Studies on the Chemical Epigenetic Modification of Fungus <i>Samsoniella Hepiali</i> CDB9-31

Jinli ZHAO; Hongyan YANG; Jiaqian YANG; Xinyi CHEN; Qing ZHAO; Xiaomei ZHANG

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Jinli ZHAO, Hongyan YANG, Jiaqian YANG, Xinyi CHEN, Qing ZHAO, Xiaomei ZHANG. Studies on the Chemical Epigenetic Modification of Fungus Samsoniella Hepiali CDB9-31[J]. Journal of Kunming Medical University.

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Jinli ZHAO, Hongyan YANG, Jiaqian YANG, Xinyi CHEN, Qing ZHAO, Xiaomei ZHANG. Studies on the Chemical Epigenetic Modification of Fungus Samsoniella Hepiali CDB9-31[J]. Journal of Kunming Medical University.

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Studies on the Chemical Epigenetic Modification of Fungus Samsoniella Hepiali CDB9-31

College of Basic Medicine /College of Traditional Chinese Medicine，Yunnan University of Traditional Chinese Medicine，Kunming Yunnan 650500，China

Received Date: 2025-07-10
Available Online: 2025-08-13

Abstract

Abstract

Objective To analyze the effects of the histone deacetylase inhibitor suberoylanilide hydroxamic acid （SAHA） on the secondary metabolites of the entomopathogenic fungus Samsoniella hepiali CDB9-31 using thin-layer chromatography （TLC） and high-performance liquid chromatography （HPLC）. Methods The fermentation products of Samsoniella hepiali CDB9-31 treated with epigenetic modifiers were separated and purified using methods such as silica gel column chromatography, Sephadex column chromatography and reversed-phase column chromatography. The structures of the compounds were elucidated using modern spectroscopic analysis methods. The antimicrobial activity of the obtained monomeric compounds was determined using the filter paper disc diffusion method. Results The TLC and HPLC analyses of its fermentation extracts revealed that SAHA could induce the strain to produce more diverse array of secondary metabolites, and 11 monomeric compounds were isolated and identified as follows: N'-phenyloctanediamide （1）, 5-Phenylcarbamoyl-pentanoic （2）, ergosterol （3）, 5, 8-Epidioxy-5α, 8α-ergosta-6, 22E-diene-3β-ol （4）, 1-monolinolein （5）, （4E, 8E）-2-N-（2-Hydroxypalmitoyl）-1-O-（β-D-glucopyranosyl）-9-methyl-4, 8-sphingadienine （6）, Ergosterol peroxide 3-O-β-D-glucopyranoside （7）, （22E, 24R）-7, 22-diene-3β, 5α, 6β-ergostatriol （8）, （2S, 2'R, 3R, 4E, 8E）-N-2'-Hydroxyhexadecanoyl-2-amion-9-methyl-4, 8-octadecadiene-1, 3-diol （9）, Adenosine （10）, D-Glulopyranose （11）. Compounds 1 and 2 were derivatives of SAHA, and it was speculated that the special metabolic environment of CDB9-31 caused the biotransformation of SAHA. Except for compound 3, all other compounds were isolated from this genus for the first time. The antibacterial activity results showed that six of these compounds exhibited varying degrees of inhibitory effects against at least one pathogenic bacterium. Conclusion This study has enriched the chemical diversity of secondary metabolites from the entomopathogenic fungus Samsoniella hepiali.
- Epigenetic modification,
- Entomopathogenic fungi,
- Samsoniella hepiali,
- Secondary metabolites,
- Antimicrobial activity

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References(32)

References

[1]	王记祥,马良进. 虫生真菌在农林害虫生物防治中的应用[J]. 浙江林学院学报,2009,26(2):286-291.
[2]	邵颖,丁婷,葛飞,等. 40 株虫生真菌发酵液对白色念珠菌的抑制作用[J]. 安徽农业大学学报,2005,32(3):328-331. doi: 10.3969/j.issn.1672-352X.2005.03.013
[3]	赵璇,田雨航,庞道然,等. 蛹虫草的化学成分、药理作用及产业化研究进展[J]. 中草药,2024,55(7):2413-2422.
[4]	Keller N P. Fungal secondary metabolism: regulation,function and drug discovery[J]. Nat Rev Microbiol,2019,17(3):167-180. doi: 10.1038/s41579-018-0121-1
[5]	Bharatiya P,Rathod P,Hiray A,et al. Multifarious elicitors: Invoking biosynthesis of various bioactive secondary metabolite in fungi[J]. Appl Biochem Biotechnol,2021,193(3):668-686. doi: 10.1007/s12010-020-03423-6
[6]	Ma X,Wei X,Xing S,et al. Polyketide production in a mangrove-associated fungus Diaporthe goulteri,induced by chemical epigenetic modification[J]. Nat Prod Res,2024,38(1):1-9. doi: 10.1080/14786419.2022.2102627
[7]	Teigo A,Tohru T,Takashi Y,et al. Structures of spiroindicumides A and B,unprecedented carbon skeletal spirolactones,and determination of the absolute configuration by vibrational circular dichroism exciton approach[J]. Org Lett,2013,15(17):4320-4323. doi: 10.1021/ol401741z
[8]	王晓洋,龚倩玉,许言超,等. 5-氮杂胞苷诱导内生真菌Penicillium sp. GZWMJZ-042代谢抗α-葡萄糖苷酶活性产物研究[J]. 中国抗生素杂志,2023,48(10):1118-1125. doi: 10.3969/j.issn.1001-8689.2023.10.004
[9]	Wang Y,Wang Z Q,Thanarut C,et al. Phylogeny and species delimitations in the economically,medically,and ecologically important genus Samsoniella (Cordycipitaceae,Hypocreales)[J]. MycoKeys,2023,99(99):227-250.
[10]	Toshe R,Khalid J S,Kemkuignou M B,et al. Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia.[J]. Beilstein J Org Chem,2025,21(23):327-339.
[11]	Zhang K T,Huang Z P,Xu X R,et al. Two new diketopiperazines from the Cordyceps fungus Samsoniella sp. XY4[J]. The Journal of Antibiotics,2023,76(12):735-740. doi: 10.1038/s41429-023-00662-7
[12]	邵颖,陈宏伟,柴文波,等. 蛹拟青霉发酵液中抑菌活性成分的分离纯化[J]. 食品科学,2012,33(23):116-120.
[13]	Ma J T,Dong X Y,Li Z H,et al. Antibacterial metabolites from kiwi endophytic fungus Fusarium tricinctum,a potential biocontrol strain for kiwi canker disease[J]. J Agric Food Chem,2023,71(20):7679-7688. doi: 10.1021/acs.jafc.3c00233
[14]	崔乃菠,马境谦,余河水,等. 基于刃天青微平板法检测金黄色葡萄球菌对天然产物的敏感性[J]. 天津中医药大学学报,2022,41(6):774-779.
[15]	Shi X,Li X,He X,et al. Chemical epigenetic regulation secondary metabolites derived from Aspergillus sydowii DL1045 with inhibitory activities for protein tyrosine phosphatases[J]. Molecules,2024,29(3):670. doi: 10.3390/molecules29030670
[16]	Alektiar S N,Han J,Dang Y,et al. Radical hydrocarboxylationof unactivated alkenes via photocatalytic formate activation[J]. J Am Chem Soc,2023,145(20):10991-10997. doi: 10.1021/jacs.3c03671
[17]	丁允章,孔黎春,张奕嘉,等. 紫色红曲霉Mp-21次级代谢产物抗氧化及抑制α-葡萄糖苷酶活性的研究[J]. 微生物学报,2022,62(1):103-118.
[18]	Sonfack F H D,Nanfack D A R,Tchuente T M A,et al. A new ceramide and other constituents from the fruits of Ficus lutea Vahl (Moraceae) and their chemotaxonomic significance[J]. Biochem Syst Ecol,2023,106(1):104573.
[19]	Zhang M M,Wang D,Lu F,et al. Identification of the active substances and mechanisms of ginger for the treatment of colon cancer based on network pharmacology and molecular docking[J]. BioData Min,2021,14(1):1-16. doi: 10.1186/s13040-020-00232-9
[20]	吴杰,陈丹丹,邓小林,等. 海南红树林内生真菌Endomelanconiopsis endophytica次级代谢产物及其体外生物活性[J]. 广东海洋大学学报,2023,43(4):27-33.
[21]	Li X,Gao J,Chen H,et al. Toxins from a symbiotic fungus,leptographium qinlingensis associated with dendroctonus armandi and their in vitro toxicitiesto pinus armandi seedlings[J]. Eur J Plant Pathol,2012,134(2):239-247. doi: 10.1007/s10658-012-9981-9
[22]	陈招莉,符大天,张蕾,等. 暗褐网柄牛肝菌化学成分及其抗肿瘤细胞毒活性[J]. 中成药,2023,45(10):3296-3301.
[23]	Qiu Y Z,Zhu Y Q,Lu H,et al. Secondary metabolites from the marine-derived fungus Penicillium chrysogenum Y20-2,and their pro-angiogenic activity[J]. Z Naturforsch C J Biosci,2023,8(9-10):345-352.
[24]	季宇彬,郑婷,尹姣定. 中国南海海绵Cinachyrella sp. 的化学成分研究[J]. 中国海洋药物,2018,37(2):7-12.
[25]	Jie F,Danyang Z,Qiannan X,et al. A new phenolic glycoside from Trollius chinensis Bunge with anti-inflammatory and antibacterial activities[J]. Nat Prod Res,2020,36(13):1-8.
[26]	Singh V R. Enzymatic catalysts for hydroxamic acid formation: A mini‐review[J]. ChemBioEng Revi,2023,11(2):339-347.
[27]	Bhatiya R K,Bhatiya S K,Meta P K,et al. Production and characterization of acyl transfer activity of amidase from Alcaligenes sp. MTCC 10674 for synthesis of hydroxamic acids[J]. J Microbiol Biotechnol,2013,40(1):21-27.
[28]	Vikram R S,Hitesh S,Ananta G,et al. Novel amidase catalyzed process for the synthesis of vorinostat drug[J]. J Appl Microbiol,2020,129(6):1589-1597. doi: 10.1111/jam.14753
[29]	Takei T,Yoshida M,Ohnishi Kameyama M,et al. Ergosterol peroxide,an apoptosis-inducing component isolated from sarcodon aspratus (Berk.) S. Ito[J]. Biosci Biotechnol Biochem,2005,69(1):212-215. doi: 10.1271/bbb.69.212
[30]	Shi X W,Li X J,Gao J M,et al. Fasciculols H and I,two lanostane derivatives from chinese mushroom naematoloma fasciculare[J]. Chem Biodivers,2011,8(10):1864-1870. doi: 10.1002/cbdv.201000203
[31]	Bok J W,Lermer L,Chilton J,et al. Antitumor sterols from the mycelia of cordyceps sinensis[J]. Phytochemistry,1999,51(7):891-898. doi: 10.1016/S0031-9422(99)00128-4
[32]	汪煜. 广义虫草分离鉴定及腺苷与虫草素的含量研究 [D]. 扬州: 扬州大学,2024.

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