Diterpenoids from the Buds of Pinus banksiana Lamb.

Abstract

Three new diterpenoids, namely 7α-hydroxyabieta-8,11,13,15-tetraen-18-oic acid, 7β,15,18-trihydroxyabieta-8,11,13-triene, 13,15-dihydroxypodocarpa-8,11,13-triene, and 12 other known compounds were isolated from buds of Pinus banksiana Lamb. All these compounds, except for 7-oxodehydroabietinol, were isolated for the first time from this plant. Their structures were elucidated by detailed spectroscopic studies and comparison with published data. All isolated compounds were tested for cytotoxic and antibacterial activities. Overall, two compounds, 7-oxodehydroabietinol and 18-nor-4,15-dihydroxyabieta-8,11,13-trien-7-one, showed moderate cytotoxicity against a human lung carcinoma cell line.

Antiviral Activities of Compounds Isolated from Pinus densiflora (Pine Tree) against the Influenza A Virus

“…a Recorded in methanol-d4 at 500 MHz. The structures of all known compounds isolated from the cortex and leaves of P. densiflora were elucidated by extensive analyses of spectroscopic data including NMR and MS spectra and by comparison with previously reported data as follows: (3) dehydroabietic acid [48]; (4) 12hydroxydehydroabietic acid [49]; (5) 7α-methoxydehydroabietic acid [50]; (6) 15hydroxydehydroabietic acid [51]; (7) 16-nor-15-oxodehydroabietic acid [52,53]; (8) abieta-8,11,13,15tetraen-18-oic acid [53]; (9) 7α-hydroxyabieta-8,11,13,15-tetraen-18-oic acid [54]; (10) karamatsuic acid [55]; (11) palustric acid [56]; (12) 12-methoxy-7,13-abietadien-18-oic acid [57]; (13) 7-oxo-13βhydroxyabiet-8( 14)-en-18-oic acid [58]; (14) 9,13β-epidioxy-8( 14)-abieten-18-oic acid [59]; (15) 14α,15epoxyabiet-9(11)-en-12-oxo-18-oic acid [60]; (16) 8( 14)-podocarpen-13-on-18-oic acid [51,52]; (17) 8( 14)podocarpen-7,13-dion-18-oic acid [51,52]; (18) 4-epi-trans-communol [61]; (19) 4-epi-trans-communal [62]; (20) 4-epi-trans-communic acid [63]; (21) 3β-hydroxy-12,13(E)-biformen [64]; (22) 18α,3αdihydroxy-12,13(E)-biformen [65]; (23) (13S)-15-hydroxylabd-8(17)-en-18-oic acid [66]; (24) ampelopsin [67]; (25) 5,7,4′-trihydroxy-3-methoxy-6-C-methylflavone ...…”

“…(7) 16-nor-15-oxodehydroabietic acid [52,53]; (8) abieta-8,11,13,15-tetraen-18-oic acid [53]; (9) 7α-hydroxyabieta-8,11,13,15-tetraen-18-oic acid [54];…”

Bio-Guided Isolation of Methanol-Soluble Metabolites of Common Spruce (Picea abies) Bark by-Products and Investigation of Their Dermo-Cosmetic Properties

“…7α,15-Dihydroxydehydroabietic acid was present as a minor compound in Fr.III and Fr.IV. This abietane diterpene has been previously identified in the aerial parts of Abies georgei Orr [16] and buds of Pinus banksiana Lamb together with its 7β-isomer, [17] while its 4-epi-isomer has been referred in stems of Illicium jiadifengpi [18] and air-dried fruits of Juniperus polycarpus var. seravschanica [19].…”

Qualitative Analysis Related to Palynological Characterization and Biological Evaluation of Propolis from Prespa National Park (Greece)

“…Isolation of the 7-oxo-dehydroabietinol (sample PP3) from propolis for the first time led to the further investigation of its plant source. This metabolite has been mentioned before in Pinus and Juniperus species [ 24 , 25 ]. After GC/MS analysis of different Juniperus species from PNP, it has been proven that Juniperus oxycedrus L. subsp.…”