ent-Abietane-type diterpenoids from the roots of Euphorbia ebracteolata with their inhibitory activities on LPS-induced NO production in RAW 264.7 macrophages

doi:10.1016/j.bmcl.2015.11.080

Bioorganic & Medicinal Chemistry Letters

Volume 26, Issue 1, 1 January 2016, Pages 1-5

https://doi.org/10.1016/j.bmcl.2015.11.080 Get rights and content

Abstract

Ten ent-abietane diterpenoids (1–10), including four new (1–4) and six known ones (5–10) were isolated from the roots of Euphorbia ebracteolata. Their structures were determined by 1D, 2D NMR, and HRESIMS. Compounds 2, 4, and 7 exhibited significant inhibitory activities on lipopolysaccharide (LPS)-induced nitric oxide production in RAW 264.7 macrophages with IC₅₀ values of 0.69, 1.97, and 0.88 μM, respectively. A primary structure–activity relationship was also discussed.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant NO. 81172958) and Program for Innovative Research Team of the Ministry of Education and Program for Liaoning Innovative Research Team in University. We appreciate the help of Prof. Jincai Lu at Shenyang Pharmaceutical University for identifying the plant material.

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The roots of the plant Euphorbia ebracteolata Hayata (Yue Xian Da Ji) are commonly used in traditional Chinese medicine to treat multiple diseases such as chronic liver diseases, oedema, pulmonary diseases and cancer. It is the main ingredient of the TCM called Langdu which can be prepared also from roots of E. fischeriana Steud. and occasionally from Stellera chamaejasme species. Numerous bioactive natural products have been isolated from E. ebracteolata including a large diversity of diterpenoids with anti-inflammatory and anticancer properties. One little series of compounds has been named yuexiandajisu (A, B, C, D, D₁, E, F) which comprises two casbane-, one isopimarane-, two abietane-, and two rosane-type diterpenes including a dimeric molecule. The origin, structural diversity and properties of these little-known natural products is discussed here. Several of these compounds have been identified in the roots of other Euphorbia species, notably the potent phytotoxic agent yuexiandajisu C. The abietane diterpenes yuexiandajisu D-E exhibit marked anticancer properties but their mechanism of action remains unresolved. The dimeric compound, renamed yuexiandajisu D₁, also exhibit anti-proliferative properties against cancer cell lines, unlike the rosane diterpene yuexiandajisu F. The structural or functional analogy with other diterpenoids is discussed.
Jolkinolide B: A comprehensive review of its physicochemical properties, analytical methods, synthesis and pharmacological activity
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Jolkinolide B is a typical ent-abietane-type diterpenoid, which is first found in Euphorbia jolkini. It is one of the most important active components in many toxic Euphorbia plants. In recent years, jolkinolide B has garnered increasing attention due to its high potent and multiple pharmacological activities. In order to better understand the research status of jolkinolide B, relevant information about jolkinolide B was collected from scientific databases (SciFinder Scholar, PubMed, ACS website, Elsevier, Web of Science, Google Scholar, Science Direct, and CNKI). There are few studies on chemical synthesis and biosynthesis of jolkinolide B. In addition, researchers on the activities of jolkinolide B are mostly concentrated at the cellular level, and there is a lack of research on the mechanism. In this review, the possible applications of jolkinolide B were systematically illustrated for the first time, from plant sources, physicochemical properties, analytical methods, synthesis and pharmacological activities. Jolkinolide B exhibits extensive pharmacological properties, including anticancer, anti-inflammatory, anti-osteoporosis, and anti-tuberculosis activities. Pharmacological activities of jolkinolide B were mainly focused on anticancer and anti-inflammatory activities, and the mechanism of action may be related with inhibition of JAK/STAT pathway, NF-κB pathway and PI3K/Akt/mTOR pathway. In addition, the extraction methods and analytical methods discussed in this review, will facilitate the development of novel herbal products for better healthcare solutions.
Phytochemical and pharmacological review of diterpenoids from the genus Euphorbia Linn (2012–2021)
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Euphorbia is one of the major genera in angiosperms, which is widely distributed all over the world, including Asia, Africa and Central and South America. The roots or tubers of Euphorbia are famous for medicinal purposes, especially in China. Many of them, such as Euphorbia pekinensis Rupr, Euphorbia fischeriana Steud and Euphorbia Kansui S.L.Liou ex S.B.Ho. . are used as Chinese herbal medicines.
This paper reviews the diterpenoids isolated from the genus Euphorbia species and the pharmacological activities of these compounds to evaluate its traditional use and potential future development.
Information on the studies of the genus Euphorbia Linn was collected from scientific journals, books and reports via library and electronic data search (Scifinder, Web of Science, PubMed, Elsevier, Scopus, Google Scholar, Springer, Science Direct, Wiley, ACS, CNKI and Kew Plants of the Word Online). Meanwhile, it was also obtained from published works of material medica, folk records, ethnophmacological literatures, Ph.D. and Masters dissertations.
Known as the main constituents of the genus Euphorbia Linn, Diterpenoids possess many pharmacological properties such as anti-inflammation, antiviral activities and cytotoxicity. To date, various types of diterpenoids were identified from this genus, including isopimarane, rosane, abietane, ent-kaurane, ent-atisane. cembrane, casbane, lathyrane, myrsinane, jatropholane, tigliane, ingenane, jatrophane, paraliane, pepluane, and euphoractin.
This review describes 14 types of diterpenoid isolated from 45 Euphorbia species from 2012 to 2021, a total of 615 compounds. Among them, mainly include jatrophane (171), lathyrane (92), myrsinane (62), abietane (70), ent-atisane (36), ent-kaurane (7), tigliane (26) and ingenane (19). The possible biological pathways of these compounds were presumed. At the same time, more than 10 biological activities of these compounds were summarized, such as anti-inflammation, antiviral activities and cytotoxicity.
Euphorbia diterpenoids: isolation, structure, bioactivity, biosynthesis, and synthesis (2013-2021)
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Covering: 2013 to 2021
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.
Diterpenoids from the genus Euphorbia: Structure and biological activity (2013–2019)
2021, Phytochemistry
Citation Excerpt :
Later, four abietane-type diterpenoids, fischeriolides A-D (16–19), together with 11 known diterpenoids were obtained from the same plant (Lee et al., 2016b). Six abietane-type diterpenoids, euphoroids A-C (20–22) (Han et al., 2018), ebracteolata D (23) (Ma et al., 2018), ebractenoid Q (24) (Bai et al., 2018), and ebractenoid N (25) (Liu et al., 2016c) were obtained from the roots of E. ebracteolata, and their structures were elucidated on the basis of spectroscopic data. Phytochemical investigation of whole plants of E. pilosa led to the isolation and identification of an abietane diterpenoid, euphopilolide (26) (Zhang et al., 2014).
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 diterpenoids in recent years, such as neuroprotection, antimalarial activity and inhibition of osteoclast formation. In this review, we summarize all the isolated diterpenoids from the genus Euphorbia according to their skeleton types, classify all these diterpenoids into 26 normal classes and 37 novel skeleton types, and summarize their biological activity.
Euphorbia ebracteolata Hayata (Euphorbiaceae): A systematic review of its traditional uses, botany, phytochemistry, pharmacology, toxicology, and quality control
2021, Phytochemistry
Citation Excerpt :
Furthermore, by comparing the structures and activities of 14 and 15, it could be found that the relative configuration of hydroxy groups at C-9 and C-14 also significantly influenced the anti-inflammatory activities of abietane diterpenoids (Liu et al., 2016) (Fig. 22). When the hydroxyl group at C-14 (15) is substituted by myrtenic acid moieties (32), the inhibitory activity is also enhanced (Bai et al., 2017; Liu et al., 2016) (Fig. 22). Some rosane diterpenoids, for example, ebractenoid H (45), yuexiandajisu F (48) and hugorosenol (49) had anti-inflammatory effects, with IC50 values of 19.02, 24.32, and 12.50 μM, while ebractenoid C (40), ebractenoid D (41), ebractenoid E (42), ebractenoid F (43), ebractenoid G (44), ebractenoid I (46), ebractenoid J (47), and ebractenoid O (53) exhibited more obvious anti-inflammatory effects, with IC50 values of 7.29, 5.51, 5.57, 3.33, 2.44, 7.32, 2.76, and 1.02 μM.
Euphorbia ebracteolata Hayata, as a traditional medicine, is widely distributed in China, Korea and Japan. In China, the dried root of this plant is named 'langdu'. It is traditionally used to treat oedema, skin ulcers, abdominal distension, cough, asthma, tuberculosis swelling and other diseases. Previous studies have found that the chemical constituents of E. ebracteolata are mainly concentrated in terpenoids, acetophenones, and flavonoids. Both extracts and pure compounds from E. ebracteolata were found to possess many pharmacological activities, such as anticancer, anti-inflammatory, antiviral, and antimicrobial effects. In addition, it was reported that E. ebracteolata shows toxicity. To provide inspiration for further in-depth studies on this plant, this review will provide a timely and systematic summary of E. ebracteolata in traditional uses, phytochemistry, pharmacology toxicology, and quality control.

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ent-Abietane-type diterpenoids from the roots of Euphorbia ebracteolata with their inhibitory activities on LPS-induced NO production in RAW 264.7 macrophages

Abstract

Graphical abstract

Section snippets

Acknowledgements

Fitoterapia

Carbohydrate Res.

Phytochemistry

Fitoterapia

Curr. Drug Targets Inflammation Allergy.

Acta Pharm. Sinica

Planta Med.

J. Asian Nat. Prod. Res.