Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp.
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...
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MDPI AG
2014-01-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/12/1/491 |
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doaj-924c6da51ade460390ae6ec615fd8b392020-11-24T22:16:54ZengMDPI AGMarine Drugs1660-33972014-01-0112149150710.3390/md12010491md12010491Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp.Enjuro Harunari0Chiaki Imada1Yasuhiro Igarashi2Takao Fukuda3Takeshi Terahara4Takeshi Kobayashi5Graduate School of Marine Science and Technology, Tokyo University of Marine Science and Technology, 4-5-7 Konan, Minato-ku, Tokyo 108-8477, JapanGraduate School of Marine Science and Technology, Tokyo University of Marine Science and Technology, 4-5-7 Konan, Minato-ku, Tokyo 108-8477, JapanBiotechnology Research Center, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, JapanBiotechnology Research Center, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, JapanGraduate School of Marine Science and Technology, Tokyo University of Marine Science and Technology, 4-5-7 Konan, Minato-ku, Tokyo 108-8477, JapanGraduate School of Marine Science and Technology, Tokyo University of Marine Science and Technology, 4-5-7 Konan, Minato-ku, Tokyo 108-8477, JapanHyaluromycin (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.http://www.mdpi.com/1660-3397/12/1/491rubromycinhyaluronidase inhibitormarine actinomycetesStreptomyces2-amino-3-hydroxycyclopent-2-enone |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Enjuro Harunari Chiaki Imada Yasuhiro Igarashi Takao Fukuda Takeshi Terahara Takeshi Kobayashi |
| spellingShingle |
Enjuro Harunari Chiaki Imada Yasuhiro Igarashi Takao Fukuda Takeshi Terahara Takeshi Kobayashi Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp. Marine Drugs rubromycin hyaluronidase inhibitor marine actinomycetes Streptomyces 2-amino-3-hydroxycyclopent-2-enone |
| author_facet |
Enjuro Harunari Chiaki Imada Yasuhiro Igarashi Takao Fukuda Takeshi Terahara Takeshi Kobayashi |
| author_sort |
Enjuro Harunari |
| title |
Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp. |
| title_short |
Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp. |
| title_full |
Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp. |
| title_fullStr |
Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp. |
| title_full_unstemmed |
Hyaluromycin, a New Hyaluronidase Inhibitor of Polyketide Origin from Marine Streptomyces sp. |
| title_sort |
hyaluromycin, a new hyaluronidase inhibitor of polyketide origin from marine streptomyces sp. |
| publisher |
MDPI AG |
| series |
Marine Drugs |
| issn |
1660-3397 |
| publishDate |
2014-01-01 |
| description |
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. |
| topic |
rubromycin hyaluronidase inhibitor marine actinomycetes Streptomyces 2-amino-3-hydroxycyclopent-2-enone |
| url |
http://www.mdpi.com/1660-3397/12/1/491 |
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