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Chloroform-acetone extract of the aerial parts of Euphorbia aellenii Rech. f. (Euphorbiaceae) was investigated for its diterpenoidal constituents. This led to the isolation of two new and one known cyclomyrsinol-type diterpenes 1-3. The structures were elucidated on the basis of 1D and 2D (1)H and (13)C NMR techniques, and in vitro immunomodulatory...
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... connata Boiss. is one of the latter that is restricted to Kerman, Yazd and Fars provinces. This study, as part of our continuing efforts towards the discovery of anticancer compounds, describes the isolation and structural elucidation of one known and two new diterpenes, belonging to the pentahydroxy-13(17)-epoxy-8,10(18)-myrsinadiene and tetrahydroxy-5,6-epoxy-14-oxo-jatropha-11(E)-ene classes (Figure 1) from E. connata. Structures of the compounds were elucidated on the basis of detailed NMR and mass spectroscopic analyses. ...
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Citations
... Several cyclomyrsinane (73)(74)(75)(76)(77)(78) and premyrsinane diterpenes (79)(80)(81) (Figure 14) were isolated from the acetone/dichlorometane extract of the aerial parts of E. sogdiana Popov [52]. The in vitro cytotoxic activity of the isolated diterpenes was screened against EJ-138 bladder carcinoma and Jurkat T-leukemia cell lines. ...
... In a study on the composition of E. gedrosiaca Rech.f., Aellen & Esfand., Yazdiniapour et al. isolated and identified from a dichloromethane/acetone extract of the whole plant two new myrsinanes, 83 and 84 [54] (Figure 15), and two known cyclomyrsinanes, 53 and 85 (Figures 13 and 15, respectively), previously reported from E. prolifera and E. aellenii [42,75]. The evaluation of their cytotoxicity against B16F10 and A375 melanoma cells indicated that, on both cell lines, these compounds showed cytotoxicity effects. ...
... Two new (150 and 85 Figures 15 and 19, respectively)) and one known (200) cyclomyrsinane-type diterpenes were isolated from E. aellenii Rech. f. [75,93]. In vitro immunomodulatory activity was assessed by measuring the phytohemagglutinin (PHA)-induced T-cell proliferation. ...
Euphorbia species are important sources of polycyclic and macrocyclic diterpenes, which have been the focus of natural-product-based drug research due to their relevant biological properties, including anticancer, multidrug resistance reversal, antiviral, and anti-inflammatory activities. Premyrsinane, cyclomyrsinane, and myrsinane diterpenes are generally and collectively designated as myrsinane-type diterpenes. These compounds are derived from the macrocyclic lathyrane structure and are characterized by having highly oxygenated rearranged polycyclic systems. This review aims to describe and summarize the distribution and diversity of 220 myrsinane-type diterpenes isolated in the last four decades from about 20 Euphorbia species. Some myrsinane diterpenes obtained from Jatropha curcas are also described. Discussion on their plausible biosynthetic pathways is presented, as well as isolation procedures and structural elucidation using nuclear magnetic resonance spectroscopy. Furthermore, the most important biological activities are highlighted, which include cytotoxic and immunomodulatory activities, the modulation of efflux pumps, the neuroprotective effects, and the inhibition of enzymes such as urease, HIV-1 reverse transcriptase, and prolyl endopeptidase, among other biological effects.
... Compounds 3-4 were also isolated in the acetone/dichloromethane extract (see Experimental). The compounds, based on a cyclomyrsinane skeleton, were previously reported from E. prolifera and E. aellenii [23,24]. Compounds based on cyclomyrsinane sketelon were also reported form E. falcata [25] and E. sogdiana [26] and exhibited potassium ion channel inhibitory activity [25] and cytotoxic activity on EJ-138 bladder carcinoma and Jurkat T-leukemia cells [26]. ...
Phytochemical analysis of Euphorbia gedrosiaca Rech.f., Aellen & Esfand., an Iranian endemic spurge, afforded the isolation of four myrsinane types diterpene polyesters. Two new compounds (1–2) were based on a myrsinane skeleton while the others (3–4) were known diterpenes based on a cyclomyrsinane backbone. Their chemical structures were elucidated by spectroscopic methods, including 1D and 2D NMR and HRESIMS. The isolated compounds were tested to evaluate their cell growth inhibitory activity and apoptotic effects on melanoma cell lines, B16F10 and A375. The IC50 values for compounds 1–4 were 58.45, 55.43, 86.52 and 82.27 μM, respectively, on B16F10, and 20.66, 21.88, 36.21 and 39.87 μM, respectively, on A375 cells. Non-treated cells were used as negative control (100% cell growth) and 5 nM Taxol were considered as a positive control.
... Most of the studied species contained both polycyclic and macrocyclic diterpenes and included E. lathyris [31], E. stracheyi [32], E. royleana [33], E. antiquorum [34], E. kansuensis [35,36], E. prolifera [37], E. peplus [38], E. aellenii [39], E. pilosa [40], E. saudiarabica [28], E.marginata [41], E. neriifolia [42], E. resinifera [43], E. pekinensis [44], E. hylonoma [45], E. milii [46], E. wallichii [47], and E. ebracteolata [48]. While others contained only macrocyclic diterpenes like E. esula [49], E. helioscopia [50], E. yinshanica [51], E. grandicornis [52], and E. kansui [53]. ...
... Others were E. neriifolia [42], (n = 32), E. lathyris (n = 21) [31] (n = 28), E. kansui [53] (n = 23), E. stracheyi [32] (n = 22), E. peplus [38] (n = 22), E. antiquorum [34], (n = 21) and E. marginata [41] (n = 20). While other species reported only one or two diterpenes such as E. gaditana [27] (n = 1), E. kopetdaghi [25] (n = 2), E. aellenii [39] (n = 2), E. pilosa (n = 2) and E. grandicornis (n = 2) (Table 1). Anticancer, chemoreversal abilities, and anti-inflammatory activities were the most-studied biological studies. ...
... E. aellenii jatrophane (n = 2) Antiproliferative [39] E. antiquorum ent-abietane n = 1), ent-atisane (n = 7), ingenol (n = 1), ingol (n = 16), ingol (n = 4), lathyrane (n = 3) ...
Euphorbia species have a rich history of ethnomedicinal use and ethnopharmacological applications in drug discovery. This is due to the presence of a wide range of diterpenes exhibiting great structural diversity and pharmacological activities. As a result, Euphorbia diterpenes have remained the focus of drug discovery investigations from natural products. The current review documents over 350 diterpenes, isolated from Euphorbia species, their structures, classification, biosynthetic pathways, and their structure–activity relationships for the period covering 2013–2020. Among the isolated diterpenes, over 20 skeletal structures were identified. Lathyrane, jatrophane, ingenane, ingenol, and ingol were identified as the major diterpenes in most Euphorbia species. Most of the isolated diterpenes were evaluated for their cytotoxicity activities, multidrug resistance abilities, and inhibitory activities in vitro, and reported good activities with significant half-inhibitory concentration (IC50) values ranging from 10–50 µM. The lathyranes, isopimaranes, and jatrophanes diterpenes were further found to show potent inhibition of P-glycoprotein, which is known to confer drug resistance abilities in cells leading to decreased cytotoxic effects. Structure–activity relationship (SAR) studies revealed the significance of a free hydroxyl group at position C-3 in enhancing the anticancer and anti-inflammatory activities and the negative effect it has in position C-2. Esterification of this functionality, in selected diterpenes, was found to enhance these activities. Thus, Euphorbia diterpenes offer a valuable source of lead compounds that could be investigated further as potential candidates for drug discovery.
... [9] In another study, three cyclomyrsinol diterpenes which one of them was the compound (4), were extracted from Euphorbia aellenii and their effects on the proliferation of human peripheral blood lymphocytes were investigated. [3] The results of the mentioned study showed that all these three compounds were found to inhibit lymphocyte proliferation at 50 μg/mL concentration. The immunomodulatory effects of compound (4) was more than other compounds. ...
... The immunomodulatory effects of compound (4) was more than other compounds. [3] In Zolfaghari et al. study, the cytotoxic effects of myrsinane (1) to (3) extracted from Euphorbia sogdiana Popov were investigated against Jurkat and EJ-138 cell lines. [10] The results of the mentioned study confirmed the cytotoxicity of these compounds with the IC 50 value of about 25-36 and 19-25 μM, for EJ-138 and Jurkat cell lines, respectively. ...
Background: Cyclomyrsinane diterpenes especially those extracted from various Euphorbia species have shown interesting biological properties in recent years. Because of the high prevalence of breast cancer and the challenges ahead in its treatment, the use of these compounds as potential anti cancer agents seem reasonable. Objectives: The aim of the present study was to evaluate the cytotoxic effects of some myrsinane type diterpenoids extracted from Euphorbia sogdiana Popov and determine their induced cell death mechanism. Methods: MTT assay was used to determine the cytotoxicity of six various myrsinane compounds on MCF 7 and 4T1 breast cancer cell lines. Human umbilical vein endothelial cells were used as the normal cell line too. The apoptotic effects of the structure with the most cytotoxic effects were determined using flow cytometry assay in IC50 concentration for 24 h of incubation. Results: Compound (6) showed the most cytotoxic effects with IC50 of about 8 ± 4 and 24 ± 4 μg/mL for MCF 7 and 4T1 cell lines, respectively. Furthermore, the cells treated with 5 and 10 μg/mL of compound (6) for 24 h, showed 37 and 55% of apoptotic cells. Conclusions: These surveyed compounds have the potential to be considered as useful anti-breast cancer agents due to the great cytotoxicity and apoptotic effects against these cancer cells and the fact that there was no significant cytotoxicity on normal cells.
... The species are distributed worldwide (Vasas and Hohmann, 2014) throughout tropical and temperate regions, mainly growing in southern USA, the Mediterranean basin, the Middle East, South Africa and north China. Many of them have been used as folk medicine with a long history (Wang et al., 2006;Ghanadian et al., 2013). For their extensive biological activities, Euphorbia species have been used for treatment of yellow fever (Korin et al., 2002), viral hepatitis (Hezareh, 2005), edema, ascites, warts (Wang et al., 2006), cancer , multi-drug resistance (Wesolowska et al., 2007), skin diseases, gonorrhea, and migraine (Shi et al., 2008). ...
E. fischeriana has long been used as a traditional Chinese medicine. Recent studies reported that some compounds of E. fischeriana exhibited antimicrobial and immune enhance activity. Innate immune system is essential for the immune surveillance of inner and outer threats, initial host defense responses and immune modulation. The role of natural drug compounds, including E. fischeriana, in innate immune regulation is largely unknown. Here we demonstrated that E. fischeriana compound Dpo is involved in antiviral signaling. The genome wide RNA-seq analysis revealed that the induction of ISGs by viral infection could be synergized by Dpo. Consistently, Dpo enhanced the antiviral immune responses and protected the mice from death during viral infection. Dpo however was not able to rescue STING deficient mice lethality caused by HSV-1 infection. The enhancement of ISG15 by Dpo was also impaired in STING, IRF3, IRF7, or ELF4 deficient cells, demonstrating that Dpo activates innate immune responses in a STING/IRFs/ELF4 dependent way. The STING/IRFs/ELF4 axis is therefore important for Dpo induced ISGs expression, and can be used by host to counteract infection.
... Ones isolated from E.microsciadia showed anti-angiogenic activity on vein endothelial cells in vitro by assessing capillary-like tube network formation [18]. Cyclomyrsinanes isolated from Euphorbia aellenii and E. kopetdaghi showed immunosuppressive activity against lymphocyte proliferation, IL-2 and oxidative burst activity of macrophages [19,20]. ...
Objectives
There is a significant prevalence of affective disorders including depression and anxiety in people with multiple sclerosis (MS), resulting in reduced quality of life. Since the current treatments are not generally effective, further studies are needed to find appropriate drugs to alleviate anxiety and depression symptoms in these patients.
Methods
The effects of a new analog of cyclomyrsinol diterpenes (TAMEC) isolated from Euphorbia sogdiana on the anxiety (open field and elevated plus maze test) and depressive-like behaviors (sucrose preference test and forced swim test) in EAE-induced C57BL/6 mice (EAE; a mouse model of MS) were investigated. Hippocampal tumor necrosis factor-alpha (TNF-α), interleukin (IL)-1β and IL-10 levels were also measured by ELISA.
Results
The results indicated that TAMEC treatment reduced anxiety and depression-like behavior. This drug also decreased the levels of TNF-α and IL1β and increased IL-10 level in the hippocampus.
Discussion
Taken together, our findings demonstrate that the drug we used here can reduce anxiety and depression-like symptoms in EAE-induced mice. However, more studies are still needed to validate, expand, and generalize these data.
... In previous studies, phytochemical investigations on E. aellenii led to the isolation and identification of two cycloartane triterpenes , and nine macrocyclic diterpenes including two lathyrane , two myrsinol, two tigliane , and threre cylomyrsinol diterpenes (Ghanadian et al. 2013), with immunosuppressory activities. 14-Desoxo-3b,5a,7b,10,15b-O-pentaacetyl-14a-O-benzoyl-10,18-dihydromyrsinol isolated from E. aellenii showed potent suppressive activity against oxidative burst activity of phagocytes and the lymphocyte proliferations in vitro (Vasas & Hohmann 2014). ...
... Later, 3,5,10-O-triacetyl-8-O-isobutanoyl-14-O-benzoylcyclomyrsinol was tested through T-cell proliferation assay, interleukin-2 assay, oxidative burst of phagocytes and through their cytotoxicity on two different normal cell lines. It showed potent inhibitory activity against PHA-activated lymphocyte proliferation and ROS production of macrophages with moderate interleukin-2 inhibitory activity and ignorable cytotoxic effect on normal 3T3-L1 mouse fibroblast and CC-1 rat hepatocyte cell lines (Ghanadian et al. 2013). In this research, a new lathyrane diterpene is isolated from Euphorbia aellenii and then its effect on apoptosis and the underlying molecular mechanism is investigated. ...
Euphorbia species have been used in traditional medicine in many countries for the treatment of cancer. This paper aims to evaluate the capability of a new lathyrane diterpene isolated from Euphorbia aellenii to induce apoptosis in the Caov-4 cell line to determine the underlying mechanism of its anticancer effects. A new 6(17)-epoxylathyrane diterpenes: aellinane from Euphorbia aellenii was evaluated for viability of Caov-4 cells by MTT method. Apoptosis induction by lathyrane diterpene was confirmed by annexin V-FITC/PI staining, and caspase-6 activation. The Bcl2 and Bax protein content were detected by Western blot analysis. Finally, we employed the fluorescent ROS detection kit and fluorochrome JC-1 to determine ROS levels and loss of mitochondria membrane potential (ΔΨm) in Caov-4 cells, respectively. The results show that lathyrane diterpene has significant cytotoxic effect against Caov-4 cells. The IC50 value was 45 µM. Annexin V/propidium iodide (PI) staining and caspase-6 activity assay confirmed that lathyrane diterpene is able to induce apoptosis in Caov-4 cells. The results also demonstrate that lathyrane diterpene up-regulated Bax and down-regulated Bcl-2 proteins. Moreover, apoptotic effect of lathyrane diterpene was also related to ROS production and loss of mitochondrial membrane potential (ΔΨm). This study demonstrated that lathyrane diterpene has profound activity against Caov-4 cells. Analysis of apoptosis-related proteins revealed that lathyrane diterpene triggered the mitochondrion-mediated apoptosis pathway, which led to the loss of mitochondrial membrane potential (ΔΨm) and activation of caspase 6. Therefore, we believe that lathyrane diterpene might be a promising natural compound in ovarian cancer therapy.
Two new rare trachylobane euphoratones A-B (1-2), together with five known diterpenoids (compounds 3-7), were isolated from the aerial parts of Euphorbia atoto. Their structures were unambiguously elucidated through HRESIMS, 1D and 2D NMR spectral analysis. Compounds 1, 3, 4 and 7 showed weak anti-inflammatory activities (IC50 77.49 ± 6.34, 41.61 ± 14.49, 16.00 ± 1.71 and 33.41 ± 4.52 μM, respectively), compared to the positive control quercetin (IC50 15.23 ± 0.65 μM).
Covering: 2013 to 2021As 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.
GIRK channels are activated by a large number of G protein-coupled receptors and regulate the electrical activity of neurons, cardiac atrial myocytes, and β-pancreatic cells. Abnormalities in GIRK channel function have been implicated in the pathophysiology of neuropathic pain, drug addiction, and cardiac arrhythmias. In the heart, GIRK channels are selectively expressed in the atrium, and their activation inhibits pacemaker activity, thereby slowing the heart rate. In the present study, 19 new diterpenes, falcatins A-S (1-19), and the known euphorprolitherin D (20) were isolated from Euphorbia falcata. The compounds were assayed on stable transfected HEK-hERG (Kv11.1) and HEK-GIRK1/4 (Kir3.1 and Kir3.4) cells. Blocking activity on GIRK channels was exerted by 13 compounds (61-83% at 10 μM), and, among them, five possessed low potency on the hERG channel (4-20% at 10 μM). These selective activities suggest that myrsinane-related diterpenes are potential lead compounds for the treatment of atrial fibrillation.
