Citrinadin A, a novel pentacyclic alkaloid from marine-derived fungus Penicillium citrinum
- PMID: 15330594
- DOI: 10.1021/ol048900y
Citrinadin A, a novel pentacyclic alkaloid from marine-derived fungus Penicillium citrinum
Abstract
[structure: see text] A novel pentacyclic alkaloid, citrinadin A (1), was isolated from the cultured broth of the fungus Penicillium citrinum, which was separated from a marine red alga, and the structure was elucidated by spectroscopic data. The relative stereochemistry of the pentacyclic core was assigned on the basis of NOESY data and (1)H-(1)H coupling constants, and the presence of an N,N-dimethyl-L-valine residue in 1 was determined by chiral HPLC analysis of the hydrolysate.
Similar articles
-
Absolute stereochemistry of citrinadins a and B from marine-derived fungus.J Org Chem. 2005 Nov 11;70(23):9430-5. doi: 10.1021/jo051499o. J Org Chem. 2005. PMID: 16268618
-
Scalusamides A-C, new pyrrolidine alkaloids from the marine-derived fungus Penicillium citrinum.J Nat Prod. 2005 Feb;68(2):273-6. doi: 10.1021/np049661q. J Nat Prod. 2005. PMID: 15730261
-
Perinadine A, a novel tetracyclic alkaloid from marine-derived fungus Penicillium citrinum.Org Lett. 2005 Sep 15;7(19):4261-4. doi: 10.1021/ol051695h. Org Lett. 2005. PMID: 16146402
-
Indolizidine and quinolizidine alkaloids.Nat Prod Rep. 2008 Feb;25(1):139-65. doi: 10.1039/b612166g. Epub 2007 Dec 13. Nat Prod Rep. 2008. PMID: 18250900 Review.
-
Indolizidine and quinolizidine alkaloids.Nat Prod Rep. 2004 Oct;21(5):625-49. doi: 10.1039/b310689f. Epub 2004 Sep 14. Nat Prod Rep. 2004. PMID: 15459758 Review.
Cited by
-
Antimicrobial and Cytotoxic Secondary Metabolites from a Marine-Derived Fungus Penicillium Citrinum VM6.Curr Microbiol. 2023 Dec 8;81(1):32. doi: 10.1007/s00284-023-03568-7. Curr Microbiol. 2023. PMID: 38062305
-
Enantioselective total synthesis of (-)-citrinadin A and revision of its stereochemical structure.J Am Chem Soc. 2013 Jul 31;135(30):10886-9. doi: 10.1021/ja405547f. Epub 2013 Jul 18. J Am Chem Soc. 2013. PMID: 23837457 Free PMC article.
-
Enantioselective total syntheses of citrinadins A and B. Stereochemical revision of their assigned structures.J Am Chem Soc. 2014 Oct 8;136(40):14184-92. doi: 10.1021/ja5074646. Epub 2014 Sep 29. J Am Chem Soc. 2014. PMID: 25211501 Free PMC article.
-
Structural basis of the stereoselective formation of the spirooxindole ring in the biosynthesis of citrinadins.Nat Commun. 2021 Jul 6;12(1):4158. doi: 10.1038/s41467-021-24421-0. Nat Commun. 2021. PMID: 34230497 Free PMC article.
-
Exploring the synthetic potential of epoxide ring opening reactions toward the synthesis of alkaloids and terpenoids: a review.RSC Adv. 2024 Apr 23;14(19):13100-13128. doi: 10.1039/d4ra01834f. eCollection 2024 Apr 22. RSC Adv. 2024. PMID: 38655462 Free PMC article. Review.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Research Materials