Hyaluromycin,a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp. |
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| Authors: | Enjuro Harunari Chiaki Imada Yasuhiro Igarashi Takao Fukuda Takeshi Terahara Takeshi Kobayashi |
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| Institution: | 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; E-Mails: (C.I.); (T.T.); (T.K.);2.Biotechnology Research Center, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan; E-Mails: (Y.I.); (T.F.) |
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| Abstract: | 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. |
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| Keywords: | rubromycin hyaluronidase inhibitor marine actinomycetes Streptomyces 2-amino-3-hydroxycyclopent-2-enone |
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