Novel indole diketopiperazine stereoisomers from a marine-derived fungus Aspergillus sp.

References

• Barrow CJ, Cai P, Snyder JK, Sedlock DM, Sun HH, Cooper R. 1993. WIN 64821, a new competitive antagonist to substance P, isolated from an Aspergillus species: structure determination and solution conformation. J Org Chem. 58(22):6016–6021. doi:10.1021/jo00074a031.
   Web of Science ®Google Scholar
• Belin P, Moutiez M, Lautru S, Seguin J, Gondry M. 2012. The nonribosomal synthesis of diketopiperazines in trna-dependent cyclodipeptide synthase pathways. Nat Prod Rep. 29(9):961–979. doi:10.1039/c2np20010d.
   PubMed Web of Science ®Google Scholar
• Borgman P, Lopez RD, Lane AL. 2019. The expanding spectrum of diketopiperazine natural product biosynthetic pathways containing cyclodipeptide synthases. Org Biomol Chem. 17(9):2305–2314. doi:10.1039/c8ob03063d.
   PubMed Web of Science ®Google Scholar
• Fujimoto H, Sumino M, Okuyama E, Ishibashi M. 2004. Immunomodulatory constituents from an Ascomycete, Chaetomium seminudum. J Nat Prod. 67(1):98–102. doi:10.1021/np0302201.
   PubMed Web of Science ®Google Scholar
• Giessen TW, Marahiel MA. 2015. Rational and combinatorial tailoring of bioactive cyclic dipeptides. Fron Microbiol. 6:785. doi:10.3389/fmicb.2015.00785.
   PubMed Web of Science ®Google Scholar
• Giessen TW, Tesmar AMV, Marahiel MA. 2013. A trna-dependent two-enzyme pathway for the generation of singly and doubly methylated ditryptophan 2,5-diketopiperazines. Biochemistry. 52(24):4274–4283. doi:10.1021/bi4004827.
   PubMed Web of Science ®Google Scholar
• Gondry M, Sauguet L, Belin P, Thai R, Amouroux R, Tellier C, Tuphile K, Jacquet M, Braud S, Courçon M, et al. 2009. Cyclodipeptide synthases are a family of trna-dependent peptide bond-forming enzymes. Nat Chem Biol. 5(6):414–420. doi:10.1038/nchembio.175.
   PubMed Web of Science ®Google Scholar
• Gu BB, Gui YH, Liu L, Su ZY, Jiao WH, Li L, Sun F, Wang SP, Yang F, Lin HW. 2019. A new asymmetric diketopiperazine dimer from the sponge-associated fungus Aspergillus versicolor 16F-11. Magn Reson Chem. 57(1):49–54. doi:10.1002/mrc.4780.
   PubMed Web of Science ®Google Scholar
• Jia B, Ma YM, Liu B, Chen P, Hu Y, Zhang R. 2019. Synthesis, antimicrobial activity, structure-activity relationship, and molecular docking studies of indole diketopiperazine alkaloids. Front Chem. 7:837. doi:10.3389/fchem.2019.00837.
   PubMed Web of Science ®Google Scholar
• Klas KR, Kato H, Frisvad JC, Yu F, Newmister SA, Fraley AE, Sherman DH, Tsukamoto S, Williams RM. 2018. Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi. Nat Prod Rep. 35(6):532–558. doi:10.1039/C7NP00042A.
   PubMed Web of Science ®Google Scholar
• Li GY, Yang T, Luo YG, Chen XZ, Fang DM, Zhang GL. 2009. Brevianamide J, a new indole alkaloid dimer from fungus Aspergillus versicolor. Org Lett. 11(16):3714–3717. doi:10.1021/ol901304y.
   PubMed Web of Science ®Google Scholar
• Ma YM, Liang XA, Kong Y, Jia B. 2016. Structural diversity and biological activities of indole diketopiperazine alkaloids from fungi. J Agric Food Chem. 64(35):6659–6671. doi:10.1021/acs.jafc.6b01772.
   PubMed Web of Science ®Google Scholar
• Mishra A, Choi J, Choi SJ, Baek KH. 2017. Cyclodipeptides: an overview of their biosynthesis and biological activity. Molecules. 22(10):1796. doi:10.3390/molecules22101796.
   PubMed Web of Science ®Google Scholar
• Nishiuchi K, Ohashi H, Nishioka K, Yamasaki M, Furuta M, Mashiko T, Tomoshige S, Ohgane K, Kamisuki S, Watashi K. 2022. Synthesis and antiviral activities of neoechinulin B and its derivatives. J Nat Prod. 85(1):284–291. doi:10.1021/acs.jnatprod.1c01120.
   PubMed Web of Science ®Google Scholar
• Sedlock DM, Barrow CJ, Brownell JE, Hong A, Gillum AM, Houck DR. 1994. WIN 64821, a novel neurokinin antagonist produced by an Aspergillus sp. II. Biological activity. J Antibiot. 47(4):399–410. doi:10.7164/antibiotics.47.399.
   PubMed Web of Science ®Google Scholar
• Shende VV, Khatri Y, Newmister SA, Sanders JN, Lindovska P, Yu F, Doyon TJ, Kim J, Houk KN, Movassaghi M, et al. 2020. Structure and function of nzeb, a versatile C–C and C-N bond forming diketopiperazine dimerase. J Am Chem Soc. 142(41):17413–17424. doi:10.1021/jacs.0c06312.
   PubMed Web of Science ®Google Scholar
• Sun S, Ma K, Tao Q, Han J, Bao L, Liu L, Liu H. 2018. Diketopiperazines and 2h-pyran-2-ones with antioxidant activity from the rice fermented with aspergillus luchuensis. Fitoterapia. 125:266–272. doi:10.1016/j.fitote.2018.01.016.
   PubMed Web of Science ®Google Scholar
• Varoglu M, Corbett TH, Valeriote FA, Crews P. 1997. Asperazine, a selective cytotoxic alkaloid from a sponge-derived culture of aspergillus niger. J Org Chem. 62(21):7078–7079. doi:10.1021/jo970568z.
   PubMed Web of Science ®Google Scholar
• Wang F, Hua H, Pei Y, Chen D, Jing Y. 2006. Triterpenoids from the resin of styrax tonkinensis and their antiproliferative and differentiation effects in human leukemia HL-60 cells. J Nat Prod. 69(5):807–810. doi:10.1021/np050371z.
   PubMed Web of Science ®Google Scholar
• Wang FQ, Tong QY, Ma HR, Xu HF, Hu S, Ma W, Xue YB, Liu JJ, Wang JP, Song HP, et al. 2015. Indole diketopiperazines from endophytic Chaetomium sp 88194 induce breast cancer cell apoptotic death. Sci Rep. 5:9294. doi:10.1038/srep09294.
   PubMed Web of Science ®Google Scholar
• Wen H, Liu X, Zhang Q, Deng Y, Zang Y, Wang J, Liu J, Zhou Q, Hu L, Zhu H. 2018. Three new indole diketopiperazine alkaloids from aspergillus ochraceus. Chem Biodivers. 15(4):e1700550. doi:10.1002/cbdv.201700550.
   PubMed Web of Science ®Google Scholar
• Wibowo JT, Ahmadi P, Rahmawati SI, Bayu A, Putra MY, Kijjoa A. 2021. Marine-derived indole alkaloids and their biological and pharmacological activities. Mar Drugs. 20(1):3. doi:10.3390/md20010003.
   PubMed Web of Science ®Google Scholar
• Yang J, Gong L, Guo M, Jiang Y, An F. 2021. Bioactive indole diketopiperazine alkaloids from the marine endophytic fungus Aspergillus sp. YJ191021. Mar Drugs. 19(3):157. doi:10.3390/md19030157.
   PubMed Web of Science ®Google Scholar
• Zhang YH, Geng C, Zhang XW, Zhu HJ, Shao CL, Cao F, Wang CY. 2019. Discovery of bioactive indole-diketopiperazines from the marine-derived fungus penicillium brasilianum aided by genomic information. Mar Drugs. 17(9):514. doi:10.3390/md17090514.
   PubMed Web of Science ®Google Scholar
• Zheng CJ, Park SH, Koshino H, Kim YO, Kim WG. 2007. Verticillin G, a new antibacterial compound from bionectra byssicola. J Antibiot. 60(1):61–64. doi:10.1038/ja.2007.8.
   PubMed Web of Science ®Google Scholar