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MR-566A

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Category Enzyme inhibitors
Catalog number BBF-03674
CAS
Molecular Weight 203.62
Molecular Formula C8H10ClNO3

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is produced by the strain of Trichoderma harzianus KCTC 0114BP. MR-566A inhibited mushroom enzyminase and melanin biosynthesis in B16 melanoma cells with IC50 (μmol/L) of 1.72 and 0.1, respectively.

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Synonyms SCHEMBL20203773
IUPAC Name 5-chloro-3,4-dihydroxy-3-(1-hydroxyethyl)cyclopentene-1-carbonitrile
Canonical SMILES CC(C1(C=C(C(C1O)Cl)C#N)O)O
InChI InChI=1S/C8H10ClNO3/c1-4(11)8(13)2-5(3-10)6(9)7(8)12/h2,4,6-7,11-13H,1H3
InChI Key XSQKIWCUHSTCDP-UHFFFAOYSA-N
Appearance Brown Powder
1. MR566A and MR566B, new melanin synthesis inhibitors produced by Trichoderma harzianum. I. Taxonomy, fermentation, isolation and biological activities
C H Lee, M C Chung, H J Lee, K S Bae, Y H Kho J Antibiot (Tokyo). 1997 Jun;50(6):469-73. doi: 10.7164/antibiotics.50.469.
New melanin synthesis inhibitors (MR566A and B) and six related known isocyanocyclopentenes were isolated from the fermentation broth of Trichoderma harzianum. The IC50 values of MR566A and B against mushroom tyrosinase were 1.72 and 47 microM, respectively. They inhibited melanin biosynthesis in B16 melanoma cells with MIC values of 0.1 and 2.2 microM, respectively. Also isolated from the same culture extract of T. harzianum was a new oxazole (MR93B), which showed no inhibitory activity against mushroom tyrosinase at a concentration of 1,000 microg/ml.
2. MR566A and MR566B, new melanin synthesis inhibitors produced by Trichoderma harzianum. II. Physico-chemical properties and structural elucidation
C H Lee, H Koshino, M C Chung, H J Lee, J K Hong, J S Yoo, Y H Kho J Antibiot (Tokyo). 1997 Jun;50(6):474-8. doi: 10.7164/antibiotics.50.474.
New melanin synthesis inhibitors (MR566A and B) and six related known isocyanocyclopentenes were isolated from the fermentation broth of Trichoderma harzianum, and their structures were elucidated by spectroscopic methods. The structures of novel isocyanides, MR566A (1) and B (2), were elucidated as 1-(3-chloro-1,2-dihydroxy-4-isocyano-4-cyclopenten-1-yl)etha nol, 1-(1,2,3-trihydroxy-3-isocyano-4-cyclopenten-1-yl)ethanol, respectively. The structure of novel oxazole, MR93B (9), was elucidated as 4-[(1Z)-3-hydroxy-2-hydroxymethyl-1-propen-1-yl]oxazole.

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