Glycosides of <i>Atractylodes lancea</i>

Abstract

The rhizomes of Atractylodes plants (Compositae) have been used as an important crude drug since antiquity. They are listed in the Chinese, Korean, and Japanese pharmacopoeias, and are prescribed in traditional medicine as diuretic and stomachic drugs. They are classified into two groups that contain b-eudesmol and hinesol as the main constituents of the essential oil (Atractylodes lancea and Atractylodes chinensis; so-jutsu), and atractylon as the main constituent of the essential oil (Atractylodes japonica and Atractylodes ovata; byaku-jutsu).1) However, the phylogenetic relationship between A. lancea and A. japonica is considered to be closer than that of A. japonica and A. ovata. 2,3)As for the polar constituents of the rhizome of A. lancea, nine sesquiterpenoid glycosides (atractyloside A to I), L-tryptophan, and syringin were reported by Yahara et al. 4) On the other hand, we reported the isolation and the characterization of eight sesquiterpenoid glycosides, including atractyloside A-E, G, and a compound with a secoguaiane skeleton, a monoterpenoid glucoside, seven aromatic compound glycosides, and L-phenylalanine from the water-soluble portion of A. japonica. 5) In the present study, we undertook a reexamination of the water-soluble portion of the rhizome of A. lancea.The dried rhizome of A. lancea, which was cultivated in the Tokyo Metropolitan Medical Plants Garden, was extracted with methanol, and the methanolic extract was suspended in water and successively extracted with ether and ethyl acetate. The aqueous layer was chromatographed on Amberlite XAD-II to give water and methanol eluate fractions. The methanol eluate fraction was chromatographed on Sephadex LH-20, and subjected to a combination of silica gel, Lobar RP-8 column chromatography, and HPLC. Then, 16 sesquiterpenoid glycosides (1-16), four monoterpenoid glucosides (17-20), two hemiterpenoid glycosides (21, 22), an alkyl glycoside (23), five aromatic compound glycosides (24-28), an acetylene derivative compound glucoside (29), two nucleosides (30, 31), and L-tryptophan (32) were isolated. Among them, five sesquiterpenoid glycosides (7-9,

Biosynthesis and function of polyacetylenes and allied natural products

“…Both Atractylodes lancea (so-jutsu) and Atractylodes ovata (byaku-jutsu) are important medicinal plants from Japan, China, and Korea and are often prescribed without distinction. The 1-O-β-D-glucopyranoside of (2E,8E)-2,8-decadiene-4,6-diyne-1,10-diol (24Q) was extracted from rhizomes of A. lancea [288]. In contrast, A. ovata produces an unusual β-D-apiofuranosyl-(1 6)-β-D-glucopyranoside linked at the alternate 8-hydroxyl site 24R, which together with the identified terpene natural products and phylogenic analysis supports the assignment of A. ovata as a unique species.…”

Socioeconomic impact of traditional Korean medicine, Pyeongwee-San (KMP6) as an anti-allergic inflammatory drug

“…Atractylodes rhizoma has been used for eliminating dampness, strengthening the spleen, expelling wind, and clearing away cold in traditional Korean medicine for centuries (Kimura et al, 2006). As for the chemical constituents of the Atractylodes rhizoma, many sesquiterpenoid glycosides and essential oils were reported (Kitajima et al, 2003). It contains sesquiterpenoids (1.5-3.0% by weight), such as atractylenolide -I, -II, and -III, atractylon, and 3â-acetoxyatractylon, as well as polyacetylene compounds, such as (6E,12E)-tetradecadiene-8,-10-diyne-1,3-diol mono acetate, (6E,12E)-tetradecadiene-8,10-diyne-1,3-diol, and 6-methyl-2-geranyl-p-benzoquinone (Sakurai et al, 1993).…”

Astonishing diversity of natural surfactants: 7. Biologically active hemi‐ and monoterpenoid glycosides

“…Two rare hemiterpene cyclohexyl glucosides, 57 and 58, were isolated from the water-soluble portion of rhizome methanolic extracts of Atractylodes lancea and A. japonica (49). Simmondsin 59 is an unusual 2(cyanomethylene)cyclohexyl glucoside from Simmondsia californica (50).…”