Two new diketopiperazines (1, 2), one new polyprenol (3), together with 19 known compounds (4–22) were obtained from the EtOAc extract of Bionectria sp. Y1085, an endophytic fungus isolated from the plant Huperzia serrata. Their structures were elucidated by extensive NMR and MS analysis. Bionectin D (1) is a rare diketopiperazine with a single methylthio substitution at the α-carbon of cyclized amino acid residue. The antibacterial activity of compounds was assayed against Escherichia coli, Staphylococcus aureus, and Salmonella typhimurium ATCC 6539, and some metabolites (1, 2, 10, 11, and 14) exhibited evident antibacterial activity.
Subscribe to Journal
Get full journal access for 1 year
only $24.92 per issue
All prices are NET prices.
VAT will be added later in the checkout.
Rent or Buy article
Get time limited or full article access on ReadCube.
All prices are NET prices.
Saleem M, Ali MS, Hussain S, Jabbar A, Ashraf M, Lee YS. Marine natural products of fungal origin. Nat Prod Rep. 2007;24:1142–52.
Strobel G, Daisy B, Castillo U, Harper J. Natural products from endophytic microorganisms. J Nat Prod. 2004;67:257–68.
Stringlis IA, Zhang H, Pieterse CMJ, Bolton MD, de Jonge R. Microbial small molecules–weapons of plant subversion. Nat Prod Rep. 2018;35:410–33.
Zhang HW, Song YC, Tan RX. Biology and chemistry of endophytes. Nat Prod Rep. 2006;23:753–71.
Kharwar RN, Mishra A, Gond SK, Stierle A, Stierle D. Anticancer compounds derived from fungal endophytes: their importance and future challenges. Nat Prod Rep. 2011;28:1208–28.
Kaul S, Gupta S, Ahmed M, Dhar MK. Endophytic fungi from medicinal plants: a treasure hunt for bioactive metabolites. Phytochem Rev. 2012;11:487–505.
Ferreira A, Rodrigues M, Fortuna A, Falcao A, Alves G. Huperzine A from Huperzia serrata: a review of its sources, chemistry, pharmacology and toxicology. Phytochem Rev 2016;15:51–85.
Chen YM, Yang YH, Li XN, Zou C, Zhao PJ. Diterpenoids from the endophytic fungus Botryosphaeria sp. P483 of the chinese herbal medicine Huperzia serrata. Molecules. 2015;20:16924–32.
Yu FX, Chen Y, Yang YH, Zhao PJ. Four new dimeric spiro-azaplilone derivatives cochliodones E-H from the entophytic fungus Chaetomium sp. M336. Phytochem Lett. 2016;16:263–7.
Zheng CJ, Kim YH, Kim WG. Glioperazine B, as a new antimicrobial agent against Staphylococcus aureus, and glioperazine C: two new dioxopiperazines from Bionectra byssicola. Biosci Biotechnol Biochem. 2007;71:1979–83.
Usami Y, Yamaguchi J, Numata A, Gliocladins A–C. and glioperazine: cytotoxic dioxo– or trioxopiperazine metabolites from a Gliocladium sp. separated from a sea hare. Heterocycles. 2004;63:1123–9.
Zhao WY, et al. Three new dioxopiperazine metabolites from a marine-derived fungus Aspergillus fumigatus Fres. Nat Prod Res. 2010;24:953–7.
Dong JY, He HP, Shen YM, Zhang KQ. Nematicidal epipolysulfanyldioxopiperazines from Gliocladium roseum. J Nat Prod. 2005;68:1510–3.
Zheng CJ, Kim CJ, Bae KS, Kim YH, Kim WG, Bionectins A-C. epidithiodioxopiperazines with anti-MRSA activity, from Bionectra byssicola F120. J Nat Prod. 2006;69:1816–19.
Nishida H, Huang XH, Tomoda H, Omura S. Glisoprenins, new inhibitors of acyl-CoA: cholesterol acyltransferase produced by Gliocladium sp. FO-1513. II. Structure elucidation of glisoprenins A and B. J Antibiot. 1992;45:1669–76.
Hegde VR, et al. Neurokinin receptor inhibitors: fermentation, isolation, physico-chemical properties, structure and biological activity. J Antibiot. 1997;50:983–91.
Chu CY, Vukov R. Determination of the structure of butyl rubber by NMR spectroscopy. Macromolecules. 1985;18:1423–30.
Son BW, Jensen PR, Kauffman CA, Fenical W. New cytotoxic epidithiodioxopiperazines related to verticillin A from a marine isolate of the fungus Penicillium. Nat Prod Lett. 1999;13:213–22.
Wei W, et al. An antibacterial metabolite from Lasiodiplodia pseudotheobromae F2. Phytochemistry. 2014;100:103–9.
Dong JY, Zhou W, Li L, Li GH, Liu YJ, Zhang KQ. A new epidithiodioxopiperazine metabolite isolated from Gliocladium roseum YMF1.00133. Chin Chem Lett. 2006;17:922–4.
Chu M, et al. Inhibition of c-fos proto-oncogene induction by Sch 52900 and Sch 52901, novel diketopiperazine produced by Gliocladium sp. J Antibiot. 1995;48:1440–45.
Chen Y, Guo H, Du Z, Liu XZ, Che Y, Ye X. Ecology-based screen identifies new metabolites from a Cordyceps-colonizing fungus as cancer cell proliferation inhibitors and apoptosis inducers. Cell Prolif. 2009;42:838–47.
Che YS, Liu XZ, Ye X, Guo HJ, Chen YL, Liu SC. Method for preparing gliocladicillin C and application thereof. CN101805699, no. 2009-10077302-101805699. 2009;February:17.
Evidente A, Iacobellis NS, Sisto A. Isolation of indole-3-acetic acid methyl ester, a metabolite of indole-3-acetic acid from Pseudomonas amygdali. Experientia. 1993;49:182–3.
Yan XJ, Suzuki M, Ohnishi-Kameyama M, Sada Y, Nakanishi T, Nagata T. Extraction and identification of antioxidants in the roots of Yacon (Smallanthus sonchifolius). J Agric Food Chem. 1999;47:4711–3.
Zhao PJ, Wang HX, Li GH, Li HD, Liu J, Shen YM. Secondary metabolites from endophytic Streptomyces sp. Lz531. Chem Biodivers. 2007;4:899–904.
Koga J, et al. Cerebrosides A and C, sphingolipid elicitors of hypersensitive cell death and phytoalexin accumulation in rice plants. J Biol Chem. 1998;273:31985–91.
Yang T, Wang CH, Liu HJ, Chou GX, Cheng XM, Wang ZT. A new antioxidant compound from Capparis spinose. Pharm Biol. 2010;48:589–94.
Saleem R, Ahmad M, Naz A, Siddiqui H, Ahmad SI, Faizi S. Hypertensive and toxicological study of citric acid and other constituents from Tagetes patula roots. Arch Pharm Res. 2004;27:1037–42.
Yue JM, Chen SN, Lin ZW, Sun HD. Sterols from the fungus Lactarium volemus. Phytochemistry. 2001;56:801–6.
This study was financially supported by the National Natural Science Foundation of China (31760018, 31560016), the Applied Basic Research Foundation of Yunnan Province (2018FA006 and 2017FA016), and National Key R&D Program of China (2017YFD0201104).
Conflict of interest
The authors declare that they have no conflict of interest.
Publisher’s note: Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
About this article
Cite this article
Yang, YH., Yang, DS., Li, GH. et al. Antibacterial diketopiperazines from an endophytic fungus Bionectria sp. Y1085. J Antibiot 72, 752–758 (2019). https://doi.org/10.1038/s41429-019-0209-5
Journal of Fungi (2020)