Mycotrienol I

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Mycotrienol I
Category Bioactive by-products
Catalog number BBF-01976
CAS 81904-15-6
Molecular Weight 455.54
Molecular Formula C26H33NO6

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Description

Mycotrienol I is a polyene macrolide compound produced by Str. rishiriensis T-23. It has anti-fungal and anti-leukemia activity.

Specification

Synonyms Ansatrienol A; (4E,6S,7S,8R,10E,12E,14E,16R)-6,8-dihydroxy-16-methoxy-5,7-dimethyl-19-azabicyclo[18.3.1]tetracosa-1(23),4,10,12,14,20-hexaene-18,22,24-trione
Storage Store at -20°C
IUPAC Name (5R,6E,8E,10E,13R,14S,15S,16E)-13,15-dihydroxy-5-methoxy-14,16-dimethyl-2-azabicyclo[18.3.1]tetracosa-1(23),6,8,10,16,20-hexaene-3,22,24-trione
Canonical SMILES CC1C(CC=CC=CC=CC(CC(=O)NC2=CC(=O)C=C(C2=O)CCC=C(C1O)C)OC)O
InChI InChI=1S/C26H33NO6/c1-17-10-9-11-19-14-20(28)15-22(26(19)32)27-24(30)16-21(33-3)12-7-5-4-6-8-13-23(29)18(2)25(17)31/h4-8,10,12,14-15,18,21,23,25,29,31H,9,11,13,16H2,1-3H3,(H,27,30)/b5-4+,8-6+,12-7+,17-10+/t18-,21-,23+,25+/m0/s1
InChI Key KDVQXJCAPWJRKD-VWMGDPEBSA-N

Properties

Appearance Yellow Powder
Antibiotic Activity Spectrum fungi
Boiling Point 710.1±60.0°C at 760 mmHg
Melting Point 94-95°C
Density 1.2±0.1 g/cm3
Solubility Soluble in Methanol, Chloroform, Ethyl acetate

Reference Reading

1. Potentiation of mitomycin C, 6-mercaptopurine, bleomycin, cis-diamminedichloroplatinum and 5-fluorouracil by mycotrienins and mycotrienols
M Kuwano, K Ikezaki, K Mamizuka, S Komiyama, H Seto, N Otake, M Sugita, T Yamaguchi, T Kishiye, H Fukawa, et al. Gan. 1983 Oct;74(5):759-66.
Mycotrienins I and II and mycotrienols I and II are ansamycin antibiotics containing a triene structure, isolated from Streptomyces rishiriensis. An amphotericin B-resistant clone (AMBR-1) derived from cultured Chinese hamster V79 cells was cross-resistant to mycotrienins I and II, but not to mycotrienol I or II. These four ansamycin antibiotics were found to potentiate significantly the action of some anti-cancer agents including 5-fluorouracil, cis-diamminedichloroplatinum, bleomycin, mitomycin C and 6-mercaptopurine against cultured V79 cells. The action of adriamycin was not potentiated. These four ansamycin antibiotics showed a synergism spectrum similar to that of smaller polyene antibiotics.

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