Drimane sesquiterpenoids from a wetland soil-derived fungus Aspergillus calidoustus TJ403-EL05

doi:10.1007/s13659-022-00349-w

应用天然产物 ›› 2022, Vol. 12 ›› Issue (4): 27-27.DOI: 10.1007/s13659-022-00349-w

• Short Communication • 上一篇

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

收稿日期:2022-04-20 出版日期:2022-08-24 发布日期:2022-08-12
通讯作者: Zhengxi Hu,E-mail:hzx616@126.com;Yonghui Zhang,E-mail:zhangyh@mails.tjmu.edu.cn
基金资助:
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).

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

Received:2022-04-20 Online:2022-08-24 Published:2022-08-12
Contact: Zhengxi Hu,E-mail:hzx616@126.com;Yonghui Zhang,E-mail:zhangyh@mails.tjmu.edu.cn
Supported by:
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).

摘要/Abstract

摘要： 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).

关键词: Aspergillus calidoustus, Drimane sesquiterpenoids, Structure elucidation, Anti-inflammatory activity

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).

Key words: Aspergillus calidoustus, Drimane sesquiterpenoids, Structure elucidation, Anti-inflammatory activity

Sitian Zhang, Shuyuan Mo, Fengli Li, Yaxin Zhang, Jianping Wang, Zhengxi Hu, Yonghui Zhang. Drimane sesquiterpenoids from a wetland soil-derived fungus Aspergillus calidoustus TJ403-EL05[J]. 应用天然产物, 2022, 12(4): 27-27.

参考文献

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.

[1]	Hongyan Wen, Sheng Li, Yu Zhang. Phthalide mono- and dimers from the rhizomes of Angelica sinensis and their anti-inflammatory activities[J]. 应用天然产物, 2025, 15(3): 26-26.
[2]	Gabin T. M. Bitchagno, Nathan Reynolds, Monique S. J. Simmonds. Diterpene chemical space of Aeollanthus buchnerianus Briq. aerial part[J]. 应用天然产物, 2025, 15(1): 6-6.
[3]	Shi-Yan Feng, Na Jiang, Jia-Ying Yang, Lin-Yao Yang, Jiang-Chao Du, Xuan-Qin Chen, Dan Liu, Rong-Tao Li, Jin-Dong Zhong. Antiviral and anti-inflammatory activities of chemical constituents from twigs of Mosla chinensis Maxim[J]. 应用天然产物, 2024, 14(3): 26-26.
[4]	Orawan Jongsomjainuk, Jutatip Boonsombat, Sanit Thongnest, Hunsa Prawat, Paratchata Batsomboon, Sitthivut Charoensutthivarakul, Saroj Ruchisansakun, Kittipong Chainok, Jitnapa Sirirak, Chulabhorn Mahidol, Somsak Ruchirawat. Kaemtakols A–D, highly oxidized pimarane diterpenoids with potent anti-inflammatory activity from Kaempferia takensis[J]. 应用天然产物, 2023, 13(6): 55-55.
[5]	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.
[6]	Yang Yu, Yang Wang, Gui-Chun Wang, Cheng-Yong Tan, Yi Wang, Jin-Song Liu, Guo-Kai Wang. Andropanilides A-C, the novel labdane-type diterpenoids from Andrographis paniculata and their anti-inflammation activity[J]. 应用天然产物, 2023, 13(5): 31-31.
[7]	Xun Wei, Jia-Luo Huang, Hua-Hua Gao, Fang-Yu Yuan, Gui-Hua Tang, Sheng Yin. New halimane and clerodane diterpenoids from Croton cnidophyllus[J]. 应用天然产物, 2023, 13(3): 21-21.
[8]	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.
[9]	Mohammad Sanad Abu-Darwish, Célia Cabral, Zulfigar Ali, Mei Wang, Shabana I. Khan, Melissa R. Jacob, Surendra K. Jain, Babu L. Tekwani, Fazila Zulfiqar, Ikhlas A. Khan, Hatem Taifour, Lígia Salgueiro, Thomas Efferth. Salvia ceratophylla L. from South of Jordan: new insights on chemical composition and biological activities[J]. 应用天然产物, 2020, 10(5): 307-316.
[10]	Yin-E Zhi, Xu-Jie Qin, Hui Liu, Yuan Zeng, Wei Ni, Li He, Zu-Ding Wang, Hai-Yang Liu. Structurally Diverse Polymethylated Phloroglucinol Meroterpenoids from Baeckea frutescens[J]. 应用天然产物, 2018, 8(6): 431-439.
[11]	Ce Kuang, Shu-Xi Jing, Yan Liu, Shi-Hong Luo, Sheng-Hong Li. Drimane Sesquiterpenoids and Isochromone Derivative from the Endophytic Fungus Pestalotiopsis sp. M-23[J]. 应用天然产物, 2016, 6(3): 155-160.
[12]	Wen-Ting Chen, Lin-Fu Liang, Xu-Wen Li, Wei Xiao, Yue-Wei Guo. Further New Highly Oxidative Cembranoids from the Hainan Soft Coral Sarcophyton trocheliophorum[J]. 应用天然产物, 2016, 6(2): 97-102.
[13]	Hao Wen, Yan Li, Xingzhong Liu, Wencai Ye, Xinsheng Yao, Yongsheng Che. Fusagerins A-F, New Alkaloids from the Fungus Fusarium sp.[J]. 应用天然产物, 2015, 5(4): 195-203.
[14]	Frank Surup, Eric Kuhnert, Elena Liscinskij, Marc Stadler. Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii(Xylariaceae)[J]. 应用天然产物, 2015, 5(3): 167-173.
[15]	Xiao-Yan YANG, Tao FENG, Jian-Hai DING, Zheng-Hui LI, Yan LI, Qiong-Ying FAN, Ji-Kai LIU. Two new drimane sesquiterpenoids from cultures of the basidiomycete Trichaptum biforme[J]. 应用天然产物, 2013, 3(4): 154-157.

Drimane sesquiterpenoids from a wetland soil-derived fungus Aspergillus calidoustus TJ403-EL05

Drimane sesquiterpenoids from a wetland soil-derived fungus Aspergillus calidoustus TJ403-EL05

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价