Citation: Tan Yingzi, Guo Zhikai, Zhu Mengyue, Shi Jing, Li Wei, Jiao Ruihua, Tan Renxiang, Ge Huiming. Anti-inflammatory spirobisnaphthalene natural products from a plant-derived endophytic fungus Edenia gomezpompae[J]. Chinese Chemical Letters, ;2020, 31(6): 1406-1409. doi: 10.1016/j.cclet.2020.03.059 shu

Anti-inflammatory spirobisnaphthalene natural products from a plant-derived endophytic fungus Edenia gomezpompae

Tan Yingzi ^a,1 ,
Guo Zhikai ^b,d,1 ,
Zhu Mengyue ^a ,
Shi Jing ^a ,
Li Wei ^a ,
Jiao Ruihua ^a ,
Tan Renxiang ^a,c ,
Ge Huiming ^a,*,

a.
State Key Laboratory of Pharmaceutical Biotechnology, Institute of Functional Biomolecules, School of Life Sciences, Nanjing University, Nanjing 210023, China
b.
Hainan Key Laboratory of Tropical Microbe Resources, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China
c.
State Key Laboratory Cultivation Base for TCM Quality and Efficacy, Nanjing University of Chinese Medicine, Nanjing 210023, China
d.
Hainan Academy of Tropical Agricultural Resource, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China

hmge@nju.edu.cn

Received Date: 14 February 2020
Revised Date: 9 March 2020
Accepted Date: 23 March 2020
Available Online: 27 March 2020

Figures(4)

Spirobisnaphthalenes comprise a relatively rare family of natural products that are normally isolated from fungi and occasionally from plants. Here we reported the discovery of seven new preussomerintype spirobisnaphthalenes, preussomerins YT1-YT7 (1-7), and seven known ones (8-14), from the endophytic fungus Edenia gomezpompae, enriching the structural diversity of this family of natural products. Their structures were established by 1D and 2D NMR spectroscopy, HRESIMS analysis and comparison with previously reported compounds, with the absolute configurations of compounds 1 and 2 being further confirmed by single-crystal X-ray diffraction using Cu Kα radiation. The antiinflammatory activities of all isolates were assessed by measuring the production of NO in LPS-induced RAW264.7 macrophage cells. Among them, compounds 8 and 13 exhibited potent inhibitory activities on the production of NO, with IC₅₀ values of 2.61 and 1.32 μmol/L, respectively.
- Endophytic fungus,
- Spirobisnaphthalene natural products,
- Preussomerin-type,
- Structure elucidation,
- Anti-inflammatory activity
1. [1]
  Y.S. Cai, Y.W. Guo, K. Krohn, Nat. Prod. Rep. 27(2010) 1840-1870. doi: 10.1039/c0np00031k
2. [2]
  H. Jiang, S.G. Ma, Y. Li, et al., Bioorg. Med. Chem. Lett. 26(2016) 4832-4836. doi: 10.1016/j.bmcl.2016.08.019
3. [3]
  A. Wisetsai, R. Lekphrom, J. Boonmak, et al., Org. Lett. 21(2019) 8344-8348. doi: 10.1021/acs.orglett.9b03122
4. [4]
  H.A. Weber, J.B. Gloer, J. Org. Chem. 56(1991) 4355-4360. doi: 10.1021/jo00014a007
5. [5]
  S.H. Chen, D.N. Chen, R.L. Cai, et al., J. Nat. Prod. 79(2016) 2397-2402. doi: 10.1021/acs.jnatprod.6b00639
6. [6]
  J.Y. Dong, H.C. Song, J.H. Li, et al., J. Nat. Prod. 71(2008) 952-956. doi: 10.1021/np800034g
7. [7]
  C.L. Liu, C.L. Yang, Y.J. Zeng, et al., Chin. Chem. Lett. 30(2019) 44-46. doi: 10.1016/j.cclet.2018.10.030
8. [8]
  H. Han, Z.K. Guo, B. Zhang, et al., Chin. J. Nat. Med. 17(2019) 475-480.
9. [9]
  S.Y. Ma, Y.S. Xiao, B. Zhang, et al., Org. Lett. 19(2017) 6208-6211. doi: 10.1021/acs.orglett.7b03113
10. [10]
  Y.S. Xiao, B. Zhang, M. Zhang, et al., Org. Biomol. Chem. 15(2017) 3909-3916. doi: 10.1039/C7OB00614D
11. [11]
  Z.K. Guo, R. Wang, W. Huang, et al., Beilstein J. Org. Chem.10(2014) 2677-2682. doi: 10.3762/bjoc.10.282
12. [12]
  C.L. Yang, H.M. Wu, C.L. Liu, et al., J. Nat. Prod. 82(2019) 792-797. doi: 10.1021/acs.jnatprod.8b00705
13. [13]
  Z.K. Guo, C.J. Gai, C.H. Cai, et al., Mar. Drugs 15(2017) 381. doi: 10.3390/md15120381
14. [14]
  M.L. Macías-Rubalcava, B.E. Herna'ndez-Bautista, M. Jime'nez-Estrada, et al., Phytochemistry 69(2008) 1185-1196. doi: 10.1016/j.phytochem.2007.12.006
15. [15]
  M.L. Macías-Rubalcava, M.E. Ruiz-Velasco Sobrino, C. Mele'ndez-Gonza'lez, et al., J. Agric. Food Chem. 62(2014) 3553-3562. doi: 10.1021/jf500965k
16. [16]
  T. Masayuki, W. Hiroshi, H. Kenzo, et al., Jpn. Kokai Tokkyo Koho, JP 2003026684 A, 2003.
17. [17]
  S. Sakemi, T. Inagaki, K. Kaneda, et al., J. Antibiot. 48(1995) 134-142. doi: 10.7164/antibiotics.48.134
18. [18]
  S. Martinez-Luis, G. Della-Togna, P.D. Coley, et al., J. Nat. Prod. 71(2008) 2011-2014. doi: 10.1021/np800472q
19. [19]
  K. Pudhom, T. Teerawatananond, J. Nat. Prod. 77(2014) 1962-1966. doi: 10.1021/np500068y
1. [1]
  Aimin Fu , Chunmei Chen , Qin Li , Nanjin Ding , Jiaxin Dong , Yu Chen , Mengsha Wei , Weiguang Sun , Hucheng Zhu , Yonghui Zhang . Niduenes A−F, six functionalized sesterterpenoids with a pentacyclic 5/5/5/5/6 skeleton from endophytic fungus Aspergillus nidulans. Chinese Chemical Letters, 2024, 35(9): 109100-. doi: 10.1016/j.cclet.2023.109100
2. [2]
  Chunmao Yuan , Yanrong Zeng , Lei Huang , Yu Mou , Jun Jin , Ping Yi , Yanmei Li , Xiaojiang Hao . Hymoins A–C, three unusual polycyclic polyprenylated acylphloroglucinols with lipid-lowering activity from Hypericum monogynum. Chinese Chemical Letters, 2025, 36(3): 109859-. doi: 10.1016/j.cclet.2024.109859
3. [3]
  Jinyan Zhang , Fen Liu , Qian Jin , Xueyi Li , Qiong Zhan , Mu Chen , Sisi Wang , Zhenlong Wu , Wencai Ye , Lei Wang . Discovery of unusual phloroglucinol–triterpenoid adducts from Leptospermum scoparium and Xanthostemon chrysanthus by building blocks-based molecular networking. Chinese Chemical Letters, 2024, 35(6): 108881-. doi: 10.1016/j.cclet.2023.108881
4. [4]
  Qi Tan , Run-Zhu Fan , Wencong Yang , Ge Zou , Tao Chen , Jianying Wu , Bo Wang , Sheng Yin , Zhigang She . (+)/(−)-Mycosphatide A, a pair of highly oxidized polyketides with lipid-lowering activity from the mangrove endophytic fungus Mycosphaerella sp. SYSU-DZG01. Chinese Chemical Letters, 2024, 35(9): 109390-. doi: 10.1016/j.cclet.2023.109390
5. [5]
  Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
6. [6]
  Xiaoyao Ma , Jinling Zhang , Ge Fang , He Gao , Jie Gao , Li Fu , Yuanyuan Hou , Gang Bai . Förster resonance energy transfer reveals phillygenin and swertiamarin concurrently target AKT on different binding domains to increase the anti-inflammatory effect. Chinese Chemical Letters, 2024, 35(5): 108823-. doi: 10.1016/j.cclet.2023.108823
7. [7]
  Wenjia Wang , Xingyue He , Xiaojie Wang , Tiantian Zhao , Osamu Muraoka , Genzoh Tanabe , Weijia Xie , Tianjiao Zhou , Lei Xing , Qingri Jin , Hulin Jiang . Glutathione-depleted cyclodextrin pseudo-polyrotaxane nanoparticles for anti-inflammatory oxaliplatin (Ⅳ) prodrug delivery and enhanced colorectal cancer therapy. Chinese Chemical Letters, 2024, 35(4): 108656-. doi: 10.1016/j.cclet.2023.108656
8. [8]
  Xiongbo Song , Jinwen Xiao , Juan Wu , Li Sun , Long Chen . Decellularized amniotic membrane promotes the anti-inflammatory response of macrophages via PI3K/AKT/HIF-1α pathway. Chinese Chemical Letters, 2025, 36(1): 109844-. doi: 10.1016/j.cclet.2024.109844
9. [9]
  Yun-Feng Liu , Hui-Fang Du , Ya-Hui Zhang , Zhi-Qin Liu , Xiao-Qian Qi , Du-Qiang Luo , Fei Cao . Chaeglobol A, an unusual octocyclic sterol with antifungal activity from the marine-derived fungus Chaetomium globosum HBU-45. Chinese Chemical Letters, 2025, 36(3): 109858-. doi: 10.1016/j.cclet.2024.109858
10. [10]
  Deli Chen , Jiawen Li , Xudong Xu , Zhaocui Sun , Yun Yang , Minghui Xu , Hanqiao Liang , Junshan Yang , Hui Meng , Guoxu Ma , Jianhe Wei . Plant-microbial interactions inspired the discovery of novel sesquiterpenoid dimeric skeletons of hidden natural products from Hibiscus tiliaceus. Chinese Chemical Letters, 2024, 35(10): 109451-. doi: 10.1016/j.cclet.2023.109451
11. [11]
  Guo-Ping Yin , Ya-Juan Li , Li Zhang , Ling-Gao Zeng , Xue-Mei Liu , Chang-Hua Hu . Citrinsorbicillin A, a novel homotrimeric sorbicillinoid isolated by LC-MS-guided with cytotoxic activity from the fungus Trichoderma citrinoviride HT-9. Chinese Chemical Letters, 2024, 35(8): 109035-. doi: 10.1016/j.cclet.2023.109035
12. [12]
  Run-Han Li , Tian-Yi Dang , Wei Guan , Jiang Liu , Ya-Qian Lan , Zhong-Min Su . Evolution exploration and structure prediction of Keggin-type group IVB metal-oxo clusters. Chinese Chemical Letters, 2024, 35(5): 108805-. doi: 10.1016/j.cclet.2023.108805
13. [13]
  Zhengzheng LIU , Pengyun ZHANG , Chengri WANG , Shengli HUANG , Guoyu YANG . Synthesis, structure, and electrochemical properties of a sandwich-type {Co₆}-cluster-added germanotungstate. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1173-1179. doi: 10.11862/CJIC.20240039
14. [14]
  Zhexin Chen , Yuqing Shi , Fang Zhong , Kai Zhang , Furong Zhang , Shenghong Xie , Zhongbin Cheng , Qian Zhou , Yi-You Huang , Hai-Bin Luo . Discovery of amentoflavone as a natural PDE4 inhibitor with anti-fibrotic effects. Chinese Chemical Letters, 2025, 36(4): 109956-. doi: 10.1016/j.cclet.2024.109956
15. [15]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
16. [16]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
17. [17]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
18. [18]
  Chunlei Dai , Liying Wang , Xinru You , Yi Zhao , Zhong Cao , Jun Wu . Coffee-derived self-anti-inflammatory polymer as drug nanocarrier for enhanced rheumatoid arthritis treatment. Chinese Chemical Letters, 2025, 36(3): 109869-. doi: 10.1016/j.cclet.2024.109869
19. [19]
  Jian Song , Shenghui Wang , Qiuge Liu , Xiao Wang , Shuo Yuan , Hongmin Liu , Saiyang Zhang . N-Benzyl arylamide derivatives as novel and potent tubulin polymerization inhibitors against gastric cancers: Design, structure–activity relationships and biological evaluations. Chinese Chemical Letters, 2025, 36(2): 109678-. doi: 10.1016/j.cclet.2024.109678
20. [20]
  Xue-Jiao Wang , Jun-Li Xin , Hong Xiang , Ze-Yu Zhao , Yu-Hang He , Haibo Wang , Guangyao Mei , Yi-Cheng Mao , Juan Xiong , Jin-Feng Hu . Holotrichones A and B, potent anti-leukemic lindenane-type sesquiterpene trimers with unprecedented complex carbon skeletons from a rare Chloranthus species. Chinese Chemical Letters, 2024, 35(12): 109682-. doi: 10.1016/j.cclet.2024.109682

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(1259)
HTML views(74)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142