A new myrsinol-type diterpene polyester fromEuphorbia dracunculoidesLam

Abstract

A new myrsinol-type diterpene polyester, 14-deoxo-3β-O-propinoyl-2α,5α,7β,15β-tetra-O-acetyl-14α-O-benzoyl-myrsinol (1), and its known analogue, 14-deoxo-3β-O-prorionyl-5α,15β-di-O-acetyl-7β-O-nicotinoyl-myrsinol-14β-acetate (2), together with a monoterpenoid, pubinernoid A (3), two indole alkaloids, neoechinulin A (4) and dihydroxyisoechinulin A (5), two benzene derivatives, siringin (6) and (3-methoxyphenyl) acetic acid (7), were isolated from the 70% acetone extract of the aerial parts of Euphorbia dracunculoides Lam. Their structures were elucidated on the basis of spectroscopic evidence and comparison with literature reports. The absolute configuration of 1 was deduced by comparing experimental and calculated ECD spectra. Among them, compounds 4 and 5 were first obtained from the plant source. In addition, the (13)C NMR data of compound 2 was reported for the first time.

Characterization of Diterpenes from Euphorbia prolifera and Their Antifungal Activities against Phytopathogenic Fungi

“…The ethyl acetate-soluble part of the methanol extract of the roots parts of E. prolifera was fractionated by silica gel column chromatography and MPLC and further purified by HPLC to afford six new ( 1 – 6 ) and two known ( 7 and 8 ) diterpenoids (Figure ). The known compounds were identified by comparison of spectroscopic data with those reported in the literature as 2α,5α,7β,15β-tetra- O -acetyl-3β- O -propinoyl-14α- O -benzoyl-14-deoxomyrsinol, 7 , and 3β- O -propionyl-5α,10,15β-tri- O -acetyl-14β- O -nicotinoyl-7-oxo-10,18-dihydromyrsinol, 8 …”

LC-ESI QToF MS Non-Targeted Screening of Latex Extracts of Euphorbia seguieriana ssp. seguieriana Necker and Euphorbia cyparissias and Determination of Their Potential Anticancer Activity

“…In the ES extract, four pairs of isobaric compounds were detected: two compounds with molecular formula C 36 H 46 O 12 — 7 at t R = 7.12 and 13 at t R = 8.39 min—and two compounds with molecular formula C 41 H 48 O 12 — 18 at t R = 9.62 and 22 at t R = 10.69 min—while only one Euphorbia /Euphorbiaceae premyrsinane with a corresponding molecular formula has been identified from each pair so far [ 44 , 51 , 52 , 53 , 61 ], in addition to two compounds with molecular formula C 36 H 48 O 12 — 10 at t R = 7.33 and 14 at t R = 8.77 min—corresponding to two known premyrsinanes [ 46 , 47 , 57 ], and two compounds with molecular formula C 36 H 50 O 8 — 29 at t R = 13.92 min and 30 at t R = 14.13 min—whose mass spectra showed fragment ions corresponding to the loss of a water molecule, as well as fragment ions 313, 295, and 267. The only compound with the same molecular formula so far identified in the genus Euphorbia belongs to the PE type of diterpene esters [ 70 , 71 , 72 , 73 ].…”

Myrsinane-Type Diterpenes: A Comprehensive Review on Structural Diversity, Chemistry and Biological Activities

“…From the 70% aqueous Me 2 CO extract of E. dracunculoides Lam., several new myrsinane- ( 183 , 184 – 187 ) [ 102 , 103 , 104 ], premyrsinane- ( 188 – 190 ) [ 105 ], and cyclomyrsinane-type ( 191 – 193 ) ( Figure 21 ) [ 105 ] diterpenes were isolated, together with known compounds that were previously obtained from other Euphorbia species [ 37 , 66 , 67 ]. Also, from E. erythradenia Bioss., a new myrsinane was isolated 194 ( Figure 21 ) but without biological activity unlike the tetrahydroingenol diterpenes isolated from this plant [ 106 ].…”