Oxygenated sesquiterpenes from the wood of Juniperus oxycedrus

Barrero, Alejandro F.; Sánchez, Juan Francisco López; Oltra, J. Enrique; Altarejos, Joaquı́n; Ferrol, Nuria; Barragán, Armando

doi:10.1016/0031-9422(91)84207-9

Cited by 35 publications

(20 citation statements)

References 10 publications

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“…FC of fraction N 1.5 (b.p. 348C/0.8 mbar, 0.22 g) gave 14 fractions with the following main constituents (in elution order): vitispiranes 56, 57, (E)- (21) and (Z)-tagetone (26), fenchyl acetate (45), elsholtzia ketone (35), bornyl acetate (55), pinocamphone (23), pinocarvone (24), myrtenal (33), isopinocamphone (28), p-methylacetophenone (29), (E)-non-3-en-2-one (17), the oxepanone 30, terpinen-4-ol (31), neo-dihydrocarveol (37), the menthenol 40, linalol (12), and trans-pinocarveol (19). New compounds are given in boldface.…”

Section: Introductionmentioning

confidence: 99%

“…The oxidation products of calamenene, the tetralones 97 and 128 were found in lavender oil 27. 121, 125, Sesquichamaenol (138),45 and the rearranged cadinanes, gleenol (109)35 and b-oplopenone (115),39 are known as constituents of Juniperus species. The muuroladienol 120 was one of 14 cadinene derivatives obtained on photosensitized oxidation of d-cadinene (98) 41.…”

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confidence: 99%

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Constituents of commercial Labdanum oil

et al. 1998

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Commercial Labdanum oil contains more than 300 constituents. 186 compounds (154 from the neutral part, 32 from the acidic part), representing about 95% of the oil, were identi®ed mainly by their NMR spectra. Typical for the Labdanum oil in the C 15 to C 20 region are aromadendrane (23%), cadinane (9%) and labdane (7%) derivatives, mostly oxidized. The main constituents in this region are ledene (92, 9.3%), allo-

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Section: Introductionmentioning

confidence: 99%

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confidence: 99%

Constituents of commercial Labdanum oil

et al. 1998

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“…cubenol (9), 15) epi-cubenol (10), 16,17) cubebol (11), 16,17) epicubebol (12), 18) gleenol (13), 19) b-elemol (14), 20) cryptomerione (15), 21) 7 (14),10-bisaboladien-1-ol-4-one (16), 22) 2,7(14),10-bisabolatrien-1-ol-4-one (17), 23) 7 (14),10-bisaboladien-1,4-diol (18), 24) cryptomeridiol (19), 25) sandracopimaradiene (20), 26) sandaracopimarinal (21), 27) sandaracopimarinol (22), 28) sandaracopimaric acid (23), 29) 8 [14],15-pimaradiene-3-ol (24), 30) 18-nor-8 [14],15-isopimaradien-4-ol (25), 31) sandaracopimarinol acetate (26), 31) 16-phyllocladanol (27), 32) 7,13-abietadiene (28), 33) abietatriene (29), 34) ferruginol (30), 35) 6,7-dehydroferruginol (31), 36) sugiol (32), 37) hinokiol (33), 37) 19-hydroxyferruginol …”

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A New Abietane and Two Dimeric Abietane Diterpenes from the Black Heartwood of <i>Cryptomeria japonica</i>

Arihara

Umeyama

Bando

et al. 2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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The Japanese cedar, Cryptomeria japonica D. DON. (Taxodiaceae) is a widely distributed conifer called sugi in Japanese. This wood is the most popular building material for Japanese housing. Although many cedar cores are reddish brown, about 20% are black, as a result of genetic factors, physical damage, infection of fungus, etc., and are called kurojin in Japanese. Chemical research on the terpene components of cedar cores is limited to the reddish brown ones. [1][2][3][4][5][6][7][8][9] This prompted us to examined the terpene constituents of black heartwood.Shaved chips (3.92 kg) of black heartwood were exhaustively extracted with MeOH at room temperature for 4 weeks. The extract was partitioned between H 2 O and EtOAc. Repeated separation of the EtOAc-soluble portion by chromatography over ordinary-phase silica gel and reverse-phase silica gel furnished a novel abietane, sugikurojin A (1), dimeric abietanes, and sugikurojins B (2) and C (3), along with known compounds formosaninol (4), 10) a-muurolene (5), 11) d-cadinene (6), 12) calamenene (7), 13,14) T-cadinol (8), 15) cubenol (9), 15) epi-cubenol (10), 16,17) cubebol (11), 16,17) 21) 7(14),10-bisaboladien-1-ol-4-one (16), 22) 2,7(14),10-bisabolatrien-1-ol-4-one (17), 23) 7 (14),10-bisaboladien-1,4-diol (18) A-C (1-3) were isolated from the black heartwood of Cryptomeria japonica. The structure of sugikurojin A was deduced to be 19-hydroxy-6,7-dehydroferruginol on the basis of extensive NMR experiments. Sugikurojin B was a dimer of 6,7-dihydroxyferruginol and 6,7-dehydroferruginol with a 6-O-11 linkage. Sugikurojin C was a dimeric ferruginol with 6-O-7 and 7-O-6 linkages. Also obtained in this investigation were the known compounds formosaninol (4), 15 sesquiterpenes (5-19), 16 diterpenes (20-35), three phenylpropanoids (36-38), and a phenolic compound (39).

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“…Our group [30] has used this kind of rearrangement in a synthesis of (−)-gleenol (60) and (−)-axenol (59) from (R)-(−)-carvone (58) ( Figure 2). (−)-Gleenol has been isolated from Picea glehni [31], P. koraiensis [32], Criptomeria japonica [33], Juniperus oxycedrus [34], and the brown alga Taonia atomaria [35]. The enantiomer, (+)-gleenol, and its C-6 epimer, (+)-axenol, have been isolated from New Zealand Eurypon sponge species.…”

Section: Scheme 11mentioning

confidence: 99%

Synthesis of Sesquiterpenes via Silicon-Guided Rearrangement of Epoxydecalins

Blay

Collado

Garcı́a

et al. 2008

Natural Product Communications

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A survey of the rearrangement of methyldecalins via C-5 carbocation intermediates, with special attention to the silicon-guided rearrangement of epoxydecalins is provided. A TMS group properly positioned on either C-1 or C-9 promotes the acidic rearrangement of 10-methyl-4,5-epoxydecalins and 10-methyl-5,6-epoxydecalins with exclusive migration toward C-5 of the methyl or methylene groups linked directly to C-10. The application of this biomimetic approach to the synthesis of a number of spirocyclic and eremophilane sesquiterpenes is reported.

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Oxygenated sesquiterpenes from the wood of Juniperus oxycedrus

Cited by 35 publications

References 10 publications

Constituents of commercial Labdanum oil

Constituents of commercial Labdanum oil

A New Abietane and Two Dimeric Abietane Diterpenes from the Black Heartwood of <i>Cryptomeria japonica</i>

Synthesis of Sesquiterpenes via Silicon-Guided Rearrangement of Epoxydecalins

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