广西师范大学学报(自然科学版) ›› 2026, Vol. 44 ›› Issue (6): 146-155.doi: 10.16088/j.issn.1001-6600.2025112003

• 药用资源研究 • 上一篇    下一篇

一株虎舌红来源内生真菌Talaromyces sp.次级代谢产物及抗菌活性研究

吴茜1,2,3,4, 唐海媚1,2,3,4, 植卓坚1,2,3,4, 陈幸1,2,3,4, 王文丽1,2,3,4, 曹越智1,2,3,4, 任佳慧1,2,3,4, 徐伟锋1,2,3,4, 杨瑞云1,2,3,4*   

  1. 1.药用资源化学与药物分子工程教育部重点实验室(广西师范大学), 广西 桂林 541004;
    2.广西药用资源化学与药物分子工程重点实验室(广西师范大学), 广西 桂林 541004;
    3.特色药用资源化学广西高校工程研究中心(广西师范大学), 广西 桂林 541004;
    4.广西师范大学 化学与药学学院, 广西 桂林 541004
  • 收稿日期:2025-11-20 修回日期:2026-01-22 出版日期:2026-11-05 发布日期:2026-11-10
  • 通讯作者: 杨瑞云(1978—),女,广西桂林人,广西师范大学研究员,博士。E-mail: yang_rui_yun@163.com
  • 基金资助:
    广西科技计划(桂科AD25069038);广西自然科学基金(2023GXNSFAA026228, 2025GXNSFAA069913)

Secondary metabolites of an endophytic fungus Talaromyces sp. from Ardisia mamillata Hance and their antibacterial and antifungal activities

Wu Qian1,2,3,4, Tang Haimei1,2,3,4, Zhi Zhuojian1,2,3,4, Chen Xing1,2,3,4, Wang Wenli1,2,3,4, Cao Yuezhi1,2,3,4, RenJiahui1,2,3,4, Xu Weifeng1,2,3,4, Yang Ruiyun1,2,3,4*   

  1. 1. Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Education of China (Guangxi Normal University), Guilin Guangxi 541004, China;
    2. Guangxi Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University), Guilin Guangxi 541004, China;
    3. Guangxi University Engineering Research Center for Chemistry of Characteristic Medicinal Resources (Guangxi Normal University), Guilin Guangxi 541004, China;
    4. School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin Guangxi 541004, China
  • Received:2025-11-20 Revised:2026-01-22 Online:2026-11-05 Published:2026-11-10

摘要: 本文研究一株虎舌红来源内生真菌Talaromyces sp. HSHL-F40的次级代谢产物及抗菌活性。采用柱色谱及半制备高效液相色谱等技术对该菌的大米发酵产物进行分离纯化,通过NMR、HR-ESI-MS等波谱技术对化合物进行结构鉴定,从中共分离鉴定出17个化合物,分别为:(2E,5E)-4-oxo-2-propylidene-5,7-octadienoic acid(1)、peniciisocoumarin H (2)、penicimarin C (3)、penicilloxalone B (4)、(R)-3-((3S,4S)-3,4-dihydroxypentyl)-8-hydroxyisochroman-1-one (5)、(R)-3-((R)-4,5-dihydroxypentyl)-8-hydroxyisochroman-1-one (6)、talaroisocoumarin A(7)、peniciisocoumarin F (8)、aspergillumarins B (9)、aspergillumarin A (10)、(3S,4S)-sclerotinin A (11)、3-(hydroxymethyl)-6,8-dimethoxy-2H-1-benzopyran-2-one (12)、talarohydrazone B (13)、sequoiamonascin C (14)、vermistatin (15)、4-hydroxy-2-methoxyacetanilide (16)、(E)-3-(2,5-dioxo-3-(propan-2-ylidene)pyrrolidin-1-yl)acrylic acid (17),其中,化合物1为新化合物,其余化合物均为首次从虎舌红来源的内生真菌中分离得到。抗菌活性测试结果显示,化合物13对金黄色葡萄球菌、枯草芽孢杆菌、巨大芽孢杆菌均表现出较好的抑制作用,最低抑制浓度(minimal inhibitory concentration,MIC)值均为8 mg/L;化合物1对荔枝炭疽病菌具有中等抗菌活性,MIC值为32 mg/L。

关键词: 虎舌红, 内生真菌, 蓝状菌, 次级代谢产物, 抗菌活性

Abstract: This study investigated the secondary metabolites of the endophyticfungus Talaromyces sp. HSHL-F40 isolated from Ardisia mamillata Hance and their antibacterial and antifungal activities. Seventeen compounds were isolated from the rice fermentation of the fungus by using column chromatography and semi-preparative HPLC. Their structures were identified as(2E,5E)-4-oxo-2-propylidene-5,7-octadienoic acid(1), peniciisocoumarin H (2), penicimarin C (3), penicilloxalone B (4), (R)-3-((3S, 4S)-3, 4-dihydroxypentyl)-8-hydroxyisochroman-1-one (5), (R)-3-((R)-4, 5-dihydroxypentyl)-8-hydroxyisochroman-1-one (6), talaroisocoumarin A (7), peniciisocoumarin F (8), aspergillumarins B (9), aspergillumarin A (10), (3S, 4S)-sclerotinin A (11), 3-(hydroxymethyl)-6, 8-dimethoxy-2H-1-benzopyran-2-one (12), talarohydrazone B(13), sequoiamonascin C (14), vermistatin (15), 4-hydroxy-2-methoxyacetanilide (16), and (E)-3-(2, 5-dioxo-3-(propan-2-ylidene)pyrrolidin-1-yl)acrylic acid (17), by using NMR and HR-ESI-MS. Among these, compound 1 is a new compound, and the other compounds were isolated from the endophytic fungi of Ardisia mamillata Hance for the first time. Compound13 exhibited antibacterial activity against Staphylococcus aureus, Bacillus subtilis and Bacillus megaterium, with MIC values of 8 mg/L. Antifungal assays revealed that compound 1 showed moderate inhibitory activity against Colletotrichum fructicola, with an MIC value of 32 mg/L.

Key words: Ardisia mamillata Hance, endophytic fungi, Talaromyces sp., secondary metabolites, antibacterial and antifungal activity

中图分类号:  O629.9

[1] Tsang C C, Tang J Y M, Lau S K P, et al. Taxonomy and evolution of Aspergillus, Penicillium and Talaromyces in the omics era: past, present and future[J]. Computational and Structural Biotechnology Journal, 2018, 16: 197-210. DOI:10.1016/j.csbj.2018.05.003.
[2] 孙剑秋, 阮永明, 金世宇, 等. 篮状菌属的重要性及其分类学研究概况[J]. 菌物研究, 2021, 19(2): 83-93. DOI:10.13341/j.jfr.2020.1374.
[3] Lan D H, Wu B. Chemistry and bioactivities of secondary metabolites from the genus Talaromyces[J]. Chemistry & Biodiversity, 2020, 17(8): e2000229. DOI:10.1002/cbdv.202000229.
[4] 安婷, 谭慧, 郭蓉, 等. 篮状菌属次级代谢产物结构及活性的研究进展[J]. 中国抗生素杂志, 2024, 49(9): 961-985. DOI:10.13461/j.cnki.cja.007753.
[5] 陈仲巍, 林凤娇, 陈彬彬, 等. 篮状菌属微生物次级代谢产物研究进展[J]. 生物资源, 2022, 44(4): 362-369. DOI:10.14188/j.ajsh.2022.04.004.
[6] Zhai M M, Li J, Jiang C X, et al. The bioactive secondary metabolites from Talaromyces species[J]. Natural Products and Bioprospecting, 2016, 6(1): 1-24. DOI:10.1007/s13659-015-0081-3.
[7] Lei L R, Gong L Q, Jin M Y, et al. Research advances in the structures and biological activities of secondary metabolites from Talaromyces[J]. Frontiers in Microbiology, 2022, 13: 984801. DOI:10.3389/fmicb.2022.984801.
[8] Frisvad J C, Yilmaz N, Thrane U, et al. Talaromyces atroroseus, a new species efficiently producing industrially relevant red pigments[J]. PLoS One, 2013, 8(12): e84102. DOI:10.1371/journal.pone.0084102.
[9] 凌育赵, 刘经亮, 吴晓天, 等. 虎舌红根茎三萜皂苷类成分的研究[J]. 中成药, 2019, 41(9): 2139-2144. DOI:10.3969/j.issn.1001-1528.2019.09.025.
[10]Mo T X, Huang X S, Zhang W X, et al. A series of meroterpenoids with rearranged skeletons from an endophytic fungus Penicillium sp. GDGJ-285[J]. Organic Chemistry Frontiers, 2021, 8(10): 2232-2241. DOI:10.1039/D1QO00173F.
[11]Zhou J T, Wu Q, Zhao J X, et al. Sucurchalasins a and B, sulfur-containing heterodimers of a cytochalasan and a macrolide from the endophytic fungus Aspergillus spelaeus GDGJ-286[J]. Journal of Natural Products, 2024, 87(9): 2327-2334. DOI:10.1021/acs.jnatprod.4c00489.
[12]Mo T X, Lv L X, Huang X S, et al. A series of meroterpenoids with highly oxygenated skeletons from the endophytic fungus Penicillium sp. and their anti-inflammatory activities[J]. Phytochemistry, 2025, 236: 114493. DOI:10.1016/j.phytochem.2025.114493.
[13]李本超, 梁艳, 覃小芽, 等. 广豆根内生真菌GDG-178代谢产物研究[J]. 广西师范大学学报(自然科学版), 2021, 39(2): 139-143. DOI:10.16088/j.issn.1001-6600.2020060902.
[14]Wiegand I, Hilpert K, Hancock R E W. Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances[J]. Nature Protocols, 2008, 3(2): 163-175. DOI:10.1038/nprot.2007.521.
[15]Yang R Y, Li C Y, Lin Y C, et al. Lactones from a brown Alga endophytic fungus (No. ZZF36) from the South China Sea and their antimicrobial activities[J]. Bioorganic & Medicinal Chemistry Letters, 2006, 16(16): 4205-4208. DOI:10.1016/j.bmcl.2006.05.081.
[16]Bai M, Zheng C J, Huang G L, et al. Bioactive meroterpenoids and isocoumarins from the mangrove-derived fungus Penicillium sp. TGM112[J]. Journal of Natural Products, 2019, 82(5): 1155-1164.
[17]Qi J, Shao C L, Li Z Y, et al. Isocoumarin derivatives and benzofurans from a sponge-derived Penicillium sp. fungus[J]. Journal of Natural Products, 2013, 76(4): 571-579. DOI:10.1021/np3007556.
[18]Ren Y, Chao L H, Sun J, et al. Two new polyketides from the fungus Penicillium oxalicum MHZ153[J]. Natural Product Research, 2019, 33(3): 347-353. DOI:10.1080/14786419.2018.1452001.
[19]Li K Y, Zhu Q F, Ao J L, et al. New meroterpenoid and isocoumarins from the fungus Talaromyces amestolkiae MST1-15 collected from coal area[J]. Molecules, 2022, 27(23): 8223. DOI:10.3390/molecules27238223.
[20]Chen S H, Liu Y Y, Liu Z M, et al. Isocoumarins and benzofurans from the mangrove endophytic fungus Talaromyces amestolkiae possess α-glucosidase inhibitory and antibacterial activities[J]. RSC Advances, 2016, 6(31): 26412-26420. DOI:10.1039/C6RA02566H.
[21]Ma M Z, Yi W W, Qin L, et al. Talaromydien a and talaroisocoumarin A, new metabolites from the marine-sourced fungus Talaromyces sp. ZZ1616[J]. Natural Product Research, 2022, 36(1): 460-465. DOI:10.1080/14786419.2020.1779265.
[22]钟晋谦, 陈玉婵, 陈闪冲, 等. 深海真菌Neoroussoella sp.固体发酵物中次生代谢产物及其生物活性研究[J]. 天然产物研究与开发, 2021, 33(7): 1165-1171. DOI:10.16333/j.1001-6880.2021.7.011.
[23]Li S D, Wei M Y, Chen G Y, et al. Two new dihydroisocoumarins from the endophytic fungus Aspergillus sp. collected from the South China Sea[J]. Chemistry of Natural Compounds, 2012, 48(3): 371-373. DOI:10.1007/s10600-012-0254-9.
[24]Ngan N T T, Quang T H, Kim K W, et al. Anti-inflammatory effects of secondary metabolites isolated from the marine-derived fungal strain Penicillium sp. SF-5629[J]. Archives of Pharmacal Research, 2017, 40(3): 328-337. DOI:10.1007/s12272-017-0890-5.
[25]Huang H B, Li Q, Feng X J, et al. Structural elucidation and NMR assignments of four aromatic lactones from a mangrove endophytic fungus (No. GX4-1B)[J]. Magnetic Resonance in Chemistry, 2010, 48(6): 496-499. DOI:10.1002/mrc.2605.
[26]Wu J J, Wang W X, Yang Y H, et al. Phenylhydrazone alkaloids from the deep-sea cold seep derived fungus Talaromyces amestolkiae HDN21-0307[J]. Journal of Natural Products, 2024, 87(5): 1407-1415.
[27]Stierle D B, Stierle A A, Bugni T. Sequoiamonascins A: D: novel anticancer metabolites isolated from a redwood endophyte[J]. ChemInform, 2003, 34(40): 200340221. DOI:10.1002/chin.200340221.
[28]Kawai K I, Komai S I, Hosoe T, et al. New vermistatin derivatives isolated from Penicillium simplicissimum[J]. Heterocycles, 2005, 65(11): 2771. DOI:10.3987/com-05-10523.
[29]Findlay J A, Li G Q, Miller J D, et al. Insect toxins from spruce endophytes[J]. Canadian Journal of Chemistry, 2003, 81(4): 284-292. DOI:10.1139/v03-044.
[30]Miao F, Yang R, Chen D D, et al. Isolation, identification and antimicrobial activities of two secondary metabolites of Talaromyces verruculosus[J]. Molecules, 2012, 17(12): 14091-14098. DOI:10.3390/molecules171214091.
[31]Murugappan S, Dastari S, Jungare K, et al. Hydrazide-hydrazone/hydrazone as enabling linkers in anti-cancer drug discovery: a comprehensive review[J]. Journal of Molecular Structure, 2024, 1307: 138012. DOI:10.1016/j.molstruc.2024.138012.
[32]Li Y F, Yang S M, Zhang S, et al. Discovery of novel 3-phenylhydrazone coumarin derivatives as potential antifungal agents against phytopathogenic fungi[J]. Food Chemistry, 2025, 486: 144655. DOI:10.1016/j.foodchem.2025.144655.
[1] 贾辉, 卢杏红, 吕东艳, 梁家萍, 徐伟锋. 一株海鞘来源真菌Penicilliumsp.次级代谢产物及抗菌活性研究[J]. 广西师范大学学报(自然科学版), 2026, 44(2): 199-210.
[2] 陈雪玉, 施慧露, 黄秋菊, 边迅, 骆海玉. 烟云彩螽肠道细菌的分离鉴定及抗菌活性菌株筛选[J]. 广西师范大学学报(自然科学版), 2025, 43(6): 204-214.
[3] 傅春青, 梁春祥, 梁莉芬, 高程海, 刘永宏, 徐新亚. 嗜盐真菌Cladosporium cladosporioides GXIMD 00533次级代谢产物及其生物活性研究[J]. 广西师范大学学报(自然科学版), 2025, 43(2): 247-257.
[4] 徐紫薇, 邓业成, 骆海玉, 邓志勇, 韦坚芬, 黄玲玉, 甘萍贵. 鸡屎藤内生真菌活性菌株筛选及其抗菌活性物质研究[J]. 广西师范大学学报(自然科学版), 2025, 43(1): 31-38.
[5] 刘铭希, 李奇聪, 冉川, 张丝, 施慧露, 邓志勇, 骆海玉, 邓业成. 柑橘溃疡病菌的分离鉴定及其微生物源抑制剂筛选[J]. 广西师范大学学报(自然科学版), 2025, 43(1): 39-47.
[6] 韦坚芬, 邓志勇, 邓业成, 骆海玉, 蒙思妤, 徐紫薇, 施瑶, 梁文垦. 草珊瑚内生真菌SgG4抗植物病原真菌的活性物质研究[J]. 广西师范大学学报(自然科学版), 2024, 42(2): 175-182.
[7] 肖泽恩, 邹思华, 江娇, 罗海梅, 黄锡山, 刘永宏, 谭振. 木榄内生真菌Penicillium sp. GXIMD00006的次级代谢产物及其降血糖活性研究[J]. 广西师范大学学报(自然科学版), 2023, 41(6): 150-157.
[8] 李奇聪, 陈洁萍, 欧艳绍, 杨树贤, 邓志勇, 骆海玉, 邓业成. 柑橘内生真菌LJZ-Y-11次生代谢产物抑菌活性研究[J]. 广西师范大学学报(自然科学版), 2023, 41(1): 155-163.
[9] 李本超, 梁艳, 覃小芽, 莫土香, 徐照隆, 李俊, 杨瑞云. 广豆根内生真菌GDG-178代谢产物研究[J]. 广西师范大学学报(自然科学版), 2021, 39(2): 139-143.
[10] 覃玉月, 刘晓波, 徐照隆, 莫土香, 李俊, 杨瑞云. 广豆根内生真菌Xylaria sp. GDGJ-368代谢产物研究[J]. 广西师范大学学报(自然科学版), 2020, 38(5): 71-77.
[11] 徐伟锋,姚飞华,梁学锋,郑娜,杨瑞云,李俊. 广豆根内生真菌GDG-180代谢产物研究[J]. 广西师范大学学报(自然科学版), 2017, 35(1): 58-61.
[12] 黄婉云, 殷鹏龙, 李虹, 彭湘艳, 苏桂发. 喹诺酮-二茂铁杂合物的合成及生物活性研究[J]. 广西师范大学学报(自然科学版), 2016, 34(2): 111-115.
[13] 周德雄, 王歆竹, 徐伟峰, 杨瑞云, 邵长伦, 李俊. 短指软珊瑚Sinularia sp.内生真菌Ta31-2代谢产物研究(Ⅱ)[J]. 广西师范大学学报(自然科学版), 2014, 32(4): 91-95.
[14] 杨瑞云, 黄忠京, 邵长伦, 李俊, 佘志刚, 林永成. 南海马尾藻内生真菌No.ZZF36代谢产物研究[J]. 广西师范大学学报(自然科学版), 2010, 28(2): 53-56.
Viewed
Full text


Abstract

Cited

  Shared   
  Discussed   
No Suggested Reading articles found!
版权所有 © 广西师范大学学报(自然科学版)编辑部
地址:广西桂林市三里店育才路15号 邮编:541004
电话:0773-5857325 E-mail: gxsdzkb@mailbox.gxnu.edu.cn
本系统由北京玛格泰克科技发展有限公司设计开发