Three new amide derivatives from the fungus Alternaria brassicicola

doi:10.1007/s13659-023-00391-2

Natural Products and Bioprospecting ›› 2023, Vol. 13 ›› Issue (4): 28-28.DOI: 10.1007/s13659-023-00391-2

• SHORT COMMUNICATION • Previous Articles Next Articles

Three new amide derivatives from the fungus Alternaria brassicicola

Fengli Li¹, Saisai Gu², Sitian Zhang¹, Shuyuan Mo¹, Jieru Guo³, Zhengxi Hu¹, Yonghui Zhang¹

1. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, China;
2. Department of Pharmacy, Union Hospital, Tongji Medical college, Huazhong University of Science and Technology, Wuhan, 430022, China;
3. Department of Pharmacy, Tongji Hospital, Tongji Medical college, Huazhong University of Science and Technology, Wuhan, 430033, China

Received:2023-07-24 Online:2023-10-08 Published:2023-08-24
Contact: Jieru Guo,E-mail:guojieru314@163.com;Zhengxi Hu,E-mail:hzx616@126.com;Yonghui Zhang,E-mail:zhangyh@mails.tjmu.edu.cn
Supported by:
This project was financially supported by the National Program for Support of Top-notch Young Professionals (No. 0106514050), the National NSFC (Nos. 82273811 and 82104043), the National Key R&D Program of China (No. 2021YFA0910500), the National NSF for Distinguished Young Scholars (No. 81725021), the Innovative Research Groups of the National NSFC (No. 81721005), and the Academic Frontier Youth Team of HUST (No. 2017QYTD19).

Three new amide derivatives from the fungus Alternaria brassicicola

Fengli Li¹, Saisai Gu², Sitian Zhang¹, Shuyuan Mo¹, Jieru Guo³, Zhengxi Hu¹, Yonghui Zhang¹

1. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, China;
2. Department of Pharmacy, Union Hospital, Tongji Medical college, Huazhong University of Science and Technology, Wuhan, 430022, China;
3. Department of Pharmacy, Tongji Hospital, Tongji Medical college, Huazhong University of Science and Technology, Wuhan, 430033, China

通讯作者: Jieru Guo,E-mail:guojieru314@163.com;Zhengxi Hu,E-mail:hzx616@126.com;Yonghui Zhang,E-mail:zhangyh@mails.tjmu.edu.cn
基金资助:
This project was financially supported by the National Program for Support of Top-notch Young Professionals (No. 0106514050), the National NSFC (Nos. 82273811 and 82104043), the National Key R&D Program of China (No. 2021YFA0910500), the National NSF for Distinguished Young Scholars (No. 81725021), the Innovative Research Groups of the National NSFC (No. 81721005), and the Academic Frontier Youth Team of HUST (No. 2017QYTD19).

Abstract

Abstract: Three new amide derivatives (alteralkaloids A–C, 1–3) and three known alkaloids (4–6) were afforded after phytochemical investigation of fungus Alternaria brassicicola. The structures of these compounds were confirmed by NMR spectroscopic and HRESIMS data. Furthermore, the absolute configuration of 1 was determined using the single-crystal X-ray diffraction analysis. Compounds 1–3 belong to a class of amide derivatives that have not been found in nature before, sharing the same characteristic signals of the butyl moiety and amide group. These isolated compounds mentioned above were tested for the cytotoxic activity.

Key words: Alternaria brassicicola, Secondary metabolites, Amide derivatives, Structural elucidation

摘要： Three new amide derivatives (alteralkaloids A–C, 1–3) and three known alkaloids (4–6) were afforded after phytochemical investigation of fungus Alternaria brassicicola. The structures of these compounds were confirmed by NMR spectroscopic and HRESIMS data. Furthermore, the absolute configuration of 1 was determined using the single-crystal X-ray diffraction analysis. Compounds 1–3 belong to a class of amide derivatives that have not been found in nature before, sharing the same characteristic signals of the butyl moiety and amide group. These isolated compounds mentioned above were tested for the cytotoxic activity.

关键词: Alternaria brassicicola, Secondary metabolites, Amide derivatives, Structural elucidation

Fengli Li, Saisai Gu, Sitian Zhang, Shuyuan Mo, Jieru Guo, Zhengxi Hu, Yonghui Zhang. Three new amide derivatives from the fungus Alternaria brassicicola[J]. Natural Products and Bioprospecting, 2023, 13(4): 28-28.

Fengli Li, Saisai Gu, Sitian Zhang, Shuyuan Mo, Jieru Guo, Zhengxi Hu, Yonghui Zhang. Three new amide derivatives from the fungus Alternaria brassicicola[J]. 应用天然产物, 2023, 13(4): 28-28.

References

1. Lou J, Fu L, Peng Y, Zhou L. Metabolites from Alternaria fungi and their bioactivities. Molecules. 2013;18:5891–935.
2. Ye K, Ai HL, Liu JK. Identification and bioactivities of secondary metabolites derived from endophytic fungi isolated from ethnomedicinal plants of Tujia in Hubei Province: a review. Nat Prod Bioprospect. 2021;11:185–205.
3. Toghueo RMK. Anti-leishmanial and anti-inflammatory agents from endophytes: a review. Nat Prod Bioprospect. 2019;9:311–28.
4. Kim MY, Sohn JH, Ahn JS, Oh H. Alternaramide, a cyclic depsipeptide from the marine-derived fungus Alternaria sp. SF-5016. J Nat Prod. 2009;72:2065–8.
5. Li F, Lin S, Zhang S, Pan L, Chai C, Su JC, Yang B, Liu J, Wang J, Hu Z, Zhang Y. Modified fusicoccane-type diterpenoids from Alternaria brassicicola. J Nat Prod. 2020;83:1931–8.
6. Wang HL, Li R, Li J, He J, Cao ZY, Kurtan T, Mandi A, Zheng GL, Zhang W. Alternarin A, a drimane meroterpenoid, suppresses neuronal excitability from the coral-associated fungi Alternaria sp. ZH-15. Org Lett. 2020;22:2995–8.
7. Wu JC, Hou Y, Xu Q, Jin XJ, Chen Y, Fang J, Hu B, Wu QX. (+/-)-Alternamgin, a pair of enantiomeric polyketides, from the endophytic fungi Alternaria sp. MG1. Org Lett. 2019;21:1551–4.
8. Zou J, Zhang S, Zhao H, Wang YH, Zhou ZQ, Chen GD, Hu D, Li N, Yao XS, Gao H. Biotransformation of alpha-asarone by Alternaria longipes CGMCC 3.2875. Chin J Nat Med. 2021;19:700–5.
9. Hu Z, Sun W, Li F, Guan J, Lu Y, Liu J, Tang Y, Du G, Xue Y, Luo Z, Wang J, Zhu H, Zhang Y. Fusicoccane-derived diterpenoids from Alternaria brassicicola: investigation of the structure–stability relationship and discovery of an IKKβ inhibitor. Org Lett. 2018;20:5198–202.
10. Leyte-Lugo M, Richomme P, Poupard P, Pena-Rodriguez LM. Identification and quantification of a phytotoxic metabolite from Alternaria dauci. Molecules. 2020;25:4003–14.
11. Li F, Pan L, Lin S, Zhang S, Li H, Yang B, Liu J, Wang J, Hu Z, Zhang Y. Fusicoccane-derived diterpenoids with bridgehead double-bond-containing tricyclo[9.2.1.0^3,7]tetradecane ring systems from Alternaria brassicicola. Bioorg Chem. 2020;100:103887.
12. Yang CL, Wu HM, Liu CL, Zhang X, Guo ZK, Chen Y, Liu F, Liang Y, Jiao RH, Tan RX, Ge HM. Bialternacins A–F, aromatic polyketide dimers from an endophytic Alternaria sp. J Nat Prod. 2019;82:792–7.
13. Dalinova A, Chisty L, Kochura D, Garnyuk V, Petrova M, Prokofieva D, Yurchenko A, Dubovik V, Ivanov A, Smirnov S, Zolotarev A, Berestetskiy A. Isolation and bioactivity of secondary metabolites from solid culture of the fungus, Alternaria sonchi. Biomolecules. 2020;10:81–98.
14. Tang Y, Xue Y, Du G, Wang J, Liu J, Sun B, Li XN, Yao G, Luo Z, Zhang Y. Structural revisions of a class of natural products: scaffolds of aglycon analogues of fusicoccins and cotylenins isolated from fungi. Angew Chem Int Ed. 2016;55:4069–73.
15. Li F, Sun W, Guan J, Lu Y, Zhang S, Lin S, Liu J, Gao W, Wang J, Hu Z, Zhang Y. Alterbrassicicene A, a highly transformed fusicoccane-derived diterpenoid with potent PPAR-γ agonistic activity from Alternaria brassicicola. Org Lett. 2018;20:7982–6.
16. Li F, Lin S, Zhang S, Hao X, Li XN, Yang B, Liu J, Wang J, Hu Z, Zhang Y. Alterbrassinoids A–D: fusicoccane-derived diterpenoid dimers featuring different carbon skeletons from Alternaria brassicicola. Org Lett. 2019;21:8353–7.
17. Kuo PC, Hwang TL, Lin YT, Kuo YC, Leu YL. Chemical constituents from Lobelia chinensis and their anti-virus and anti-inflammatory bioactivities. Arch Pharm Res. 2011;34:715–22.
18. Kim SB, Chang BY, Hwang BY, Kim SY, Lee MK. Pyrrole alkaloids from the fruits of Morus alba. Bioorg Med Chem Lett. 2014;24:5656–9.
19. Chen CJ, Deng AJ, Liu C, Shi R, Qin HL, Wang AP. Hepatoprotective activity of Cichorium endivia L. extract and its chemical constituents. Molecules. 2011;16:9049–66.

[1]	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]. Natural Products and Bioprospecting, 2025, 15(2): 17-17.
[2]	Olusesan Ojo, Idris Njanje, Dele Abdissa, Tarryn Swart, Roxanne L. Higgitt, Rosemary A. Dorrington. Newly isolated terpenoids (covering 2019-2024) from Aspergillus species and their potential for the discovery of novel antimicrobials [J]. Natural Products and Bioprospecting, 2025, 15(2): 19-19.
[3]	Ismail Ware, Katrin Franke, Andrej Frolov, Kseniia Bureiko, Elana Kysil, Maizatulakmal Yahayu, Hesham Ali El Enshasy, Ludger A. Wessjohann. Comparative metabolite analysis of Piper sarmentosum organs approached by LC-MS-based metabolic profiling [J]. Natural Products and Bioprospecting, 2024, 14(4): 30-30.
[4]	Weiwei Peng, Qi Huang, Xin Ke, Wenxuan Wang, Yan Chen, Zihuan Sang, Chen Chen, Siyu Qin, Yuting Zheng, Haibo Tan, Zhenxing Zou. Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5 [J]. Natural Products and Bioprospecting, 2024, 14(1): 8-8.
[5]	Kritika Jalota, Vikas Sharma, Chiti Agarwal, Suruchi Jindal. Eco-friendly approaches to phytochemical production: elicitation and beyond [J]. Natural Products and Bioprospecting, 2024, 14(1): 5-5.
[6]	Li Wu, Ning Yang, Meng Guo, Didi Zhang, Reza A. Ghiladi, Hasan Bayram, Jun Wang. The role of sound stimulation in production of plant secondary metabolites [J]. Natural Products and Bioprospecting, 2023, 13(6): 40-40.
[7]	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]. Natural Products and Bioprospecting, 2023, 13(3): 17-17.
[8]	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]. Natural Products and Bioprospecting, 2021, 11(6): 651-658.
[9]	Ke Ye, Hong-Lian Ai, Ji-Kai Liu. Identification and Bioactivities of Secondary Metabolites Derived from Endophytic Fungi Isolated from Ethnomedicinal Plants of Tujia in Hubei Province: A Review [J]. Natural Products and Bioprospecting, 2021, 11(2): 185-205.
[10]	Xia Wang, Xing-Rong Peng, Jing Lu, Gui-Lin Hu, Ming-Hua Qiu. New Dammarane Triterpenoids, Caffruones A-D, from the Cherries of Coffea arabica [J]. Natural Products and Bioprospecting, 2018, 8(6): 413-418.
[11]	Gao-Wei Li, Han Liu, Feng Qiu, Xiao-Juan Wang, Xin-Xiang Lei. Residual Dipolar Couplings in Structure Determination of Natural Products [J]. Natural Products and Bioprospecting, 2018, 8(4): 279-295.
[12]	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]. Natural Products and Bioprospecting, 2018, 8(2): 121-129.
[13]	Rui Chu, Luo-Sheng Wan, Xing-Rong Peng, Mu-Yuan Yu, Zhi-Run Zhang, Lin Zhou, Zhong-Rong Li, Ming-Hua Qiu. Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans [J]. Natural Products and Bioprospecting, 2016, 6(4): 217-223.
[14]	Ming-Ming Zhai, Jie Li, Chun-Xiao Jiang, Yan-Ping Shi, Duo-Long Di, Phillip Crews, Quan-Xiang Wu. The Bioactive Secondary Metabolites from Talaromyces species [J]. Natural Products and Bioprospecting, 2016, 6(1): 1-24.
[15]	Frank Surup, Eric Kuhnert, Elena Liscinskij, Marc Stadler. Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii(Xylariaceae) [J]. Natural Products and Bioprospecting, 2015, 5(3): 167-173.

Three new amide derivatives from the fungus Alternaria brassicicola

Three new amide derivatives from the fungus Alternaria brassicicola

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments