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Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2016, 18, 3, 496-499

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One-Step Semisynthesis of a Segetane Diterpenoid from a Jatrophane Precursor via a Diels–Alder Reaction

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† State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, 132 Lanhei Road, Kunming 650201, P. R. China
‡ Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States
§ University of Chinese Academy of Sciences, Beijing 100049, P. R. China
Cite this: Org. Lett. 2016, 18, 3, 496-499
Publication Date (Web):January 19, 2016
https://doi.org/10.1021/acs.orglett.5b03473
Copyright © 2016 American Chemical Society
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Abstract

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A novel segetane diterpenoid (1) and four jatrophane diterpenoids (2–5) were isolated from an acetone extract of Euphorbia peplus. Due to quantity limitations, we prepared 1 via a Diels–Alder reaction, an approach motivated by this compound’s biosynthetic pathway and successfully performed X-ray analysis of 1. Furthermore, in an in vitro activity test, 1 exhibited moderate anti-inflammatory activity, whereas both its precursor (2) and the relevant intermediate (2a, IC50 = 1.56 μM) exhibited significant anti-inflammatory activity.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.5b03473.

  • X-ray data for compound 1 (CIF)

  • Experimental section, X-ray crystallographic data of 1, spectroscopic spectra of compound 1–5, 2a, and 3a (PDF)

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Cited By

This article is cited by 13 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. Taotao Ling, Walter H. Lang, Jane Craig, Malia B. Potts, Amit Budhraja, Joseph Opferman, John Bollinger, Julie Maier, Travis D. Marsico, Fatima Rivas. Studies of Jatrogossone A as a Reactive Oxygen Species Inducer in Cancer Cellular Models. Journal of Natural Products 2019, 82 (5) , 1301-1311. DOI: 10.1021/acs.jnatprod.8b01087.
  3. Zhen-Peng Mai, Gang Ni, Yan-Fei Liu, Li Li, Jia-Yuan Li, De-Quan Yu. Heliojatrones A and B, Two Jatrophane-Derived Diterpenoids with a 5/10 Fused-Ring Skeleton from Euphorbia helioscopia: Structural Elucidation and Biomimetic Conversion. Organic Letters 2018, 20 (10) , 3124-3127. DOI: 10.1021/acs.orglett.8b01215.
  4. Mao Li, Virginie Carreras, Angela Jalba, and Thierry Ollevier . Asymmetric Diels–Alder Reaction of α,β-Unsaturated Oxazolidin-2-one Derivatives Catalyzed by a Chiral Fe(III)-Bipyridine Diol Complex. Organic Letters 2018, 20 (4) , 995-998. DOI: 10.1021/acs.orglett.7b03939.
  5. Luo-Sheng Wan, Rui Chu, Xing-Rong Peng, Guo-Lei Zhu, Mu-Yuan Yu, Lei Li, Lin Zhou, Shuang-Yang Lu, Jin-Run Dong, Zhi-Run Zhang, Yan Li, and Ming-Hua Qiu . Pepluane and Paraliane Diterpenoids from Euphorbia peplus with Potential Anti-inflammatory Activity. Journal of Natural Products 2016, 79 (6) , 1628-1634. DOI: 10.1021/acs.jnatprod.6b00206.
  6. Luo-Sheng Wan, Yin Nian, Chen-Jun Ye, Li-Dong Shao, Xing-Rong Peng, Chang-An Geng, Zhi-Li Zuo, Xiao-Nian Li, Jian Yang, Ming Zhou, and Ming-Hua Qiu . Three Minor Diterpenoids with Three Carbon Skeletons from Euphorbia peplus. Organic Letters 2016, 18 (9) , 2166-2169. DOI: 10.1021/acs.orglett.6b00787.
  7. Xing-Lin Xie, Run-Zhu Fan, Rong Hu, Si-Yuan Luo, Gui-Hua Tang, Sheng Yin. Euphoresulanes A–M, structurally diverse jatrophane diterpenoids from Euphorbia esula. Bioorganic Chemistry 2020, 98, 103763. DOI: 10.1016/j.bioorg.2020.103763.
  8. 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.
  9. Lie-Feng Ma, Yue Zhang, Xuan Zhang, Meng-Jia Chen, Zha-Jun Zhan, Wei-Guang Shan. A new tetracyclic diterpenoid from the seeds of Euphorbia lathyris. Journal of Chemical Research 2020, 7, 174751981990110. DOI: 10.1177/1747519819901101.
  10. Zhenpeng Mai, Gang Ni, Yanfei Liu, Zhao Zhang, Li Li, Naihong Chen, Dequan Yu. Helioscopianoids A–Q, bioactive jatrophane diterpenoid esters from Euphorbia helioscopia. Acta Pharmaceutica Sinica B 2018, 8 (5) , 805-817. DOI: 10.1016/j.apsb.2018.03.011.
  11. Zhen-Peng Mai, Gang Ni, Yan-Fei Liu, Li Li, Guo-Ru Shi, Xin Wang, Jia-Yuan Li, De-Quan Yu. Heliosterpenoids A and B, two Novel Jatrophane-Derived Diterpenoids with a 5/6/4/6 Ring System from Euphorbia helioscopia. Scientific Reports 2017, 7 (1) DOI: 10.1038/s41598-017-04399-w.
  12. 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.
  13. James R. Hanson. Diterpenoids of terrestrial origin. Natural Product Reports 2017, 34 (10) , 1233-1243. DOI: 10.1039/C7NP00040E.

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