Communesin B

Communesin B
Names
	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
CAS Number	148439-46-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	24713764;
PubChem CID	44575539;
CompTox Dashboard (EPA)	DTXSID001017735 ;
	InChI InChI=1S/C32H36N4O2/c1-5-6-7-15-24(37)35-18-16-31-21-12-8-9-13-22(21)33-28-32(31)17-19-36(29(31)35)26(27-30(2,3)38-27)20-11-10-14-23(25(20)32)34(28)4/h5-15,26-29,33H,16-19H2,1-4H3/b6-5+,15-7+/t26-,27+,28+,29+,31-,32-/m0/s1 Key: XZFSMUXVAYCHFO-RPCCRITPSA-N;
	SMILES C/C=C/C=C/C(=O)N1CC[C@]23[C@H]1N4CC[C@@]25c6c(cccc6N([C@H]5Nc7c3cccc7)C)[C@H]4[C@@H]8C(O8)(C)C;
Properties
Chemical formula	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). Infobox references

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]

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]

References

^ Crawley SL, Funk RL (September 2003). "A synthetic approach to nomofungin/communesin B". Organic Letters. 5 (18): 3169–3171. doi:10.1021/ol034407v. PMID 12943379.
^ Nicoletti R, Trincone A (February 2016). "Bioactive Compounds Produced by Strains of Penicillium and Talaromyces of Marine Origin". Marine Drugs. 14 (2): 37. doi:10.3390/md14020037. PMC 4771990. PMID 26901206.
^ Pompeo, Matthew M.; Cheah, Jaime H.; Movassaghi, Mohammad (2019-09-11). "Total Synthesis and Anti-Cancer Activity of All Known Communesin Alkaloids and Related Derivatives". Journal of the American Chemical Society. 141 (36): 14411–14420. doi:10.1021/jacs.9b07397. ISSN 0002-7863. PMC 6743222. PMID 31422662.
^ ^a ^b ^c Wei X, Wang WG, Matsuda Y (March 2022). "Branching and converging pathways in fungal natural product biosynthesis". Fungal Biology and Biotechnology. 9 (1): 6. doi:10.1186/s40694-022-00135-w. PMC 8902786. PMID 35255990.
^ Pompeo MM, Cheah JH, Movassaghi M (September 2019). "Total Synthesis and Anti-Cancer Activity of All Known Communesin Alkaloids and Related Derivatives". Journal of the American Chemical Society. 141 (36): 14411–14420. doi:10.1021/jacs.9b07397. PMC 6743222. PMID 31422662.
^ ^a ^b ^c Lin HC, Chiou G, Chooi YH, McMahon TC, Xu W, Garg NK, Tang Y (March 2015). "Elucidation of the concise biosynthetic pathway of the communesin indole alkaloids". Angewandte Chemie. 54 (10): 3004–3007. doi:10.1002/anie.201411297. PMC 4409825. PMID 25571861.

[1] Crawley SL, Funk RL (September 2003). "A synthetic approach to nomofungin/communesin B". Organic Letters. 5 (18): 3169–3171. doi:10.1021/ol034407v. PMID 12943379.

[2] Nicoletti R, Trincone A (February 2016). "Bioactive Compounds Produced by Strains of Penicillium and Talaromyces of Marine Origin". Marine Drugs. 14 (2): 37. doi:10.3390/md14020037. PMC 4771990. PMID 26901206.

[3] Pompeo, Matthew M.; Cheah, Jaime H.; Movassaghi, Mohammad (2019-09-11). "Total Synthesis and Anti-Cancer Activity of All Known Communesin Alkaloids and Related Derivatives". Journal of the American Chemical Society. 141 (36): 14411–14420. doi:10.1021/jacs.9b07397. ISSN 0002-7863. PMC 6743222. PMID 31422662.

[:0-4] Wei X, Wang WG, Matsuda Y (March 2022). "Branching and converging pathways in fungal natural product biosynthesis". Fungal Biology and Biotechnology. 9 (1): 6. doi:10.1186/s40694-022-00135-w. PMC 8902786. PMID 35255990.

[5] Pompeo MM, Cheah JH, Movassaghi M (September 2019). "Total Synthesis and Anti-Cancer Activity of All Known Communesin Alkaloids and Related Derivatives". Journal of the American Chemical Society. 141 (36): 14411–14420. doi:10.1021/jacs.9b07397. PMC 6743222. PMID 31422662.

[:1-6] Lin HC, Chiou G, Chooi YH, McMahon TC, Xu W, Garg NK, Tang Y (March 2015). "Elucidation of the concise biosynthetic pathway of the communesin indole alkaloids". Angewandte Chemie. 54 (10): 3004–3007. doi:10.1002/anie.201411297. PMC 4409825. PMID 25571861.

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