Journal
MARINE DRUGS
Volume 12, Issue 1, Pages 491-507Publisher
MDPI AG
DOI: 10.3390/md12010491
Keywords
rubromycin; hyaluronidase inhibitor; marine actinomycetes; Streptomyces; 2-amino-3-hydroxycyclopent-2-enone
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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-C-13(2)]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.-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.
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