Communesin B
Chemical compound
From Wikipedia, the free encyclopedia
Communesin B is a cytotoxic chemical compound isolated from Penicillium strains found on the marine alga Ulva intestinalis.[1][2] It exhibits cytotoxicity in vitro against human lung carcinoma, prostate carcinoma, colorectal carcinoma, cervical adenocarcinoma, and breast adenocarcinoma cell lines.[3]
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| Preferred IUPAC name
(2E,4E)-1-{(3aR,8aR,13bR,16aS,17S)-17-[(2R)-3,3-Dimethyloxiran-2-yl]-9-methyl-2,3,8a,9,14,15-hexahydro-8H-13,16-methanobenzo[c]indolo[3,2-j]pyrrolo[3,2-e][2,6]naphthyridin-1(16aH)-yl}hexa-2,4-dien-1-one | |
| Identifiers | |
3D model (JSmol) |
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CompTox Dashboard (EPA) |
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| Properties | |
| C32H36N4O2 | |
| Molar mass | 508.666 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthesis
Communesin B is a dimeric indole alkaloid with a hexadienoyl moiety originating from polyketide synthesis.[4] Biosynthesis starts with two L-tryptophan molecules processed by different pathways. The first pathway involves a decarboxylation step catalyzed by CnsB to produce tryptamine. The second pathway starts the synthesis of 4-L-dimethylallyl tryptophan by CnsF followed by further processing of CnsA and CnsD to form aurantioclavine.[4] These two indole-containing fragments are combined through a radical oxidative coupling by CnsC, a cytochrome P450 enzyme, to form the core scaffold of communesin alkaloids.[5] CnsE transfers a methyl group to the indole nitrogen, and CnsJ creates an epoxide ring on the dimethylallyl substituent off the ring structure to form communesin I.[6] Separately, CnsI synthesizes a hexadienoyl group using acetyl-CoA as a starting material and extending it with two malonyl-CoA units.[6] Then, CnsK performs N-acylation with the CnsI-synthesized hexadienoyl chain to form communesin B.[6]
