Sasanquol, a 3,4-seco-triterpene alcohol from sasanqua oil, and its anti-inflammatory effect.

A novel 3,4-seco-triterpene alcohol, named sasanquol, was isolated from the non-saponifiable lipid of sasanqua oil from the seeds of Camellia sasanqua. Its structure was established to be 3,4-seco-D:B-friedobacchara-4,21-dien-3-ol by spectroscopic methods. This is the first example of naturally occurring triterpene with a D:B-friedobaccharane skeleton. The 50% inhibitory dose of this compound against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear inflammation (1 microgram per ear) in mice was 0.4 mg per ear.

Inhibitory effect of heliantriol C; a component of edible Chrysanthemum, on tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin.

Two hydroxy taraxastane-type triterpenes, faradiol and heliantriol C, have been isolated from the ligulate flowers of Chrysanthemum morifolium Ramat. var. sinense Makino fa. esculentum Makino, the edible Chrysanthemum. These compounds showed strong inhibitory activity against 12-O-tetradecanoyl-phorbol-13-aetate (TPA)-induced inflammation in mice. At 0.2 µmol/mouse, these compounds markedly inhibited the promoting effect of TPA (1 µg/mouse) on skin tumor formation followed by 7,12-dimethylbenz[a]anthracene (50 µg/mouse).

Triterpene alcohols from camellia and sasanqua oils and their anti-inflammatory effects.

The nonsaponifiable lipids of camellia and sasanqua oils from the seeds of Camellia japonica L. and C. sasanqua THUNB., respectively, were investigated for their triterpene alcohol constituents. This led to the isolation of twenty-seven triterpene alcohols of which seven were novel naturally occurring compounds, tirucalla-5,7,24-trien-3 beta-ol (1), lemmaphylla-7,21-dien-3 beta-ol (2), isoeuphol (3), isotirucallol (4), (24R)-24,25-epoxybutyrospermol (5) and its 24S-epimer (6), and isoaglaiol (7). The structures were determined by spectroscopic and chemical methods. The inhibitory effects of 3, 4 a mixture of 5 and 6, a mixture of 7 and its 24S-epimer (aglaiol), and eight known triterpene alcohols isolated in this study were evaluated in ear inflammation in mice induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The 50% inhibitory dose of these triterpenes for TPA-induced inflammation (1 microgram per ear) was 0.2-0.9 mg/ear.

Triterpene alcohols from the flowers of compositae and their anti-inflammatory effects.

Eleven tabular and nine ligulate flowers from 15 species of Compositae plants were investigated for their triterpene alcohol constituents. This led to the isolation and identification of 11 triterpene alcohols as follows: heliaol, taraxasterol, psi-taraxasterol, alpha-amyrin, beta-amyrin, lupeol, taraxerol, cycloartenol, 24-methyl-enecycloartanol, tirucalla-7,24-dienol and dammaradienol. The tabular flowers of Calendula officinalis, Carthamus tinctorius, Cosmos bipinnatus, Chrysanthemum morifolium, Helianthus annuus and Matricaria matricarioides showed a characteristic feature by containing helianol as the most predominant component (29-86%) in the triterpene alcohol fractions. The triterpene alcohols from Compositae flowers were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate-induced inflammation (1 microgram per ear) in mice. All of these showed marked inhibitory activity, and their 50% inhibitory dose was 0.1-0.8 mg per ear.

Inhibitory effect of taraxastane-type triterpenes on tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin.

Two taraxastane-type hydroxy triterpenes, taraxasterol and faradiol, isolated from the flowers of Compositae plants Cynara scolymus (artichoke) and Chrysanthemum morifilolium (chrysanthemum), respectively, showed strong inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice. At 2.0 mumol/mouse, these compounds inhibited markedly the tumor-promoting effect of TPA (1 microgram/mouse) on skin tumor formation following initiation with 7,12-dimethylbenz[alpha]anthracene (50 micrograms/mouse).

Inhibitory effect of oral administration of Monascus pigment on tumor promotion in two-stage carcinogenesis in mouse skin.

Monascus pigment was extracted from red malted rice, Monascus anka. It has been used as coloring matter for foodstuffs in Japan and certain Asian countries. Oral administration of Monascus pigment suppressed the tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in mice following initiation by 7,12-dimethylbenz[a]anthracene.

Some lupane-type triterpenes inhibit tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in two-stage carcinogenesis in mouse skin.

We have found that several lupane-type triterpenes, including lupeol, its acetate, betulin and betulinic acid, inhibit 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation, and that betulinic acid inhibits tumor promotion in two-stage carcinogenesis in mice. Among seven lupane-type triterpenes assayed, these compounds inhibited the inflammatory activity induced by TPA in mice. The 50 % inhibitory dose of these compounds for TPA-induced inflammation was 0.4-4.0 µmol. Furthermore, topical application of lupeol, lupeol 3-acetate and betulin markedly suppressed the tumor-promoting effect of TPA (1 µg/mouse) in mouse skin initiated with 7,12-dimethyl-benz[a]anthracene (50 µg/mouse), at a grade corresponding to that of betulinic acid.

(+)-Alpha-viniferin, an anti-inflammatory compound from Caragana chamlagu root.

The roots of Caragana chamlagu Lamarck (Leguminosae) are used as an anti-neuralgic, anti-rheumatic, anti-arthritic, etc. in the folk medicine of Korea. An ether extract was fractionated with monitoring of the anti-inflammatory activity, and the active principle was elucidated as (+)-alpha-viniferin on the basis of spectroscopic data, including two-dimensional nuclear magnetic resonance and circular dichroism spectra.