ACS Publications. Most Trusted. Most Cited. Most Read
Crispenes F and G, cis-Clerodane Furanoditerpenoids from Tinospora crispa, Inhibit STAT3 Dimerization

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Nat. Prod. 2018, 81, 2, 236-242
    Article

    Crispenes F and G, cis-Clerodane Furanoditerpenoids from Tinospora crispa, Inhibit STAT3 Dimerization
    Click to copy article linkArticle link copied!

    View Author Information
    † Department of Pharmaceutical Chemistry, University of Dhaka, Dhaka-1000, Bangladesh
    ‡ School of Cancer and Pharmaceutical Science, King’s College London, 150 Stamford Street, London SE1 9NH, U.K.
    *Tel: +88 01 819-253698. Fax: +88 02 9667222. E-mail: [email protected] (C. M. Hasan).
    *Tel: +442078481891. Fax: +442078484295. E-mail: [email protected] (K. M. Rahman).
    Other Access OptionsSupporting Information (1)

    Journal of Natural Products

    Cite this: J. Nat. Prod. 2018, 81, 2, 236–242
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jnatprod.7b00377
    Published February 3, 2018
    Copyright © 2018 The American Chemical Society and American Society of Pharmacognosy
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Two new cis-clerodane-type furanoditerpenes, crispenes F and G (1 and 2), together with seven known compounds, were isolated from the stems of Tinospora crispa. Crispenes F and G (1 and 2) inhibited STAT3 dimerization in a cell-free fluorescent polarization assay and were found to have significant cytotoxicity against a STAT3-dependent MDA-MB 231 breast cancer cell line, while being inactive in a STAT3-null A4 cell line. These two compounds share structural similarities with a previously reported STAT3 inhibitor, crispene E, isolated from the same plant. Molecular docking studies suggested that the molecules inhibit STAT3 by interacting with its SH2 domain.

    Copyright © 2018 The American Chemical Society and American Society of Pharmacognosy

    Subjects

    what are subjects

    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. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jnatprod.7b00377.

    • HPLC methods, molecular modeling images and 1H and 13C NMR spectra of isolated compounds (PDF)

    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

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai
    powered by  Scite

    This article is cited by 20 publications.

    1. Sio-Hong Lam, Hui-Kang Liu, Shih-Yuan Chung, Jia-Ling Chang, Mao-Xuan Hong, Sheng-Chu Kuo, Chih-Chuang Liaw. Diterpenoids and Their Glycosides from the Stems of Tinospora crispa with Beta-Cell Protective Activity. Journal of Natural Products 2023, 86 (6) , 1437-1448. https://doi.org/10.1021/acs.jnatprod.3c00114
    2. Jinyun Dong, Xiang-Dong Cheng, Wei-Dong Zhang, Jiang-Jiang Qin. Recent Update on Development of Small-Molecule STAT3 Inhibitors for Cancer Therapy: From Phosphorylation Inhibition to Protein Degradation. Journal of Medicinal Chemistry 2021, 64 (13) , 8884-8915. https://doi.org/10.1021/acs.jmedchem.1c00629
    3. Weiyi Wang, Jing Yang, Yan-Yan Liao, Gang Cheng, Jing Chen, Shaowei Mo, Li Yuan, Xiang-Dong Cheng, Jiang-Jiang Qin, Zongze Shao. Aspeterreurone A, a Cytotoxic Dihydrobenzofuran–Phenyl Acrylate Hybrid from the Deep-Sea-Derived Fungus Aspergillus terreus CC-S06-18. Journal of Natural Products 2020, 83 (6) , 1998-2003. https://doi.org/10.1021/acs.jnatprod.0c00189
    4. Hauke Löcken, Cinzia Clamor, Klaus Müller. Napabucasin and Related Heterocycle-Fused Naphthoquinones as STAT3 Inhibitors with Antiproliferative Activity against Cancer Cells. Journal of Natural Products 2018, 81 (7) , 1636-1644. https://doi.org/10.1021/acs.jnatprod.8b00247
    5. Yuxiao Li, Shichao Zheng, Hongrui Li, Yanhong Li, Ziliang Wang, Wei Wang, Bowen Zheng, Xishan Bai, Xiangzhong Huang. Two new clerodane diterpenoids with analgesic activity from the roots of Paratinospora sagittata (Oliv.) Wei Wang. Natural Product Research 2025, 26 , 1-10. https://doi.org/10.1080/14786419.2025.2484254
    6. Minky Mukhija, Sonia Kamboj, Jyoti Monga, Devkant Sharma, Anurag Bhargava. Terpenes on the Frontline. 2025, 299-328. https://doi.org/10.4018/979-8-3693-6972-2.ch011
    7. Serges H. Ngalaha Ediah, Elodie Gaële Matheuda, Brio Azonsop Kefossang, Yves M.Mba Nguekeu, Takeshi Kodama, Saw Yu Yu Hnin, Zhuang Qian, Maurice Ducret Awouafack, Apollinaire Tsopmo, Hiroyuki Morita, Mathieu Tene. A new antibacterial neo-clerodane diterpenoid and other constituents from Chasmanthera dependens Hochst. (Menispermaceae) and their chemotaxonomic significance. Biochemical Systematics and Ecology 2025, 118 , 104922. https://doi.org/10.1016/j.bse.2024.104922
    8. Yang-Li Zhu, Li Deng, Xin-Yan Dai, Jia-Qi Song, Yan Zhu, Ting Liu, Xiang-Qian Kong, Li-Jun Zhang, Hai-Bing Liao. Tinopanoids K-T, clerodane diterpenoids with anti-inflammatory activity from Tinospora crispa. Bioorganic Chemistry 2023, 140 , 106812. https://doi.org/10.1016/j.bioorg.2023.106812
    9. Ehfazul Haque, Md. Sazzadul Bari, Labony Khandokar, Juhaer Anjum, Ibrahim Jantan, Veronique Seidel, Md. Areeful Haque. An updated and comprehensive review on the ethnomedicinal uses, phytochemistry, pharmacological activity and toxicological profile of Tinospora crispa (L.) Hook. f. & Thomson. Phytochemistry Reviews 2023, 22 (1) , 211-273. https://doi.org/10.1007/s11101-022-09843-y
    10. Jin‐Qiu You, Yi‐Nan Liu, Jun‐Su Zhou, Xin‐Yu Sun, Chun Lei, Qing Mu, Jing‐Ya Li, Ai‐Jun Hou. cis ‐Clerodane Diterpenoids with Structural Diversity and Anti‐inflammatory Activity from Tinospora crispa. Chinese Journal of Chemistry 2022, 40 (24) , 2882-2892. https://doi.org/10.1002/cjoc.202200433
    11. Cristina Forzato, Patrizia Nitti. New Diterpenes with Potential Antitumoral Activity Isolated from Plants in the Years 2017–2022. Plants 2022, 11 (17) , 2240. https://doi.org/10.3390/plants11172240
    12. Jing Yang, Lingling Wang, Xiaoqing Guan, Jiang-Jiang Qin. Inhibiting STAT3 signaling pathway by natural products for cancer prevention and therapy: In vitro and in vivo activity and mechanisms of action. Pharmacological Research 2022, 182 , 106357. https://doi.org/10.1016/j.phrs.2022.106357
    13. Bharat Singh, Sheenu Nathawat, Ram A. Sharma. Ethnopharmacological and phytochemical attributes of Indian Tinospora species: A comprehensive review. Arabian Journal of Chemistry 2021, 14 (10) , 103381. https://doi.org/10.1016/j.arabjc.2021.103381
    14. Fatema Tabassum, Choudhury Mahmood Hasan, Mohammad Mehedi Masud, Shirin Jamshidi, Khondaker Miraz Rahman, Monira Ahsan. Indole alkaloids from the leaves of Ravenia spectabilis engl. with activity against pancreatic cancer cell line. Phytochemistry 2021, 186 , 112744. https://doi.org/10.1016/j.phytochem.2021.112744
    15. Zita G. Ríos-Malváez, Ma-Angeles Cano-Herrera, Juan Carlos Dávila-Becerril, Gustavo Mondragón-Solórzano, María Teresa Ramírez-Apan, David Morales-Morales, Joaquín Barroso-Flores, Jonnathan G. Santillán-Benítez, M.V. Basavanag Unnamatla, Marco Antonio García-Eleno, Nelly González-Rivas, Erick Cuevas-Yañez. Synthesis, characterization and cytotoxic activity evaluation of 4-(1,2,3-triazol-1-yl) salicylic acid derivatives. Journal of Molecular Structure 2021, 1225 , 129149. https://doi.org/10.1016/j.molstruc.2020.129149
    16. Sujitra Hanthanong, Siwattra Choodej, Thammarat Aree, Khanitha Pudhom. Two new rearranged clerodane diterpenes from Thai Tinospora baenzigeri. Journal of Natural Medicines 2021, 75 (1) , 201-206. https://doi.org/10.1007/s11418-020-01450-5
    17. Arvind Singh Negi. Anti-Breast Cancer Terpenoids of Natural Origins. 2021, 29-68. https://doi.org/10.1016/B978-0-12-821277-6.00003-9
    18. Huihui Cao, Wenqiang Zhang, Dongyi Liu, Manting Hou, Shiyu Liu, Wenkai He, Jiawei Lin, Meng Shao. Identification, in vitro evaluation and modeling studies of the constituents from the roots of Arnebia euchroma for antitumor activity and STAT3 inhibition. Bioorganic Chemistry 2020, 96 , 103655. https://doi.org/10.1016/j.bioorg.2020.103655
    19. Kyle A. Pelot, David M. Hagelthorn, Young J. Hong, Dean J. Tantillo, Philipp Zerbe. Diterpene Synthase‐Catalyzed Biosynthesis of Distinct Clerodane Stereoisomers. ChemBioChem 2019, 20 (1) , 111-117. https://doi.org/10.1002/cbic.201800580
    20. Sobia Tabassum, Rashda Abbasi, Nafees Ahmad, Ammad Ahmad Farooqi. Targeting of JAK-STAT Signaling in Breast Cancer: Therapeutic Strategies to Overcome Drug Resistance. 2019, 271-281. https://doi.org/10.1007/978-3-030-20301-6_14
    Download PDF
    Go to Journal of Natural Products
    Get e-Alerts
    Get e-Alerts

    Journal of Natural Products

    Cite this: J. Nat. Prod. 2018, 81, 2, 236–242
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jnatprod.7b00377
    Published February 3, 2018
    Copyright © 2018 The American Chemical Society and American Society of Pharmacognosy
    Request reuse permissions

    Article Views

    1589

    Altmetric

    -

    Citations

    20
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.