Macrocyclic diterpenoids from Euphorbia hyberna L. subsp. insularis and their reaction with oxyphilic reagents

Appendino, Giovanni; Spagliardi, Paola; Ballero, Mauro; Seu, G

doi:10.1016/s0367-326x(02)00213-7

Cited by 22 publications

(7 citation statements)

References 10 publications

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“…These results are consistent with previous phytochemical investigations conducted on these species [61][62][63][64] (see Table S1 in supporting informations). In addition, while deoxyphorbol or dideoxyphorbol esters were commonly isolated from Euphorbia spp.…”

Section: Analysis Of Euphorbia Extracts Using Targeted Lc-ms 2 Methodssupporting

confidence: 95%

LC-MS2-Based dereplication of Euphorbia extracts with anti-Chikungunya virus activity

et al. 2015

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Recently, phorbol esters from Euphorbiaceae have been shown to elicit potent and selective antiviral activity on the replication of Chikungunya virus (CHIKV) in cell culture. With the objective to found new compounds with anti-CHIKV activities, 45 extracts from various plant parts of 11 Mediterranean Euphorbia and one Mercurialis species were evaluated for selective inhibition of CHIKV replication. All EtOAc extracts, especially those prepared from latex, exhibited significant and selective antiviral activity in a Chikungunya virus-cell-based assay. An LC-MS(2) dereplication method was then developed to investigate whether known diterpenoids with anti-CHIKV activity, such as the potent anti-CHIKV 12-O-tetradecanoylphorbol-13-acetate (TPA), phorbol-12,13-didecanoate, and prostratin as well as 24 other commercially available diterpenoids of tigliane-, ingenane-, and daphnane-type for which the anti-CHIKV activity have been established in advance (Nothias-Scaglia et al. 2015), were present in the Euphorbia extracts. Only ingenol-3-mebutate, 13-O-isobutyryl-12-deoxyphorbol-20-acetate, and ingenol-3,20-dibenzoate, all exhibiting weak anti-CHIKV activities, were detected in the EtOAc extracts of Euphorbia peplus, Euphorbia segetalis ssp. pinea, and Euphorbia pithyusa ssp. pithyusa. Given the potent anti-CHIKV activities of these Euphorbia extracts, the present study suggested that their antiviral activities are probably due to untargeted diterpenoids.

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Section: Analysis Of Euphorbia Extracts Using Targeted Lc-ms 2 Methodssupporting

confidence: 95%

LC-MS2-Based dereplication of Euphorbia extracts with anti-Chikungunya virus activity

et al. 2015

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“…Euphorbia hyberna [22], a Mediterranean plant specimen without previous established antiviral activity. Although its chemical structure is quite different from phorbol esters, some biological correlations are possible, as our data indicate that SJ23B antagonizes HIV-1 latency through activation of classical PKCs in HIV-1 latently infected Jurkat cells.…”

Section: Sj23b Is a Diterpene With A Jatrophane Skeleton And A Lactonmentioning

confidence: 99%

SJ23B, a jatrophane diterpene activates classical PKCs and displays strong activity against HIV in vitro

Bedoya

Márquez

Martínez

et al. 2009

Biochemical Pharmacology

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Existence of virus reservoirs makes the eradication of HIV infection extremely difficult. Current drug therapies neither eliminate these viral reservoirs nor prevent their formation. Consequently, new strategies are needed to target these reservoirs with the aim of decreasing their size. We analysed a series of jatrophane diterpenes isolated from Euphorbia hyberna and we found that one of them, SJ23B, induces the internalization of the HIV-1 receptors CD4, CXCR4 and CCR5 and prevents R5 and X4 viral infection in human primary T cells at the nanomolar range. Moreover, SJ23B is a potent antagonist of HIV-1 latency. Using Jurkat-LAT-GFP cells, a model for HIV-1 latency, we found that prostratin and SJ23B activate HIV-1 gene expression, with SJ23B being at least 10-fold more potent than prostratin. SJ23B did not elicit transforming foci activity in NIH 3T3 cells but is a potent activator of PKCalpha and delta as measured by in vitro kinase assays and by cellular translocation experiments. By using isoform-specific PKC inhibitors we found that cPKCs are critical for SJ23B-induced HIV-1 reactivation. We also showed that both SJ23B-induced IkappaBalpha degradation and NF-kappaB activation were inhibited by the classical PKC inhibitor, Gö6976. Accordingly, SJ23B synergizes with ionomycin to translocate PKCalpha to the plasma membrane and to activate the NF-kappaB pathway. Moreover, SJ23B activates both NF-kappaB and Sp1-dependent transcriptional activities in primary T cells. We have shown that diterpene jatrophanes represent a new member of anti-AIDS agents that could be developed for mitigating HIV reactivation.

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“…[2] The biological activities of the genus, including antitumor, antiviral, cytotoxic properties and different vascular effects, are generally attributed to the presence of specific types of diterpenes, both macrocyclic and polycyclic derivatives. [3–5] The skin irritant and tumor-promoting properties of tigliane, ingenane and dephanane diterpenes of this plant are well known. Considerable attention has recently been given to the macrocyclic diterpenes because of their high chemical diversity and therapeutically relevant bioactivity.…”

Section: Introductionmentioning

confidence: 99%

Triterpenes from Euphorbia rigida

et al. 2010

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Macrocyclic diterpenoids from Euphorbia hyberna L. subsp. insularis and their reaction with oxyphilic reagents

Cited by 22 publications

References 10 publications

LC-MS2-Based dereplication of Euphorbia extracts with anti-Chikungunya virus activity

LC-MS2-Based dereplication of Euphorbia extracts with anti-Chikungunya virus activity

SJ23B, a jatrophane diterpene activates classical PKCs and displays strong activity against HIV in vitro

Triterpenes from Euphorbia rigida

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