Daphnane-Type Diterpene Orthoesters and their Biological Activities

Abstract

Daphnane orthoesters are the active ingredients of plant remedies from the Western, Chinese and African traditional medicine, and have provided important tools to investigate medicinally relevant processes like tumour promotion, apoptosis, neurotrophism, and VR1 activation. The occurrence, biological activity, and molecular pharmacology of these compounds will be reviewed.

Chemical constituents investigation of Daphne tangutica

“…This observation suggested that compound 1 does not possess the ortho-ester group on ring C, which was found in most known daphnane diterpene derivatives. By thus far, the reports on the naturally occurring daphnane diterpenes without this unusual feature are very limited [8,9]. Another notable difference between compound 1 and those known analogs found in the ring A [10][11][12].…”

“…In our present study, two new daphnane derivatives (1 and 2), together with 28 known compounds, including six daphnane diterpenes, vesiculosin (3) [9], isovesiculosin (4) [9], gniditrin (5) [10], gnidicin (6) [10], daphnetoxin (7) [11] and excoecariatoxin (8) [12], nine coumarines, umbelliferone [13] (9), daphnoretin (10) [14], daphneticin (11) [5b], isodaphneticin (12) [15], daphnetin (13) [5c], daphnorin (14) [5c], daphnin (15) [16], daphnetin 8-O-β-D-glucopyranoside (16) [16] and daphneside (17) [16], six lignans, (−)-piperitol (18) [17] [19], (−)-pinoresinol glucoside (22) [18] and syringaresinol 4′,4″-di-O-β-D-glucopyranoside (23) [19], five phenylpropanoid derivatives, caffeic acid octadecyl ester (24) [20], trans-ferulic acid (25) [21], isoferulic acid (26) [22], icariside H 1 (27) [23] and syringin (28) [24], a steroid, β-sitosterol (29) and a small molecular compound, methyl phydroxy benzonate (30) [20] were purified and structurally identified. This is the first time that 13 known compounds, including 3,4,6,12,14,17,22,[24]...…”

“…Previous phytochemical research on D. tangutica has revealed that daphnane diterpenes, coumarines as well as lignans are major principles isolated from this plant [3][4][5]. Among those reported secondary metabolites, daphnane diterpenes are structurally unique compounds only found in the families of Euphorbiaceae and Thymelaeaceae, and have been documented as the irritant and toxic principles of these plants with a wide spectrum of activities including abortifacient, neurotrophic, insecticidal, tumor promoting, antileukaemia and anticancer [6][7][8].…”

Plants from The Genus Daphne: A Review of its Traditional Uses, Phytochemistry, Biological and Pharmacological Activity

“…They represent the main type of known plant orthoesters and they exhibit numerous biological activities (53)(54)(55). This group of molecules also contains acutilobins, which are found in some Daphne plant species, such as D. acutiloba (Figure 4).…”

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

“…[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. 1), a representative daphnane diterpene, is the irritant in the latex of Euphorbia resinifera.…”