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.
Keywords: rubromycin; hyaluronidase inhibitor; marine actinomycetes; Streptomyces; 2-amino-3-hydroxycyclopent-2-enone
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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.
Harunari E, Imada C, Igarashi Y, Fukuda T, Terahara T, Kobayashi T. Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp.. Marine Drugs. 2014; 12(1):491-507.
Harunari, Enjuro; Imada, Chiaki; Igarashi, Yasuhiro; Fukuda, Takao; Terahara, Takeshi; Kobayashi, Takeshi. 2014. "Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp.." Mar. Drugs 12, no. 1: 491-507.