The native production of the sesquiterpene isopterocarpolone by Streptomyces sp. RM-14-6

Natural Product Research

Volumn 28, Issue 5, 2014, Pages 337-339

  Shaaban, Khaled A ^a   Singh, Shanteri ^a   Elshahawi, Sherif I ^a   Wang, Xiachang ^a   Ponomareva, Larissa V ^a   Sunkara, Manjula ^b   Copley, Gregory C ^b   Hower, James C ^b   Morris, Andrew J ^b   Kharel, Madan K ^a   Thorson, Jon S ^a  

^a University of Kentucky   (United States)

^b UNIVERSITY OF KENTUCKY   (United States)

Author keywords

bacteria; biosynthesis; cyclase; isoprenoid; natural products; terpene

Indexed keywords

5 EPIARISTOLOCHENE; ARISTOLOCHENE; GEOSMIN; SESQUITERPENE; SESQUITERPENE ISOPTEROCARPOLONE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIUM ISOLATE; BIOSYNTHESIS; CYTOTOXICITY ASSAY; DRUG ISOLATION; DRUG STRUCTURE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; ISOLATION AND PURIFICATION; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; ONE DIMENSIONAL NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; STEREOCHEMISTRY; STREPTOMYCES; TWO DIMENSIONAL NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

BACTERIA (MICROORGANISMS); STREPTOMYCES; STREPTOMYCES SP.;

MOLECULAR STRUCTURE; NAPHTHOLS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SESQUITERPENES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STREPTOMYCES;

EID: 84896389019     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786419.2013.855932     Document Type: Article

References (12)

1. Ding L, Amier A, Fiebig HH, Lin WH, Peschel G, Hertweck C. 2012. Kandenols A-E, eudesmenes from an endophytic Streptomyces sp. of the mangrove tree Kandelia candel. J Nat Prod. 75:2223-2227.
2. Gerber NN, Lechevalier HA. 1965. Geosmin, an earthly-smelling substance isolated from actinomycetes. Appl Microbiol. 13:935-938.
3. Jiang J, He X, Cane DE. 2006. Geosmin biosynthesis. Streptomyces coelicolor germacradienol/germacrene D synthase converts farnesyl diphosphate to geosmin. Am Chem Soc. 128:8128-8129.
4. Kitajima J, Kamoshita A, Ishikawa T, Takano A, Fukuda T, Isoda S, Ida Y. 2003. Glycosides of Atractylodes lancea. Chem Pharm Bull. 51:673-678.
5. Kumar N, Ravindra B, Seshadri T. 1974. Terpenoids of Pterocarpus santalinus heartwood. Phytochemistry. 13:633-636.
6. Laatsch H. 2012. AntiBase 2012: the natural compound identifier. Weinheim, Germany: Wiley-VCH.
7. Meguro A, Tomita T, Nishiyama M, Kuzuyama T. 2013. Identification and characterization of bacterial diterpene cyclases that synthesize the cembrane skeleton. Chembiochem. 14:316-321.
8. Nakano C, Kudo F, Eguchi T, Ohnishi Y. 2011. Genome mining reveals two novel bacterial sesquiterpene cyclases: (-)-germacradien-4-ol and (-)-epi-alpha-bisabolol synthases from Streptomyces citricolor. Chembiochem. 12:2271-2275.
9. Rising KA, Starks CM, Noel JP, Chappell J. 2000. Demonstration of germacrene A as an intermediate in 5-epi-aristolochene synthase catalysis. J Am Chem Soc. 122:1861-1866.
10. Shaaban KA, Wang X, Elshahawi SI, Ponomareva LV, Sunkara M, Copley GC, Hower JC, Morris AJ, Kharel MK, Thorson JS. 2013. Herbimycins D-F, ansamycin analogues from Streptomyces sp. RM-7-15. J Nat Prod. 76:1619-1626.
11. Wang X, Shaaban KA, Elshahawi SI, Ponomareva LV, Sunkara M, Zhang Y, Copley GC, Hower JC, Morris AJ, Kharel MK, Thorson JS. 2013. Frenolicins C-G, Pyranonaphthoquinones from Streptomyces sp. RM-4-15. J Nat Prod. 76:1441-1447.
12. Whitehead IM, Threlfall DR, Ewing DF. 1989. 5-Epi-aristolochene is a common precursor of the sesquiterpenoid phytoalexins capsidiol and debneyol. Phytochemistry. 28:775-779.