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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Nat. Prod. 2016, 79, 6, 1628-1634

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Pepluane and Paraliane Diterpenoids from Euphorbia peplus with Potential Anti-inflammatory Activity

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† State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People’s Republic of China
§ University of Chinese Academy of Sciences, Beijing 100049, People’s Republic of China
*Tel: +86-871-65223327. Fax: +86-871-65223255. E-mail: [email protected].
Cite this: J. Nat. Prod. 2016, 79, 6, 1628-1634
Publication Date (Web):May 20, 2016
https://doi.org/10.1021/acs.jnatprod.6b00206
Copyright © 2016 The American Chemical Society and American Society of Pharmacognosy
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Abstract

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Twelve new diterpenoids based on two rare skeletal types, namely, paralianones A–D (1–4) and pepluanols A–H (5–12), along with five known compounds, were isolated from an acetone extract of Euphorbia peplus. Their structures were proposed based on 1D and 2D NMR spectroscopic data analysis. These diterpenoids were evaluated for potential anti-inflammatory activity in a lipopolysaccharide-stimulated mouse macrophage cellular model. Compounds 3, 4, 11, 13, and 16 displayed moderate inhibitory effects on NO inhibition, with IC50 values ranging from 29.9 to 38.3 μM.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jnatprod.6b00206.

  • 1D, 2D, and HRESIMS spectra of compounds 1–12 (PDF)

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Cited By

This article is cited by 12 publications.

  1. Jun-Cheng Su, Wen Cheng, Jian-Guo Song, Yuan-Lin Zhong, Xiao-Jun Huang, Ren-Wang Jiang, Yao-Lan Li, Man-Mei Li, Wen-Cai Ye, Ying Wang. Macrocyclic Diterpenoids from Euphorbia helioscopia and Their Potential Anti-inflammatory Activity. Journal of Natural Products 2019, 82 (10) , 2818-2827. DOI: 10.1021/acs.jnatprod.9b00519.
  2. Yue Liang, Lijun An, Zhaoyu Shi, Xuke Zhang, Chunfeng Xie, Muhetaer Tuerhong, Zhaohui Song, Yasushi Ohizumi, Dongho Lee, Ling Shuai, Jing Xu, Yuanqiang Guo. Bioactive Diterpenoids from the Stems of Euphorbia antiquorum. Journal of Natural Products 2019, 82 (6) , 1634-1644. DOI: 10.1021/acs.jnatprod.9b00134.
  3. Luo-Sheng Wan, Yin Nian, Xing-Rong Peng, Li-Dong Shao, Xiao-Nian Li, Jian Yang, Ming Zhou, Ming-Hua Qiu. Pepluanols C–D, Two Diterpenoids with Two Skeletons from Euphorbia peplus. Organic Letters 2018, 20 (10) , 3074-3078. DOI: 10.1021/acs.orglett.8b01114.
  4. Yan-Ni Chen, Qing-Yun Lu, Dong-Mei Li, Ying-Yao Li, Xue-Xue Pu, Bo-Ting Li, Xiao-Han Tang, Hong-Yu Tang, Shuai Liu, Lei Yang, Yu Zhang, Ying-Tong Di, Xin Fang, Xiao-Jiang Hao. Three new diterpenoids from Euphorbia peplus. Natural Product Research 2020, , 1-7. DOI: 10.1080/14786419.2020.1749609.
  5. Maryam Fattahian, Mustafa Ghanadian, Zulfiqar Ali, Ikhlas A. Khan. Jatrophane and rearranged jatrophane-type diterpenes: biogenesis, structure, isolation, biological activity and SARs (1984–2019). Phytochemistry Reviews 2020, 58 DOI: 10.1007/s11101-020-09667-8.
  6. Lijun An, Yue Liang, Xueyuan Yang, Huimei Wang, Jie Zhang, Muhetaer Tuerhong, Dihua Li, Chunyan Wang, Dongho Lee, Jing Xu, Ling Shuai, Jin Jin, Yuanqiang Guo. NO inhibitory diterpenoids as potential anti-inflammatory agents from Euphorbia antiquorum. Bioorganic Chemistry 2019, 92, 103237. DOI: 10.1016/j.bioorg.2019.103237.
  7. Navneet Kishore, Pradeep Kumar, Karuna Shanker, Akhilesh Kumar Verma. Human disorders associated with inflammation and the evolving role of natural products to overcome. European Journal of Medicinal Chemistry 2019, 179, 272-309. DOI: 10.1016/j.ejmech.2019.06.034.
  8. Jin-Hai Yu, Dong-Xiang Wu, Zhi-Pu Yu, Yu-Peng Li, Yin-Yin Wang, Shu-Juan Yu, Hua Zhang. New e:b-Friedo-Hopane Type Triterpenoids from Euphorbia peplus with Simiarendiol Possessing Significant Cytostatic Activity against HeLa Cells by Induction of Apoptosis and S/G2 Cell Cycle Arrest. Molecules 2019, 24 (17) , 3106. DOI: 10.3390/molecules24173106.
  9. Yan-Fei Liu, Shi-Shan Yu. Survey of natural products reported by Asian research groups in 2016. Journal of Asian Natural Products Research 2017, 19 (11) , 1047-1072. DOI: 10.1080/10286020.2017.1391229.
  10. Abbes Benmerache, Abdulmagid Alabdul Magid, Amira Labed, Ahmed Kabouche, Laurence Voutquenne-Nazabadioko, Jane Hubert, Hamid Morjani, Zahia Kabouche. Isolation and characterisation of cytotoxic compounds from Euphorbia clementei Boiss.. Natural Product Research 2017, 31 (18) , 2091-2098. DOI: 10.1080/14786419.2016.1277345.
  11. Jiantao Zhang, Huanfeng Jiang, Shifa Zhu. Cascade One-Pot Synthesis of Indanone-Fused Cyclopentanes from the Reaction of Donor-Acceptor Cyclopropanes and Enynals via a Sequential Hydrolysis/Knoevenagel Condensation/[3+2] Cycloaddition. Advanced Synthesis & Catalysis 2017, 359 (17) , 2924-2930. DOI: 10.1002/adsc.201700345.
  12. James R. Hanson. Diterpenoids of terrestrial origin. Natural Product Reports 2017, 34 (10) , 1233-1243. DOI: 10.1039/C7NP00040E.

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