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Mar. Drugs 2014, 12(1), 491-507; doi:10.3390/md12010491

Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp.

1,* , 1
1 Graduate School of Marine Science and Technology, Tokyo University of Marine Science and Technology, 4-5-7 Konan, Minato-ku, Tokyo 108-8477, Japan 2 Biotechnology Research Center, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan
* Author to whom correspondence should be addressed.
Received: 7 November 2013 / Revised: 28 December 2013 / Accepted: 31 December 2013 / Published: 21 January 2014
(This article belongs to the Special Issue Advances and New Perspectives in Marine Biotechnology)
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Hyaluromycin (1), a new member of the rubromycin family of antibiotics, was isolated from the culture extract of a marine-derived Streptomyces sp. as a HAase inhibitor on the basis of HAase activity screening. The structure of 1 was elucidated through the interpretation of NMR data for the compound and its 3″-O-methyl derivative in combination with an incorporation experiment with [1,2-13C2]acetate. The compound’s absolute configuration was determined by the comparison of its circular dichroism (CD) spectrum with those of other rubromycins. Hyaluromycin (1) consists of a γ-rubromycin core structure possessing a 2-amino-3-hydroxycyclopent-2-enone (C5N) unit as an amide substituent of the carboxyl function; both structural units have been reported only from actinomycetes. Hyaluromycin (1) displayed approximately 25-fold more potent hyaluronidase inhibitory activity against hyaluronidase than did glycyrrhizin, a known inhibitor of plant origin.
Keywords: rubromycin; hyaluronidase inhibitor; marine actinomycetes; Streptomyces; 2-amino-3-hydroxycyclopent-2-enone rubromycin; hyaluronidase inhibitor; marine actinomycetes; Streptomyces; 2-amino-3-hydroxycyclopent-2-enone
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Harunari, E.; Imada, C.; Igarashi, Y.; Fukuda, T.; Terahara, T.; Kobayashi, T. Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp.. Mar. Drugs 2014, 12, 491-507.

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