Cabon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. X. Pimaradienes

Wenkert, Ernest; Buckwalter, Brian L.

doi:10.1021/ja00767a070

Cited by 213 publications

(68 citation statements)

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“…1, the CHCl 3 extract was further subjected to ether extraction, SiO 2 column chromatography, and reversed phase HPLC, or a combination of silica gel column chromatography and reversed phase HPLC, resulting in the isolation of the most active compound (4) and other five compounds (1-3, 5, 6). Their structures were elucidated as communic acid (1), 17) sandaracopimaric acid (2), 18,19) (13S)-15-hydroxylabd-8(17)-en-19-oic acid (3), 20) deoxypodophyllotoxin (4), 21) 14-hydroxyisopimaric acid (=calliphyllin) (5), 22) and 7-hydroxysandaracopimaric acid (6) 23) on the basis of spectral analyses (½ D , EI-MS, 1 H-and 13 C-NMR, together with 2D NMR (COSY, NOESY, HMQC, and HMBC experiments)). Their structures were confirmed by comparison with reported spectroscopic data, their chemical structures being shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

Isolation of Apoptosis- and Differentiation-Inducing Substances toward Human Promyelocytic Leukemia HL-60 Cells from Leaves ofJuniperus taxifolia

Muto

Tomokuni

Haramoto

et al. 2008

Bioscience, Biotechnology, and Biochemistry

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Section: Resultsmentioning

confidence: 99%

Isolation of Apoptosis- and Differentiation-Inducing Substances toward Human Promyelocytic Leukemia HL-60 Cells from Leaves ofJuniperus taxifolia

Muto

Tomokuni

Haramoto

et al. 2008

Bioscience, Biotechnology, and Biochemistry

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“…nce that quaternary anti carbons are deshielded relative to quaternary syn carbons. Consider the three isomeric pimaradienes 1-3 (8). The step from the Ass9 to the A' olefin constitutes a syn + anti change for C(13), and results in a 1.9 pprn downfield shift.…”

Section: Elimination Of the I3-diaxial P-hydrogen Bymentioning

confidence: 99%

A reinterpretation of beta, gamma, and delta substituent effects on ¹³C chemical shifts

Beierbeck¹,

Saunders²

1976

Can. J. Chem.

109

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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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Cabon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. X. Pimaradienes

Cited by 213 publications

References 0 publications

Isolation of Apoptosis- and Differentiation-Inducing Substances toward Human Promyelocytic Leukemia HL-60 Cells from Leaves ofJuniperus taxifolia

Isolation of Apoptosis- and Differentiation-Inducing Substances toward Human Promyelocytic Leukemia HL-60 Cells from Leaves ofJuniperus taxifolia

A reinterpretation of beta, gamma, and delta substituent effects on ¹³C chemical shifts

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

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Cabon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. X. Pimaradienes

Cited by 213 publications

References 0 publications

Isolation of Apoptosis- and Differentiation-Inducing Substances toward Human Promyelocytic Leukemia HL-60 Cells from Leaves ofJuniperus taxifolia

Isolation of Apoptosis- and Differentiation-Inducing Substances toward Human Promyelocytic Leukemia HL-60 Cells from Leaves ofJuniperus taxifolia

A reinterpretation of beta, gamma, and delta substituent effects on 13C chemical shifts

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

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A reinterpretation of beta, gamma, and delta substituent effects on ¹³C chemical shifts