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      Three new ent-abietane diterpenoids from the roots of Euphorbia fischeriana and their cytotoxicity in human tumor cell lines

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          Abstract

          Abstract

          Three new ent-abietane diterpenoids, termed fischerianoids A–C ( 1– 3), were isolated and identified from the ethyl acetate extracts of roots of the medicinally valuable plant Euphorbia fischeriana. The planar and relative structures of 1– 3 were established via high-resolution electrospray ionisation mass spectrometry and one- and two-dimensional nuclear magnetic resonance spectroscopic analyses, and the absolute configuration of 1 was further established via X-ray crystallography experiment. Compounds 1– 3 showed selective inhibitory potency against certain human tumor cell lines with IC 50 values ranging from 8.50 ± 0.13 to 35.52 ± 0.08 μM.

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          The online version of this article (10.1007/s12272-019-01151-y) contains supplementary material, which is available to authorized users.

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          Absolute structure and absolute configuration

          H. Flack, G Bernardinelli (1999)
          Fundamental notions concerning absolute structure and absolute configuration, and their determination from single-crystal diffraction measurements, are presented and reviewed. A glossary of terms with definitions useful in this field is provided. For absolute structure and its determination, the separate but interacting influences of the structure and the inversion-distinguishing power of an X-ray diffraction experiment with dispersive scatterers are examined. Important experimental and algorithmic details of the current methods used for absolute-structure determination are provided. Characterization of crystals for absolute-structure determination and of molecules for absolute-configuration determination are treated. Attention is given to the analysis of absolute structure and absolute configuration in twinned crystals.
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            SHELXL: high-resolution refinement.

            Fabian Schneider, George M. Sheldrick (1996)
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              Diterpenoids from the roots of Euphorbia fischeriana.

              Bo Wang, Rong Huang, Bing Wang … (2006)
              From the dried roots of Euphorbia fischeriana, seven new diterpenoids, 3alpha,17-dihydroxy-ent-pimara-8(14),15-diene (1), 7beta,11beta,12beta-trihydroxy-ent-abieta-8(14),13(15)-dien-16,12-olide (2), 17-acetoxyjolkinolide B (3), 13beta-hydroxy-ent-abiet-8(14)-en-7-one (4), 12-deoxyphorbaldehyde-13-acetate (5) 12-deoxyphorbaldehyde-13-hexadecacetate (6), and 12-deoxyphorbol-13-(9Z)-octadecanoate-20-acetate (7), and two known compounds, 12-deoxyphorbol-13-decanoate (8) and prostratin (9), were isolated. The structures of the new compounds were elucidated on the basis of spectroscopic analysis. The structure of compound 1 was confirmed by single-crystal X-ray crystallography. Compounds 3 and 8 exhibited potent cytotoxic activity to Ramos B cells with IC50 values of 0.023 and 0.0051 microg/mL, respectively.
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                Author and article information

                Contributors
                Guanghui Lv: +18772836076 , lvguanghui0725@163.com
                Xintao Chen: +18772836076 , m18772836076@163.com
                Journal
                Journal ID (nlm-ta): Arch Pharm Res
                Journal ID (iso-abbrev): Arch. Pharm. Res
                Title: Archives of Pharmacal Research
                Publisher: Pharmaceutical Society of Korea (Seoul )
                ISSN (Print): 0253-6269
                Publication date (Electronic): 17 April 2019
                Publication date PMC-release: 17 April 2019
                Publication date (Print): 2019
                Volume: 42
                Issue: 6
                Pages: 512-518
                Affiliations
                [1 ]ISNI 0000 0004 1799 2448, GRID grid.443573.2, Department of Pharmacy, Taihe Hospital, , Hubei University of Medicine, ; Shiyan, 442000 People’s Republic of China
                [2 ]ISNI 0000 0004 0368 7223, GRID grid.33199.31, 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
                Article
                Publisher ID: 1151
                DOI: 10.1007/s12272-019-01151-y
                PMC ID: 6562045
                PubMed ID: 30997601
                SO-VID: f37e0adc-e9e6-4e40-b973-86a054486f4c
                Copyright © © The Author(s) 2019
                License:

                Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License ( http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.

                History
                Date received : 3 January 2019
                Date accepted : 1 April 2019
                Funding
                Funded by: the Program for Foundation of Health and Family Planning Commission of Hubei Province
                Award ID: WJ2017F079
                Award Recipient :
                Funded by: the Soft Science Project of Taihe Hospital
                Award ID: 2017rkt12
                Award Recipient :
                Categories
                Subject: Research Article
                Custom metadata
                issue-copyright-statement © The Pharmaceutical Society of Korea 2019

                Keywords: ent-abietane diterpenoids,euphorbia fischeriana,structural elucidation,cytotoxicity
                Data availability:
                Keywords: ent-abietane diterpenoids, euphorbia fischeriana, structural elucidation, cytotoxicity

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