Vibralactone derivatives isolated from co-cultures of the basidiomycetes Stereum hirsutum and Boreostereum vibrans

doi:10.1007/s13659-025-00505-y

Natural Products and Bioprospecting ›› 2025, Vol. 15 ›› Issue (2): 20-20.DOI: 10.1007/s13659-025-00505-y

• ORIGINAL ARTICLE • Previous Articles

Vibralactone derivatives isolated from co-cultures of the basidiomycetes Stereum hirsutum and Boreostereum vibrans

Jinjuan Wei, Zhe-Xi Li, Gao-Ke Peng, Xinyang Li, He-Ping Chen, Ji-Kai Liu

School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan, 430074, China

Received:2025-01-28 Accepted:2025-03-07 Online:2025-05-17 Published:2025-04-25
Contact: He-Ping Chen, E-mail:chenhp@mail.scuec.edu.cn;Ji-Kai Liu, E-mail:liujikai@mail.scuec.edu.cn
Supported by:
This work was financially supported by the National Natural Science Foundation of China (Grant number 82473810) and the Fundamental Research Funds for the Central Universities, South-Central Minzu University (Grant No. CPT22033). The authors thank the Analytical & Measuring Center, School of Pharmaceutical Sciences, South-Central Minzu University for the spectra test, and the Bioactivity Screening Center of Natural Products, Kunming Institute of Botany, CAS for biological activity screening.

Vibralactone derivatives isolated from co-cultures of the basidiomycetes Stereum hirsutum and Boreostereum vibrans

Jinjuan Wei, Zhe-Xi Li, Gao-Ke Peng, Xinyang Li, He-Ping Chen, Ji-Kai Liu

School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan, 430074, China

通讯作者: He-Ping Chen, E-mail:chenhp@mail.scuec.edu.cn;Ji-Kai Liu, E-mail:liujikai@mail.scuec.edu.cn
基金资助:
This work was financially supported by the National Natural Science Foundation of China (Grant number 82473810) and the Fundamental Research Funds for the Central Universities, South-Central Minzu University (Grant No. CPT22033). The authors thank the Analytical & Measuring Center, School of Pharmaceutical Sciences, South-Central Minzu University for the spectra test, and the Bioactivity Screening Center of Natural Products, Kunming Institute of Botany, CAS for biological activity screening.

Abstract

Abstract: The basidiomycetes Stereum hirsutum and Boreostereum vibrans are two fungi of the same genus. In this study, chemical investigation on the co-cultures of the two congeneric fungi led to the isolation of eleven new vibralactone derivatives, hirsutavibrins A-K (1-11). The structures of 1-11 were elucidated by extensive NMR and HRESIMS spectroscopic analysis, and computational methods. Hirsutavibrins A (1) and B (2) showed weak cytotoxicity against the human lung cancer cell line A549. Hirsutavibrin D (4) showed moderate anti-nitric oxide activity in murine monocytic RAW 264.7 macrophages. This work not only expands the members of vibralactone derivatives with variable configurations but also opens a new avenue for fungal co-culturing study between congeneric fungi.

Key words: Stereum hirsutum, Boreostereum vibrans, Basidiomycetes, Co-culture, Vibralactone derivatives

摘要： The basidiomycetes Stereum hirsutum and Boreostereum vibrans are two fungi of the same genus. In this study, chemical investigation on the co-cultures of the two congeneric fungi led to the isolation of eleven new vibralactone derivatives, hirsutavibrins A-K (1-11). The structures of 1-11 were elucidated by extensive NMR and HRESIMS spectroscopic analysis, and computational methods. Hirsutavibrins A (1) and B (2) showed weak cytotoxicity against the human lung cancer cell line A549. Hirsutavibrin D (4) showed moderate anti-nitric oxide activity in murine monocytic RAW 264.7 macrophages. This work not only expands the members of vibralactone derivatives with variable configurations but also opens a new avenue for fungal co-culturing study between congeneric fungi.

关键词: Stereum hirsutum, Boreostereum vibrans, Basidiomycetes, Co-culture, Vibralactone derivatives

Jinjuan Wei, Zhe-Xi Li, Gao-Ke Peng, Xinyang Li, He-Ping Chen, Ji-Kai Liu. Vibralactone derivatives isolated from co-cultures of the basidiomycetes Stereum hirsutum and Boreostereum vibrans[J]. Natural Products and Bioprospecting, 2025, 15(2): 20-20.

References

[1] Feng L, Shang R-R, Wang XJ, Li L, Li X, Gong Y-X, Shi L-Y, Wang JW, Qian ZY, Tan NH, Wang Z. The natural alkaloid (-)-N-Hydroxyapiosporamide suppresses colorectal tumor progression as an NF-κB pathway inhibitor by targeting the TAK1-TRAF6 Complex. J Nat Prod. 2023;86:1449-62.
[2] Chen Y, Li Q, Li Y, Zhang W, Liang Y, Fu A, Wei M, Sun W, Chen C, Zhang Y, Zhu H. Quadriliterpenoids A - I, nine new 4,4-dimethylergostane and oleanane triterpenoids from Aspergillus quadrilineatus with immunosuppressive inhibitory activity. Nat Prod Bioprospect. 2024;14:59.
[3] Ma R, Feng XY, Tang JJ, Ha W, Shi YP. 5α-Epoxyalantolactone from Inula macrophylla attenuates cognitive deficits in scopolamine-induced Alzheimer’s disease mice model. Nat Prod Bioprospect. 2024;14:39.
[4] Peng W, Huang Q, Ke X, Wang W, Chen Y, Sang Z, Chen C, Qin S, Zheng Y, Tan H, Zou Z. Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5. Nat Prod Bioprospect. 2024;14:8.
[5] Sresuksai K, Sawadsitang S, Jantaharn P, Noppawan P, Churat A, Suwannasai N, Mongkolthanaruk W, Senawong T, Tontapha S, Moontragoon P, Amornkitbamrung V, McCloskey S. Antiproliferative polyketides from fungus Xylaria cf. longipes SWUF08-81 in different culture media. Nat Prod Bioprospect. 2024;14:6.
[6] Zhou L, Akbar S, Wang MX, Chen HP, Liu JK. Tetra-, penta-, and hexa-nor-lanostane triterpenes from the medicinal fungus Ganoderma australe. Nat Prod Bioprospect. 2022;12:32.
[7] Zhang JJ, Tang X, Moore BS. Genetic platforms for heterologous expression of microbial natural products. Nat Prod Rep. 2019;36:1313-32.
[8] Schueffler A, Anke T. Fungal natural products in research and development. Nat Prod Rep. 2014;31:1425-48.
[9] Liu SL, Zhou L, Chen HP, Liu JK. Sesquiterpenes with diverse skeletons from histone deacetylase inhibitor modified cultures of the basidiomycete Cyathus stercoreus (Schwein) De Toni HFG134. Phytochemistry. 2022;195:113048.
[10] Hu Z, Ye Y, Zhang Y. Large-scale culture as a complementary and practical method for discovering natural products with novel skeletons. Nat Prod Rep. 2021;38:1775-93.
[11] Starnovskaya SS, Nesterenko LE, Popov RS, Kirichuk NN, Chausova VE, Chingizova EA, Chingizov AR, Isaeva MP, Yurchenko EA, Yurchenko AN. Metabolite profiles of Paragliomastix luzulae (formerly named as Acremonium striatisporum) KMM 4401 and its co-cultures with Penicillium hispanicum KMM 4689. Nat Prod Bioprospect. 2024;14:38.
[12] Lyu HN, Liu HW, Keller NP, Yin WB. Harnessing diverse transcriptional regulators for natural product discovery in fungi. Nat Prod Rep. 2020;37:6-16.
[13] Xu Y, Du X, Yu X, Jiang Q, Zheng K, Xu J, Wang P. Recent advances in the heterologous expression of biosynthetic gene clusters for marine natural products. Mar Drugs. 2022;20:341.
[14] Wang QY, Chen HP, Wu KY, Li X, Liu JK. Antibacterial and β-amyloid precursor protein-cleaving enzyme 1 inhibitory polyketides from the fungus Aspergillus chevalieri. Front Microbiol. 2022;13:1051281.
[15] Tang Y, Zhao ZZ, Yao JN, Feng T, Li ZH, Chen HP, Liu JK. Irpeksins A-E, 1,10-seco-eburicane-type triterpenoids from the medicinal fungus Irpex lacteus and Their Anti-NO Activity. J Nat Prod. 2018;81:2163-8.
[16] Tang Y, Zhao ZZ, Hu K, Feng T, Li ZH, Chen HP, Liu JK. Irpexolidal represents a class of triterpenoid from the fruiting bodies of the medicinal fungus Irpex lacteus. J Org Chem. 2019;84:1845-52.
[17] Li X, Chen HP, Zhou L, Fan J, Awakawa T, Mori T, Ushimaru R, Abe I, Liu JK. Cordycicadins A-D, antifeedant polyketides from the entomopathogenic fungus Cordyceps cicadae JXCH1. Org Lett. 2022;24:8627-32.
[18] Wang QY, Chen HP, Tao H, Li X, Zhao Q, Liu JK. Penidaleodiolides A and B, cage-like polyketides with neurotransmission-regulating activity from the soil fungus Penicillium daleae L3SO. Org Lett. 2024;26:7632-7.
[19] Liu DZ, Wang F, Liao TG, Tang JG, Steglich W, Zhu HJ, Liu JK. Vibralactone: a lipase inhibitor with an unusual fused β-lactone produced by cultures of the basidiomycete Boreostereum vibrans. Org Lett. 2006;8:5749-52.
[20] Jiang MY, Wang F, Yang XL, Fang LZ, Dong ZJ, Zhu HJ, Liu JK. Derivatives of vibralactone from cultures of the basidiomycete Boreostereum vibrans. Chem Pharm Bull. 2008;56:1286-8.
[21] Jiang MY, Zhang L, Dong ZJ, Yang ZL, Leng Y, Liu JK. Vibralactones D-F from cultures of the basidiomycete Boreostereum vibrans. Chem Pharm Bull. 2010;58:113-6.
[22] Wang GQ, Wei K, Feng T, Li ZH, Zhang L, Wang QA, Liu JK. Vibralactones G-J from cultures of the basidiomycete Boreostereum vibrans. J Asian Nat Prod Res. 2012;14:115-20.
[23] Chen HP, Zhao ZZ, Li ZH, Dong ZJ, Wei K, Bai X, Zhang L, Wen CN, Feng T, Liu JK. Novel Natural oximes and oxime esters with a vibralactone backbone from the basidiomycete Boreostereum vibrans. Chemistryopen. 2016;5:142-9.
[24] Zhao PJ, Yang YL, Du LC, Liu JK, Zeng Y. Elucidating the biosynthetic pathway for vibralactone: a pancreatic lipase inhibitor with a fused bicyclic β-lactone. Angew Chem Int Ed. 2013;52:2298-302.
[25] Yang YL, Zhou H, Du G, Feng KN, Feng T, Fu XL, Liu JK, Zeng Y. A monooxygenase from Boreostereum vibrans catalyzes oxidative decarboxylation in a divergent vibralactone biosynthesis pathway. Angew Chem Int Ed. 2016;55:5463-6.
[26] Feng KN, Yang YL, Xu YX, Zhang Y, Feng T, Huang SX, Liu JK, Zeng Y. A hydrolase-catalyzed cyclization forms the fused bicyclic β-lactone in vibralactone. Angew Chem Int Ed. 2020;59:7209-13.
[27] Feng KN, Zhang Y, Zhang MF, Yang YL, Liu JK, Pan LF, Zeng Y. A flavin-monooxygenase catalyzing oxepinone formation and the complete biosynthesis of vibralactone. Nat Commun. 2023;14:3436.
[28] Nistanaki SK, Boralsky LA, Pan RD, Nelson HM. A concise total synthesis of (±)-vibralactone. Angew Chem Int Ed. 2019;58:1724-6.
[29] Zhao ZZ, Zhang F, He HJ, Wang Y, Du JH, Wang ZZ, Chen H, Liu JK, Stereuins AF. Isopentenyl benzene congeners with antibacterial and neurotrophic activities from Stereum hirsutum HFG27. Phytochemistry. 2024;228: 114253.
[30] Zhao ZZ, Han KY, Li Z-H, Feng T, Chen HP, Liu JK. Cytotoxic ergosteroids from the fungus Stereum hirsutum. Phytochemistry Lett. 2019;30:143-9.
[31] Zhao ZZ, Zhao X, Si YY, Wang ZZ, Sun YJ, Chen HP, Feng WS, Liu JK. Structure elucidation of linear triquinane sesquiterpenoids, hirsutuminoids A-Q, from the fungus Stereum hirsutum and their activities. Phytochemistry. 2022;200: 113227.
[32] Wang G, Ran H, Fan J, Keller NP, Liu Z, Wu F, Yin W-B. Fungal-fungal cocultivation leads to widespread secondary metabolite alteration requiring the partial loss-of-function VeA1 protein. Sci Adv. 2022;8:eabo6094.
[33] Yao L, Zhu LP, Xu XY, Tan LL, Sadilek M, Fan H, Hu B, Shen XT, Yang J, Qiao B, Yang S. Discovery of novel xylosides in co-culture of basidiomycetes Trametes versicolor and Ganoderma applanatum by integrated metabolomics and bioinformatics. Sci Rep. 2016;6:33237.
[34] Yu G, Ge X, Wang Y, Mo X, Yu H, Tan L, Yang S. Discovery of novel terpenoids from the basidiomycete Pleurotus ostreatus through genome mining and coculture optimization. J Agric Food Chem. 2023;71:11110-23.
[35] Shen XT, Mo XH, Zhu LP, Tan LL, Du FY, Wang QW, Zhou YM, Yuan XJ, Qiao B, Yang S. Unusual and highly bioactive sesterterpenes synthesized by Pleurotus ostreatus during coculture with Trametes robiniophila Murr. Appl Environ Microbiol. 2019;85:e00293-e319.
[36] Xiong J, Zhou PJ, Jiang HW, Huang T, He YH, Zhao ZY, Zang Y, Choo YM, Wang X, Chittiboyina AG, Pandey P, Hamann MT, Li J, Hu JF. Forrestiacids A and B, pentaterpene inhibitors of acl and lipogenesis: extending the limits of computational NMR methods in the structure assignment of complex natural products. Angew Chem Int Ed. 2021;60:22270-5.
[37] Chen HP, Jiang MY, Zhao ZZ, Feng T, Li ZH, Liu JK. Vibralactone biogenesis-associated analogues from submerged cultures of the fungus Boreostereum vibrans. Nat Prod Bioprospect. 2018;8:37-45.

Vibralactone derivatives isolated from co-cultures of the basidiomycetes Stereum hirsutum and Boreostereum vibrans

Vibralactone derivatives isolated from co-cultures of the basidiomycetes Stereum hirsutum and Boreostereum vibrans

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 5

Recommended Articles

Metrics

Comments

[1]	Asih Triastuti, Marieke Vansteelandt, Fatima Barakat, Carlos Amasifuen, Patricia Jargeat, Mohamed Haddad. Untargeted metabolomics to evaluate antifungal mechanism: a study of Cophinforma mamane and Candida albicans interaction [J]. Natural Products and Bioprospecting, 2023, 13(1): 1-1.
[2]	He-Ping Chen, Meng-Yuan Jiang, Zhen-Zhu Zhao, Tao Feng, Zheng-Hui Li, Ji-Kai Liu. Vibralactone Biogenesis-Associated Analogues from Submerged Cultures of the Fungus Boreostereum vibrans [J]. Natural Products and Bioprospecting, 2018, 8(1): 37-45.
[3]	Kun Wei, Gang-Qiang Wang, Xue Bai, Yan-Fen Niu, He-Ping Chen, Chun-Nan Wen, Zheng-Hui Li, Ze-Jun Dong, Zhi-Li Zuo, Wen-Yong Xiong, Ji-Kai Liu. Structure-Based Optimization and Biological Evaluation of Pancreatic Lipase Inhibitors as Novel Potential Antiobesity Agents [J]. Natural Products and Bioprospecting, 2015, 5(3): 129-157.
[4]	He-Ping Chen, Zhen-Zhu Zhao, Rong-Hua Yin, Xia Yin, Tao Feng, Zheng-Hui Li, Kun Wei, Ji-Kai Liu. Six New Vibralactone Derivatives from Cultures of the Fungus Boreostereum vibrans [J]. Natural Products and Bioprospecting, 2014, 4(5): 271-276.
[5]	Jian-Hai DING, Tao FENG, Zheng-Hui LI, Liang LI, Ji-Kai LIU. Twelve new compounds from the basidiomycete Boreostereum vibrans [J]. Natural Products and Bioprospecting, 2012, 2(5): 200-205.