Abstract
A new prenylated naphthoquinone antibiotic, fumaquinone (5,7-dihydroxy-2-methoxy-3-methyl-6-(3-methyl-but-2-enyl)[1,4]naphthoquinone) was isolated from cultures of Streptomyces fumanus (LL-F42248). Its chemical structure was determined primarily by NMR spectroscopy. Preliminary feeding experiments indicated the naphthoquinone is of polyketide origin, while the O-methyl and aromatic C-methyl groups are derived from methionine.
Similar content being viewed by others
Article PDF
References
Kuzuyama T, Seto H . Diversity of the biosynthesis of the isoprene units. Nat Prod Rep 20: 171–183 ( 2003)
Shin-Ya K, Imai S, Furihata K, Hayakawa Y, Kato Y, Vanduyne GD, Clardy J, Seto H . Isolation and structural elucidation of an antioxidative agent, naphterpin. J Antibiot 43: 444–447 ( 1990)
Wessels P, Gohrt A, Zeeck A, Drautz H, Zahner H . Metabolic products of microorganisms, 260. Naphthgeranines, new naphthoquinone antibiotics from Streptomyces sp. J Antibiot 44: 1013–1018 ( 1991)
Funayama S, Ishibashi M, Anraku Y, Komiyama K, Ōmura S . Structures of novel antibiotics, furaquinocins A and B. Tetrahedron Lett 30: 7427–7430 ( 1989)
Ishibashi M, Funayama S, Anraku Y, Komiyama K, Ōmura S . Novel antibiotics, furaquinocins C, D, E, F, G and H. J Antibiot 44: 390–395 ( 1991)
Pathirana C, Jensen PR, Fenical W . Marinone and debromomarinone: Antibiotic sesquiterpenoid naphthoquinones of a new structure class from a marine bacterium. Tetrahedron Lett 33: 7663–7666 ( 1992)
Kalaitzis JA, Hamano Y, Nilsen G, Moore BS . Biosynthesis and structural revision of neomarinone. Org Lett 5: 4449–4452 ( 2003)
Fukuda DS, Mynderse JS, Baker PJ, Berry DM, Boeck LD, Yao RC, Mertz FP, Nakatsukasa WM, Mab J, Ott J, Counter FT, Ensminger PW, Allen NE, Alborn WE, Hobbs JN . A80915, A new antibiotic complex produced by Streptomyces aculeolatus. Discovery, taxonomy, fermentation, isolation, characterization, and antibacterial evaluation. J Antibiot 43: 623–633 ( 1990)
Carter GT, Nietsche JA, Goodman JJ, Torrey MJ, Dunne TS, Borders DB, Testa RT . LL-F42248α, a novel chlorinated pyrrole antibiotic. J Antibiot 40: 233–236 ( 1987)
Charan RD, Schlingmann G, Bernan VS, Feng X, Carter GT . Additional pyrrolomycins from cultures of Streptomyces fumanus. J Nat Prod 68: 277–279 ( 2005)
Funayama S, Ishibashi M, Komiyama K, Ōmura S . Biosynthesis of furaquinocins A and B. J Org Chem 55: 1132–1133 ( 1990)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Charan, R., Schlingmann, G., Bernan, V. et al. Fumaquinone, a New Prenylated Naphthoquinone from Streptomyces fumanus. J Antibiot 58, 271–274 (2005). https://doi.org/10.1038/ja.2005.32
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/ja.2005.32
Keywords
This article is cited by
-
Species-specific secondary metabolism by actinomycetes of the genus Phytohabitans and discovery of new pyranonaphthoquinones and isatin derivatives
The Journal of Antibiotics (2023)
-
Bisprenyl naphthoquinone and chlorinated calcimycin congener bearing thiazole ring from an actinomycete of the genus Phytohabitans
The Journal of Antibiotics (2022)