Fellutamide

Fellutamide A

Fellutamide B

Fellutamides are tripeptide derivatives from Penicillium fellutanum and other fungi. They are potent proteasome inhibitor that stimulates nerve growth factor synthesis in vitro.^[1]^[2]

Fellutamides A and F were first isolated from Aspergillus versicolor.^[3]^[4] Fellutamides C and D were first isolated from an undescribed Metulocladosporiella (Chaetothyriales).^[5]

Fellutamide B strongly inhibits the growth of the tuberculosis-causing bacterium Mycobacterium tuberculosis.^[6] Its biosynthetic pathway has been determined in the filamentous fungus Aspergillus nidulans.^[7]

References

^ Hines J, Groll M, Fahnestock M, Crews CM (May 2008). "Proteasome inhibition by fellutamide B induces nerve growth factor synthesis". Chemistry & Biology. 15 (5): 501–12. doi:10.1016/j.chembiol.2008.03.020. PMC 2485210. PMID 18482702.
^ Yamaguchi K, Tsuji T, Wakuri S, Yazawa K, Kondo K, Shigemori H, Kobayashi J (February 1993). "Stimulation of nerve growth factor synthesis and secretion by fellutamide A in vitro". Bioscience, Biotechnology, and Biochemistry. 57 (2): 195–9. doi:10.1271/bbb.57.195. PMID 7763492.
^ Lee, Yoon-Mi; Dang, Hung The; Hong, Jong-Ki; Lee, Chong-O.; Bae, Kyung-Sook; Kim, Dong-Kyoo; Jung, Jee-H. (2010). "A Cytotoxic Lipopeptide from the Sponge-Derived Fungus Aspergillus versicolor". Bulletin of the Korean Chemical Society. 31: 205–208. doi:10.5012/bkcs.2010.31.01.205.
^ Lee, Yoon-Mi; Dang, Hung The; Li, Jianlin; Zhang, Ping; Hong, Jong-Ki; Lee, Chong-O.; Jung, Jee-H. (2011). "A Cytotoxic Fellutamide Analogue from the Sponge-Derived Fungus Aspergillus versicolor". Bulletin of the Korean Chemical Society. 32 (10): 3817–3820. doi:10.5012/bkcs.2011.32.10.3817.
^ Xu, Deming; Ondeyka, John; Harris, Guy H.; Zink, Deborah; Kahn, Jennifer Nielsen; Wang, Hao; Bills, Gerald; Platas, Gonzalo; Wang, Wenxian; Szewczak, Alexander A.; Liberator, Paul; Roemer, Terry; Singh, Sheo B. (2011). "Isolation, Structure, and Biological Activities of Fellutamides C and D from an Undescribed Metulocladosporiella (Chaetothyriales) Using the Genome-Wide Candida albicans Fitness Test". Journal of Natural Products. 74 (8): 1721–1730. doi:10.1021/np2001573. PMID 21761939.
^ Lin G, Li D, Chidawanyika T, Nathan C, Li H (September 2010). "Fellutamide B is a potent inhibitor of the Mycobacterium tuberculosis proteasome". Archives of Biochemistry and Biophysics. 501 (2): 214–20. doi:10.1016/j.abb.2010.06.009. PMC 2930046. PMID 20558127.
^ Yeh HH, Ahuja M, Chiang YM, Oakley CE, Moore S, Yoon O, Hajovsky H, Bok JW, Keller NP, Wang CC, Oakley BR (August 2016). "Resistance Gene-Guided Genome Mining: Serial Promoter Exchanges in Aspergillus nidulans Reveal the Biosynthetic Pathway for Fellutamide B, a Proteasome Inhibitor". ACS Chemical Biology. 11 (8): 2275–84. doi:10.1021/acschembio.6b00213. PMC 6457343. PMID 27294372.

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[1] Hines J, Groll M, Fahnestock M, Crews CM (May 2008). "Proteasome inhibition by fellutamide B induces nerve growth factor synthesis". Chemistry & Biology. 15 (5): 501–12. doi:10.1016/j.chembiol.2008.03.020. PMC 2485210. PMID 18482702.

[2] Yamaguchi K, Tsuji T, Wakuri S, Yazawa K, Kondo K, Shigemori H, Kobayashi J (February 1993). "Stimulation of nerve growth factor synthesis and secretion by fellutamide A in vitro". Bioscience, Biotechnology, and Biochemistry. 57 (2): 195–9. doi:10.1271/bbb.57.195. PMID 7763492.

[3] Lee, Yoon-Mi; Dang, Hung The; Hong, Jong-Ki; Lee, Chong-O.; Bae, Kyung-Sook; Kim, Dong-Kyoo; Jung, Jee-H. (2010). "A Cytotoxic Lipopeptide from the Sponge-Derived Fungus Aspergillus versicolor". Bulletin of the Korean Chemical Society. 31: 205–208. doi:10.5012/bkcs.2010.31.01.205.

[4] Lee, Yoon-Mi; Dang, Hung The; Li, Jianlin; Zhang, Ping; Hong, Jong-Ki; Lee, Chong-O.; Jung, Jee-H. (2011). "A Cytotoxic Fellutamide Analogue from the Sponge-Derived Fungus Aspergillus versicolor". Bulletin of the Korean Chemical Society. 32 (10): 3817–3820. doi:10.5012/bkcs.2011.32.10.3817.

[5] Xu, Deming; Ondeyka, John; Harris, Guy H.; Zink, Deborah; Kahn, Jennifer Nielsen; Wang, Hao; Bills, Gerald; Platas, Gonzalo; Wang, Wenxian; Szewczak, Alexander A.; Liberator, Paul; Roemer, Terry; Singh, Sheo B. (2011). "Isolation, Structure, and Biological Activities of Fellutamides C and D from an Undescribed Metulocladosporiella (Chaetothyriales) Using the Genome-Wide Candida albicans Fitness Test". Journal of Natural Products. 74 (8): 1721–1730. doi:10.1021/np2001573. PMID 21761939.

[6] Lin G, Li D, Chidawanyika T, Nathan C, Li H (September 2010). "Fellutamide B is a potent inhibitor of the Mycobacterium tuberculosis proteasome". Archives of Biochemistry and Biophysics. 501 (2): 214–20. doi:10.1016/j.abb.2010.06.009. PMC 2930046. PMID 20558127.

[7] Yeh HH, Ahuja M, Chiang YM, Oakley CE, Moore S, Yoon O, Hajovsky H, Bok JW, Keller NP, Wang CC, Oakley BR (August 2016). "Resistance Gene-Guided Genome Mining: Serial Promoter Exchanges in Aspergillus nidulans Reveal the Biosynthetic Pathway for Fellutamide B, a Proteasome Inhibitor". ACS Chemical Biology. 11 (8): 2275–84. doi:10.1021/acschembio.6b00213. PMC 6457343. PMID 27294372.

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