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Literature DB >> 16737291

Azamerone, a terpenoid phthalazinone from a marine-derived bacterium related to the genus Streptomyces (Actinomycetales).

Ji Young Cho¹, Hak Cheol Kwon, Philip G Williams, Paul R Jensen, William Fenical.

Abstract

A novel meroterpenoid, azamerone, was isolated from the saline culture of a new marine-derived bacterium related to the genus Streptomyces. Azamerone is composed of an unprecedented chloropyranophthalazinone core with a 3-chloro-6-hydroxy-2,2,6-trimethylcyclohexylmethyl side chain. The structure was rigorously determined by NMR spectroscopy and X-ray crystallography. A possible biosynthetic origin of this unusual ring system is proposed. [structure: see text]

Entities: Chemical

Mesh：

Substances：
Terpenes
azamerone

Year: 2006 PMID： 16737291 PMCID： PMC2596804 DOI： 10.1021/ol060630r

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

16 in total

Review 1. Marine actinomycete diversity and natural product discovery.

Authors: Paul R Jensen; Tracy J Mincer; Philip G Williams; William Fenical
Journal: Antonie Van Leeuwenhoek Date: 2005-01 Impact factor: 2.271

2. Culturable marine actinomycete diversity from tropical Pacific Ocean sediments.

Authors: Paul R Jensen; Erin Gontang; Chrisy Mafnas; Tracy J Mincer; William Fenical
Journal: Environ Microbiol Date: 2005-07 Impact factor: 5.491

3. Structural studies on new depsipeptide antibiotics, variapeptin and citropeptin.

Authors: M Nakagawa; Y Hayakawa; K Furihata; H Seto
Journal: J Antibiot (Tokyo) Date: 1990-05 Impact factor: 2.649

4. New cytotoxic salinosporamides from the marine Actinomycete Salinispora tropica.

Authors: Philip G Williams; Greg O Buchanan; Robert H Feling; Christopher A Kauffman; Paul R Jensen; William Fenical
Journal: J Org Chem Date: 2005-08-05 Impact factor: 4.354

5. Antibiotic terpenoid chloro-dihydroquinones from a new marine actinomycete.

Authors: Irma E Soria-Mercado; Alejandra Prieto-Davo; Paul R Jensen; William Fenical
Journal: J Nat Prod Date: 2005-06 Impact factor: 4.050

6. Antineoplastic agents 430. Isolation and structure of cribrostatins 3, 4, and 5 from the republic of maldives cribrochalina species.

Authors: G R Pettit; J C Knight; J C Collins; D L Herald; R K Pettit; M R Boyd; V G Young
Journal: J Nat Prod Date: 2000-06 Impact factor: 4.050

Review 7. Diversity of the biosynthesis of the isoprene units.

Authors: Tomohisa Kuzuyama; Haruo Seto
Journal: Nat Prod Rep Date: 2003-04 Impact factor: 13.423

8. Synthesis and cytotoxicity of 1-substituted 2-methyl-1H-imidazo[4,5-g]phthalazine-4,9-dione derivatives.

Authors: Jin Sung Kim; Hyun-Jung Lee; Myung-Eun Suh; Hea-Young Park Choo; Sang Kook Lee; Hyen Joo Park; Choonmi Kim; Sang Woo Park; Chong-Ock Lee
Journal: Bioorg Med Chem Date: 2004-07-01 Impact factor: 3.641

9. Structures of new antibiotics napyradiomycins.

Authors: K Shiomi; H Nakamura; H Iinuma; H Naganawa; K Isshiki; T Takeuchi; H Umezawa; Y Iitaka
Journal: J Antibiot (Tokyo) Date: 1986-04 Impact factor: 2.649

10. Natural abundance nitrogen-15 nuclear magnetic resonance spectral studies on selected donors.

Authors: N Someswara Rao; G Babu Rao; B N Murthy; M Maria Das; T Prabhakar; M Lalitha
Journal: Spectrochim Acta A Mol Biomol Spectrosc Date: 2002-10 Impact factor: 4.098

29 in total

1. Nitropyrrolins A-E, cytotoxic farnesyl-α-nitropyrroles from a marine-derived bacterium within the actinomycete family Streptomycetaceae.

Authors: Hak Cheol Kwon; Ana Paula D M Espindola; Jin-Soo Park; Alejandra Prieto-Davó; Mickea Rose; Paul R Jensen; William Fenical
Journal: J Nat Prod Date: 2010-11-23 Impact factor: 4.050

Azamerone, a terpenoid phthalazinone from a marine-derived bacterium related to the genus Streptomyces (Actinomycetales).

Review 1. Marine actinomycete diversity and natural product discovery.

2. Culturable marine actinomycete diversity from tropical Pacific Ocean sediments.

3. Structural studies on new depsipeptide antibiotics, variapeptin and citropeptin.

4. New cytotoxic salinosporamides from the marine Actinomycete Salinispora tropica.

5. Antibiotic terpenoid chloro-dihydroquinones from a new marine actinomycete.

6. Antineoplastic agents 430. Isolation and structure of cribrostatins 3, 4, and 5 from the republic of maldives cribrochalina species.

Review 7. Diversity of the biosynthesis of the isoprene units.

8. Synthesis and cytotoxicity of 1-substituted 2-methyl-1H-imidazo[4,5-g]phthalazine-4,9-dione derivatives.

9. Structures of new antibiotics napyradiomycins.

10. Natural abundance nitrogen-15 nuclear magnetic resonance spectral studies on selected donors.

1. Nitropyrrolins A-E, cytotoxic farnesyl-α-nitropyrroles from a marine-derived bacterium within the actinomycete family Streptomycetaceae.

2. Meroterpenoid natural products from Streptomyces bacteria - the evolution of chemoenzymatic syntheses.

Review 3. Cyclization of aromatic polyketides from bacteria and fungi.

Review 4. Heteroatom-Heteroatom Bond Formation in Natural Product Biosynthesis.

5. Bioactive compounds from marine actinomycetes.

6. Erythrolic acids A-E, meroterpenoids from a marine-derived Erythrobacter sp.

7. Actinoranone, a cytotoxic meroterpenoid of unprecedented structure from a marine adapted Streptomyces sp.

8. Formation of the pyridazine natural product azamerone by biosynthetic rearrangement of an aryl diazoketone.

9. Enantioselective Synthesis of Azamerone.

10. The ammosamides: structures of cell cycle modulators from a marine-derived Streptomyces species.