New diterpenoids from the stems of <i>Euphorbia antiquorum</i> growing in Vietnam

Tran, Thanh-Nha; Sichaem, Jirapast; Nguyen, Van-Kieu; Nguyen, Huu-Hung; Cao, Truong-Tam; Nguyen, Thi-Phuong; Giau, Vo Van; Niamnont, Nakorn; Nguyen, Ngoc-Hong; Duong, Thuc‐Huy

doi:10.1080/14786419.2020.1789634

Cited by 9 publications

(11 citation statements)

References 20 publications

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“…All compounds ( 32 – 34 ) displayed no cytotoxicity effect against K562, compared to acarbose (IC 50 = 162.50 µM). It was also noted that the activities of these compounds were due to the presence of hydroxyl groups at C-16 and C-17, which are their bioactive functionalities [ 54 ]. Ent-atisane-3 β ,16 α ,17-triol ( 36 ), from the root extracts of E. kansuensis, showed no inhibition of NO (IC 50 > 50 µM compared to quercetin (IC 50 = 10.80 µM) [ 35 ].…”

Section: Pharmacological Activities and Structure–activity Relationship (Sar)mentioning

confidence: 99%

“…Melanin synthesis activity, inhibitory (α-glucosidase), inhibitory (NO production) [34,[54][55][56] E. dracunculoides tigliane (n = 1), myrsinol (n = 2) Cytotoxic [57,58] E. ebracteolata rosane (n = 5) Lipase inhibitory [48] E. esula jatrophane (n = 41) Antimalarial [34,59] E. fischeriana ent-abietane (n = 4), meroterpenoid (n = 5), tigliane (n = 5) Cytotoxic [30,[60][61][62][63] E. gaditana gaditanone (n = 1) Not evaluated [27] E. glomerulans jatrophane (n = 17) MDR-chemoreversal [29] E. grandicornis tigliane (n = 2)…”

Section: Occurrence Of Euphorbia Diterpenesmentioning

confidence: 99%

“…Shaker et al [33] described the isolation of new ent-atisane diterpenoids, euphoroylean F (30) and euphoroylean G (31), from the whole-plant extract of E. royleana. Tran et al [54] investigated stem extracts of E. antiquorum and reported the isolation of ent-atisanes diterpenoids (32)(33)(34)(35)). An et al [56] reported the isolation of euphorin A (37), euphorin B (38) and ent-(3α,5β,8α,9β,10α,12α)-3-hydroxyatis-16-en-14-one (41) from stem extracts of E. antiquorum.…”

Section: Ent-atisanes Ent-isopimaranes Cembranes and Labdanesmentioning

confidence: 99%

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Euphorbia Diterpenes: An Update of Isolation, Structure, Pharmacological Activities and Structure–Activity Relationship

et al. 2021

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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.

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Section: Pharmacological Activities and Structure–activity Relationship (Sar)mentioning

confidence: 99%

Section: Occurrence Of Euphorbia Diterpenesmentioning

confidence: 99%

Section: Ent-atisanes Ent-isopimaranes Cembranes and Labdanesmentioning

confidence: 99%

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Euphorbia Diterpenes: An Update of Isolation, Structure, Pharmacological Activities and Structure–Activity Relationship

et al. 2021

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“…Euphorbia antiquorum L., a medicinal plant, has traditionally been used for various treatments, for example, the latex has been used for emetic, purgative, and diuretic treatments, and the fresh stems for treatment of skin sores, scabies, and toothache [1][2][3]. Previous chemical studies on E. antiquorum in Thailand, Vietnam, and China have reported the wealth of diterpenoids, including lathyane, ent-atisane, ent-abietane, and ent-kaurane types [3][4][5][6][7][8]. Those isolated compounds showed various biological activities including cytotoxic, antiinflammatory, anti-HIV activities, and the inhibition of nitric oxide (NO) production [9].…”

Section: Introductionmentioning

confidence: 99%

Alpha-Glucosidase Inhibitory Diterpenes from Euphorbia antiquorum Growing in Vietnam

Tran

Dao²,

Tran³

et al. 2021

Molecules

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Bioactive-guided phytochemical investigation of Euphorbia antiquorum L. growing in Vietnam led to the isolation of five ent-atisanes, one seco-ent-atisane, and one lathyrane (ingol-type). The structures were elucidated as ent-1α,3α,16β,17-tetrahydroxyatisane (1), ethyl ent-3,4-seco-4,16β,17-trihydroxyatisane-3-carboxylate (2), ent-atisane-3-oxo-16β,17-acetonide (3), ent-3α-acetoxy-16β,17-dihydroxyatisane (4), ent-16β,17-dihydroxyatisane-3-one (5), calliterpenone (6), and ingol 12-acetate (7). Their chemical structures were unambiguously determined by analysis of one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) and high resolution mass spectrometry, as well as by comparison with literature data. Among them, 1 is a new compound while 2 is an ethylated artifact of ent-3,4-seco-4,16β,17-trihydroxyatisane-3-carboxylic acid, a new compound. Isolates were evaluated for alpha-glucosidase inhibition. Compound 3 showed the most significant inhibitory activity against alpha-glucosidase with an IC50 value of 69.62 µM. Further study on mechanism underlying yeast alpha-glucosidase inhibition indicated that 3 could retard the enzyme function by noncompetitive.

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“…One of the compounds abovementioned, copetdaghinane A, inhibits the growth of MCF-7 breast cancer cells through the mitochondrial apoptotic pathway activation(Riahi et al 2020). On the other hand, none of the compounds in Euphorbia antiquorum root extracts showed cytotoxic activity(Tran et al 2022). Fraction compounds of Euphorbia umbellata latex hexane extracts have caused morphological changes compatible with apoptosis induction against leukemic cells, such as cell cycle alteration, depolarized cell population increase, and caspase 3/7 activation.…”

mentioning

confidence: 99%

In vitro Cytogenetic Effects of the Euphorbia grisophylla Aerial Parts Aqueous Extract in Human Peripheral Lymphocytes

Polat

İla

2022

Preprint

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The effects of the aqueous extract obtained from the aerial parts of Euphorbia grisophylla M.L.S.Khan, a herbaceous member of the Euphorbiaceae family, which is common in other parts of the world outside the Antarctic continent, on genotoxic, cytotoxic, and oxidative parameters were investigated. Experiments were carried out under short-term and in vitro conditions with sublethal concentrations of the test substance extract. According to the first results, the plant extract did not significantly affect the oxidative stress indicators in cell culture. Similarly, it increased the micronucleus ratio in lymphocytes insignificantly, but the concentration-effect relationship is significant in the 24-hour treatment. Again, the test substance did not induce an evident reversion-type mutation in the Ames test. However, the percentage of damaged cells in the Comet test and the genetic damage index increased significantly except for the lowest concentration. The cytotoxic effect observed in the context of the same pattern with these findings is remarkable. In conclusion, the slightly clastogenic and cytotoxic effect of Euphorbia grisophylla aqueous extract, not based on the oxidative attack, may provide a new projection for further research, like cancer therapy.

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New diterpenoids from the stems of Euphorbia antiquorum growing in Vietnam

Cited by 9 publications

References 20 publications

Euphorbia Diterpenes: An Update of Isolation, Structure, Pharmacological Activities and Structure–Activity Relationship

Euphorbia Diterpenes: An Update of Isolation, Structure, Pharmacological Activities and Structure–Activity Relationship

Alpha-Glucosidase Inhibitory Diterpenes from Euphorbia antiquorum Growing in Vietnam

In vitro Cytogenetic Effects of the Euphorbia grisophylla Aerial Parts Aqueous Extract in Human Peripheral Lymphocytes

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