Three new pyrrole alkaloids from the endophytic fungus Albifimbria viridis

doi:10.1007/s13659-022-00327-2

应用天然产物 ›› 2022, Vol. 12 ›› Issue (1): 1-5.DOI: 10.1007/s13659-022-00327-2

• •

Three new pyrrole alkaloids from the endophytic fungus Albifimbria viridis

Pan-Pan Wei, Jia-Cheng Ji, Xu-Jun Ma, Zheng-Hui Li, Hong-Lian Ai, Xin-Xiang Lei, Ji-Kai Liu

School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, People's Republic of China

收稿日期:2021-09-04 修回日期:2021-11-08 出版日期:2022-02-24 发布日期:2022-03-12
通讯作者: Hong-Lian Ai, Xin-Xiang Lei, Ji-Kai Liu
基金资助:
National Natural Science Foundation of China (31870513), Zheng-Hui Li, National Aerospace Science Foundation of China (32000011), Hong-Lian Ai.

Three new pyrrole alkaloids from the endophytic fungus Albifimbria viridis

Pan-Pan Wei, Jia-Cheng Ji, Xu-Jun Ma, Zheng-Hui Li, Hong-Lian Ai, Xin-Xiang Lei, Ji-Kai Liu

School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, People's Republic of China

Received:2021-09-04 Revised:2021-11-08 Online:2022-02-24 Published:2022-03-12
Contact: Hong-Lian Ai, Xin-Xiang Lei, Ji-Kai Liu
Supported by:
National Natural Science Foundation of China (31870513), Zheng-Hui Li, National Aerospace Science Foundation of China (32000011), Hong-Lian Ai.

摘要/Abstract

摘要： Three new pyrrole alkaloids albifipyrrols A-C (1-3), were isolated from the endophytic fungus Albifimbria viridis collected from the Chinese medicinal plant. Their structures were elucidated by extensive NMR and HRESIMS spectrometric analyses. All compounds were evaluated for immunosuppressive activity. Fortunately, compound 2 exhibits certain inhibition specifically against the LPS-induced proliferation of B lymphocyte cells with IC₅₀ value 16.16 μM.

关键词: Pyrrole alkaloids, Coptis chinensis, Endophytic fungus, Albifimbria viridis, Immunosuppressive activity

Abstract: Three new pyrrole alkaloids albifipyrrols A-C (1-3), were isolated from the endophytic fungus Albifimbria viridis collected from the Chinese medicinal plant. Their structures were elucidated by extensive NMR and HRESIMS spectrometric analyses. All compounds were evaluated for immunosuppressive activity. Fortunately, compound 2 exhibits certain inhibition specifically against the LPS-induced proliferation of B lymphocyte cells with IC₅₀ value 16.16 μM.

Key words: Pyrrole alkaloids, Coptis chinensis, Endophytic fungus, Albifimbria viridis, Immunosuppressive activity

Pan-Pan Wei, Jia-Cheng Ji, Xu-Jun Ma, Zheng-Hui Li, Hong-Lian Ai, Xin-Xiang Lei, Ji-Kai Liu. Three new pyrrole alkaloids from the endophytic fungus Albifimbria viridis[J]. 应用天然产物, 2022, 12(1): 1-5.

参考文献

1. Chen HP, Zhao ZZ, Cheng GG, Zhao K, Han KY, Zhou L, Feng T, Li ZH, Liu JK. Immunosuppressive nor-isopimarane diterpenes from cultures of the fungicolous fungus Xylaria longipes HFG1018. J Nat Prod. 2020;83:401-12.
2. Lleo A, Invernizzi P, Gao B, Podda M, Gershwin ME. Definition of human autoimmunity-autoantibodies versus autoimmune disease. Autoimmun Rev. 2010;9:A259-66.
3. Gao Y, Duan FF, Liu L, Peng XG, Meng XG, Ruan HL. Hypothemycin-type resorcylic acid lactones with immunosuppressive activities from a Podospora sp. J Nat Prod. 2021;84:483-94.
4. Feng T, Duan KT, He SJ, Wu B, Zheng YS, Ai HL, Li ZH, He J, Zuo JP, Liu JK. Ophiorrhines A and B, two immunosuppressive monoterpenoid indole alkaloids from Ophiorrhiza japonica. Org Lett. 2018;20:7926-8.
5. Shou QY, Fu RZ, Tan Q, Shen ZW. Geranylated flavonoids from the roots of Campylotropis hirtella and their immunosuppressive activities. J Agric Food Chem. 2009;57:6712-9.
6. Kiuchi M, Adachi K, Kohara T, Minoguchi M, Hanano T, Aoki Y, Mishina T, Arita M, Nakao N, Ohtsuki M, Hoshino Y, Teshima K, Chiba K, Sasaki S, Fujita T. Synthesis and immunosuppressive activity of 2-substituted 2-aminopropane-1,3-diols and 2-aminoethanols. J Med Chem. 2000;43:2946-61.
7. Ujam NT, Ajaghaku DL, Okoye FBC, Esimone CO. Antioxidant and immunosuppressive activities of extracts of endophytic fungi isolated from Psidium guajava and Newbouldia laevis. Phytomedicine Plus. 2021;1:100028.
8. D'Alessio R, Bargiotti A, Carlini O, Colotta F, Ferrari M, Gnocchi P, Isetta A, Mongelli N, Motta P, Rossi A, Rossi M, Tibolla M, Vanotti E. Synthesis and immunosuppressive activity of novel prodigiosin derivatives. J Med Chem. 2000;43:2557-65.
9. Liu J, Li H, Chen KX, Zuo JP, Guo YW, Tang W, Li XW. Design and synthesis of marine phidianidine derivatives as potential immunosuppressive agents. J Med Chem. 2018;61:11298-308.
10. Johnston A. Equivalence and interchangeability of narrow therapeutic index drugs in organ transplantation. Eur J Hosp Pharm. 2013;20:302-7.
11. Smith JM, Nemeth TL, McDonald RA. Current immunosuppressive agents:efficacy, side effects, and utilization. Pediatr Clin N Am. 2003;50:1283-300.
12. Gordaliza M, Faircloth GT, Castro MA, Miguel del Corral JM, López-Vázquez ML, San FA. Immunosuppressive cyclolignans. J Med Chem. 1996;39:2865-8.
13. Li G, Kusari S, Lamshoft M, Schuffler A, Laatsch H, Spiteller M. Antibacterial secondary metabolites from an endophytic fungus, Eupenicillium sp. LG41. J Nat Prod. 2014;77:2335-41.
14. Lin X, Lu C, Huang Y, Zheng Z, Su W, Shen Y. Endophytic fungi from a pharmaceutical plant, Camptotheca acuminata:isolation, identification and bioactivity. World J Microbiol Biotechnol. 2007;23:1037-40.
15. Chen HJ, Awakawa T, Sun JY, Wakimoto T, Abe I. Epigenetic modifierinduced biosynthesis of novel fusaric acid derivatives in endophytic fungi from Datura stramonium L. Nat Prod Bioprospect. 2013;3:20-3.
16. Feng L, Wang J, Liu S, Zhang XJ, Bi QR, Hu YY, Wang Z, Tan NH. Colletopeptides A-D, anti-inflammatory cyclic tridepsipeptides from the plant endophytic fungus Colletotrichum sp. S8. J Nat Prod. 2019;82:1434-41.
17. Kuang C, Jing SX, Liu Y, Luo SH, Li SH. Drimane sesquiterpenoids and Isochromone derivative from the endophytic fungus Pestalotiopsis sp. M-23. Nat Prod Bioprospect. 2016;6:155-60.
18. Kim D, Simborio HL, Reyes AW, Min W, Lee HJ, Lee J, Chang H, Kim D. Antibacterial effects of Coptis chinensis Franch against Brucella abortus. J Agric Life Sci. 2014;48:107-14.
19. Fan DL, Xiao XH, Ma XJ. Calorimetric study of the effect of protoberberine alkaloids in Coptis chinensis Franch on Staphylococcus aureus growth. Thermochim Acta. 2008;480:49-52.
20. Zhang XH, Zhang DJ, Liu JL, Pan HY, Qin JC, Zhang YH. Antifungal effects of volatile organic compounds from the endophytic fungus Cryptosporiopsis ericae Cc-HG-7 isolated from Coptis chinensis Franch. Biocontrol Sci Technol. 2018;28:496-508.

[1]	Wei-Ye Wu, Xun Wei, Qiong Liao, Yi-Fan Fu, Lei-Ming Wu, Lei Li, Shu-Qi Wu, Qing-Ren Lu, Fang-Yu Yuan, Dong Huang, Zhang-Hua Sun, Tao Yuan, Gui-Hua Tang. Structurally diverse polyketides and alkaloids produced by a plant-derived fungus Penicillium canescens L1[J]. 应用天然产物, 2025, 15(3): 22-22.
[2]	Yu Chen, Qin Li, Yongqi Li, Wenyi Zhang, Yu Liang, Aimin Fu, Mengsha Wei, Weiguang Sun, Chunmei Chen, Yonghui Zhang, Hucheng Zhu. Quadriliterpenoids A-I, nine new 4,4-dimethylergostane and oleanane triterpenoids from Aspergillus quadrilineatus with immunosuppressive inhibitory activity[J]. 应用天然产物, 2024, 14(6): 59-59.
[3]	Yin-Zhong Fan, Chun Tian, Shun-Yao Tong, Qing Liu, Fan Xu, Bao-Bao Shi, Hong-Lian Ai, Ji-Kai Liu. The antifungal properties of terpenoids from the endophytic fungus Bipolaris eleusines[J]. 应用天然产物, 2023, 13(6): 43-43.
[4]	Ning-Ning Wang, Chun-Yu Liu, Tian Wang, Yue-Lan Li, Ke Xu, Hong-Xiang Lou. Two New Quinazoline Derivatives from the Moss Endophytic Fungus Aspergillus sp. and Their Anti-inflammatory Activity[J]. 应用天然产物, 2021, 11(1): 105-110.
[5]	Xiao-Zheng Su, Jian-Wei Tang, Kun Hu, Xiao-Nian Li, Han-Dong Sun, Pema-Tenzin Puno. Arthrinins E-G, Three Botryane Sesquiterpenoids from the Plant Endophytic Fungus Arthrinium sp. HS66[J]. 应用天然产物, 2020, 10(4): 201-207.
[6]	Wen-Jie Sun, Hong-Tao Zhu, Tian-Yuan Zhang, Meng-Yue Zhang, Dong Wang, Chong-Ren Yang, Yi-Xuan Zhang, Ying-Jun Zhang. Two New Alkaloids from Fusarium tricinctum SYPF 7082, an Endophyte from the Root of Panax notoginseng[J]. 应用天然产物, 2018, 8(5): 391-396.
[7]	Rong Chen, Jian-Wei Tang, Xing-Ren Li, Miao Liu, Wen-Ping Ding, Yuan-Fei Zhou, Wei-Guang Wang, Xue Du, Han-Dong Sun, Pema-Tenzin Puno. Secondary Metabolites from the Endophytic Fungus Xylaria sp. Hg1009[J]. 应用天然产物, 2018, 8(2): 121-129.

Three new pyrrole alkaloids from the endophytic fungus Albifimbria viridis

Three new pyrrole alkaloids from the endophytic fungus Albifimbria viridis

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 7

编辑推荐

Metrics

本文评价