Lathyrane-Type Diterpenoids from the Seeds of Euphorbia lathyris L. with Inhibitory Effects on NO Production in RAW 264.7 Cells.

Published on Oct 1, 2018in Chemistry & Biodiversity2.039
· DOI :10.1002/CBDV.201800144
Jin Woo Lee13
Estimated H-index: 13
(CBNU: Chungbuk National University),
Qinghao Jin13
Estimated H-index: 13
(CBNU: Chungbuk National University)
+ 6 AuthorsBang Yeon Hwang37
Estimated H-index: 37
(CBNU: Chungbuk National University)
: Bioactivity-guided fractionation of the methanolic extract from the seeds of Euphorbia lathyris led to the isolation of 18 lathyrane-type diterpenoids including a new one, Euphorbia factor L29 (1). Their chemical structures were elucidated by extensive NMR spectroscopic data including 2D-NMR and HR-ESI-MS as well as CD data. All isolates (1 - 18) were found to inhibit the nitric oxide production in LPS-induced RAW 264.7 macrophages, with their IC50 values in the range of 11.2 - 52.2 μm.
📖 Papers frequently viewed together
8 Citations
9 Authors (Jin Lu, ..., Jin-Hui Wang)
36 Citations
4 Citations
#1Jia-Xi Wang (Southwest Jiaotong University)H-Index: 2
#2Qian Wang (Southwest Jiaotong University)H-Index: 2
Last. Xian-Li Zhou (Southwest Jiaotong University)H-Index: 12
view all 6 authors...
We isolated two new lathyrane-type diterpenes L27 (1) and L28 (2) along with seven known compounds (3-9) from the seeds of Euphorbia lathyris. These compounds were identified by NMR, high-resolution electrospray ionisation (HR-ESI)-MS as well as IR spectroscopy. Compounds 1 and 2 were assigned NMR spectrums with 1H-NMR, 13C-NMR, distortionless enhancement by polarization (DEPT), correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple bond connecti...
12 CitationsSource
#1Juan Hua (CAS: Chinese Academy of Sciences)H-Index: 11
#2Shi-Hong Luo (CAS: Chinese Academy of Sciences)H-Index: 6
Last. Xue-Mei Niu (Ministry of Education)H-Index: 16
view all 10 authors...
Three new macrocyclic diterpenoids, euphoscopoids A - C (1 - 3), including two new jatrophanes and a new lathyrane, were isolated from the whole plant of Euphorbia helioscopia. Their structures were elucidated by spectroscopic methods. Antifeedant and cytotoxic activities of these isolates were evaluated. All compounds showed significant antifeedant activity against a generalist plant-feeding insect, Helicoverpa armigera, with EC50 values ranging from 2.05 to 4.34 mu g/cm(2). In addition, compou...
6 CitationsSource
#1Li Wang (CAS: Chinese Academy of Sciences)H-Index: 8
#2Ya-Tuan Ma (CAS: Chinese Academy of Sciences)H-Index: 6
Last. Yong Zhao (YNNU: Yunnan Normal University)H-Index: 14
view all 9 authors...
A new lathyrane diterpenoid ester, euphordracunculin C (1), together with a phenolic amide, 4-hydroxy-N-[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-3-methoxybenzamide (2), was isolated from the aerial parts of Euphorbia dracunculoides. The structure of the new compound was elucidated on the basis of spectroscopic analysis including 1D and 2D NMR techniques.
6 CitationsSource
#1Jin Woo Lee (CBNU: Chungbuk National University)H-Index: 13
#2Qinghao Jin (CBNU: Chungbuk National University)H-Index: 13
Last. Bang Yeon Hwang (CBNU: Chungbuk National University)H-Index: 37
view all 9 authors...
Bioactivity-guided fractionation of the MeOH extract from the roots of Euphorbia kansui resulted in the isolation of two new jatrophane-type diterpenoids, kanesulones A (1) and B (2), together with six known jatrophane-type diterpenoids (3–8) and ten known ingenane-type diterpenoids (9–18). Their chemical structures were elucidated on the basis of spectroscopic data interpretation, especially 1D and 2D NMR such as HMQC, HMBC, COSY and NOESY, and HRESIMS data as well as CD analysis. Compounds 1–8...
22 CitationsSource
#1Jin Woo Lee (CBNU: Chungbuk National University)H-Index: 13
#2Chul Lee (CBNU: Chungbuk National University)H-Index: 16
Last. Bang Yeon Hwang (CBNU: Chungbuk National University)H-Index: 37
view all 12 authors...
Bioactivity-guided isolation of a methanolic extract of Euphorbia fischeriana led to the isolation of four new abietane-type diterpenoids, fischeriolides A–D (1–4), together with 11 known diterpenoids. Their structures were elucidated based on the interpretation of 1D and 2D NMR spectroscopic and HRESIMS data. The absolute configuration of compound 3 was determined by single-crystal X-ray diffraction analysis and electronic circular dichroism methods. Compounds 5–9 exhibited inhibitory effects o...
28 CitationsSource
#1Shanshan Yang (TJU: Tianjin University)H-Index: 2
#2Jiachen Sun (Tianjin University of Traditional Chinese Medicine)H-Index: 1
Last. Yaozhou Zhang (TJU: Tianjin University)H-Index: 2
view all 5 authors...
Euphorbia lathyris has been known traditionally for its anticancer activity. However, for weakly polar compositions of Euphorbia lathyris, there is a lack of comprehensive chromatographic purification methods. Therefore, it is necessary to establish an efficient bioassay-guided off-line 2D HPLC method for isolation and identification of anticancer compounds from the Euphorbia lathyris ethyl acetate extract. In the present study, preparative separation in the first dimension was performed on a ba...
3 CitationsSource
#1Wei Jiao (CAS: Chinese Academy of Sciences)H-Index: 10
#2Zhongmin Wan (CAS: Chinese Academy of Sciences)H-Index: 1
Last. Huawu Shao (CAS: Chinese Academy of Sciences)H-Index: 17
view all 11 authors...
Five series of 37 new acylate and epoxide derivatives (3–39) of Euphorbia factor L3, a lathyrol diterpene isolated from Euphorbia lathyris, were designed by modifying the hydroxyl moiety of C-3, C-5, or C-15. Chemoreversal effects of the acylates on multidrug resistance (MDR) were evaluated in breast cancer multidrug-resistant MCF-7/ADR cells that overexpress P-glycoprotein (P-gp). Eight derivatives exhibited greater chemoreversal ability than verapamil (VRP) against adriamycin (ADR) resistance....
22 CitationsSource
#1Cátia Vieira (University of Lisbon)H-Index: 1
#2Noélia Duarte (University of Lisbon)H-Index: 21
Last. Maria-José U. Ferreira (University of Lisbon)H-Index: 30
view all 7 authors...
Abstract Aiming to optimize macrocyclic lathyrane-type diterpenes as effective Pgp modulators, the phytochemical study of the methanolic extract of Euphorbia boetica aerial parts was carried out. Two new macrocyclic 6,17-epoxylathyrane-type diterpenes, named epoxyboetiranes A ( 1 ) and B ( 2 ), along with three known analogues ( 3 – 5 ) were isolated. Epoxyboetirane A ( 1 ), a triacetate isolated in large amounts, was hydrolyzed to give epoxylathyrol ( 6 ). In order to study the effect of the su...
26 CitationsSource
#1Jin Lu (SPU: Shenyang Pharmaceutical University)H-Index: 4
#2Guoyu Li (XMU: Xinjiang Medical University)H-Index: 1
Last. Jin-Hui Wang (SPU: Shenyang Pharmaceutical University)H-Index: 18
view all 9 authors...
Abstract Ten lathyrane-type diterpenoids named Euphorbia Factor L 12 –L 21 ( 1 – 10 ) and twelve known diterpenoids ( 11 – 22 ) were isolated from seeds of Euphorbia lathyris . The structures of these compounds were determined by extensive spectroscopic (UV, IR, HRESIMS, 1D and 2D NMR) analyses. In addition, the configuration of Euphorbia Factor L 12 ( 1 ) was further confirmed by X-ray crystallographic and circular dichroism (CD) analyses. A putative biogenetic relationship to these compounds w...
36 CitationsSource
#1Andrea Vasas (University of Szeged)H-Index: 23
#2Judit Hohmann (University of Szeged)H-Index: 39
244 CitationsSource
Cited By5
#1Yang Xu (SPU: Shenyang Pharmaceutical University)H-Index: 2
#2Peiyu Tang (SPU: Shenyang Pharmaceutical University)
Last. Lixia Chen (SPU: Shenyang Pharmaceutical University)H-Index: 24
view all 7 authors...
Abstract null null Euphorbiaceae is one of the largest families of higher plants, including 7500 species, and many of them are used as medicines in China. From 2013 to 2019, a total of 455 previously undescribed diterpenoids were isolated from 53 species of Euphorbia, and some skeleton types were first discovered from the genus Euphorbia. Most of the diterpenoids isolated from Euphorbia spp. have been tested for their biological activity, and some of them were first reported for Euphorbia diterp...
#1Meijuan Hou (Shanxi Medical University)
#2Yiqiong Zhang (Shanxi Medical University)
Last. Anjia Chen (Shanxi Medical University)H-Index: 7
view all 7 authors...
In this study, a hydrophobic interaction electrokinetic chromatography method has been developed for simultaneous separation and determination of three diterpenoids in Euphorbiae Lathyris L.: Euphorbia factor L1 , Euphorbia factor L2 and Euphorbia factor L3 . After optimization of separation conditions, the electrolyte solution was 5.0 mM ammonium acetate buffer containing 30 mM sodium dodecyl sulfate in a 60% (v/v) methanol (pH 6.86), 25 kV of electric field across the capillary was applied at ...
#1Ya-Li Wang (SPU: Shenyang Pharmaceutical University)H-Index: 7
#2Zhuorui Song (SPU: Shenyang Pharmaceutical University)
Last. Lixia Chen (SPU: Shenyang Pharmaceutical University)H-Index: 24
view all 8 authors...
Abstract Twelve previously undescribed diterpenoids, euplarisans A-L (1-12), including one premyrsinane and eleven lathyranes, along with ten known analogues 13-22 were isolated from the seeds of Euphorbia lathyris. Their chemical structures were delineated by spectroscopic analysis and single-crystal X-ray diffraction. Interestingly, both 5 and 6 possessed an unusual trans-gem-dimethylcyclopropane as structural features and compound 8 was elucidated as premyrsinane-type diterpenoid. Meanwhile, ...
1 CitationsSource
#9Fei Liu (CAS: Chinese Academy of Sciences)H-Index: 27
Two novel lathyrane-type diterpenoids, the Euphorbia factors L2a (1) and L2b (2), and their stereoisomer Euphorbia factor L2 (3) were obtained from seeds of Euphorbia lathyris. Both Euphorbia factors L2a and L2b possess an unprecedented trans-gem-dimethylcyclopropane as structural feature. Also, the Euphorbia factor L2a is the first example of a lathyrane diterpenoid with an endocyclic 12(Z)-double bond. The structures of the molecules and their absolute configurations were elucidated by compreh...
1 CitationsSource
#1Vincent A. Ricigliano (ARS: Agricultural Research Service)H-Index: 11
#2Vincent P. Sica (UNCG: University of North Carolina at Greensboro)H-Index: 8
Last. Nicholas H. Oberlies (UNCG: University of North Carolina at Greensboro)H-Index: 59
view all 6 authors...
Abstract Plants in the genus Euphorbia produce a wide variety of pharmacologically active diterpenoids with anticancer, multidrug resistance reversal, and antiviral properties. Some are the primary industrial source of ingenol mebutate, which is approved for treatment of the precancerous skin condition actinic keratosis. Similar to other high value phytochemicals, Euphorbia diterpenoids accumulate at low concentrations in planta and chemical synthesis produces similarly low yields. We establishe...
3 CitationsSource