Three new spirostanol glycosides from Helleborus thibetanus.

An ongoing chemical investigation on n-BuOH extract of roots and rhizomes of Helleborus thibetanus afforded three new spirostanol glycosides (1-3). Their structures were elucidated by extensive analysis of 1 D, 2 D NMR spectra, together with IR and MS methods and acid hydrolysis. This is the first report of the isolation of spirostanol glycoside with xylose at C-24 of the aglycone in Helleborus.

New minor spirostanol glycosides from Helleborus thibetanus.

Phytochemical reinvestigation of the dried roots and rhizomes of Helleborus thibetanus afforded four new minor spirostanol glycosides (1-4) and four known spirostanol glycosides (5-8). Their structures were determined on the basis of spectroscopic analyses, including 1D and 2D NMR experiments, together with HR-ESI-MS and IR measurements and the results of acid hydrolysis.

Two new lignan glycosides from the fruits of Pyrus ussuriensis.

Two new lignan glycosides, ussuriensislignan A (1) and ussuriensislignan B (2), together with seventeen known compounds (3-19), were isolated from the fruits of Pyrus ussuriensis. Their structures were determined by various spectroscopic methods. This is the first report of the isolation of lignans (compounds 1-3) from the genus Pyrus, and compounds 3-6, 12-16 were reported from Pyrus for the first time.

Three new steroidal saponins from Helleborus thibetanus.

Three new steroidal saponins including two spirostanol glycosides (1-2) and one furostanol glycoside 1-sulphate (3) were isolated from the dried roots and rhizomes of Helleborus thibetanus. Structures of the compounds were determined on the basis of extensive use of 1-D and 2-D NMR experiments, together with HR-ESI-MS and IR measurements, as well as the results of acid hydrolysis. Compounds 1-2 represented steroidal saponins with an unusual substitution pattern, which possessed a double bond at C-25 and were glycosylated at 1-OH.

cDNA clone and expression analysis of α-Tropomyosin during Japanese flounder (Paralichthys olivaceus) metamorphosis.

Tropomyosin (TM) plays a critical role in skeletal and cardiac muscle development and function. To assess the functional significance of α-TM in Japanese flounder (Paralichthys olivaceus) development and metamorphosis, cDNA from Japanese flounder was cloned and α-TM mRNA measured during development and metamorphosis. The full-length cDNA is 1 191 bp, including a 5'-untranslated region of 114 bp, a 3'-UTR of 222 bp, and an open reading frame of 855 bp encoding a polypeptide of 284 amino acids. Real-time quantitative PCR revealed that α-TM mRNA is initially expressed in unfertilized ovum, indicating the α-TM gene is maternal. Relatively low mRNA levels were observed in different embryonic stages. A higher level of α-TM mRNA was detected 3 days post hatching (dph), while the highest level was measured at 29 dph (metamorphic climax) after which it declined towards the end of metamorphosis. The expression of α-TM mRNA was up-regulated in thyroid hormone-treated larvae at 36 dph, but there was no marked difference at other stages when compared to control animals. After thiourea treatment, the expression of α-TM mRNA declined slightly. These data provide basic information that can be utilized in further studies into the role of α-TM in P. olivaceus development and metamorphosis.

Polygonumosides A-D, stilbene derivatives from processed roots of Polygonum multiflorum.

Four new stilbene derivatives, polygonumosides A-D (1-4), were isolated from the processed roots of Polygonum multiflorum. Their structures were elucidated by spectroscopic analysis, including 1D and 2D NMR and ECD. Polygonumosides A (1) and B (2), possessing an unprecedented tetracyclic skeleton, were assigned as 2S- and 2R-2-(4-hydroxyphenyl)-9,10,11-trihydroxy-2H-benzo[c]furo[2,3-f]chromen-7(3H)-one-4-O-ß-d-glucopyranosides, respectively, while polygonumosides C (3) and D (4) were assigned as a pair of diastereomeric stilbene glucoside dimers.

Two new phenylpropanoid glycosides from the roots of Aruncus sylvester.

Two new phenylpropanoid glycosides, 1,3,4-tri-O-(E)-caffeoyl-ß-d-glucopyranoside (1) and 1,4-di-O-(E)-caffeoyl-ß-d-glucopyranoside (2), along with four known phenylpropanoid glycosides (3-6), were isolated from the roots of Aruncus sylvester. The structures of 1 and 2 were elucidated using various spectroscopic methods. Compounds 1 and 2 displayed significant scavenging activity of 2,2-diphenyl-1-picrylhydrazyl free radicals with IC50 values of 110 and 258 µM (ascorbic acid: IC50 = 574 µM).

Estrogenic properties of six compounds derived from Eucommia ulmoides Oliv. and their differing biological activity through estrogen receptors α and ß.

Eucommia ulmoides Oliv. (Du-zhong), a well known Chinese herbal medicine, has been increasingly used as a nutraceutical supplement. The aim of this study was to identify and characterise novel estrogenic compounds in E. ulmoides. We report that six compounds, namely pinoresinol 4'-O-ß-d-glucopyranoside, pinoresinol di-O-ß-d-glucopyranoside, aucubin, wogonin, baicalein, and α-O-ß-d-glucopyranosyl-4,2',4'-trihydroxydihydrochalcone, activated estrogen receptor (ER)-dependent transcription of both transfected and endogenous target genes. Strikingly, these compounds exhibited significant difference in ER subtype (α vs. ß) selectivity. Cell proliferation and ER subcellular localisation analyses also demonstrated that they mediated the estrogenic effects by the genomic action of ERα. This study suggests that E. ulmoides is a rich source of new selective estrogen receptor modulators and evaluations of its health benefit and safety as a food additive should take into account the diverse phytoestrogen activities of the individual components.

Rapid characterization of triterpene saponins from Conyza blinii by liquid chromatography coupled with mass spectrometry.

Conyza blinii Le'vl is a medicinal herb used for the treatment of inflammation in Chinese folk medicine. Its major bioactive constituents are triterpene saponins, most of which contain 6-8 sugar residues. In this report, electrospray ionization tandem mass spectrometry fragmentation behaviors of bisdesmosidic triterpene saponins (conyzasaponin A, B, and C) were studied in both positive and negative ion modes with an ion-trap mass spectrometer. In full scan mass spectrometry, these saponins gave predominant [M-H](-) and [M+Na](+) ions, which determined the molecular weights. In tandem mass spectrometry (MS(n), n = 2-4), the [M-H](-) and [M+Na](+) ions yielded fragments [Y(0α)-H](-) and [B(α)+Na](+), which were diagnostic for the structures of the triterpene skeleton and sugar chains. The structural elucidation was approved by accurate mass data using IT-TOF-MS. An interpretation guideline based on MS(n) (n = 2-4) diagnostic ions was proposed in order to elucidate the chemical structures of unknown triterpene saponins in C. blinii extract. The saponins in C. blinii were separated by liquid chromatography with a methanol/acetonitrile/water solvent system, and then analyzed by ion-trap and IT-TOF mass spectrometers. Based on the interpretation guideline, a total of 35 triterpenoid saponins were tentatively identified. Among them, 15 saponins had been previously reported, and the other 20 saponins were reported from Conyza species for the first time. This study indicates that LC/MS is a powerful technology for the rapid characterization of complicated saponins in herbal extracts.

The anti-inflammatory activities of Tanshinone IIA, an active component of TCM, are mediated by estrogen receptor activation and inhibition of iNOS.

Tanshinone IIA (Tan IIA) is a major compound extracted from a traditional herbal medicine Salvia miltiorrhiza BUNGE, which is used to treat cardiovascular diseases, cerebrovascular diseases and postmenopausal syndrome. It has also been shown to possess anti-inflammatory activity. Since Tan IIA has a similar structure to that of 17beta-estradiol (E(2)), the present study was undertaken to characterize the estrogenic activity of Tan IIA and to demonstrate a functional role of this activity in RAW 264.7 cells. In transient transfection assay, Tan IIA (10 microM) increases ERE-luciferase activity in an estrogen receptor (ER) subtype-dependent manner when either ERalpha or ERbeta were co-expressed in Hela cells. In LPS-induced RAW 264.7 cells, Tan IIA exerts anti-inflammatory effects by inhibition of iNOS gene expression and NO production, as well as inhibition of inflammatory cytokine (IL-1beta, IL-6, and TNF-alpha) expression via ER-dependent pathway. Therefore, it could serve as a potential selective estrogen receptor modulator (SERM) to treat inflammation-associated neurodegenerative and cardiovascular diseases without increasing the risk of breast cancer.

New aliphatic nitro-compounds from Indigofera carlesii.

An investigation of aliphatic nitro-compounds in Indigofera carlesii resulted in the identification of two blended novel compounds: 2-O-acryl-3,6-di-O-(3-nitropropanoyl)-alpha-d-glucopyranose and 6-O-acryl-2,3-di-O-(3-nitropropanoyl)-alpha-d-glucopyranose. The structures of the new compounds were elucidated on basis of spectral analysis.

[The quality specification of grape seed extract].

This paper reiviewed the current situation of quality control of grape seed extract in domestic and international market. Considering the fact that there is no national or industrial technical specifications established for the extract product, the authors suggested that two sets of quality specifications should be established for the grape seed extract. The two sets of specifications are: the high purity grape seed extract should contain polyphenol NLT 95%, monomer NLT 10%; and the grape seed extract with ordinary quality should have a procyanidolic value NLT 95, and monomer NLT 6%.

[Phytochemical and pharmacological research progress in Leontopodium medicinal plants].

This paper reviewed the phytochemical and pharmacological research progress in Leontopodium medicinal plants, including the resource distribution, the chemical constitutes, the pharmacological activities and clinical application. The review has provided some information for the study and development of Leontopodium medicinal plants in future.

A nobel cyanogenic glycoside from Semiaquilegia adoxoides.

Phytochemical investigation of Semiaquilegia adoxoides was initiated in view of its common usage in traditional Chinese medicine and the scarcity of previous phytochemical studies. Fractionation of an ethanol extract from the roots of this plant led to the isolation and identification of a novel cyanogenic glycoside, 2-(beta-D-glucopyranosyloxy)-4-hydroxybenzeneacetonitrile (1). The structure of 1 was elucidated on the basis of IR, FAB-MS, 1D and 2D NMR spectral analysis.

Two new quinoline glycoalkaloids from Echinops gmelinii.

Two new glycosidic quinoline alkaloids, 1-methyl-4-methoxy-8-(beta-D-glucopyranosyloxy)-2(1H)-quinolinone (1) and 4-methoxy-8-(beta-D-glucopyranosyloxy)-2(1H)-quinolinone (2), have been isolated from the 1-butanol extract of the aerial parts of Echinops gmelinii (Compositae). Structural elucidation of the two new glycoalkaloids was based on their 1H, 13C, DEPT, HSQC, COSY, HMBC NMR spectra and high-resolution FAB-MS data. These two compounds are rare examples of quinoline alkaloidal glycosides from natural sources.