Agarwood oil and spikenard extract were examined for their sedative activity using a spontaneous vapor administration system. It was shown that inhalation of agarwood oil vapor sedated mice. The main volatile constituents of the oil were found to be benzylacetone [agarwood oil from a Hong Kong market (1)], or alpha-gurjunene and (+)-calarene [agarwood oil made in Vietnam (2)]. A hexane extract of spikenard contained a lot of calarene, and its vapor inhalation had a sedative effect on mice. Individual principles benzylacetone, calarene, and alpha-gurjunene were administered to mice, which reproduced the result of the corresponding oil or extract. However, the most effective dose of the compounds was lower than their original content in the oil and extract (benzylacetone 0.1%, calarene 0.17%, alpha-gurjunene 1.5%).

Agarwood ('Jinkoh' in Japanese) is a famous incense and is used as a sedative, analgesic and digestive in Kampo medicine. From agarwood, characteristic sesquiterpenes [2][3][4][5][6][7][8] and chromone derivatives [9][10][11][12][13][14][15][16] have been isolated. These compounds, together with the pyrolyzation products, constitute a pleasant odor when agarwood is burnt, 17,18) and combinations of these compounds make up various qualities of agarwood. Although the resinous part of agarwood is formed by decay, injury, etc., of the tree of the Aquilaria species (Thymelaeaceae), this process has not been understood in detail. Examination of the chemical constituents of the damaged wood would offer valuable information for understanding the bioorganic process of agarwood formation. In the present paper, we describe the isolation and structure elucidation of four new chromone derivatives (1-4), together with seven known chromones, from the MeOH extract of withered wood of A. sinensis, an original plant of agarwood (Chart 1). Results and DiscussionWithered wood of A. sinensis GILG grown in Taiwan was extracted with MeOH, and the MeOH extract was fractionated to hexane-, AcOEt-and BuOH-soluble fractions. The hexane-soluble fraction was separated by silica gel column chromatography to yield a new 2-(2-phenylethyl)-chromone 1, together with five known compounds: flindersiachromone, 9) AH 3 , 10) AH 4 , 10) AH 5 10) and AH 6 . 10) The AcOEtsoluble fraction was separated by silica gel and reversedphase silica gel column chromatography to yield a new 2-(2-phenylethyl)chromone 2, two new 2-(2-phenylethyl)-5,6,7,8-tetrahydrochromones 3 and 4, and two known dimeric chromones AH 10 11) and AH 14 12) (Chart 1). The structures of the known compounds were confirmed by comparison of the physical and spectral data with those reported.Compound 1 10) except for the carbons of the chromone system. From the heteronuclear multiple bond connectivity (HMBC) spectrum (Fig. 1), the hydroxyl group was located at C-5 because the hydroxyl proton (d H 12.77) and the proton at C-3 (d H 6.11) correlated with the same carbon at C-4a (d C 111.31). The methoxyl group was located at C-6, because the aromatic carbon (d C 144.18) which correlated with the methoxyl protons (d H 3.85) also correlated with the hydroxyl proton (d H 12.77) at C-5. Thus, compound 1 was determined to be 5-hydroxy-6-methoxy-2-(2-phenylethyl)chromone.Compound 2 was obtained as a white powder with the molecular formula of C 17 H 14 O 4 . The presence of a chromone ring was suggested from the UV and IR spectra. The 13 C-NMR spectrum of 2 (Table 2) was very similar to that of AH 3 10) except for the methylenes (C-7Ј, C-8Ј): one of the methylenes was replaced by an oxymethine group (d C 71.37). This was confirmed by the presence of ABX-type signals at d H 3.14 (1H, dd, Jϭ14.3, 4.6 Hz), 3.20 (1H, dd, Jϭ14.3, 8.7 Hz) and d H 5.53 (1H, dd, Jϭ8.7, 4.6 Hz) in the 1 H-NMR (Table 1). The oxymethine group was located at C-7Ј, because the oxymethine proton (d H 5.53) correlated with the ...

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Valerena-4,7(11)-diene and beta-maaliene were isolated from spikenard for the first time, and the effects of inhaling these compounds were investigated. Both compounds reduced the locomotor activity of mice dose-dependently, even at a low dose. Valerena-4,7(11)-diene had a particularly profound effect, with the strongest sedative activity observed at a dose of 0.06%. Caffeine-treated mice that showed an area under the curve (AUC) for locomotor activity that was double that of controls were calmed to normal levels by administration of valerena-4,7(11)-diene. The continuous sleep time of pentobarbital-treated mice was prolonged by about 2.7 times with valerena-4,7(11)-diene, an effect similar to that of chlorpromazine administered orally.

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An ethanol extract of Helichrysum maracandicum showed antiproliferative activity against cultured cells of SENCAR mouse in an in vitro assay, and activity-guided fractionation of the extract resulted in the isolation of isosalipurposide as an active substance. Naringenin chalcone, the aglycone of isosalipurposide, also showed strong antiproliferative activity. An in vivo assay of two-stage carcinogenesis on mouse skin revealed that epidermal application of isosalipurposide resulted in delayed formation of papillomas. Western blot analysis showed that the expression of p38 mitogen-activated protein kinase was suppressed by the administration of naringenin chalcone or isosalipurposide, which might be related to the anticarcinogenic activity.

cDNA cloning of a monoterpene synthase from Perilla frutescens whose steam-distilled oil contains 92.9% perillaketone, was performed by the PCR method using primers designed based on limonene synthase. The fulllength nucleotide sequence of this cDNA consisted of 1978 bp including a 1827-bp translational region encoding a deduced protein of 608 amino acids, which was similar to that of limonene synthase from P. frutescens (85% identity). Functional expression of this clone in Escherichia coli yielded an active monoterpene synthase enzyme, which converted geranyl diphosphate into 53.8% myrcene, 20.9% sabinene, 19.8% linalool and 5.5% limonene. As for the extraction of reaction products, we performed SPME (solid phase micro extraction) as well as conventional solvent extraction, and compared these two extraction methods.Key words Perilla frutescens; myrcene synthase; homology-based cDNA cloning; Labiatae; monoterpene synthase; essential oil Bold alphabets indicate the genes which regulating the biosynthetic steps, black arrows indicate promotion, and white arrows indicate inhibition, of the indicated biosynthetic step.