Cochlioquinone B

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Cochlioquinone B
Category Enzyme inhibitors
Catalog number BBF-04197
CAS 32450-26-3
Molecular Weight 472.61
Molecular Formula C28H40O6
Purity >99% by HPLC

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Description

It is the minor component of a bioactive pigment isolated from Bipolaris cynodontis and Cochliobolus miyabeanus. It is an NADH-ubiquinone reductase inhibitor. It is also a phytotoxic agent inhibiting root growth. It is closely related to cochlioquinone A which inhibits diacylglycerol acyltransferase and exhibits anti-angiogenic and nematocidal activity. It is an antagonist of the human chemokine receptor, CCR5, in HIV-1.

Specification

Synonyms 20-De(acetyloxy)-11-deoxy-20-oxo-cochlioquinone A; 9-(1,3-Dimethyl-2-oxopentyl)-1,2,3,4aα,5,6,6a,12,12aα,12b-decahydro-3β-(1-hydroxy-1-methylethyl)-6aβ,12bβ-dimethyl-pyrano[3,2-a]xanthene-8,11-dione Stereoisomer; (3R,4aR,6aR,12aR,12bR)-9-[(1S,3S)-1,3-Dimethyl-2-oxopentyl]-1,2,3,4a,5,6,6a,12,12a,12b-decahydro-3-(1-hydroxy-1-methylethyl)-6a,12b-dimethylpyrano[3,2-a]xanthene-8,11-dione
Storage Store at -20°C
IUPAC Name (3R,4aR,6aR,12aR,12bR)-3-(2-hydroxypropan-2-yl)-6a,12b-dimethyl-9-[(2S,4S)-4-methyl-3-oxohexan-2-yl]-1,2,3,4a,5,6,12,12a-octahydropyrano[3,2-a]xanthene-8,11-dione
Canonical SMILES CCC(C)C(=O)C(C)C1=CC(=O)C2=C(C1=O)OC3(CCC4C(C3C2)(CCC(O4)C(C)(C)O)C)C
InChI InChI=1S/C28H40O6/c1-8-15(2)23(30)16(3)17-13-19(29)18-14-20-27(6)11-9-21(26(4,5)32)33-22(27)10-12-28(20,7)34-25(18)24(17)31/h13,15-16,20-22,32H,8-12,14H2,1-7H3/t15-,16-,20+,21+,22+,27+,28+/m0/s1
InChI Key NTPNSKLZWVYKGK-WWURSIHSSA-N
Source Bipolaris leersia

Properties

Appearance Yellow Crystal
Boiling Point 579.4±50.0°C (Predicted)
Melting Point 168-169°C
Density 1.17±0.1 g/cm3 (Predicted)
Solubility Soluble in Ethanol, Methanol, Acetone

Reference Reading

1.Cytotoxic cochlioquinone derivatives from the endophytic fungus Bipolaris sorokiniana derived from Pogostemon cablin.
Wang M1, Sun ZH2, Chen YC2, Liu HX2, Li HH2, Tan GH2, Li SN2, Guo XL3, Zhang WM2. Fitoterapia. 2016 Apr;110:77-82. doi: 10.1016/j.fitote.2016.02.005. Epub 2016 Feb 11.
Chemical investigation of the liquid culture of the endophytic fungus Bipolaris sorokiniana A606, which was isolated from the medicinal plant Pogostemon cablin resulted in the isolation of four new cytotoxic compounds, named isocochlioquinones D-E (1-2) and cochlioquinones G-H (3-4), along with five known cochlioquinone analogues (5-9). Their structures were determined on the basis of extensive spectroscopic analysis. Isocochlioquinone D (1) possessed a rare benzothiazin-3-one moiety and cochlioquinone G (3) was the first example of cochlioquinones bearing an indole-4,7-dione fragment. All of the isolates (1-9) were evaluated for their cytotoxic activities against MCF-7, NCI-H460, SF-268 and HepG-2 tumor cell lines by the sulforhodamine B (SRB) assay. Compounds 4 and 6-9, featuring a cochlioquinone core, exhibited potent cytotoxicities in vitro against the four tumor cell lines, and a preliminary structure-activity relationship of these compounds was also discussed.

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