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Literature DB >> 14709083

Schulzeines A-C, new alpha-glucosidase inhibitors from the marine sponge Penares schulzei.

Kentaro Takada¹, Taisuke Uehara, Yoichi Nakao, Shigeki Matsunaga, Rob W M van Soest, Nobuhiro Fusetani.

Abstract

Three new alpha-glucosidase inhibitors, schulzeines A-C (1-3), were isolated from the marine sponge Penares schulzei. Their structures were elucidated by spectral analysis and chemical degradations to be the isoquinoline alkaloids, encompassing two amino acids, and C(28) fatty acid, the last of which was sulfated. Absolute stereochemistry of schulzeines was determined by application of the modified Mosher analysis to fragments obtained by chemical degradation. Schulzeines A-C inhibit alpha-glucosidase with IC(50) values of 48-170 nM.

Entities: Chemical Gene

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Year: 2004 PMID： 14709083 DOI： 10.1021/ja037368r

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

11 in total

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Authors: Alejandro M S Mayer; Abimael D Rodríguez; Roberto G S Berlinck; Mark T Hamann
Journal: Comp Biochem Physiol C Toxicol Pharmacol Date: 2007-02-09 Impact factor: 3.228

Schulzeines A-C, new alpha-glucosidase inhibitors from the marine sponge Penares schulzei.

Review 1. Astonishing diversity of natural surfactants: 4. Fatty acid amide glycosides, their analogs and derivatives.

3. INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Review 4. Survey of marine natural product structure revisions: a synergy of spectroscopy and chemical synthesis.

5. An unusual reactivity of BBr(3): Accessing tetrahydroisoquinoline units from N-phenethylimides.

6. Total synthesis of the alpha-glucosidase inhibitors schulzeine A, B, and C and a structural revision of schulzeine A.

7. Palladium-Catalyzed Enantioselective Relay Heck Arylation of Enelactams: Accessing α,β-Unsaturated δ-Lactams.

Review 8. New one-pot methodologies for the modification or synthesis of alkaloid scaffolds.

9. N-(9,11-Dimeth-oxy-4-oxo-2,3,4,6,7,11b-hexa-hydro-1H-pyrido[2,1-a]isoquinolin-3-yl)benzamide.

10. α-glucosidase inhibitors from plants: A natural approach to treat diabetes.