Short Communication |
|
|
|
|
|
Drimane sesquiterpenoids from a wetland soil-derived fungus Aspergillus calidoustus TJ403-EL05 |
Sitian Zhang, Shuyuan Mo, Fengli Li, Yaxin Zhang, Jianping Wang, Zhengxi Hu, Yonghui Zhang |
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 |
|
|
Abstract Soil-derived fungi represent an insufficiently tapped reservoir for discovering new and bioactive natural products (NPs), and despite an ever-increasing number of unknown NPs have been discovered over the past few decades, much of the hidden biosynthetic potential is still in an urgent need to be disclosed. In this research, a chemical investigation was performed on a wetland soil-derived fungus Aspergillus calidoustus TJ403-EL05, leading to the isolation of a total of fourteen drimane sesquiterpenoids (1-14), incorporating three new ones, namely ustusols F-H (1-3). Their structures, comprising absolute configurations, were completely authenticated by widespread spectroscopic data, quantum chemical 13C NMR and ECD calculations, and X-ray crystallography experiments. Compound 14 exhibited moderate anti-inflammatory activity by inhibiting the LPS-induced NO release (IC50=25.6 μM).
|
Keywords
Aspergillus calidoustus
Drimane sesquiterpenoids
Structure elucidation
Anti-inflammatory activity
|
Fund:This project was supported financially by the National Natural Science Foundation for Distinguished Young Scholars (No. 81725021), the National Natural Science Foundation of China (Nos. 81573316 and 31870326), the Innovative Research Groups of the National Natural Science Foundation of China (No. 81721005), the Fundamental Research Funds for the Central Universities (No. 2020kfyXJJS083), the National Key R&D Program of China (No. 2021YFA0910500), the Research and Development Program of Hubei Province (No. 2020BCA058), and the Chinese Medicine Research Foundation of Health Commission of Hubei Province (No. ZY2021Z019). |
Corresponding Authors:
Zhengxi Hu,E-mail:hzx616@126.com;Yonghui Zhang,E-mail:zhangyh@mails.tjmu.edu.cn
E-mail: hzx616@126.com;zhangyh@mails.tjmu.edu.cn
|
Issue Date: 12 August 2022
|
|
|
1. Newman DJ, Cragg GM. Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. J Nat Prod. 2020;83:770-803. 2. Hamed A, Ismail M, El-Metwally MM, Frese M, Ibrahim TMA, El-Haddad AF, Sewald N, Shaaban M. Diverse polyketides and alkaloids from Penicillium sp. KHMM:structural elucidation, biological and molecular docking studies. Z Naturforsch C. 2019;74:131-7. 3. Stähelin HF. The history of cyclosporin A (Sandimmune®) revisited:another point of view. Experientia. 1996;52:5-13. 4. Liu M, Zhang X, Shen L, Sun W, Lin S, Liu J, Cao F, Qi C, Wang J, Hu Z, Zhang Y. Bioactive polyketide-terpenoid hybrids from a soil-derived fungus Bipolaris zeicola. J Org Chem. 2021;86:10962-74. 5. Li H, Xu D, Sun W, Yang B, Li F, Liu M, Wang J, Xue Y, Hu Z, Zhang Y. HPLC-DAD-directed isolation of linearly fused prenylated indole alkaloids from a soil-derived Aspergillus versicolor. J Nat Prod. 2019;82:2181-8. 6. Mo S, Yin J, Ye Z, Li F, Lin S, Zhang S, Yang B, Yao J, Wang J, Hu Z, Zhang Y. Asperanstinoids A-E:undescribed 3,5-dimethylorsellinic acid-based meroterpenoids from Aspergillus calidoustus. Phytochemistry. 2021;190:112892. 7. Zhuravleva OI, Afiyatullov SS, Denisenko VA, Ermakova SP, Slinkina NN, Dmitrenok PS, Kim NY. Secondary metabolites from a marine-derived fungus Aspergillus carneus Blochwitz. Phytochemistry. 2012;80:123-31. 8. Kwon J, Lee H, Seo YH, Yun J, Lee J, Kwon HC, Guo Y, Kang JS, Kim JJ, Lee D. Cytotoxic drimane sesquiterpenoids isolated from Perenniporia maackiae. J Nat Prod. 2018;81:1444-50. 9. Xu K, Zhou Q, Li XQ, Luo T, Yuan XL, Zhang ZF, Zhang P. Cadinane-and drimane-type sesquiterpenoids produced by Paecilomyces sp. TE-540, an endophyte from Nicotiana tabacum L., are acetylcholinesterase inhibitors. Bioorg Chem. 2020;104:104252. 10. Shiono Y, Hiramatsu F, Murayama T, Koseki T, Funakoshi T, Ueda K, Yasuda H. Two drimane-type sesquiterpenes, Strobilactones A and B, from the liquid culture of the edible mushroom Strobilurus ohshimae. Z Naturforsch B. 2007;62:1585-9. 11. Rajab MS, Ndegwa JM. 11α-Hydroxy muzigadiolide, a novel drimane sesquiterpene from the stem bark of Warburgia ugandensis. Bull Chem Soc Ethiop. 2000;14:45-9. 12. Sakio Y, Hirano YJ, Hayashi M, Komiyama K, Ishibashi M. Dendocarbins A-N, new drimane sesquiterpenes from the Nudibranch Dendrodoris carbunculosa. J Nat Prod. 2001;64:726-31. 13. Urones JG, Díez D, Gómez PM, Marcos IS, Basabe P, Moro RF. Chemistry of zamoranic acid. Part 10 Homochiral hemisynthesis of pereniporin A. J Chem Soc Perkin Trans. 1997;1:1815-8. 14. Ding JH, Ding ZG, Chunyu WX, Zhao JY, Wang HB, Liu SW, Wang F. Three new drimane sesquiterpenoids from cultures of the fungus Penicillium sp. J Asian Nat Prod Res. 2017;19:780-5. 15. Zhou H, Zhu T, Cai S, Gu Q, Li D. Drimane sesquiterpenoids from the mangrove-derived fungus Aspergillus ustus. Chem Pharm Bull. 2011;59:762-6. |
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
|
Shared |
|
|
|
|
|
Discussed |
|
|
|
|