Chemical constituents of Euphorbia peplus

doi:10.1016/j.bse.2021.104307

Biochemical Systematics and Ecology

Volume 98, October 2021, 104307

https://doi.org/10.1016/j.bse.2021.104307 Get rights and content

Highlights

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Eight compounds (1–8) were isolated from Euphorbia peplus.
•
The structure of a previously undescribed jatrophane type diterpenoid (1) was established.
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It is the first report of isolation of compound 5 from the genus Euphorbia.
•
Chemotaxonomic significance of these compounds was described.

Abstract

Phytochemical investigation of the whole plant of Euphorbia peplus Linn. led to the isolation of previously uncharacterized jatrophane type diterpenoid euphopepluanone L (1), along with seven known compounds, including three diterpenes (2–4), three bisnorsesquiterpenes (5–7), and a monoterpene (8). Their chemical structures were established based on extensive spectroscopic analysis. Compounds 3 (20-deoxyingenol) and 5–8 were firstly isolated from E. peplus, while PBI 345 (5) reported from the genus for the first time. Furthermore, the chemotaxonomic significance of the isolates was discussed.

Section snippets

Subject and source

The genus Euphorbia (Euphorbiaceae) is one of the largest genera of flowering plants containing more than 2000 species (Ernst et al., 2015). Plants of this genus are easily distinguishable by their irritant milky latex and their specialized inflorescences. There are about 80 species of the genus found in China (Editorial Committee of Flora of China, 1997), of which 32 are used in folk herb (Peng et al., 2012). E. peplus Linn. is a small annual weed that is native to Mediterranean coast and

Previous work

Previous phytochemical investigations on Euphorbia genus have mainly focused on diterpenoids which are considered as a taxonomic marker of the genus (Shi et al., 2008; Vasas and Hohmann, 2014). Several decades chemical studies on E. peplus have yielded a series of diterpenoids with abietane (Chen et al., 2020a), euphoperfoliane (Chen et al., 2020b), jatrophane (Chen et al., 2021a, 2021b; Hua et al., 2017; Hohmann et al., 1999b, 2000; Jakupovic et al., 1998; Song et al., 2010; Yang et al., 2021

Extraction and isolation

The air-dried whole parts of E. peplus (24 kg) were powdered and extracted with methanol thrice at room temperature. The extract was suspended in water and extracted with petroleum ether, and ethyl acetate. The ethyl acetate extract (660 g) was subjected to a silica gel column using petroleum ether/ethyl acetate (100:0 to 0:100, v/v) as eluent to obtain 10 fractions, F1–F10.

Fraction F6 (53 g) was subjected to MCI gel with MeOH-H₂O (40:60–100:0) to give 7 fractions. F6.5 (5.7 g) was separated by

Chemotaxonomic significance

In the present phytochemical investigation, eight compounds were isolated from the whole plants of E. peplus, including four diterpenoids (1−4), three bisnorsesquiterpenes (5–7) and a monoterpene (8). These results enriched the chemical profile of E. peplus and provided evidence for chemotaxonomic analysis of genus Euphorbia.

Diterpenoids are characteristic component of the genus Euphorbia (Vasas and Hohmann, 2014), and previous phytochemical studies on E. peplus have shown that jatrophane and

Declaration of competing interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgements

This research was supported by the National Natural Science Foundation of China under Grant (numbers 31872666); National Key R&D Program of China under Grant (number 2018YFA0900600); Special Fund for Talent Introduction of Kunming Institute of Botany, CAS (to Xin Fang); and Key R&D Program of Yunnan under Grant (2019ZF011-2).

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Phytochemical investigation into the medium polar fraction of the ethanol extract of Euphorbia peplus led to the identification of 32 diterpenoids with five structural types. Compounds 1–5 and 7–11 are reported for the first time, while the configuration of 6,7-epoxy group of 6 was revised to be β-oriented. Compounds 1–5 feature a rare structural variation of the double bond at Δ¹ migrating to Δ¹⁽¹⁰⁾ in the tigliane-type diterpenoid family. Biologically, compound 21 was found to be the only one to show moderate cytotoxic activity, associated with the presence of a benzoyloxy residue at C-16. Besides, compounds 4, 8, 12, 13, 16, and 19 show significant inhibitory activities against NO production induced by LPS in RAW264.7 macrophage cells, with IC₅₀ values within 2–5 μM. Structure-activity relationship (SAR) analysis revealed that the ingenane-type diterpenoids have the best anti-inflammatory activity, and the esterification at 3-OH or 5-OH is crucial. Further biological researches demonstrated that 13, the predominant metabolite in this plant, exerts anti-inflammatory effects by blocking the activation of NF-κB and MAPK signaling pathways.
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The compound also treats skin diseases (Lai et al., 2018). This compound has been isolated and identified from a number of plant species such as Lactuca indica, Gynura nepalensis, Rumphella sp., Toona sinensis, Nelumbo nucifera, Saussurea medusa, Saussurea pulchella, Psychotria yunnanensis, Isatis tinctoria, Euphorbia peplus, Leonurus japonicus, Humulus japonicus, Capsella bursa-pastoris, and Thesium chinense (Min et al., 2021; Xu et al., 2020; Yin et al., 2020; Peng et al., 2019; Ahn et al., 2013). Although the medicinal and allelopathic potentials have well documented (Hossen et al., 2021c), there is no report on the identification and allelopathic activity of this substance from E. floribundus.
Allelopathic compounds can play a vital role in protecting the environment from pollution by synthetic herbicides. Compounds isolated from plant species with allelopathic potential can be used as natural herbicides to control weeds and help reduce environmental pollution. Elaeocarpus floribundus has been reported to contain allelopathic compounds. Aqueous methanolic extracts of the leaves of this plant showed strong growth inhibitory potential against two test species (monocotyledonous Italian ryegrass and dicotyledonous alfalfa) in plants- and dose-dependent technique. Several extensive chromatographic separations of the E. floribundus leaf extracts yielded four active compounds 1, 2, 3, and 4 (novel compound). All the identified compounds showed strong growth inhibitory potential against cress. The concentrations caused for 50% growth limitation (I₅₀ values) of the cress seedlings were in the range 500.4–1913.1 μM. The findings indicate that the identified compounds might play a pivotal function in the allelopathic potential of E. floribundus tree. This report is the first on elaeocarpunone and its allelopathic potential.
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As the characteristic metabolites of Euphorbia plants, Euphorbia diterpenoids have always been a hot topic in related science communities due to their intriguing structures and broad bioactivities. In this review, we intent to provide an in-depth and extensive coverage of Euphorbia diterpenoids reported from 2013 to the end of 2021, including 997 new Euphorbia diterpenoids and 78 known ones with latest progress. Multiple aspects will be summarized, including their occurrences, chemical structures, bioactivities, and syntheses, in which the structure–activity relationship and biosynthesis of this class will be discussed for the first time.

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Chemical constituents of Euphorbia peplus

Highlights

Abstract

Section snippets

Subject and source

Previous work

Extraction and isolation

Chemotaxonomic significance

Declaration of competing interest

Acknowledgements

Saudi Pharmaceut. J.

Phytochemistry

Bioorg. Chem.

Org. Biomol. Chem.

J. Ethnopharmacol.

Phytochemistry

Phytochemistry

Phytochemistry

Biochem. Systemat. Ecol.

Phytochemistry

Chin. J. Nat. Med.

Phytochemistry

Org. Lett.

Org. Lett.

Org. Lett.

Three new diterpenoids from Euphorbia peplus

Nat. Prod. Res.

Jatrophane diterpenoids from the seeds of Euphorbia peplus with potential bioactivities in lysosomal-autophagy pathway

Nat. Prod. Bioprospect.

Lagaspholones Aand B: two new jatropholane-type diterpenes from Euphorbia lagascae

Org. Lett.