-070, Brazil., Borges RM; Instituto de Pesquisas de Produtos Naturais Walter Mors, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ 21941-617, Brazil., Bielinski VA; Synthetic Biology and Bioenergy Group, J. Craig Venter Institute, La Jolla, California 92037, United States.; Instituto de Química, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ 21941-617, Brazil., Padilla G; Instituto de Ciências Biomédicas, Universidade de São Paulo, São Paulo, SP 05508-070, Brazil., Pupo MT; Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP 05508-070, Brazil. |
| المصدر: | Journal of natural products [J Nat Prod] 2024 Mar 22; Vol. 87 (3), pp. 491-500. Date of Electronic Publication: 2024 Feb 29. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Society of Pharmacognosy Country of Publication: United States NLM ID: 7906882 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6025 (Electronic) Linking ISSN: 01633864 NLM ISO Abbreviation: J Nat Prod Subsets: MEDLINE |
| أسماء مطبوعة: | Original Publication: Cincinnati, American Society of Pharmacognosy. |
| مواضيع طبية MeSH: | Sesquiterpenes*/chemistry , Streptomyces*/metabolism, Terpenes/metabolism ; Cyclization |
| مستخلص: | In nature, the vast majority of sesquiterpenes are produced by type I mechanisms, and glycosylated sesquiterpenes are rare in actinobacteria. Streptomyces olindensis DAUFPE 5622 produces the sesquiterpenes olindenones A-G, a new class of rearranged drimane sesquiterpenes. Olindenones B-D are oxygenated derivatives of olindenone A, while olindenones E-G are analogs glycosylated with dideoxysugars. 13 C-isotope labeling studies demonstrated olindenone A biosynthesis occurs via the methylerythritol phosphate (MEP) pathway and suggested the rearrangement is only partially concerted. Based on the structures, one potential mechanism of olindenone A formation proceeds by cyclization of the linear terpenoid precursor, likely occurring via a terpene cyclase-mediated type II mechanism whereby the terminal alkene of the precursor is protonated, triggering carbocation-driven cyclization followed by rearrangement. Diphosphate hydrolysis may occur either before or after cyclization. Although a biosynthetic route is proposed, the terpene cyclase gene responsible for producing olindenones currently remains unidentified. |
| المشرفين على المادة: | 0 (Sesquiterpenes) 0 (Terpenes) |
| SCR Organism: | Streptomyces olindensis |
| تواريخ الأحداث: | Date Created: 20240229 Date Completed: 20240325 Latest Revision: 20240325 |
| رمز التحديث: | 20240325 |
| DOI: | 10.1021/acs.jnatprod.3c00752 |
| PMID: | 38422010 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 1520-6025 |
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| DOI: | 10.1021/acs.jnatprod.3c00752 |