<i>Euphorbia</i> Diterpenes: Isolation, Structure, Biological Activity, and Synthesis (2008–2012)

Vasas, Andrea; Hohmann, Judit

doi:10.1021/cr400541j

Cited by 420 publications

(397 citation statements)

References 157 publications

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“…In previous studies, it was shown that phorbol esters, such as the TPA (13) from Croton tiglium (Euphorbiaceae) and phorbol-12,13-didecanoate (11), were the most potent inhibitors of CHIKV replication to date [11]. Euphorbia species are characterized by their ability to produce lower diterpenoids belonging to the tigliane, ingenane, jatrophane along with other types of diterpene ester [28,32]. Thus, in a dereplication perspective, an LC-MS 2 -based method was developed to search for the presence of these known inhibitors along with their related commercially available lower diterpenoids, in these Euphorbia extracts.…”

Section: Evaluation Of Euphorbia Extracts Against Chikv Replicationmentioning

confidence: 99%

“…Diterpenoids isolated from Euphorbia species represent a unique group of structurally diverse compounds that possess remarkable biological activities [28][29][30][31][32], such as potent antiviral activity against human immunodeficiency virus (HIV) for tigliane- [33], ingenane- [29,34,35] and macrocyclic-type esters [36][37][38], or powerful P-glycoprotein modulation activity for macrocyclic diterpene esters [39,40].…”

Section: Introductionmentioning

confidence: 99%

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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: Evaluation Of Euphorbia Extracts Against Chikv Replicationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2015

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“…[1][2][3] Daphnane is a major class of diterpenes and has received considerable attention due to its important pharmacological activity. [4][5][6] Resiniferatoxin (1, Fig.…”

Section: Introductionmentioning

confidence: 99%

Radical-Mediated Three-Component Reaction: A Study toward the Total Synthesis of Resiniferatoxin

Urabe

2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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This review summarizes the efforts to develop a radical-mediated three-component reaction and its application to a convergent approach to synthesize the 5/7/6-tricyclic framework (ABC-rings) of the densely functionalized dephnane diterpene, resiniferatoxin. The α-alkoxy bridgehead radical species, which was designed as the radical donor of the three-component reaction, was generated from O,Se-and O,Te-acetals under two different conditions. The generated α-alkoxy bridgehead radical effectively underwent the threecomponent reaction with α,β-unsaturated ketones and allyltributyltin/aldehyde under each of the conditions, giving rise to a wide variety of multiply functionalized 2,3-trans disubstituted cyclopentenone moieties. One of the established reactions was utilized as the key assembling reaction of the ABC-tricyclic framework of resiniferatoxin. The reaction of the bridgehead radical of the highly functionalized 6-membered C-ring, the 5-membered A-ring, and an allyltributyltin derivative effectively produced the C4-branched AC-rings. The last B-ring was constructed from the coupling adduct in two steps through the 7-endo cyclization, delivering the tricyclic framework possessing the correct C8 and 9-stereocenters of resiniferatoxin. The present methods demonstrate the power of the three-component reaction using an α-alkoxy bridgehead radical in a convergent approach to the complex architectures of daphnane diterpenes.

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“…They are widely distributed in plant kingdom and microorganisms (Frija et al 2011;Hanson 2013Hanson , 2015. Diterpenoids have interesting structures and various biological activities such as anti-tumor, anti-microorganism and anti-inflammation, which have been attracted considerable research interest (Vasas and Hohmann 2014;Gonzalez 2015). Several drugs with diterpenoid structures are available, such as retinol, retinal, phytol and taxol.…”

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confidence: 99%

Naturally occurring furanoditerpenoids: distribution, chemistry and their pharmacological activities

et al. 2016

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Furanoditerpenoids are a special group of diterpenoids composing of one or more furan rings, which are rarely found in nature. This review aims to survey the various naturally occurring furanoditerpenoids and their pharmacological activities. A fairly large number of furanoditerpenoids have been reported from the families Euphorbiaceae, Fabaceae and Lamiaceae, and a few ones from the families Asteraceae, Codoniaceae, Dioscoreaceae, Fossombroniaceae, Jamesoniellaceae, Meliaceae, Menispermaceae, Olacaceae, Psathyrellaceae, Sapindaceae and Scapaniaceae. Their distribution correlates strongly with the taxonomic divisions. Most of these plants are widely used in traditional medicines, and furanoditerpenoids have therefore been disclosed with a wide range of bioactivities including anti-cancer, antiinflammation and anti-microorganism. To structure this review, the furanoditerpenoids were classified into seven types, including clerodane-type (Type I), labdane-type (Type II), cassane-type (Type III), abietane-type (Type IV), spongian-type (Type V), prenylbisabolane-type (Type VI) and miscellaneous type (Type VII). On the basis of 170 references, this review covers the distribution, phytochemistry, synthesis and pharmacological activities of furanoditerpenoids, describing 444 compounds. The information provided in this review might shed light on further research and development of furanoditerpenoids as potential therapeutic agents.

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

Cited by 420 publications

References 157 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

Radical-Mediated Three-Component Reaction: A Study toward the Total Synthesis of Resiniferatoxin

Naturally occurring furanoditerpenoids: distribution, chemistry and their pharmacological activities

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