Panunoids A-D, four new prenylhydroquinone derivatives isolated from the fungus Panus rudis

doi:10.1007/s13659-025-00562-3

应用天然产物 ›› 2026, Vol. 16 ›› Issue (1): 9-9.DOI: 10.1007/s13659-025-00562-3

Panunoids A-D, four new prenylhydroquinone derivatives isolated from the fungus Panus rudis

Yun Liu¹, Jian-Qiang Zhao¹, Yan-Long Yang², Han-Bing Yuan¹, Yan-Ming Wang^1,3,4, Jun Yuan^1,3,4

1. Jiangsu Key Laboratory of Regional Specific Resource Pharmaceutical Transformation, Huaiyin Institute of Technology, Huai'an 223003, China;
2. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China;
3. National & Local Joint Engineering Research Center for Mineral Salt Deep Utilization, Huaiyin Institute of Technology, Huai'an 223003, China;
4. Key Laboratory for Palygorskite Science and Applied Technology of Jiangsu Province, Huaiyin Institute of Technology, Huai'an 223003, China

收稿日期:2025-07-21 出版日期:2026-02-14 发布日期:2026-03-25
通讯作者: Yan-Ming Wang,E-mail:823113328@qq.com;Jun Yuan,E-mail:yuanj_hyit@163.com
基金资助:
This work was supported by Major Program of Natural Science Foundation of the Higher Education Institutions of Jiangsu Province of China (No. 24KJA360001) and Open Project of Jiangsu Provincial Key Laboratory of Palygorskite Science and Applied Technology (No. HPZ202402).

Panunoids A-D, four new prenylhydroquinone derivatives isolated from the fungus Panus rudis

Yun Liu¹, Jian-Qiang Zhao¹, Yan-Long Yang², Han-Bing Yuan¹, Yan-Ming Wang^1,3,4, Jun Yuan^1,3,4

1. Jiangsu Key Laboratory of Regional Specific Resource Pharmaceutical Transformation, Huaiyin Institute of Technology, Huai'an 223003, China;
2. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China;
3. National & Local Joint Engineering Research Center for Mineral Salt Deep Utilization, Huaiyin Institute of Technology, Huai'an 223003, China;
4. Key Laboratory for Palygorskite Science and Applied Technology of Jiangsu Province, Huaiyin Institute of Technology, Huai'an 223003, China

Received:2025-07-21 Online:2026-02-14 Published:2026-03-25
Contact: Yan-Ming Wang,E-mail:823113328@qq.com;Jun Yuan,E-mail:yuanj_hyit@163.com
Supported by:
This work was supported by Major Program of Natural Science Foundation of the Higher Education Institutions of Jiangsu Province of China (No. 24KJA360001) and Open Project of Jiangsu Provincial Key Laboratory of Palygorskite Science and Applied Technology (No. HPZ202402).

摘要/Abstract

摘要： A chemical constituent study on the fermented rice substrate of basidiomycetous fungus Panus rudis led to the isolation of four previously undescribed prenylhydroquinone derivatives compounds (1-4) and eight known compounds (5-12). Among them, compound 3 featured a rare benzothiazole derivative with hydroxy substituted 3-methyl-1-butenyl substitution on the benzene ring, and the absolute configurations of 7 and 12 were elucidated as unreported ones. Their structures were identified by the interpretation of 1D and 2D NMR spectroscopy, HRESIMS data, X-ray single-crystal diffraction, and comparison of calculated and experimental ECD spectra. The plausible biosynthetic pathways for 1-7 are proposed. Cytotoxicity evaluation was conducted on 1 and 3-12 against two cancer cell lines (A-549 and HepG2). The results demonstrated that 1, 3-6, 8, 9, and 12 exhibited weak cytotoxicity against both two cell lines. Among them, 8 and 12 showed dose-dependent inhibitory effects, and their IC₅₀ values at 72 h were obtained.

关键词: Panus rudis, Solid-state fermentation, Benzothiazole derivatives, Cytotoxicity

Abstract: A chemical constituent study on the fermented rice substrate of basidiomycetous fungus Panus rudis led to the isolation of four previously undescribed prenylhydroquinone derivatives compounds (1-4) and eight known compounds (5-12). Among them, compound 3 featured a rare benzothiazole derivative with hydroxy substituted 3-methyl-1-butenyl substitution on the benzene ring, and the absolute configurations of 7 and 12 were elucidated as unreported ones. Their structures were identified by the interpretation of 1D and 2D NMR spectroscopy, HRESIMS data, X-ray single-crystal diffraction, and comparison of calculated and experimental ECD spectra. The plausible biosynthetic pathways for 1-7 are proposed. Cytotoxicity evaluation was conducted on 1 and 3-12 against two cancer cell lines (A-549 and HepG2). The results demonstrated that 1, 3-6, 8, 9, and 12 exhibited weak cytotoxicity against both two cell lines. Among them, 8 and 12 showed dose-dependent inhibitory effects, and their IC₅₀ values at 72 h were obtained.

Key words: Panus rudis, Solid-state fermentation, Benzothiazole derivatives, Cytotoxicity

Yun Liu, Jian-Qiang Zhao, Yan-Long Yang, Han-Bing Yuan, Yan-Ming Wang, Jun Yuan. Panunoids A-D, four new prenylhydroquinone derivatives isolated from the fungus Panus rudis[J]. 应用天然产物, 2026, 16(1): 9-9.

参考文献

[1] Wei F, Hong YZ, Liu JJ, et al. Gongronella sp induces overproduction of laccase in Panus rudis. J Basic Microbiol. 2010;50(1):98–103. https://doi.org/10.1002/jobm.200900155.
[2] Zhang M, Wu F, Wei ZY, et al. Characterization and decolorization ability of a laccase from Panus rudis. Enzyme Microb Technol. 2006;39(1):92–7. https://doi.org/10.1016/j.enzmictec.2005.09.012.
[3] Yue L, Chen JL, Tuo YL, et al. Taxonomy and phylogeny of Panus (Polyporales, Panaceae) in China and its relationship with allies. MycoKeys. 2024;105:267–94. https://doi.org/10.3897/mycokeys.105.121025.
[4] Gressler M, Löhr NA, Schäfer T, et al. Mind the mushroom: natural product biosynthetic genes and enzymes of Basidiomycota. Nat Prod Rep. 2021;38(4):702–22. https://doi.org/10.1039/d0np00077a.
[5] Yang YL, Zhou M, Yang L, et al. A mushroom P450-monooxygenase enables regio- and stereoselective biocatalytic synthesis of epoxycyclohexenones. Angew Chem Int Ed. 2023;62(49):202313817. https://doi.org/10.1002/anie.202313817.
[6] Song JG, Ha LS, Ki DW, et al. Chemical constituents of the culture broth of Panus rudis. Mycobiology. 2021;49(6):604–6. https://doi.org/10.1080/12298093.2021.2004663.
[7] Lee YY, Ullah HMA, Ha LS, et al. Isopanepoxydone inhibits oxidative damage in murine alveolar macrophages via NRF2 and NLRP3 inflammasome. Immunopharmacol Immunotoxicol. 2022;44(3):347–54. https://doi.org/10.1080/08923973.2022.2047197.
[8] Yu HP, Hao XJ, Gao YG, et al. Precursor-directed biosynthesis of panepoxydone derivatives with nitric oxide production inhibitory activity. ChemBioChem. 2025;26(1):202400691. https://doi.org/10.1002/cbic.202400691.
[9] Porco JA, Su S, Lei XG, et al. Total synthesis and structure assignment of (+)-hexacyclinol. Angew Chem Int Ed Engl. 2006;45(35):5790–2. https://doi.org/10.1002/anie.200602854.
[10] Rychnovsky SD. Predicting NMR spectra by computational methods: structure revision of hexacyclinol. Org Lett. 2006;8(13):2895–8. https://doi.org/10.1021/ol0611346.
[11] Williams AJ, Elyashberg ME, Blinov KA, et al. Applying computer-assisted structure elucidation algorithms for the purpose of structure validation: revisiting the NMR assignments of hexacyclinol. J Nat Prod. 2008;71(4):581–8. https://doi.org/10.1021/np070557t.
[12] Li L, Wang YZ, Chen NX, et al. Exploring diversity through dimerization in natural products by a rational tandem mass-based molecular network strategy. Org Lett. 2023;25(22):4016–21. https://doi.org/10.1021/acs.orglett.3c01038.
[13] Ding JH, Li ZH, Feng T, et al. A new cadinane sesquiterpenoid from cultures of the Basidiomycete Panus conchatus. Nat Prod Res. 2018;32(19):2333–7. https://doi.org/10.1080/14786419.2017.1413559.
[14] Wang SX, Chen BS, Zhang ZJ, et al. Isolation, structural elucidation and biosynthetic pathway of bioactive prenyl quinone compounds from Panus lecomtei based on untargeted metabolomics combined with molecular networking. Food Chem. 2025;463:9. https://doi.org/10.1016/j.foodchem.2024.141275.
[15] Wang SX, Zhao RL, Guo C, et al. New neroterpenoid compounds from the culture of mushroom Panus lecomtei. Chin J Nat Med. 2020;18(4):268–72. https://doi.org/10.1016/s1875-5364(20)30033-9.
[16] Palasarn S, Tanyapanyachon P, Vichai V, et al. Chromene dimers from cultures of Basidiomycete Panus similis. J Nat Prod. 2025;88(3):777–84. https://doi.org/10.1021/acs.jnatprod.4c01475.
[17] Gong ZH, Wu ZY, Yang Q, et al. Influences of lactic acid bacteria strains on the flavor profiles, metabolites and quality characteristics of red yeast rice produced by solid-state fermentation. Food Res Int. 2024;197:115172. https://doi.org/10.1016/j.foodres.2024.115172.
[18] He JY, Li M, Gao MX, et al. Differential volatile compounds between rice and tartary buckwheat by solid-state fermentation with Monascus purpureus. Int J Food Microbiol. 2025;435:111181. https://doi.org/10.1016/j.ijfoodmicro.2025.111181.
[19] Zhang BB, Xing HB, Jiang BJ, et al. Using millet as substrate for efficient production of monacolin K by solid-state fermentation of Monascus ruber. J Biosci Bioeng. 2018;125(3):333–8. https://doi.org/10.1016/j.jbiosc.2017.10.011.
[20] Zhu JS, Lu F, Liu DD, et al. The process of solid-state fermentation of soybean meal: antimicrobial activity, fermentation heat generation and nitrogen solubility index. J Sci Food Agric. 2024;104(6):3228–34. https://doi.org/10.1002/jsfa.13209.
[21] Peng WW, Huang Q, Ke X, et al. Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5. Nat Prod Bioprospect. 2024;14(1):13. https://doi.org/10.1007/s13659-024-00429-z.
[22] Wu WY, Wei X, Liao Q, et al. Structurally diverse polyketides and alkaloids produced by a plant-derived fungus Penicillium canescens L1. Nat Prod Bioprospect. 2025;15(1):12. https://doi.org/10.1007/s13659-025-00503-0.
[23] Yin Q, Han JY, Yang GX, et al. New sesquiterpenoids with anti-inflammatory effects from phytopathogenic fungus Bipolaris sorokiniana 11134. Nat Prod Bioprospect. 2025;15(1):13. https://doi.org/10.1007/s13659-025-00508-9.
[24] Liu S, Sun CZ, Ha Y, et al. Novel antibacterial alkaloids from the Mariana Trench-derived actinomycete Streptomyces sp. SY2255. Tetrahedron Lett. 2024;137:154935. https://doi.org/10.1016/j.tetlet.2024.154935.
[25] Ichihara A, Kimura R, Sakamura S. Synthesis of 7-desoxypanepoxydol. Agric Biol Chem. 1975;39(2):555–6. https://doi.org/10.1080/00021369.1975.10861634.
[26] Shotwell JB, Koh B, Choi HW, et al. Inhibitors of NF-κB signaling: design and synthesis of a biotinylated isopanepoxydone affinity reagent. Bioorg Med Chem Lett. 2002;12(23):3463–6. https://doi.org/10.1016/s0960-894x(02)00769-2.
[27] Vásquez R, Rios N, Solano G, et al. Lentinoids A-D, new natural products isolated from Lentinus strigellus. Molecules. 2018;23(4):773. https://doi.org/10.3390/molecules23040773.
[28] Wang QL, She XG, Ren XF, et al. The first asymmetric total synthesis of several 3,4-dihydroxy-2,2-dimethyl-chroman derivatives. Tetrahedron Asymmetry. 2004;15(1):29–34. https://doi.org/10.1016/j.tetasy.2003.10.040.
[29] Zheng YB, Zhao BB, Lu CH, et al. Isolation, structure elucidation and apoptosis-inducing activity of new compounds from the edible fungus Lentinus striguellus. Nat Prod Commun. 2009;4(4):501–6.
[30] Fan XL, Cao YG, Zeng MN, et al. Six new compounds from the herbaceous stems of Ephedra intermedia Schrenket C. A. meyer and their lung-protective activity. Molecules. 2024;29(2):432. https://doi.org/10.3390/molecules29020432.
[31] Collins DO, Ruddock PLD, de Grassea JC, et al. Microbial transformation of cadina-4,10(15)-dien-3-one, aromadendr-1(10)-en-9-one and methyl ursolate by Mucor plumbeus ATCC 4740. Phytochemistry. 2002;59(5):479–88. https://doi.org/10.1016/s0031-9422(01)00486-1.
[32] Husain SM, Schätzle MA, Lüdeke S, et al. Unprecedented role of hydronaphthoquinone tautomers in biosynthesis. Angew Chem Int Ed. 2014;53(37):9806–11. https://doi.org/10.1002/anie.201404560.
[33] Zhang R, He JW, Dong ZW, et al. Genomic and experimental data provide new insights into luciferin biosynthesis and bioluminescence evolution in fireflies. Sci Rep. 2020;10(1):15882. https://doi.org/10.1038/s41598-020-72900-z.
[34] Gao Y, Yang J, Yang XL, et al. Novel dibenzofuran and biphenyl phytoalexins from Sorbus pohuashanensis suspension cell and their antimicrobial activities. Fitoterapia. 2021;152:104914. https://doi.org/10.1016/j.fitote.2021.104914.
[35] Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09, Revision D. 01. Gaussian: Wallingford CT. 2009.

Panunoids A-D, four new prenylhydroquinone derivatives isolated from the fungus Panus rudis

Panunoids A-D, four new prenylhydroquinone derivatives isolated from the fungus Panus rudis

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	Shuang-Shuang Xie, Xiang Yu, Qi-Mei Tie, Jing-Ke Zhang, Bei-Bei Zhang, Meng-Nan Zeng, Xiao-Ke Zheng, Wei-Sheng Feng. Six pairs of enantiomeric prenylated flavonoids with cytotoxic activities from Epimedium sagittatum Maxim[J]. 应用天然产物, 2025, 15(4): 31-31.
[2]	Yong-Ge Fu, Yi-Qi Huang, Zhi-Hong Xu, Xia Liu, Xing-Wei Yang. Polyprenylated acylphloroglucinols from Garcinia species and structural revision of seven analogues[J]. 应用天然产物, 2025, 15(4): 34-34.
[3]	Pengkun Li, Qin Li, Aimin Fu, Yang Xiao, Chunmei Chen, Hucheng Zhu, Changxing Qi, Wei Wei, Yuan Zhou, Yonghui Zhang. Emestrin-type epipolythiodioxopiperazines from Aspergillus nidulans with cytotoxic activities by regulating PI3K/AKT and mitochondrial apoptotic pathways[J]. 应用天然产物, 2025, 15(2): 17-17.
[4]	Dong-Yang Wang, Ming-Xing Li, Yan-Chao Xu, Peng Fu, Wei-Ming Zhu, Li-Ping Wang. Dibohemamines I-O from Streptomyces sp. GZWMJZ-662, an endophytic actinomycete from the medicinal and edible plant Houttuynia cordata Thunb.[J]. 应用天然产物, 2025, 15(1): 9-9.
[5]	Yue-Mei Chen, Nan-Kai Cao, Si-Si Zhu, Meng Ding, Hai-Zhen Liang, Ming-Bo Zhao, Ke-Wu Zeng, Peng-Fei Tu, Yong Jiang. Euchrestifolines A-O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifolia[J]. 应用天然产物, 2025, 15(1): 5-5.
[6]	Alica Fischle, Mika Lutsch, Florian Hübner, Linda Sch?ker-Hübner, Lina Schürmann, Finn K. Hansen, Svetlana A. Kalinina. Micro-scale screening of genetically modified Fusarium fujikuroi strain extends the apicidin family[J]. 应用天然产物, 2024, 14(6): 51-51.
[7]	Qi-Xiu Hai, Kun Hu, Su-Ping Chen, Yang-Yang Fu, Xiao-Nian Li, Han-Dong Sun, Hong-Ping He, Pema-Tenzin Puno. Silvaticusins A-D: ent-kaurane diterpenoids and a cyclobutane-containing ent-kaurane dimer from Isodon silvaticus[J]. 应用天然产物, 2024, 14(5): 45-45.
[8]	Shuyuan Mo, Ziming Zhao, Zi Ye, Zhihong Huang, Yaxin Zhang, Wanqi Yang, Jianping Wang, Zhengxi Hu, Yonghui Zhang. New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti[J]. 应用天然产物, 2023, 13(3): 17-17.
[9]	Li Hou, Cui-Xuan Mei, Chun-Mao Yuan, Gui-Hua Tang, Duo-Zhi Chen, Qing Zhao, Hong-Ping He, Ming-Ming Cao, Xiao-Jiang Hao. Five new limonoids isolated from Walsura robusta[J]. 应用天然产物, 2023, 13(2): 7-7.
[10]	Ya-Li Hu, Xing-Ren Li, Gang Xu. Carascynol A, a hybrid of caryophyllane-type terpenoid and a C₆ unit degraded by polyprenylated acylphloroglucinols from Hypericum ascyron[J]. 应用天然产物, 2022, 12(6): 38-38.
[11]	Xin Zhang, Yun-Bao Ma, Xiao-Feng He, Tian-Ze Li, Chang-An Geng, Li-Hua Su, Shuang Tang, Zhen Gao, Ji-Jun Chen. Artemyrianosins A–J, cytotoxic germacrane-type sesquiterpene lactones from Artemisia myriantha[J]. 应用天然产物, 2022, 12(3): 16-16.
[12]	Natividad Herrera Cano, Sebastian A. Andujar, Cristina Theoduloz, Daniel A. Wunderlin, Ana N. Santiago, Guillermo Schmeda-Hirschmann, Ricardo D. Enriz, Gabriela E. Feresin. Arylated analogues of cypronazole: fungicidal effect and activity on human fibroblasts. Docking analysis and molecular dynamics simulations[J]. 应用天然产物, 2022, 12(2): 9-9.
[13]	Ruo-Song Zhang, Yang-Yang Liu, Pei-Feng Zhu, Qiong Jin, Zhi Dai, Xiao-Dong Luo. Furostanol Saponins from Asparagus cochinchinensis and Their Cytotoxicity[J]. 应用天然产物, 2021, 11(6): 651-658.
[14]	Patrick O. Sakyi, Richard K. Amewu, Robert N. O. A. Devine, Emahi Ismaila, Whelton A. Miller, Samuel K. Kwofie. The Search for Putative Hits in Combating Leishmaniasis: The Contributions of Natural Products Over the Last Decade[J]. 应用天然产物, 2021, 11(5): 489-544.
[15]	Chen Shi, Yue-Ling Peng, Juan He, Zheng-Hui Li, Ji-Kai Liu, Tao Feng. Structures, Chemical Conversions, and Cytotoxicity of Tricholopardins C and D, Two Tricholoma Triterpenoids from the Wild Mushroom Tricholoma pardinum[J]. 应用天然产物, 2021, 11(2): 235-241.