13C NMR data for abieta‐7,13‐diene diterpenoids

Feliciano, Arturo San; Corral, José M. Miguel del; Gordaliza, Marina; Salinero, M. A.

doi:10.1002/mrc.1260310910

Cited by 20 publications

(16 citation statements)

References 6 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 …”

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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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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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“…1). 11) Rosin (colophony), Resina Pini of Pinus sp., is the residue left after distilling off the volatile oil from the oleoresin (turpentine) obtained from Pinus sp., Pinus palustris Miller, Pinus pinaster Aiton, Pinus sylvestris Linne, Pinus laricio Poiret, Pinus longifolia Roxburgh, Pinus densiflora Siebold et Zuccarini, and Pinus thunbergii Parlatore. About 90% of the rosin is resin acids, and about 90% of resin acids is abietic acid.…”

Section: Resultsmentioning

confidence: 99%

Abietic Acid from Resina Pini of Pinus Species as a Testosterone 5.ALPHA.-Reductase Inhibitor

Roh

Park

Kim

2010

JOURNAL OF HEALTH SCIENCE

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The 50% ethanol extracts from Resina Pini of Pinus sp. (Pinaceae) showed more potent inhibitory activity against testosterone 5α-reductase prepared from rat prostate than those from several medicinal plants used for the treatment of androgen-dependent diseases such as benign prostatic hyperplasia. The fraction responsible for this activity was purified, and the active constituent was isolated and identified as abietic acid, a diterpene resin acid, which exhibited potent testosterone 5α-reductase inhibitory activity. Methyl abietate was substantially inactive against testosterone 5α-reductase, whereas other diterpene resin acids, pimaric acid and neoabietic acid, were as active as abietic acid against testosterone 5α-reductase, indicating that the negatively charged anionic carboxyl group on the molecule is an important structural moiety for the inhibitory activity. These findings suggest that a nonsteroidal anionic diterpene compound of natural origin may have the potential to act as a transition state analogue inhibitor of testosterone 5α-reductase in the treatment of androgendependent diseases.

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“…C-methyl group andˇ(axial, C-19) for the carbomethoxyl substituent, as was rigorously established from the chemical shift values of the C-18 (υ 28.2-28.4) and C-19 (υ 177.6-177.7) carbons. 5,6 Further extension of the C-3, C-4, C-5, C-18 and C-19 structural fragment was sorted out since the H-5˛proton showed contour peaks with the C-1, C-3, C-4, C-6, C-7, C-10 and C-20 carbons, the H-3˛proton (υ 1.01-1.08) was connected, among others, with the C-2 carbon (υ 18.9-19.9) and the C-8 carbon showed connectivities with the C-6 and C-7 methylene protons. In addition, the C-20 methyl protons (singlet at υ 0.81-1.15, see Table 1) were correlated with the C-1, C-5, C-9 and C-10 carbons, thus confirming their assignments.…”

Section: Resultsmentioning

confidence: 99%

“…In all the compounds studied, the A-ring possesses a chair conformation ( 4 C 1 ), as was deduced from the vicinal coupling constant values of the C-1, C-2 and C-3 methylene protons (see Table 1), but the B-ring shows a different conformation in each substance. In 1 the B-ring has a half-chair conformation ( 10 C 7 ), whereas in 2, 3 and 4 it has a twisted-boat conformation with the flaps at C-6 and C-9 ( 6.9 B), at C-5 and C-8 (B 5,8 ), and at C-7 and C-10 ( 7,10 B), respectively. These conclusions are in agreement with the 3 J values observed for the C-5 methine and C-6 and C-7 methylene protons (Table 1), and also with the allylic coupling between the H-7ˇand H-17 protons in 4 ( 4 J D 2.4 Hz) and with the NOESY spectra (e.g.…”

Section: Resultsmentioning

confidence: 99%

Complete assignments of1H and13C NMR spectra of four hispanane diterpenoids

Rodrı́guez¹,

Savona

2000

Magn. Reson. Chem.

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¹³C NMR data for abieta‐7,13‐diene diterpenoids

Abstract: 13C NMR data for several abieta-7,13-diene diterpenoids are reported. The most significant effects caused by the change in the stereochemistry at C-4 and other structural modifications are discussed.

Cited by 20 publications

References 6 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>

Abietic Acid from Resina Pini of Pinus Species as a Testosterone 5.ALPHA.-Reductase Inhibitor

Complete assignments of1H and13C NMR spectra of four hispanane diterpenoids

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