Diterpenoids from isodon flavidus

Zhao, Qin; Tian, Jie; Yue, Jian; Chen, Shao-Nong; Lin, Zhong Wen; Sun, Han

doi:10.1016/s0031-9422(97)00608-0

Cited by 47 publications

(38 citation statements)

References 11 publications

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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 …”

unclassified

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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unclassified

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 structural elucidation and identification of these compounds were based on spectral data analysis including MS, 1D and 2D NMR. The seven abietane diterpenoids included one new abietane diterpenoid, 20(10!5)-abeo-4,5-seco-5(10), 6,8,11,13-abietapentaene-3-one (1), and six known abietane diterpenoids, 12-hydroxyabieta-6,8,11,13-tetraene-3-one (2), abieta-8,11,13-triene-3b,12-diol (hinokiol) (3) (Zhao et al, 1998), abietatriene-3b-ol (4) (Urones et al, 1988;Chamy et al, 1991), 11,12-dihydroxy-8,11,13-abietatriene-3,7-dione (5) (Li et al, 2003), 11-hydroxy-12-methoxyabieta-8,11,13-triene-3,7-dione (6) (Yang et al, 1998), and 3b,11-dihydroxy-12-methoxyabieta-8,11,13-triene-7-one (7) (Li et al, 2002;Orihara et al, 2002;Monacelli et al, 2002) (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Abietane diterpenoids synthesized by suspension-cultured cells of Cephalotaxus fortunei

Zhang

Cao

et al. 2011

Phytochemistry Letters

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“…Fraction C-2 was separated by chromatotron eluting with a gradient between hexane and EtOAc to afford compounds 3 (115.3 mg), 4 (93.7 mg) 6 and 5 (13.6 mg) 11 . Similarly, fraction C-3 was separated by chromatotron eluting with a gradient between hexane and EtOAc to yield compound 6 (14.8 mg) 12 . The VLC fraction F was rechromatographed on silica gel, using a gradient system of hexane, CH 2 Cl 2 and MeOH as eluents to yield five fractions (F-1-5).…”

Section: Extraction and Separation Of Compoundsmentioning

confidence: 99%

Chemical Constituents From the Roots of Bombax Anceps

Sichaem

Siripong

Khumkratok

et al. 2010

J. Chil. Chem. Soc.

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The phytochemical investigation of the roots of Bombax anceps (Bombacaceae) led to the isolation of one new dihydrobenzodioxine derivative, bombaxoin (1) along with ten known compounds. All structures of the isolated compounds were established by means of spectral analyses. Compound 2 showed the highest antioxidant activity (DPPH), while compound 8 showed the highest potential inhibitors activity toward AChE and BChE. In addition, all of the compounds were inactive to cytotoxic activity (KB and HeLa cell lines).

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Diterpenoids from isodon flavidus

Cited by 47 publications

References 11 publications

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

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

Abietane diterpenoids synthesized by suspension-cultured cells of Cephalotaxus fortunei

Chemical Constituents From the Roots of Bombax Anceps

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