Two new diterpenes from Euphorbia kansuensis

Wang, Huan; Zhang, Xiaofeng; Zhou, Yan; Peng, Shu‐Lin; Zhou, Dangwei; Ding, Li‐Sheng

doi:10.1016/j.fitote.2008.01.008

Cited by 21 publications

(5 citation statements)

References 9 publications

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“…Fifteen known diterpenoids, namely, ingenol ( 3 ) [12], (3 β ,12 α )-3,12-dihydroxyisopimara-7,15-dien-2-one ( 7 ) [8], ent -l6 α ,17-dihydroxyatisan-3-one ( 9 ) [11], ent -(3 α ,5 β ,8 α ,9 β ,10 α ,12 α )-3-hydroxyatis-16-en-14-one ( 10 ) [8], ent -(5 β ,8 α ,9 β ,10 α ,11 α ,12 α )-11-hydroxyatis-16-ene-3,14-dione ( 11 ) [8], ent -(5 β ,8 α ,9 β ,10 α ,11 α ,12 α )-3,14-dioxoatis-16-en-11-yl acetate ( 12 ) [8], jolkinolide E ( 13 ) [13, 14], 7 β -hydroxy- ent -abieta-8(14),13(15)-dien-12 α ,16-olide ( 14 ) [15], pekinenal ( 15 ) [16], pekinenin A ( 16 ) [17], pekinenin D ( 17 ) [18], ent -l6 β ,17-isopropylidenedioxy kauran-3 β -ol ( 18 ) [19], jolkinol A ( 19 ) [20], jolkinol A′ ( 20 ) [20], and 3 β ,5 α ,20-trihydroxy-15 β -cinnamoyloxy-14-oxolathyra-6 Z ,12 E -diene ( 21 ) [21], were also isolated and identified by comparison of their spectroscopic data with those reported values in the literatures.…”

Section: Resultsmentioning

confidence: 99%

Antifeedant and Antiviral Diterpenoids from the Fresh Roots of Euphorbia jolkinii

Huang

Luo

et al. 2014

Nat. Prod. Bioprospect.

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The perennial herbaceous plant Euphorbia jolkinii (Euphorbiaceae) is a noxious weed widely distributed in the grasslands of northwestern Yunnan and has greatly threatened the local biodiversity. Phytochemical investigation on the fresh roots of E. jolkinii afforded six new diterpenoids 1, 2, 4–6, and 8, together with fifteen known diterpenoids. Their structures were elucidated on the basis of 1D and 2D NMR and other spectroscopic methods. Casbane, lathyrane, abietane, and ent-kaurane diterpenoids were reported from this plant for the first time. Selected compounds were evaluated for their antifeedant and anti-RSV (respiratory syncytial virus) activities. Compound 2 and ingenol (3) exhibited moderate antifeedant activity against a generalist insect herbivore, Spodoptera exigua, with EC50 values of 17.88 and 17.71 μg/cm2 respectively. Compound 19 showed significant anti-RSV activity, with 50 % inhibition (IC50) value of 10.0 μM and selective index of 8.0. Compounds 1 and 2 were less active against RSV virus, both with IC50 value of 25 μM, and with selective indices of 1.0 and 3.2 respectively. These findings provided new evidence for the biological functions and utilization of the diversified diterpenoid metabolites in the roots of this rich but harmful plant.Graphical AbstractElectronic supplementary materialThe online version of this article (doi:10.1007/s13659-014-0009-3) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Antifeedant and Antiviral Diterpenoids from the Fresh Roots of Euphorbia jolkinii

Huang

Luo

et al. 2014

Nat. Prod. Bioprospect.

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“…Wang et al isolated two lathyrane diterpenes ( 61 and 62 ) from the ethanol extract of the roots of Euphorbia kansuensis. The roots of this plant have been used in Tibetan medicine as a cholagog and purgative and in cases of pyretolysis and apocenosis …”

Section: Isolated Diterpenoidsmentioning

confidence: 99%

“…The roots of this plant have been used in Tibetan medicine as a cholagog and purgative and in cases of pyretolysis and apocenosis. 48 Jiao et al isolated a new lathyrane diterpenoid (euphorbia factor L 8 , 58) from the seeds of E. lathyris. Its absolute configuration was determined by single-crystal X-ray diffraction.…”

Section: Lower Diterpenoidsmentioning

confidence: 99%

Euphorbia Diterpenes: Isolation, Structure, Biological Activity, and Synthesis (2008–2012)

2014

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“…Yan et al [ 35 ] described the isolation of atisane-type diterpenoid; atisane-3-oxo-16 α ,17-diol ( 6 ) from ethanol root extracts of E. kansuensis . Lathyranes-type diterpenoids were isolated from the ethanol root extracts of E. kansuensis by Wang et al [ 90 ]. 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.…”

Section: Higher Diterpenesmentioning

confidence: 99%

“…Drummond et al [89] reviewed the isolation, structure, and bioactivity of various ent-atisanes diterpenoids from different genera, including Euphorbia discovered between 1965 and 2020. Ye et al [32] isolated new diterpenenoids; ent-11β-hydroxyabieta-8( 14),13( 15)-dien-16,12-olide (3) (abietane), ent-atis-16-ene-3,14-dione (29) (ent-atisane) in addition to ingenane type diterpenes; (90) and lathyranes (249-261) from the roots extracts of E. stracheyi. [32].…”

Section: Ent-atisanes Ent-isopimaranes Cembranes and Labdanesmentioning

confidence: 99%

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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Two new diterpenes from Euphorbia kansuensis

Cited by 21 publications

References 9 publications

Antifeedant and Antiviral Diterpenoids from the Fresh Roots of Euphorbia jolkinii

Antifeedant and Antiviral Diterpenoids from the Fresh Roots of Euphorbia jolkinii

Euphorbia Diterpenes: Isolation, Structure, Biological Activity, and Synthesis (2008–2012)

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

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