海洋真菌Talaromyces sp. UJNMF0655代谢产物的结构鉴定与生物活性

doi:10.6040/j.issn.1671-7554.0.2025.1192

摘要/Abstract

摘要： 目的研究海榄雌Avicennia marina(Forssk.)Vierh.根部沉积物来源真菌Talaromyces sp. UJNMF0655的次级代谢产物及其生物活性。方法采用正相硅胶色谱、反相硅胶色谱、Sephadex凝胶色谱、高效液相色谱等方法对目标真菌发酵物的乙酸乙酯提取物进行分离纯化,结合化合物的理化性质、波谱数据、文献报道等进行结构鉴定,并评价其抗菌、神经保护、抗氧化活性。结果从海洋真菌Talaromyces sp. UJNMF0655的次级代谢产物中分离鉴定了9个聚酮类化合物:talaroisochromane A(1)、talaroisochromane B(2)、penicillide(3)、paecilin L(4)、paecilin E(5)、paecilin N(6)、paecilin P(7)、paecilin F(8)、paecilin A(9),其中8个化合物(1-2,4-9)为二聚体结构,化合物1和2是新化合物。活性结果显示,化合物9对S. aureus有抑菌活性,化合物3在50 μmol/L时能够明显减少高糖引起的RSC96细胞损伤。结论海洋真菌Talaromyces sp. UJNMF0655能够产生丰富的二聚体类成分,说明该菌具有开发抗菌和神经保护先导化合物的潜力。

关键词: 海洋真菌, Talaromyces sp. UJNMF0655, 代谢产物, 二聚色原酮, 生物活性

Abstract: Objective To investigate the secondary metabolites and their bioactivities of Talaromyces sp. UJNMF0655, a fungus isolated from the root sediment of the mangrove Avicennia marina(Forssk.)Vierh. Methods The ethyl acetate extract of the target fungus fermentation broth was isolated and purified using various chromatographic techniques, including normal-phase silica gel chromatography, reversed-phase silica gel chromatography, Sephadex gel chromatography, and high-performance liquid chromatography(HPLC). The structures of the isolated compounds were elucidated through comprehensive analysis of their physicochemical properties, spectroscopic data, and comparison with literature reports, while their antimicrobial, neuroprotective, and antioxidant activities were evaluated. Results Nine polyketide compounds were isolated and identified from the secondary metabolites of the marine fungus Talaromyces sp. UJNMF0655: talaroisochromane A(1), talaroisochromane B(2), penicillide(3), paecilin L(4), paecilin E(5), paecilin N(6), paecilin P(7), paecilin F(8), and paecilin A(9). Among these, eight compounds(1-2, 4-9)featured dimeric structures, and compounds 1 and 2 were new natural products. Bioactivity results indicated that compound 9 exhibited certain antibacterial activity against S. aureus, and compound 3, at a concentration of 50 μmol/L, significantly reduced high glucose-induced damage in RSC96 cells. Conclusion The marine fungus Talaromyces sp. UJNMF0655 is capable of producing abundant dimeric metabolites, demonstrating the potential of UJNMF0655 to develop lead compounds with antimicrobial and neuroprotective activities.

Key words: Marine fungus, Talaromyces sp. UJNMF0655, Metabolites, Dimeric chromanones, Bioactivity

中图分类号:

R914.4

李梓豪,黄珊珊,张燕,张华,王春莹,李明悦,徐秀丽,鲍洁. 海洋真菌Talaromyces sp. UJNMF0655代谢产物的结构鉴定与生物活性[J]. 山东大学学报 (医学版), 2026, 64(5): 19-28.

LI Zihao, HUANG Shanshan, ZHANG Yan, ZHANG Hua, WANG Chunying, LI Mingyue, XU Xiuli, BAO Jie. Structures and bioactivities of metabolites of marine fungus Talaromyces sp. UJNMF0655[J]. Journal of Shandong University (Health Sciences), 2026, 64(5): 19-28.

参考文献

[1] Lan DH, Wu B. Chemistry and bioactivities of secondary metabolites from the genus Talaromyces[J]. Chem Biodivers, 2020, 17(8): e2000229. doi: 10.1002/cbdv.202000229
[2] Nicoletti R, Bellavita R, Falanga A, et al. The outstanding chemodiversity of marine-derived Talaromyces[J]. Biomolecules, 2023, 13(7): 1021. doi: 10.3390/biom13071021
[3] 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. AN Ting, TAN Hui, GUO Rong, et al. Research progress on the structure and activity of secondary metabolites of Talaromyces sp. [J] Chin J Antibiot, 2024, 49(9): 961-985.
[4] Yilmaz N, Visagie CM, Houbraken J, et al. Polyphasic taxonomy of the genus Talaromyces [J]. Stud Mycol, 2014, 78: 175-341. doi: 10.1016/j.simyco.2014.08.001
[5] Zhai MM, Li J, Jiang CX, et al. The bioactive secondary metabolites from Talaromyces species [J]. Nat Prod Bioprospect, 2016, 6(1): 1-24.
[6] Nicoletti R, Salvatore MM, Andolfi A, et al. Secondary metabolites of mangrove-associated strains of Talaromyces [J]. Mar Drugs, 2018, 16(1): 12. doi: 10.3390/md16010012
[7] 曾红, 王荫荫, 翟慧娟, 等. 海洋真菌Arthrinium sp. UJNMF0008代谢产物的研究 [J]. 天然产物研究与开发, 2019, 31(7): 1211-1215. ZENG Hong, WANG Yinyin, ZHAI Huijuan, et al. Secondary metabolites of marine fungus Arthrinium sp. UJNMF0008 [J]. Nat Prod Res Dev 2019, 31(7): 1211-1215.
[8] Komai SI, Hosoe T, Itabashi T, et al. New penicillide derivatives isolated from Penicillium simplicissimum [J]. J Nat Med, 2006, 60(3): 185-190.
[9] Wei PP, Ai HL, Shi BB, et al. Paecilins F-P, new dimeric chromanones isolated from the endophytic fungus Xylaria curta E10, and structural revision of paecilin A [J]. Front Microbiol, 2022, 13: 922444.doi: 10.3389/fmicb.2022.922444
[10] Kumla D, Aung TS, Buttachon S, et al. A new dihydrochromone dimer and other secondary metabolites from cultures of the marine sponge-associated fungi Neosartorya fennelliae KUFA 0811 and Neosartorya tsunodae KUFC 9213 [J]. Mar Drugs, 2017, 15(12): 375. doi: 10.3390/md15120375
[11] Álvarez-Constantino AM, Álvarez-Pérez A, VarelaJA, et al. Chemoselective Ru-catalyzed oxidative lactamization vshydroamination of alkynylamines: insights from experimental and density functional theory studies[J]. J Org Chem, 2023, 88(2): 1185-1193.
[12] Zhang FL, Ma CT, Wang WX, et al. Insights into the natural occurrence of monomeric and dimeric chromanone lactones [J]. Org Lett, 2025, 27(28): 7482-7487.
[13] Guo ZY, She ZG, Shao CL, et al. ¹H and ¹³C NMR signal assignments of paecilin A and B, two new chromone derivatives from mangrove endophytic fungus Paecilomyces sp.(tree 1-7)[J]. Magn Reson Chem, 2007, 45(9): 777-780.
[14] Valdomir G, Senthilkumar S, Ganapathy D, et al. Enantioselective total synthesis of chromanone lactone homo- and heterodimers [J]. Chem Asian J, 2018, 13(15): 1888-1891.
[15] da Silva PHF, de Souza MP, Bianco EA, et al. Antifungal polyketides and other compounds from Amazonian endophytic Talaromyces fungi [J]. J Brazil Chem Soc, 2018, 29(3): 622-630.
[16] Gu GW, Zhang T, Zhao JY, et al. New dimeric chromanone derivatives from the mutant strains of Penicillium oxalicum and their bioactivities [J]. RSC Adv, 2022, 12(35): 22377-22384.
[17] Cao HY, Yi C, Sun SF, et al. Anti-inflammatory dimeric tetrahydroxanthones from an endophytic Muyocopron laterale[J]. J Nat Prod, 2022, 85(1): 148-161.
[18] Kikuchi H, Isobe M, Kurata S, et al. New dimeric and monomeric chromanones, gonytolides D-G, isolated from the fungus Gonytrichum sp. [J]. Tetrahedron, 2012, 68(31): 6218-6223.
[19] Kikuchi H, Isobe M, Sekiya M, et al. Structures of the dimeric and monomeric chromanones, gonytolides A-C, isolated from the fungus Gonytrichum sp. and their promoting activities of innate immune responses [J]. Org Lett, 2011, 13(17): 4624-4627.
[20] Wu JW, Chen DD, Li Q, et al. Metabolomics-guided discovery of new dimeric xanthones from co-cultures of mangrove endophytic fungi Phomopsis asparagi DHS-48 and Phomopsis sp. DHS-11 [J]. Mar Drugs, 2024, 22(3):102. doi: 10.3390/md22030102
[21] Yang JX, Xu F, Huang CH, et al. Metabolites from the mangrove endophytic fungus Phomopsis sp.(#zsu-H76)[J]. Eur J Org Chem, 2010, 2010(19): 3692-3695.
[22] Pontius A, Krick A, Kehraus S, et al. Noduliprevenone: a novel heterodimeric chromanone with cancer chemopreventive potential [J]. Chemistry, 2008, 14(32): 9860-9863.
[23] Pontius A, Krick A, Mesry R, et al. Monodictyochromes A and B, dimeric xanthone derivatives from the marine algicolous fungus Monodictys putredinis [J]. J Nat Prod, 2008, 71(11): 1793-1799.
[24] Bao J, Sun YL, Zhang XY, et al. Antifouling and antibacterial polyketides from marine gorgonian coral-associa-ted fungusPenicillium sp. SCSGAF 0023 [J]. J Antibiot, 2013, 66(4): 219-223.
[25] Calcul L, Waterman C, Ma WS, et al. Screening mangrove endophytic fungi for antimalarial natural products [J]. Mar Drugs, 2013, 11(12): 5036-5050.
[26] Rönsberg D, Debbab A, Mándi A, et al. Pro-apoptotic and immunostimulatory tetrahydroxanthone dimers from the endophytic fungus Phomopsis longicolla[J]. J Org Chem, 2013, 78(24): 12409-12425.
[27] Wu XW, Iwata T, Scharf A, et al. Asymmetric synthesis of gonytolide A: strategic use of an aryl halide blocking group for oxidative coupling [J]. J Am Chem Soc, 2018, 140(18): 5969-5975.
[28] Kikuchi H, Hoshikawa T, Kurata S, et al. Design and synthesis of structure-simplified derivatives of gonytolide for the promotion of innate immune responses [J]. J Nat Prod, 2016, 79(5): 1259-1266.
[29] Li Y, Xin S, Weng R, et al. Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones [J]. Chem Sci, 2022, 13(30): 8871-8875.
[30] El-Elimat T, Figueroa M, Raja HA, et al. Biosynthetically distinct cytotoxic polyketides from Setophoma terrestris[J]. Eur J Org Chem, 2015, 2015(1): 109-121.
[31] Salvatore MM, Nicoletti R, Fiorito F, et al. Penicillides from Penicillium and Talaromyces: chemical structures, occurrence and bioactivities[J]. Molecules, 2024, 29: 3888. doi: 10.3390/molecules29163888
[32] Yu MG, Chen X, Jiang MC, et al. Two marine natural products, penicillide and verrucarin J, are identified from a chemical genetic screen for neutral lipid accumulation effectors in Phaeodactylum tricornutum[J]. Appl Microbiol Biot, 2020, 104(6): 2731-2743.
[33] Gu GW, Zhang T, Zhao JY, et al. New dimeric chromanone derivatives from the mutant strains of Penicillium oxalicum and their bioactivities[J]. RSC Adv, 2022, 12(35): 22377-22384.

多维度评价

Viewed

Full text

Abstract

Cited

Shared

Discussed