Cytotoxic jatrophane diterpenoids from the aerial parts of <i>Euphorbia helioscopia</i>

Zhou, Ming; Ma, Qiang; He, Lei; Chen, Yinhao; Zhu, Bingye; Wang, Jiahao; Yang, Qiao; Liu, Shuang; Ma, Limin

doi:10.1080/10286020.2020.1769611

Cited by 6 publications

(10 citation statements)

References 16 publications

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“…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 ]. Of this, E. esula [ 49 ] had the highest number of isolated diterpenes ( n = 44), of which the majority were jatrophane and lathyrane diterpenes, followed by E. royleana [ 33 ] ( n = 36).…”

Section: Occurrence Of Euphorbia Diterpenesmentioning

confidence: 99%

“…Phytochemical analysis of aerial extracts of E. helioscopia afforded three undescribed jatrophane diterpenoids named euphoheliphane A ( 181 ), euphoheliphane B ( 182 ), and euphoheliphane C ( 187 ) [ 50 ]. Euphoesulatin A–C ( 184 – 186 ), from E. esula, exhibited antiosteoporotic activity on BMM cells.…”

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

confidence: 99%

“…Other euphoesulatins diterpenes displayed some antiosteoporotic activities, while some, like esulone B ( 202 ), showed no activity, as demonstrated in Table 2 . The in vitro cytotoxicity studies of the compounds showed weak anticancer activities against cellossaurus cell lines (OS-RC-2), cellossaurus cell lines (Ketr-3), human kidney cell lines (769-P), cellossaurus cell lines (G401), human cell lines (GRC-1 and ACHN) with IC 50 values less than 50.00 µM compared to the positive control, doxorubicin [ 50 ]. As well, euphoractone ( 14 ) [ 59 ] displayed potent inhibition activities against human cellasaurus cell lines (H23 and H460) with IC 50 values of 21.07 mmol/L and 20.91 mmol/L, respectively, as compared to the positive control, cisplatin [ 59 ].…”

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

confidence: 99%

“…Protein kinase C activation and platelet stimulation abilities [52] E. helioscopia jatrophane (n = 10) Cytotoxic, inhibitory (nitric oxide (NO) [50,64] E. hylonoma ent-isopimarane (n = 9), ent-rosane (n = 1) Inhibitory (NO) [45] E. kansuensis…”

Section: Occurrence Of Euphorbia Diterpenesmentioning

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: Occurrence Of Euphorbia Diterpenesmentioning

confidence: 99%

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

confidence: 99%

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

confidence: 99%

Section: Occurrence Of Euphorbia Diterpenesmentioning

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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“…Euphol, a tetracyclic triterpene alcohol present in the sap of Euphorbia and in the latex of some Euphorbia species [ 15 ], showed anti-inflammatory, contraceptive, and even antitumor properties [ 16 ]. Recently, an extract of Euphorbia esula L. showed antiproliferative activity against lung, cervical, gastric, breast, and liver cancers [ 17 ], while diterpenoids isolated from an ethanolic extract of Euphorbia helioscopia showed cytotoxicity in renal cancer cell lines [ 18 ]. Interestingly, most of the studies conducted on Euphorbia focused on the presence of biologically active natural products in latex [ 19 , 20 ].…”

Section: Introductionmentioning

confidence: 99%

Antitumor Effect of the Ethanolic Extract from Seeds of Euphorbia lathyris in Colorectal Cancer

et al. 2021

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The seeds of Euphorbia lathyris have been used in traditional medicine to treat various medical conditions. However, neither all of their active biocompounds nor the molecular mechanisms underlying their therapeutic effects have been described. A new ethanolic extract of defatted flour from mature seeds of Euphorbia lathyris showed a high total polyphenol content and significant antioxidant activity. Chromatographic analysis showed that esculetin, euphorbetin, gaultherin, and kaempferol-3-rutinoside were the most abundant polyphenolic bioactive compounds. Antiproliferative assays showed a high and selective antitumor activity against colon cancer cell lines (T84 and HCT-15). In addition, a significant antiproliferative activity against glioblastoma multiforme cells was also demonstrated. Its mechanism of action to induce cell death was mediated by the overexpression of caspases 9, 3, and 8, and by activation of autophagy. Interestingly, a reduction in the migration capacity of colon cancer cells and a significant antiangiogenic effect on human umbilical vein endothelial cells were also demonstrated. Finally, the extract significantly reduced the subpopulations of cancer stem cells. This extract could be the basis to develop new therapeutic strategies for the treatment of colon cancer, although further experiments will be necessary to determine its in vivo effects.

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Phytochemical and pharmacological review of diterpenoids from the genus Euphorbia Linn (2012–2021)

Zhao

Sun

Kong

et al. 2022

Journal of Ethnopharmacology

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Cytotoxic jatrophane diterpenoids from the aerial parts of Euphorbia helioscopia

Cited by 6 publications

References 16 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

Antitumor Effect of the Ethanolic Extract from Seeds of Euphorbia lathyris in Colorectal Cancer

Phytochemical and pharmacological review of diterpenoids from the genus Euphorbia Linn (2012–2021)

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