Chemotaxonomic and chemical studies on two plants from genus of Euphorbia: Euphorbia fischeriana and Euphorbia ebracteolata

doi:10.1016/j.bse.2014.09.009

Biochemical Systematics and Ecology

Volume 57, December 2014, Pages 345-349

https://doi.org/10.1016/j.bse.2014.09.009 Get rights and content

Highlights

•
28 compounds were isolated from Euphorbia fischeriana and Euphorbia ebracteolata Hayata.
•
Acetophenone derivatives and diterpenes are the basis compounds of two plants.
•
The plants of Euphorbia have similar biosynthesis system and genetic relationship.
•
Three compounds can be designated as characteristics for plants identification.
•
It provided evidences to support two plants as the origin of the same Chinese Langdu.

Abstract

The phytochemical investigation of two plants from genus Euphorbia, Euphorbia fischeriana Steud and Euphorbia ebracteolata Hayata led to the isolation of 28 compounds. Among them, 1–3, 12–13, 20–21, 23–25, and 28 were obtained from E. fischeriana. 14–19, and 22 were acquired from E. ebracteolata. 4–11, and 26–27 were found in both of species, and 20 and 28 are isolated from E. fischeriana for the first time. In addition, acetophenone derivatives (7–9) and diterpenes (10–25) are the basis of E. fischeriana and E. ebracteolata. The abietane, atisane, and kaurane types of diterpenes and acetophenone derivatives could be regarded as good taxonomic markers for two medicinal plants, while lupane type triterpenoids，tigliane type diterpenoids and rosane diterpenes demonstrated differences of the two species.

Section snippets

Subject and source

The genus Euphorbia (Euphorbiaceae) is composed of more than 8000 species, which are distributed all over the world especially in Africa and Central and South America. In China, about 70 species have been found nationwide, of which most species and varieties are used as Traditional Chinese Medicines. Euphorbia fischeriana Steud and Euphorbia ebracteolata Hayata, two important medicinal species of the genus, are regarded to have same effects on the treatment of tuberculosis, tumour, and chronic

Chemical study

The air-dried roots of E. fischeriana and E. ebracteolata (each 10 kg) were powdered and extracted exhaustively with 95% aqueous ethanol (EtOH) under reflux for 3 h to obtain E. fischeriana extracts (EF) and E. ebracteolata extracts (EE), respectively. After evaporation of the combined EtOH extracts in vacuo, the resultant aqueous residues were suspended in water and partitioned with petroleum ether, chloroform, and ethyl acetate (EtOAc) in succession.

The petroleum ether extract (300 g) from EF

Chemotaxonomic implications

The phytochemical research of the E. fischeriana and E. ebracteolata were started in the late 1980s, and the compounds isolated from this genus include diterpenes (Che et al., 1999), acetophenone derivatives (Liu et al., 2001), triterpenoids (Liu et al., 1987), sterols (Schroeder et al., 1980), and flavones (Ma et al., 1997). Among them, diterpenes, especially abietane type diterpenes and acetophenone derivatives are the main constituents of E. fischeriana and E. ebracteolata. In our present

Acknowledgements

This research was financially supported by grants from National Natural Science Foundation of China (No. 81374061) and Program for Innovative Research Team of the Ministry of Education and Program for Liaoning Innovative Research Team in University. We also thank Prof. Jin-Cai Lu from Shenyang Pharmaceutical University for his work on identifications of the plant.

References (29)

C.T. Che et al.
Phytochemistry
(1999)
C. Chen et al.
Biochem. Syst. Ecol.
(2013)
A.R. Lal et al.
Phytochemistry
(1990)
A.R. Lal et al.
Phytochemistry
(1990)
G.A. Lane et al.
Phytochemistry
(1986)
J.L. Liu et al.
Zhongcaoyao
(2012)
L.W. Pang et al.
Neimenggu Nongye Daxue Xuebao
(2012)
G. Schroeder et al.
Phytochemistry
(1980)
D.T.A. Youssef et al.
Phytochemistry
(1998)
Chinese Pharmacopoeia Commission
Chinese pharmacopoeia
(2010)

B. Deng et al.

Nat. Prod. Res.

(2010)

G. Dräger et al.

Eur. J. Org. Chem.

(2007)

S.H. Guo et al.

Xibei nongye xuebao

(2011)

Z.J. Guo et al.

J. Chin. Med. Mater.

(2007)

Cited by (26)

Discovery of rearranged tigliane-type diterpenoids from Euphorbia ebracteolata
2024, Tetrahedron
Three novel rearranged tigliane-type diterpenoids, euphebrananes A-C (1–3), and one precursor tigliane-type diterpenoid, euphebrananes D (4), were isolated from the roots of Euphorbia ebracteolata. The structures of isolates were identified by comprehensive spectroscopy, HRESIMS, quantum chemical calculations (ECD and NMR), and X-ray crystallography. Euphebrananes A-C represented a tigliane-type diterpenoid, and a plausible biosynthetic pathway of 1–4 was proposed. In vitro, anti-inflammatory and estrogen-like activity screening showed that 1–4 exhibited weak related biological activities.
Yuexiandajisu diterpenoids from Euphorbia ebracteolata Hayata (Langdu roots): An overview
2023, Phytochemistry
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
2022, Phytochemistry
Citation Excerpt :
The method of solvent extraction, notably 95% ethanol, has been widely used for the extraction of jolkinolide B (Jia et al., 2015; Sun and Zhang, 2014; Geng et al., 2011; Wang et al., 2010; Wu et al., 2010; Bai et al., 2005; Sutthivaiyakit et al., 2000; Che et al., 1999; Morgenstern et al., 1996; Jeske et al., 1995; Daisuke and Yoshimasa, 1972). Moreover, Jian et al. obtained jolkinolide B from the aqueous extract of E. fischeriana by reflux extraction (Jian et al., 2005), and the isolation of jolkinolide B from plants by this method has also been reported in many other studies (Zhang et al., 2016b; Liang et al., 2014; Pan et al., 2011; Yan et al., 2008; Yan and Chen, 2007; Jian et al., 2005). Jian et al. studied the process of ultrasound-assisted extraction of jolkinolide B from E. fischeriana with ethanol [ω (C2H5OH) = 95%], and the indicator of the jolkinolide B extraction ratio was estimated by high-performance liquid chromatography (HPLC) (Jian et al., 2007).
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.
Eupholaricanone, A potent α-glucosidase anthracene derivative from Euphorbia larica Boiss
2022, South African Journal of Botany
Citation Excerpt :
It is widely dispersed across the globe, notably in tropical places such as Africa, the Arabian Peninsula, and Asia (Vasas and Hohmann, 2014). The majority of Euphorbia species are used to treat migraines, wounds, skin diseases, ulcers, intestinal parasites, bronchitis, asthma, cough, gastrointestinal disorders, bowel complaints, abscesses, tuberculosis, tumor, chronic tracheitis, inflamed glands (Aljubiri et al., 2021; Boudiar et al., 2010; Liang et al., 2014; Maema et al., 2016; Patel et al., 2009; Singla and Pathak, 1990; Youssouf et al., 2007) and to treat skin cancer, pulpal devitalizing agent, and keratosis (Ernst et al., 2015; Patel, Naikwade et al., 2009; Yam et al., 1997). Some Euphorbia species contains natural compounds that are being studied for their toxicity or medicinal potency, and some have been used as remedies since ancient times (Demirkiran et al., 2011; Tang et al., 2012).
A potent α-glucosidase anthracene derivative (eupholaricanone, 1), along with three known compounds lupeol (2) and lupeol acetate (3), and lup 20(29)-ene (4) was isolated as a natural product from ethyl acetate fraction of Euphorbia larica. The structure of the compound was elucidated by 1D (¹H- and ¹³C) and 2D (HSQC, HMBC, COSY and NOESY) nuclear magnetic resonance (NMR) spectroscopy and mass (QTOF-LCMS) spectrometry, and crystal structure was determined by single-crystal X-ray diffraction analysis. In vitro, compound 1 displayed potent α-glucosidase inhibitory activity with 91.60% inhibition and IC₅₀ value of 45.91 ± 0.61 µM. Furthermore, in silico structural bioinformatics tool was employed to predict the binding pattern of compound 1 in the active site of α-glucosidase where compound demonstrated excellent binding interactions with Arg213 and His351 and exhibited higher docking score than the substrate molecule. Our experimental findings and docking results indicate that this anthracene derivative could serve as a lead compound upon optimization.
Euphorboside A, a cytotoxic meroterpenoid glycoside with an unusual humulene-phloroglucinol skeleton from Euphorbia kansuensis
2021, Fitoterapia
Citation Excerpt :
Its plausible biosynthetic pathway was proposed in Scheme 1. Briefly, 4,6-dihydroxy-2-methoxy-3-methylacetophenone (2), an acylphloroglucinol derivative frequently encountered in Euphorbia plant [8–10], together with humulene were considered as two precursors. Oxidation of 2 would give 2a, while Diels-Alder reaction between Δ1 of humulene and the enone system of 2a generated the crucial intermediate i. Allylic oxidation at C-4 in i followed by glycosylation with a d-glucose finally afforded 1.
Euphorboside A (1), an unusual meroterpenoid glycoside featuring the incorporation of an acylphloroglucinol moiety into a humulene skeleton to form a 6/6/11 ring system, was isolated from the roots of Euphorbia kansuensis. Its structure was elucidated by extensive spectroscopic analysis, chemical methods, and ECD calculations. Compound 1 was screened for the cytotoxicity against nine cancer cell lines, and 1 showed marked inhibitory activities against human colon cancer RKO and human breast cancer MDA-MB-231 cell lines with IC₅₀ values of 3.70 and 4.15 μM, respectively.
Existing knowledge on Euphorbia fischeriana Steud. (Euphorbiaceae): Traditional uses, clinical applications, phytochemistry, pharmacology and toxicology
2021, Journal of Ethnopharmacology
Euphorbia fischeriana Steud. (Euphorbiaceae) is a perennial herb distributed in grassland, hill slopes or gravel hillside, with average altitude of 100–600 m. The whole grass of E. fischeriana is toxic with roots used as folk medicine to treat Zhushui, dyspepsia, abdominal distension, abdominal pain, cough, as well as external applications such as cure of scabies and tuberculosis of lymph nodes.
This systematic review aims to provide a detailed and in-depth summary about the reported advances in traditional uses, clinical applications, phytochemistry, pharmacology and toxicity of E. fischeriana, so as to offer fresh ideas and broader vision and insights for subsequent studies.
Various scientific data bases such as CNKI, Elsevier, Google Scholar, Pubmed, Science Direct, SciFinder Scholar and Web of Science were searched to collect information about E. fischeriana. Other relevant literatures were searched in ‘Flora of China Editorial Committee', ancient books, Ph.D and Masters' Dissertation to get more data of E. fischeriana.
A total of 241 chemical constituents have been identified from the roots of E. fischeriana, including diterpenoids, triterpenoids, meroterpenoids, acetophenones, flavonoids, coumarins, steroids, phenolic acids, tannins, etc. Various pharmacological activities have been demonstrated, especially anti-tumor, antibacterial, anti-inflammatory, antiviral and anti-leukemia activities. Moreover, different investigations about clinical uses and toxicology of E. fischeriana indicated that attention should be paid to its usage and dosage.
The researches of E. fischeriana are excellent, but gap still remains. As a poisonous traditional Chinese medicine, there are not enough studies on the toxicity of E. fischeriana. In addition, scholars' research on the pharmacological mechanism of E. fischeriana focuses more on the anti-tumor activity, which can be broadened in the future. Presumably, chemical constituents and biological activities of diterpenoids and trace meroterpenoids in E. fischeriana deserve further research in-depth in the future, in order to provide low toxicity and high efficiency lead compounds. Meanwhile, further studies on other medicinal aspects may lay a foundation for the comprehensive development and utilization of E. fischeriana.

View all citing articles on Scopus

View full text

Chemotaxonomic and chemical studies on two plants from genus of Euphorbia: Euphorbia fischeriana and Euphorbia ebracteolata

Highlights

Abstract

Section snippets

Subject and source

Chemical study

Chemotaxonomic implications

Acknowledgements

Phytochemistry

Biochem. Syst. Ecol.

Phytochemistry

Phytochemistry

Phytochemistry

Zhongcaoyao

Neimenggu Nongye Daxue Xuebao

Phytochemistry

Phytochemistry

Chinese pharmacopoeia

Nat. Prod. Res.

Eur. J. Org. Chem.

Xibei nongye xuebao

J. Chin. Med. Mater.