| SHORT COMMUNICATION |
|
|
|
|
|
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 |
|
|
|
|
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.
|
| Keywords
Alternaria brassicicola
Secondary metabolites
Amide derivatives
Structural elucidation
|
| Fund: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). |
|
Corresponding Authors:
Jieru Guo,E-mail:guojieru314@163.com;Zhengxi Hu,E-mail:hzx616@126.com;Yonghui Zhang,E-mail:zhangyh@mails.tjmu.edu.cn
E-mail: guojieru314@163.com;hzx616@126.com;zhangyh@mails.tjmu.edu.cn
|
|
Issue Date: 08 October 2023
|
|
|
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[9.2.1.03,7]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. |
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
| |
Shared |
|
|
|
|
| |
Discussed |
|
|
|
|
