Abietatrienes diterpenoids from Sagittaria montevidensis SSP Montevidensis

Abstract

Recebido em 1/10/08; aceito em 14/7/09; publicado na web em 25/11/09The antimicrobial properties of the hexane, hexane/EtOAc and methanol fractions of the fresh petioles of Sagittaria montevidensis ssp montevidensis (Alismataceae) were evaluated against fungi and Gram-negative and Gram-positive bacteria. A new abietatrienetype diterpenoid, 3β,7α-dihydroxi-abieta-8,11,13-triene and the known 3β-hydroxy-abieta-8,11,13-trien-7-one were isolated from the most active fraction tested and the structures of these compounds were elucidated by data including IR, EIMS, and 1D and 2D NMR spectra.

Total Syntheses of Aromatic Abietane Diterpenoids Utilizing Advances in the Pummerer Rearrangement

“…This reaction likely proceeds through formation of a benzylic carbocation after acylation of the sulfoxide by TFAA, which is in turn trapped by the trifluoroacetate counterion. Compound 1 was in agreement ( 1 H NMR, 13 C NMR, [α] D ) with the literature values , for the ent -triptobenzene T ( 1 ). This synthesis enabled the definitive assignment of the absolute configuration of this natural product where some confusion previously existed…”

“…With rapid routes established for accessing the prefunctionalized tricyclic core, our efforts shifted to the synthesis of the abietane diterpenoid natural products. Our first target was triptobenzene T ( 1 ) (Scheme ). Dimethylation of the tricyclic enone 7 provided the adduct 17 .…”

New Diterpenes from a Godavari Mangrove, Ceriops decandra

“…1). By comparison of their physical and spectroscopic data with those of literatures, the structures of four known abietanes were identified as 5,8,11,13-abietatetraen-3,7-dione [7], 3β,7α-dihydroxy-abieta-8,11,13-triene [13], 14,18-dihydroxyabieta-8,11,13-trien-7-one [14], and 15,18-dihydroxyabieta-8,11,13triene [15], respectively. All the above diterpenes were identified from this mangrove plant for the first time.…”

“…J (H a H a ) = 11.5 Hz and J (H a-H e ) = 4.0 Hz, respectively. The β-orientation of 13-OH was indicated by the similar 13 ] with a 13α-OH moiety [8] (l " Table 1).…”

Bioactive ent-Pimarane and ent-Abietane Diterpenoids from the Whole Plants of Chloranthus henryi

“…The eight known diterpenoids were identified as ent -pimar-15-ene-3α,8α-diol ( 11 ), ent -pimara-8­(14),15-diene-3α,7β-diol ( 12 ), 3β-hydroxyabieta-8,11,13-trien-7-one ( 13 ), sessilifol O ( 14 ), 3β,7α-dihydroxyabieta-8,11,13-triene ( 15 ), decandrin B ( 16 ), sessilifol D ( 17 ), and sessilifol F ( 18 ) …”