Two Novel Sesquiterpenoid Glycosides from the Rhizomes of Atractylodes lancea

Secoatractylohexone A (1), an unprecedented secoguaiane lactone glycoside featuring 6/7 cores and dihydroxy-9-guaine-3-one 11-O-β-d-glucopyranoside (2), a 9,10-unsaturated guaiene-type glycoside possessing an uncommon scaffold, were isolated from the water-soluble portion of the ethanolic extract of Atractylodes lancea rhizomes together with five known compounds (3–7). The structures of 1 and 2 were elucidated on the basis of extensive spectroscopic data and application of the CD technique. The potential biological activities of secoatractylohexone A were predicted by network pharmacology in silico, the result of which indicated that secoatractylohexone A may be used to treat type II diabetes.     

Glycosides of Atractylodes japonica

From the water-soluble portion of the methanol extract of the fresh rhizome of Atractylodes japonica, five new sesquiterpenoid glycosides, including a compound having a secoguaiane skeleton, and a new aromatic compound glycoside were isolated together with ten known compounds. Their structures were clarified by spectral investigation.     

Glycosides of Atractylodes ovata

A new coumarin glycoside and a new glycoside of an acetylene derivative were isolated from the water-soluble portion of the methanolic extract of Atractylodes ovata rhizome together with eight known compounds. Their structures were characterized as scopoletin beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside and (2E)-2-decene-4,6-diyne-1,8-diol 8-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside, respectively, based on chemical and spectroscopic investigations. A comparison of the polar constituents among Atractylodes japonica, Atractylodes lancea, and A. ovata is led to the conclusion that A. ovata is distinguishable from A. lancea and A. japonica, as also shown by phylogenetic analysis.     

New sesquiterpenoid glycoside from the rhizomes of Atractylodes lancea

Abstract

Six sesquiterpenoids and four lignans (1–10) were isolated from the n-BuOH extract of the rhizomes of Atractylodes lancea. Among them, the new sesquiterpenoid glycoside named (4?R, 5S, 7R)-hinesolone-11-O-β-?-glucopyranoside (1), along with three known compounds (2–4) were first obtained from this genus. All the isolates were elucidated by spectroscopic analyses and chemical methods, and the absolute configurations were assigned by electronic circular dichroism spectroscopy technique. In addition, the cytotoxic bioassay of compound 1 was evaluated and results showed it had no significant antitumor activity against human cancer cell lines MCF-7, HepG-2 and Hela.     

A new polyacetylene glycoside from the rhizomes of Atractylodes lancea

<正>A new polyacetylene glycoside,(1,3Z,11E)-tridecatriene-7,9-diyne-5-hydroxyl-6-O-β-D-glucopyranoside,was isolated from the rhizomes of Atractylodes lancea(Thunb.) DC.Its structure was elucidated on the basis of spectral analysis.     

Differentiation of essential oils in Atractylodes lancea and Atractylodes koreana by gas chromatography with mass spectrometry

Atractylodes rhizome is a valuable traditional Chinese medicinal herb that comprises complex several species whose essential oils are the primary pharmacologically active component. Essential oils of Atractylodes lancea and Atractylodes koreana were extracted by hydrodistillation, and the yield was determined. The average yield of essential oil obtained from A. lancea (2.91%) was higher than that from A. koreana (2.42%). The volatile components of the essential oils were then identified by a gas chromatography with mass spectrometry method that demonstrated good precision. The method showed clear differences in the numbers and contents of volatile components between the two species. 41 and 45 volatile components were identified in A. lancea and A. koreana, respectively. Atractylon (48.68%) was the primary volatile component in A. lancea, while eudesma‐4(14)‐en‐11‐ol (11.81%) was major in A. koreana. However, the most significant difference between A. lancea and A. koreana was the major component of atractylon and atractydin. Principal component analysis was utilized to reveal the correlation between volatile components and species, and the analysis was used to successfully discriminate between A. lancea and A. koreana samples. These results suggest that different species of Atractylodes rhizome may yield essential oils that differ significantly in content and composition.     

Sesquiterpenoid and C_(14)-polyacetylene glycosides from the rhizomes of Atractylodes lancea

Four new glycosides including a eudesmane-type sesquiterpenoid(1), a guaiane-type sesquiterpenoid(2), and two C_(14)-polyacetylenes(3, 4) were isolated from the rhizomes of Atractylodes lancea. Their structures were elucidated by means of spectroscopic and spectrometric analyses(UV, IR, 1D and 2D NMR, and HR-ESIMS). The absolute configurations of their aglycones were established based on the experimental and calculated electronic circular dichroism(ECD), whereas those of monosaccharide moieties were determined by the GC method after chiral derivatization. Compound 4 showed weak anti-inflammatory effects on the LPS-induced NO production in microglia BV2 cells at a concentration of10μmmolL~(-1).     

北苍术和茅苍术挥发油成分的比较

采用气相色谱-质谱联用技术分析了北苍术和茅苍术的挥发油成分,分别鉴定出47和50种化学成分,并测定了其相对含量。 采用色谱指纹图谱八强峰法和分区法,根据色谱峰的保留时间把总离子流色谱图分为5个区,比较了北苍术和茅苍术的挥发油成分。 结果表明,在总离子流色谱图Ⅳ和Ⅴ区中,从北苍术和茅苍术中均检出苍术的主要药效成分β-桉叶油醇、苍术酮和苍术素,且相对含量较高。 这表明《中国药典》将北苍术、茅苍术统称为苍术具有一定的科学性。     

Biotransformation of hinesol isolated from the crude drug Atractylodes lancea by Aspergillus niger and Aspergillus cellulosae.

Biotransformation of the sesquiterpene alcohol hinesol (1) with spasmolytic activity, which was prepared from the rhizome of Atractylodes lancea, was carried out by Aspergillus niger and Aspergillus cellulosae IFO 4040. Compound 1 was easily converted to compounds 2-9 by A. niger, and compounds 10 and 11 by A. cellulosae, respectively. Their stereostructures were established by a combination of high-resolution NMR spectral analysis, X-ray crystallographic analysis, and chemical reactions such as epoxydation.     

Glycosides of Erysimum

Summary The cardenolides of six species ofErysimum and ofSyrenia siliculosa have been studied. The cardiac glycosides erysimin and erysimoside have been found inE. altaicum, E. marschallianum, E. nuratensae, andS. siliculosa. In addition to these glycosides,E. diffusum has yielded desglucocheirotoxin, canescein, and a new cardenolide, erydiffuside,E. violascens has yielded gypsobioside, andE. cuspidatum has yielded a new glycoside cuspidoside.Khimiya Prirodnykh Soedinenii, Vol. 3, No. 2, pp. 173–178, 1967