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beta-Indomycinone

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Category Antibiotics
Catalog number BBF-01502
CAS
Molecular Weight 404.41
Molecular Formula C24H20O6

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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 Str. sp. B 8300. Beta-Indomycinone has weak activity of anti-gram positive and negative bacteria and candida albicans, it also has antioxidant activity.

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IUPAC Name 11-hydroxy-2-[(E)-2-hydroxyhex-4-en-2-yl]-5-methylnaphtho[2,3-h]chromene-4,7,12-trione
Canonical SMILES CC=CCC(C)(C1=CC(=O)C2=C(O1)C3=C(C=C2C)C(=O)C4=C(C3=O)C(=CC=C4)O)O
InChI InChI=1S/C24H20O6/c1-4-5-9-24(3,29)17-11-16(26)18-12(2)10-14-20(23(18)30-17)22(28)19-13(21(14)27)7-6-8-15(19)25/h4-8,10-11,25,29H,9H2,1-3H3/b5-4+
InChI Key IVVXCIFNKDZFST-SNAWJCMRSA-N
Appearance Yellow Solid
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; yeast
Melting Point 178°C
1. Gamma-indomycinone, a new pluramycin metabolite from a deep-sea derived actinomycete
R W Schumacher, B S Davidson, D A Montenegro, V S Bernan J Nat Prod. 1995 Apr;58(4):613-7. doi: 10.1021/np50118a024.
A new member of the pluramycin class of antibiotics, gamma-indomycinone [1], has been isolated along with the known compounds rubiflavinone C-1 [2] and beta-indomycinone [3] from the culture broth of a Streptomyces sp. obtained from a deep-sea sediment core. Each compound is composed of an anthraquinone-gamma-pyrone nucleus, but bears a different side-chain. Compounds 2 and 3 were identified by comparison of their spectral data with published data, while gamma-indomycinone [1] was characterized using 1H-nmr and mass spectrometry.
2. Isolation of β-indomycinone guided by cytotoxicity tests from Streptomyces sp. IFM11607 and revision of its double bond geometry
Kentaro Tsukahara, Kazufumi Toume, Hanako Ito, Naoki Ishikawa, Masami Ishibashi Nat Prod Commun. 2014 Sep;9(9):1327-8.
The antibiotic β-indomycinone was isolated from Streptomyces sp. IFM11607 by cytotoxicity-guided fractionation against human gastric adenocarcinoma AGS cells, and the geometry of its δ17,18-double bond was revised from E to Z based on the coupling constant.

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