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Fungichromin

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Fungichromin
Category Antifungal
Catalog number BBF-01858
CAS 6834-98-6
Molecular Weight 670.83
Molecular Formula C35H58O12
Purity >95% by HPLC

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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

A pentaene antifungal produced by streptomyces; exhibits broad spectrum antifungal and antitumor activity and, like filipin, acts via interaction with cell membrane sterols.

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Synonyms Cogomycin; Pentamycin; Lagosin; 14-Hydroxyfilipin; Antibiotic A-246; NSC-105388
Storage -20°C
IUPAC Name (3R,4S,6S,8S,10R,12R,14R,15R,16R,17E,19E,21E,23E,25E,27S,28R)-4,6,8,10,12,14,15,16,27-nonahydroxy-3-[(1R)-1-hydroxyhexyl]-17,28-dimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
Canonical SMILES CCCCCC(C1C(CC(CC(CC(CC(CC(C(C(C(=CC=CC=CC=CC=CC(C(OC1=O)C)O)C)O)O)O)O)O)O)O)O)O
InChI InChI=1S/C35H58O12/c1-4-5-11-16-29(41)32-30(42)20-26(38)18-24(36)17-25(37)19-27(39)21-31(43)34(45)33(44)22(2)14-12-9-7-6-8-10-13-15-28(40)23(3)47-35(32)46/h6-10,12-15,23-34,36-45H,4-5,11,16-21H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,22-14+/t23-,24+,25-,26+,27-,28+,29-,30+,31-,32-,33-,34-/m1/s1
InChI Key AGJUUQSLGVCRQA-SWOUQTJZSA-N
Source Streptomyces sp.
Appearance Pale Yellow to Tan Solid
Antibiotic Activity Spectrum fungi; neoplastics (Tumor)
Boiling Point 914°C at 760 mmHg
Melting Point 157-162°C
Density 1.196 g/cm3
Solubility Soluble in ethanol, methanol, DMF or DMSO.
1.Fungichromin: a substance from Streptomyces padanus with inhibitory effects on Rhizoctonia solani.
Shih HD1, Liu YC, Hsu FL, Mulabagal V, Dodda R, Huang JW. J Agric Food Chem. 2003 Jan 1;51(1):95-9.
Streptomyces padanus strain PMS-702 is an antagonist of Rhizoctonia solani AG-4, the causal agent of damping-off of cabbage. Treatment of cabbage seeds with the culture filtrate of S. padanus strain PMS-702 was effective in reducing the incidence of damping-off of cabbage. The major active ingredient from the culture filtrate of S. padanus strain PMS-702 was purified by silica gel column chromatography and identified as the polyene macrolide, fungichromin, by NMR and mass spectral data. Bioassay studies showed that fungichromin had a strong antifungal activity against R. solani AG-4, and its minimum inhibitory concentration (over 90% inhibition) was found to be 72 microg/mL. This is the first report of fungichromin from S. padanus as an active ingredient for the control of Rhizoctonia damping-off of cabbage.
2.Characterization of Streptomyces padanus JAU4234, a producer of actinomycin X₂, fungichromin, and a new polyene macrolide antibiotic.
Xiong ZQ1, Zhang ZP, Li JH, Wei SJ, Tu GQ. Appl Environ Microbiol. 2012 Jan;78(2):589-92. doi: 10.1128/AEM.06561-11. Epub 2011 Nov 4.
Strain JAU4234, identified as Streptomyces padanus, was isolated from soil collected in Jiangxi Province, China. It produced actinomycin X2, fungichromin, and a new polyene macrolide compound with antifungal activity, antifungalmycin 702. Antifungalmycin 702 had good general antifungal activity and may have potential future agricultural and/or clinical applications.

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