Ingenane and jatrophane diterpenoids from Euphorbia kansui and their antiproliferative effects

Meng, Xian‐Hua; Wang, Kai; Chai, Tian; Guo, Zhiying; Zhao, Ming; Yang, Jun‐Li

doi:10.1016/j.phytochem.2020.112257

Cited by 21 publications

(21 citation statements)

References 25 publications

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“…Chemical investigation of roots extracts of E. kansui yielded uncommon kansuingenol A–C ( 174 – 176 ) [ 65 ] possessing 6, 7-vicinal diol moiety, in addition to jatrophane type diterpenoids, kansuijatrophanol A ( 177 ) and B ( 178 ) [ 65 ] have the 11,12-vicinal diol moiety. The presence of 3,4-(methylenedioxy) cinnamyl moiety was reported for the first time in the species as seen in kansuijatrophanol C ( 179 ) and D ( 180 ) [ 65 ] jatrophane-type diterpenoids. Equally, from the whole plant ethanol extracts of E. helioscopia , euphorhelipanes A ( 244 ) and B ( 245 ) [ 99 ] diterpenoids with a 4-(5,5-dimethylheptan-2-yl)-2,7-dimethylbicyclo [4.3.0] nonane skeleton structure were isolated.…”

Section: Lower Diterpenesmentioning

confidence: 99%

“…Meng et al [ 65 ] examined the antiproliferative activities of ingenane and jatrophane diterpenoids, isolated from E. kansui against human hepatoma cancer cells (Hep-G2), human breast cancer cells (MCF-7), and human prostate cancer cells (DU145), employing the cell counting kit-8 (CCK-8) assay technique. The results showed that all the jatrophane and ingenane diterpenoids exhibited significant inhibitory activities on the cell proliferation of all the three cancer cells tested against.…”

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

confidence: 99%

“…The results showed that all the jatrophane and ingenane diterpenoids exhibited significant inhibitory activities on the cell proliferation of all the three cancer cells tested against. The IC 50 values were 30.48 μM, 6.29 μM, 4.19 μM, and 26.05 μM for 20- O -(2′ E , 4′ Z -decadienoyl) ingenol ( 97 ) and kansuijatrophanol D ( 180 ) [ 65 ], against MCF-7 and DU145 cells respectively. As regards the Hep-G2 cells, the recorded IC 50 values were 9.47 μM for kansuijatrophanol C ( 176 ), and 29.16 μM for kansuingenol B ( 178 ).…”

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

confidence: 99%

“…The structure–activity relationship suggested that jatrophane diterpenoids having 11,12-diol groups showed significant activities. For instance, in kansuijatrophanol A ( 177 ) (MCF-7; IC 50 = 21.64 µM, Hep-G2; IC 50 = 20.19 µM, DU145; IC 50 = 7.21 µM) and kansuijatrophanol B ( 178 ) (MCF-7; IC 50 = 15.25 µM, Hep-G2; IC 50 = 13.24 µM, DU145; IC 50 = 7.24 µM) [ 65 ] diterpenoids, the presence of bioactive functional group, 11, 12-diol group, had a positive effect. In addition, kansuijatrophanol C ( 179 ) (MCF-7; IC 50 = 11.25 µM, Hep-G2; IC 50 = 9.47 µM, DU145; IC 50 = 8.29 µM) with 3,4-(methylenedioxy) cinnamyl group and kansuijatrophanol D ( 180 ) (MCF-7; IC 50 = 6.29 µM, Hep-G2; IC 50 = 10.07 µM, DU145; IC 50 = 4.19 µM) with 3,4-(methylenedioxy) cinnamyl groups exhibited the highest activities.…”

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

confidence: 99%

“…In addition, kansuijatrophanol C ( 179 ) (MCF-7; IC 50 = 11.25 µM, Hep-G2; IC 50 = 9.47 µM, DU145; IC 50 = 8.29 µM) with 3,4-(methylenedioxy) cinnamyl group and kansuijatrophanol D ( 180 ) (MCF-7; IC 50 = 6.29 µM, Hep-G2; IC 50 = 10.07 µM, DU145; IC 50 = 4.19 µM) with 3,4-(methylenedioxy) cinnamyl groups exhibited the highest activities. This further suggested that the 3,4-(methylenedioxy) cinnamyl group could be responsible for the bioactive activities [ 65 ]. These observations agreed with Kulig et al’s [ 111 ] assertion that vicinal diol groups contribute significantly to the bioactivities of naturally occurring compounds possessing them.…”

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

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

confidence: 99%

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

confidence: 99%

See 3 more Smart Citations

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

et al. 2021

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Highly anticipated natural diterpenoids as an important source of new drugs in 2013–2023

Wang,

Tang,

et al. 2025

Chinese Chemical Letters

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Offline two-dimensional normal-phase × reversed-phase liquid chromatography coupled with high-resolution mass spectrometry for comprehensive analysis of chemical constituents in Euphorbia kansui

Zhang

Yang

Shen

et al. 2023

Journal of Chromatography A

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Ingenane and jatrophane diterpenoids from Euphorbia kansui and their antiproliferative effects

Cited by 21 publications

References 25 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

Highly anticipated natural diterpenoids as an important source of new drugs in 2013–2023

Offline two-dimensional normal-phase × reversed-phase liquid chromatography coupled with high-resolution mass spectrometry for comprehensive analysis of chemical constituents in Euphorbia kansui

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