Direct Identification and Quantitative Determination of Acidic and Neutral Diterpenes Using 13C-NMR Spectroscopy. Application to the Analysis of Oleoresin of Pinus nigra

Rezzi, Serge; Bighelli, Ange; Castola, Vincent; Casanova, Joseph

doi:10.1366/0003702021954890

Cited by 82 publications

(49 citation statements)

References 14 publications

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“…[14][15][16] The essential oil and the fractions of chromatography were analysed by 13 C-NMR spectroscopy, based on the pioneering work of Formacek and Kubeczka 17 and following a methodology developed and computerized in our laboratories. [14][15][16] This technique allows the direct and unequivocal identification of the main constituents of a mixture (up to 38 compounds) to a content as low as 0.5-0.3%. The computer program compared the chemical shift of each carbon of the compounds in the experimental spectrum with the spectra of pure components compiled in our spectral data library.…”

Section: Identification Of Componentsmentioning

confidence: 99%

Composition and antimicrobial activity of the essential oil of Clinopodium ascendens (Jordan) Sampaio from Madeira

Castilho

Rodrigues

et al. 2006

Flavour & Fragrance J

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1 H-and 13 C-NMR. The oil was dominated by C 3 oxygenated p-menthane derivatives: cis-isopulegone (75.2%), pulegone (6.9%), neoiso-isopulegol (6.0%) and trans-isopulegone (4.5%). The whole essential oil was tested against a variety of bacteria, both Gram-positive and Gram-negative, and two fungi; it exhibited remarkable activity against Escherichia coli and was active against Agrobacterium tumefasciens and Staphylococcus aureus and the phytopathogenic fungus Botrytis cinerea. It was ineffective against Streptococcus faecium, Streptococcus mutans and Candida albicans.

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Section: Identification Of Componentsmentioning

confidence: 99%

Composition and antimicrobial activity of the essential oil of Clinopodium ascendens (Jordan) Sampaio from Madeira

Castilho

Rodrigues

et al. 2006

Flavour & Fragrance J

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“…[21][22][23] A few constituents were identified by comparison of their spectral data (MS and/or 13 C-NMR) with those reported in the literature: (i) MS and 13 C-NMR, pmentha-1,8-dien-4-ol (37), 24 amorpha-4,11-diene (89), 19 γ-eudesmol (129), 25 manool (144) 26 and ferruginol (146); 27 (ii) MS, selina-4(15), 7(11)-diene (112); 19 iii) 13 C-NMR: α-campholenyl acetate (63), 28 longiborneol (121), 29 sesquithuriferol (120) 30 and juniper cedrol (119).…”

Section: Identification Of Componentsmentioning

confidence: 99%

Analysis ofJuniperus communis subsp.alpina needle, berry, wood and root oils by combination of GC, GC/MS and13C-NMR

et al. 2005

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The essential oils from needles, berries, wood and roots of Juniperus communis L. subsp. alpina were obtained by hydrodistillation, fractionated on column chromatography and analysed by GC, GC-MS and 13 C-NMR. Chemical compositions of wood and root oils are reported here for the first time. Eighty-two, 65, 76 and 54 components were identified, respectively, in needle, berry, wood and root oils. The chemical compositions of the essential oils from needles, berries and wood were characterized by a high proportion of monoterpene hydrocarbons. Root oil exhibited a quite different composition. Sesquiterpenes, especially those bearing a tricyclic skeleton (cedrane and longifolane), constituted the main fraction while monoterpenes were present at very low contents.

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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 Cryptomeria japonica

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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Direct Identification and Quantitative Determination of Acidic and Neutral Diterpenes Using ¹³C-NMR Spectroscopy. Application to the Analysis of Oleoresin of Pinus nigra

Cited by 82 publications

References 14 publications

Composition and antimicrobial activity of the essential oil of Clinopodium ascendens (Jordan) Sampaio from Madeira

Composition and antimicrobial activity of the essential oil of Clinopodium ascendens (Jordan) Sampaio from Madeira

Analysis ofJuniperus communis subsp.alpina needle, berry, wood and root oils by combination of GC, GC/MS and13C-NMR

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

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