NDLI: Plasticity in gilvocarcin-type C-glycoside pathways: discovery and antitumoral evaluation of polycarcin V from Streptomyces polyformus

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Organic & Biomolecular Chemistry Vol - 6 Issue - 9

Organic & Biomolecular Chemistry Vol - 6 Issue - 8

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Plasticity in gilvocarcin-type C-glycoside pathways: discovery and antitumoral evaluation of polycarcin V from Streptomyces polyformus

Content Provider	Royal Society of Chemistry (RSC)
Author	Peschel, Gundela Menzel, Klaus-Dieter Ishida, Keishi Jiang, Cheng-lin Jiang, Yi Kelter, Gerhard Li, Yi-qing Fiebig, Heinz-Herbert Hertweck, Christian Li, Ming-gang Wen, Meng-liang Huang, Xue-shi Grabley, Susanne Maier, Armin Sattler, Isabel Xu, Li-hua
Copyright Year	2008
Abstract	Gilvocarcin-type polyketide glycosides represent some of the most powerful antitumor therapeutics. Bioactivity-guided fractionation of a culture extract of Streptomyces polyformus sp. nov. (YIM 33176) yielded the known gilvocarcin V (2) and a novel related compound, polycarcin V (1). Structure elucidation by NMR and chemical derivatization revealed that the congener (1) features a C-glycosidically linked α-L-rhamnopyranosyl moiety in lieu of the D-fucofuranose. The concomitant production of two distinct furanosyl and pyranosyl C-glycosides that share the same aglycone is unprecedented in bacteria. A conversion of both isoforms via a quinone methide intermediate can be ruled out, thus pointing to two individual C-glycosylation pathways. Cytotoxicity profiling of polycarcin V in a panel of 37 tumor cell lines indicated significant antitumoral activity with a pronounced selectivity for non-small-cell lung cancer, breast cancer and melanoma cells. As the antiproliferative fingerprint is identical to that of actinomycin D, the known DNA interaction of gilvocarcins was established as a general principle of antitumorigenic activity.
Starting Page	3601
Ending Page	3605
Page Count	5
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	6
Issue Number	19
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b808633h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Quinone Aglycone Melanoma Streptomyces Biological specificity Cytotoxicity Breast cancer Dactinomycin Polyketide DNA Bacteria Nuclear magnetic resonance Non-small-cell lung carcinoma
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
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Combinatorial Biosynthetic Derivatization of the Antitumoral Agent Gilvocarcin V

Enzymatic methylation and structure-activity-relationship studies on polycarcin V, a gilvocarcin-type antitumor agent.

Enzymatic Methylation and Structure-Activity-Relationship Studies on Polycarcin V, a Gilvocarcin-Type Antitumor Agent

Gilvocarcin HE: a new polyketide glycoside from Streptomyces sp.

Cytotoxic and antioxidant marine prenylated quinones and hydroquinones

NITROGEN REPRESSION OF GILVOCARCIN V PRODUCTION IN STREPTOMYCES ARENAS 2064

Respiratory Quinone Switches from Menaquinone to Polyketide Quinone during the Development Cycle in Streptomyces sp. Strain MNU77.

Polycarcin V induces DNA-damage response and enables the profiling of DNA-binding proteins

Molecular basis of substrate specificity in family 1 glycoside hydrolases

Plasticity in gilvocarcin-type C-glycoside pathways: discovery and antitumoral evaluation of polycarcin V from Streptomyces polyformus

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