Daphnane- and Tigliane-Type Diterpenoid Esters and Orthoesters from Pimelea elongata

Abstract

Investigation of Pimelea elongata ("Lakebed Pimelea") afforded 18 tigliane- and daphnane-type diterpenes (1-18). Eight of these were new compounds: four (1-3, 5) tigliane esters and four (7, 8, 10, 11) daphnane orthoesters. The 10 known compounds were 12-O-decanoylphorbol-13-acetate (4), P. simplex subtoxin B (6), wikstroelide E (9), pimelotides A and B (12, 13), gnidiglaucin (14), simplexin (15), huratoxin (16), kirkinine D (17), and 12-β-acetoxyhuratoxin (18). The structures and relative configurations of the new compounds were determined by 1D and 2D NMR spectroscopic studies in combination with MS analyses.

Two New Diterpenoids from the Buds of Wikstroemia chamaedaphne

“…The NOESY correlations of H-7/H-8, H-7/H-20b, H-8/H-11, and H-8/H-14 indicated that H-7, H-8, H-11, H-14 and H-20b were assigned in β -orientations. A literature survey revealed that when the absolute configuration of C-9′ was R , correspondingly, 10′-CH 3 was in the α -orientation of the molecule, the chemical shift of C-10′ would appear around δ C 19.0 [ 12 , 13 ]; if the C-9′ was S configuration, the C-10′ would shift downfield to δ C 12.3 [ 4 , 5 , 13 ]. The chemical shift of C-10′ δ C 19.1 in 1 suggested the R configuration of C-9′ in 1 .…”

Antiplasmodial compounds from the stem bark of Neoboutonia macrocalyx pax

“…As confirmed from the molecular formula, the 1 H and 13 C NMR revealed that the aliphatic chain of compounds 4 and 5 contained two more and four more methylene groups than mellerin B respectively. By detailed MS and NMR data analysis, compound 4 was identified as simplexin, a known compound previously isolated from the genus Pimelea (Thymelaeaceae) including P.simplex and P. elongata and other plant species (Asada et al, 2011;Hayes et al, 2010). Compound 5 was identified as montanin, from its MS and NMR data analysis and also in comparison with data from literature.…”

A Review on Daphnane-Type Diterpenoids and Their Bioactive Studies

“…Hirseins A and B have shown inhibition of melanogenesis in B16 murine melanoma cells [22]. Glabrescin( 12 ) and Montanin ( 26 ) have been obtained from Neoboutoniaglabrescens [23]. Kirkinine D ( 25 ) and synaptolepisfactor K 7 ( 28 ) have been isolated from the S.kirkii [24].…”