Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect
ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES
ADDITION / CORRECTIONThis article has been corrected. View the notice.

Longisglucinols A–C, Structurally Intriguing Polycyclic Polyprenylated Acylphloroglucinols with Anti-inflammatory Activity from Hypericum longistylum

  • Na Zhang
    Na 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, People’s Republic of China
    More by Na Zhang
  • Zhengyi Shi
    Zhengyi Shi
    Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People’s Republic of China
    More by Zhengyi Shi
  • Qianqian Xu
    Qianqian Xu
    Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People’s Republic of China
    More by Qianqian Xu
  • Weiguang Sun
    Weiguang Sun
    Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People’s Republic of China
    More by Weiguang Sun
  • Lianghu Gu
    Lianghu Gu
    Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People’s Republic of China
    More by Lianghu Gu
  • Shuangshuang Xie
    Shuangshuang Xie
    Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People’s Republic of China
  • Yi Guo
    Yi Guo
    Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People’s Republic of China
    More by Yi Guo
  • Yulin Duan
    Yulin Duan
    Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People’s Republic of China
    More by Yulin Duan
  • Kailin Zhang
    Kailin Zhang
    Hubei Hualong Bio-chemical Pharmaceutical Co., Ltd., Wuhan 430030, People’s Republic of China
    More by Kailin Zhang
  • Changxing Qi*
    Changxing Qi
    Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People’s Republic of China
    *E-mail: [email protected] (Y. Zhang).
    More by Changxing Qi
  • , and 
  • Yonghui Zhang*
    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, People’s Republic of China
    *E-mail: [email protected] (C. Qi).
Cite this: Org. Lett. 2020, 22, 20, 7926–7929
Publication Date (Web):October 1, 2020
https://doi.org/10.1021/acs.orglett.0c02853
Copyright © 2020 American Chemical Society

    Article Views

    2551

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    Longisglucinol A (1), a polycyclic polyprenylated acylphloroglucinol (PPAP) with a new skeleton, along with two new congeners, longisglucinols B (2) and C (3), were isolated from Hypericum longistylum. Compound 1 features an unparalleled 6/6/6/5 fused ring skeleton based on a unique 8-oxa-tetracyclo-[8.3.3.01,9.03,7]cetane core. Longisglucinol A showed remarkable anti-inflammatory activity by inducing macrophage M2 polarization through the suppression of NF-κB.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.0c02853.

    • Experimental section, 1D and 2D NMR, MS, IR spectra for compounds 13, and X-ray data of 1 and 2 (PDF)

    Accession Codes

    CCDC 19743001974301 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 20 publications.

    1. Rui-Dan Hu, Wei-Yao Lin, Qian Feng, Jinru Liu, Yidi Chen, Aijia Ji, Caiyan Wang, Liping Cao, Rong Zhang, Zhongqiu Liu, Hui Cui, Qi Liang, Rong-Rong Zhang. New α-Glucosidase Inhibitors from the Whole Plant of Hypericum beanii Based on Ligand Fishing and Molecular Networking Analysis. Journal of Agricultural and Food Chemistry 2024, 72 (20) , 11452-11464. https://doi.org/10.1021/acs.jafc.4c00500
    2. Zhengyi Shi, Xueyan Duan, Fengqing Wang, Zhangrong Hou, Fei Song, Lianghu Gu, Changxing Qi, Yonghui Zhang. Maydistacins A–G, Terpestacin-type Sesterterpenoids with Anti-inflammatory Activity from the Phytopathogenic Fungus Bipolaris maydis. Journal of Natural Products 2024, 87 (1) , 68-76. https://doi.org/10.1021/acs.jnatprod.3c00786
    3. Zhengyi Shi, Xiangli Zhao, Fei Song, Zhangrong Hou, Xincai Hao, Jieru Guo, Lingjuan Sun, Hao Feng, Meng Wu, Peiling Xie, Xiaosheng Tan, Gang Chen, Changxing Qi, Yonghui Zhang. Prenyllongnols A–D, New Prenylated Acylphloroglucinols that Fight Concanavalin A-Induced Autoimmune Hepatitis. Journal of Agricultural and Food Chemistry 2023, 71 (46) , 17801-17809. https://doi.org/10.1021/acs.jafc.3c05245
    4. Jin-Yan Xie, Zi-Xuan Wang, Wu-Yang Liu, Han-Wu Liu, Ding Li, Yi-Fan Sang, Zhi Yang, Jin-Ming Gao, Xi-Tao Yan. Hyperelatolides A–D, Antineuroinflammatory Constituents with Unusual Carbon Skeletons from Hypericum elatoides. Journal of Natural Products 2023, 86 (8) , 1910-1918. https://doi.org/10.1021/acs.jnatprod.3c00226
    5. Yulin Duan, Yi Guo, Yanfang Deng, Pengfei Bu, Zhengyi Shi, Yunfang Cao, Yeting Zhang, Hong Hu, Weiguang Sun, Changxing Qi, Yonghui Zhang. Norprzewalsone A, a Rearranged Polycyclic Polyprenylated Acylphloroglucinol with a Spiro[cyclopentane-1,3′-tricyclo[7.4.0.01,6]tridecane] Core from Hypericum przewalskii. The Journal of Organic Chemistry 2022, 87 (10) , 6824-6831. https://doi.org/10.1021/acs.joc.2c00503
    6. Jin-Yan Xie, Pengfei Li, Xi-Tao Yan, Jin-Ming Gao. Discovery from Hypericum elatoides and synthesis of hyperelanitriles as α-aminopropionitrile-containing polycyclic polyprenylated acylphloroglucinols. Communications Chemistry 2024, 7 (1) https://doi.org/10.1038/s42004-023-01091-1
    7. Yulin DUAN, Zhengyi SHI, Fei SONG, Zhangrong HOU, Xiaosheng TAN, Yeting ZHANG, Xincai HAO, Gang CHEN, Changxing QI, Yonghui ZHANG. Hyparillums A and B: polycyclic polyprenylated acylphloroglucinols from Hypericum patulum. Chinese Journal of Natural Medicines 2024, 22 (3) , 273-279. https://doi.org/10.1016/S1875-5364(24)60599-6
    8. Bo Tao, Yongqi Li, Zhengyi Shi, Yulin Duan, Yi Guo, Xinye Huang, Jie Li, Yeting Zhang, Ming Chen, Fei Song, Xueqi Lan, Weiguang Sun, Lianghu Gu, Changxing Qi, Yonghui Zhang. Discovery of bioactive polycyclic polyprenylated acylphloroglucinols with adamantine/homoadamantane skeletons from Hypericum wilsonii. Phytochemistry 2024, 218 , 113953. https://doi.org/10.1016/j.phytochem.2023.113953
    9. Yongxian Cheng, Dapeng Qin. Biological Activities. 2024, 169-196. https://doi.org/10.1007/978-981-99-7329-3_14
    10. Yongxian Cheng, Dapeng Qin. Classification of Diverse Novel Phloroglucinols. 2024, 75-94. https://doi.org/10.1007/978-981-99-7329-3_7
    11. Zhengyi Shi, Jie Yin, Yang Xiao, Zhangrong Hou, Fei Song, Jianping Wang, Qingyi Tong, Changxing Qi, Yonghui Zhang. Unprecedented sesquiterpene–polycyclic polyprenylated acylphloroglucinol adduct against acute myeloid leukemia via inhibiting mitochondrial complex V. Chinese Chemical Letters 2023, 16 , 109458. https://doi.org/10.1016/j.cclet.2023.109458
    12. Gonçalo Infante Caldeira, Luís Pleno Gouveia, Rita Serrano, Olga Duarte Silva. Hypericum Genus as a Natural Source for Biologically Active Compounds. Plants 2022, 11 (19) , 2509. https://doi.org/10.3390/plants11192509
    13. Beiye Yang, Jun-Cheng Su, Lijuan Huang, Shuang Lin, Xiaoqi Jin, Xueping Lei, Zhengxi Hu, Yonghui Zhang. Hyperispirones A and B, spiro-bridged polycyclic polyprenylated acylphloroglucinols with anti-angiogenesis activity from Hypericum beanii. Organic Chemistry Frontiers 2022, 9 (13) , 3460-3466. https://doi.org/10.1039/D2QO00366J
    14. Yulin Duan, Pengfei Bu, Yi Guo, Zhengyi Shi, Yunfang Cao, Yeting Zhang, Hong Hu, Hankun Hu, Changxing Qi, Yonghui Zhang. (±)-Walskiiglucinol A, a pair of rearranged acylphloroglucinol derivative enantiomers from Hypericum przewalskii. Organic & Biomolecular Chemistry 2022, 20 (24) , 4970-4975. https://doi.org/10.1039/D2OB00562J
    15. Zhengyi Shi, Xiaosheng Tan, Hong Hu, Na Zhang, Yulin Duan, Yi Guo, Hao Feng, Lingjuan Sun, Gang Chen, Changxing Qi, Yonghui Zhang. Discovery of Undescribed Monoterpenoid Polyprenylated Acylphloroglucinols with Immunosuppressive Activities from Hypericum longistylum. Phytochemistry 2022, 198 , 113173. https://doi.org/10.1016/j.phytochem.2022.113173
    16. Zhengyi Shi, Hong Hu, Yi Guo, Yulin Duan, Yeting Zhang, Bo Tao, Pengfei Bu, Weiguang Sun, Changxing Qi, Yonghui Zhang. Discovery of 13,15- nor -polycyclic polyprenylated acylphloroglucinols from Hypericum longistylum with anti-inflammatory activity. Organic & Biomolecular Chemistry 2022, 20 (6) , 1284-1291. https://doi.org/10.1039/D1OB02107A
    17. Yan-Fei Liu, Shi-Shan Yu. Survey of natural products reported by Asian research groups in 2020. Journal of Asian Natural Products Research 2021, 23 (12) , 1115-1134. https://doi.org/10.1080/10286020.2021.2004131
    18. Beiye Yang, Jianzheng Huang, Shuang Lin, Qingyi Tong, Zeyu Yao, Fengli Li, Ying Ye, Zhengxi Hu, Yonghui Zhang. Hyperbeanone A, a 5,6- seco -spirocyclic polycyclic polyprenylated acylphloroglucinol derivative with an unprecedented skeleton from Hypericum beanii. Organic Chemistry Frontiers 2021, 8 (22) , 6411-6418. https://doi.org/10.1039/D1QO01302E
    19. Yu-xin Zhang, Zhen Ao, Yi-wen He, Jin-Yu Lu, Xin-lin Chen, Ling-yi Kong, Jian-guang Luo. Hyperpatulones C-G, new spirocyclic polycyclic polyprenylated acylphloroglucinols from the leaves of Hypericum patulum. Fitoterapia 2021, 155 , 105063. https://doi.org/10.1016/j.fitote.2021.105063
    20. Robert A. Hill, Andrew Sutherland. Hot off the Press. Natural Product Reports 2020, 37 (12) , 1556-1560. https://doi.org/10.1039/D0NP90047H