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

Abstract

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).

A Quinone Isolated from the Nest of Vespa simillima and Its Growth-Inhibitory Effect on Rat Liver Cancer Cells

“…18) In these woods, a variety of biologically active abietane-type and two pimarane-type diterpenoids have been isolated. [22][23][24][25][26][27][28][29][30][31] These reports are indicative that yellow hornets utilize these woods not only for building material for the nest but also as a chemical tool to protect the nest from microorganisms.…”

“…[22][23][24][25][26][27][28][29][30][31] However, these molecular mechanisms have not been well examined. Ross reported that an anticancer quinone classified as an abietane terpenoid exhibited apoptosis, based on morphological changes in the cancer cells.…”

Three Abietane Diterpenes and Two Diterpenes Incorporated Sesquiterpenes from the Bark of Cryptomeria japonica

“…sugikurojin B (9), 1) 6,12,15-trihydroxy-5,8,11,13-abietatetraene-7-one (10), 7) 5,6-dehydrosugiol (11), 8) trilobine (12), 9) 6,7-dehydroferruginol (13), 10) and 11,14-dihydroxy-8,11,13-abietatriene-7-one (14). 11) This paper deals with the elucidation of the structures of compounds 1-5 and the antibacterial activity of the isolated compounds against S. aureus and E. coli, together with cytotoxic activity against HL-60 and HCT-15 cell lines.…”

Abietane Diterpenoids from the Barks of Cryptomeria japonica

“…5). Furthermore, from cedar, many isopimarane diterpenes 13,14) have been obtained, but no pimarane diterpenes had been reported. From the aforementioned data, the diterpene acyloxy moiety of sugikurojin J was 7-oxo-8(14),15-isopimaradien peroxy-18-oate.…”