Abstract
Two new diketopiperazines, namely samsoniellain A (1) and samsoniellain B (2), together with two known compounds (3, 4) were isolated from Cordyceps fungus Samsoniella sp. XY4. The planar structures of 1 and 2 were determined by HRESIMS, 1D and 2D NMR spectroscopy. The absolute configurations of 1 and 2 were determined by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Results of antimicrobial activity indicated that compound 2 showed weak bacteriostatic activities against S. typhimurium χ 8956, H. influenza ATCC 10211, MRSA 2024 with the MIC values of 128, 256, and 256 μg ml−1, respectively. This is the first report about secondary metabolites of Samsoniella sp.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 12 print issues and online access
$259.00 per year
only $21.58 per issue
Buy this article
- Purchase on SpringerLink
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1038%2Fs41429-023-00662-7/MediaObjects/41429_2023_662_Fig1_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1038%2Fs41429-023-00662-7/MediaObjects/41429_2023_662_Fig2_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1038%2Fs41429-023-00662-7/MediaObjects/41429_2023_662_Fig3_HTML.png)
References
Zhou XW, Gong ZH, Su Y, Lin J, Tang KX. Cordyceps fungi: natural products, pharmacological functions and developmental products. J Pharm Pharmacol. 2009;61:279–91.
Dworecka-Kaszak B. Cordyceps fungi as natural killers, new hopes for medicine and biological control factors. Ann Parasitol. 2014;60:151–8.
Zheng P, Xia YL, Xiao GH, Xiong CH, Hu X, Zhang SW, Zheng HJ, Huang Y, Zhou Y, Wang SY, Zhao GP, Liu XZ, Leger RJS, Wang CS. Genome sequence of the insect pathogenic fungus Cordyceps militaris, a valued traditional Chinese medicine. Genome Biol. 2011;12:R116.
Lo HC, Hsieh C, Lin FY, Hsu TH. A systematic review of the mysterious caterpillar fungus Ophiocordyceps sinensis in Dong-ChongXiaCao (Dōng Chóng Xià Cǎo) and related bioactive ingredients. J Tradit Complement Med. 2013;3:16–32.
Lu YZ, Luo FF, Cen K, Xiao GH, Yin Y, Li CR, Li ZZ, Zhan S, Zhang HZ, Wang CS. Omics data reveal the unusual asexual-fruiting nature and secondary metabolic potentials of the medicinal fungus Cordyceps cicadae. BMC Genomics. 2017;18:668.
Chen XA, He X, Zhang M, Mao XM, Li YQ. An efficient genetic transformation system for Chinese medicine fungus Tolypocladium ophioglossoides. J Microbiol Methods. 2020;176:106032.
Kim HG, Song H, Yoon DH, Song BW, Park SM, Sung GH, Cho JY, Park HIL, Choi S, Song WO, Hwang KC, Kim TW. Cordyceps pruinosa extracts induce apoptosis of HeLa cells by a caspase dependent pathway. J Ethnopharmacol. 2010;128:342–51.
Xiao JH, Zhong JJ. Secondary metabolites from Cordyceps species and their antitumor activity studies. Recent Pat Biotechnol. 2007;1:123–37.
Yue GGL, Lau CBS, Fung KP, Leung PC, Ko WH. Effects of Cordyceps sinensis, Cordyceps militaris and their isolated compounds on ion transport in Calu-3 human airway epithelial cells. J Ethnopharmacol. 2008;117:92–101.
Yu HM, Wang BS, Huang SC, Duh PD. Comparison of protective effects between cultured Cordyceps militaris and natural Cordyceps sinensis against oxidative damage. J Agric Food Chem. 2006;54:3132–8.
Won SY, Park EH. Anti-inflammatory and related pharmacological activities of cultured mycelia and fruiting bodies of Cordyceps militaris. J Ethnopharmacol. 2005;96:555–61.
Li LQ, Song AX, Yin JY, Siu KC, Wong WT, Wu JY. Anti-inflammation activity of exopolysaccharides produced by a medicinal fungus Cordyceps sinensis Cs-HK1 in cell and animal models. Int J Biol Macromol. 2020;149:1042–50.
Ueda Y, Mori K, Satoh S, Dansako H, Ikeda M, Kato N. Anti-HCV activity of the Chinese medicinal fungus Cordyceps militaris. Biochem Biophys Res Commun. 2014;447:341–5.
Zhao X, Yu XH, Zhang GY, Zhang HY, Liu WW, Zhang CK, et al. Aqueous extracts of Cordyceps kyushuensis Kob induce apoptosis to exert anticancer activity. Biomed Res Int. 2018;2:1–8.
Grudniewska A, Hayashi S, Shimizu M, Kato M, Suenaga M, Imagawa H, Ito T, Asakawa Y, Ban S, Kumada T, Hashimoto T, Umeyama A. Opaliferin, a new polyketide from cultures of entomopathogenic fungus Cordyceps sp. NBRC 106954. Org Lett. 2014;16:4695–7.
Wang M, Kornsakulkarn J, Srichomthong K, Feng T, Liu JK, Isaka M, Thongpanchang C. Antimicrobial anthraquinones from cultures of the ant pathogenic fungus Cordyceps morakotii BCC 56811. J Antibiot. 2019;72:141–7.
Sun JF, Jin M, Zhou W, Diao SB, Zhou Y, Li SS, Wang X, Pan S, Jin XJ, Li G. A new ribonucleotide from Cordyceps militaris. Nat Prod Res. 2017;31:2537–43.
Xue YF, Wu LL, Ding YL, Cui XM, Han ZZ, Xu H. A new nucleoside and two new pyrrole alkaloid derivatives from Cordyceps militaris. Nat Prod Res. 2020;34:341–50.
Chu ZB, Chang J, Zhu Y, Sun X. Chemical constituents of Cordyceps cicadae. Nat Prod Commun. 2015;10:2145–6.
Mongkolsamrit S, Noisripoom W, Thanakitpipattana D, Wutikhun T, Spatafora JW, Luangsa-Ard J. Disentangling cryptic species with isaria-like morphs in Cordycipitaceae. Mycologia. 2018;110:230–57.
Chen WH, Han YF, Liang JD, Tian WY, Liang ZQ. Morphological and phylogenetic characterisations reveal three new species of Samsoniella (Cordycipitaceae, Hypocreales) from Guizhou, China. MycoKeys. 2020;74:1–15.
Liang YJ, Ariyawansa HA, Becker JO, Yang JI. The evaluation of egg-parasitic fungi Paraboeremia taiwanensis and Samsoniella sp. for the biological control of Meloidogyne enterolobii on Chinese cabbage. Microorganisms. 2020;8:828.
Pandian AT, Arivudainambi USE, Bagyalakshmi, Rajendran A. Antimicrobial potential of endophytic fungus Colletotrichum gloeosporioides associated with madhuca longifolia L. Adv Appl Res. 2011;3:1–7.
Pierens GK. 1H and 13C NMR scaling factors for the calculation of chemical shifts in commonly used solvents using density functional theory. J Comput Chem. 2014;35:1388–94.
Qu CL, Yang X, Zhang SM, et al. Study of diketopiperazines from the marine-derived Streptomyces sp. 223. Chinese J Mar Drugs. 2015;34:23–28.
He JB, Kang DW, Chen X, et al. Secondary metabolites of Streptomyces sp. KC17012 and their antibacterial activity. Nat Prod Res Dev. 2022;34:1523–9.
Wattana-Amorn P, Charoenwongsa W, Williams C, Crump MP, Apichaisataienchote B. Antibacterial activity of cyclo(L-Pro-L-Tyr) and cyclo(D-Pro-L-Tyr) from Streptomyces sp. strain 22-4 against phytopathogenic bacteria. Nat Prod Res. 2016;30:1980–3.
Acknowledgements
This work was financially supported by grants from the Natural Science Foundation of China (Nos. 31960001 and 82260687), Yunnan Provincial Science and Technology Department-Applied Basic Research Joint Special Funds of Yunnan University of Chinese Medicine (No. 202101AZ070001-204), Yunnan Province Ten Thousand People Program “Young Top Talents” Special Project (YNWR-QNBJ-2019-161).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare no competing interests.
Additional information
Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary information
Rights and permissions
About this article
Cite this article
Zhang, KT., Huang, ZP., Xu, XR. et al. Two new diketopiperazines from the Cordyceps fungus Samsoniella sp. XY4. J Antibiot 76, 735–740 (2023). https://doi.org/10.1038/s41429-023-00662-7
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1038/s41429-023-00662-7