New anti-pulmonary fibrosis prenylflavonoid glycosides from Epimedium koreanum.

Four new prenylflavonoid glycosides, namely koreanoside H-K (1-4), together with eleven known ones (5-15) were isolated from the leaves of Epimedium koreanum Nakai. Their structures were elucidated by 1D NMR, 2D NMR, HR-ESI-MS, IR and UV. The identification of the sugar moieties was carried out by means of acid hydrolysis and HPLC analysis of their derivatives. It is worth noting that compound 3 and compound 4 were elucidated to contain fucose and quinovose moieties, which were two extremely rare sugar units from the genus Epimedium. The anti-pulmonary fibrosis activity of the new compounds was evaluated using A549 cell line. Compounds 1, 2 and 4 showed significant anti-pulmonary fibrosis activities.

Isolation and structural elucidation of a low-molecular-weight polysaccharide from the roots of Panax ginseng C. A. Meyer.

A low-molecular-weight polysaccharide named MCGP-L was extracted and purified from the roots of Mountain cultivated ginseng (Panax ginseng C. A. Meyer). The polysaccharide MCGP-L was purified by molecular exclusion chromatography using the Sephadex G-25 column. The average molecular weight of MCGP-L was estimated to be 3 × 103 kDa. Monosaccharide composition analysis showed MCGP-L was composed of three kinds of monosaccharide: D-glucose, D-galactose and D-mannose. The physicochemical properties and structural characteristics of MCGP-L were investigated by the combination of chemical and instrumental analysis such as methylation analysis, High Performance Gel-Permeation Chromatography (HPGPC), High Performance Liquid Chromatography (HPLC) and Nuclear Magnetic Resonance (NMR). The backbone of MCGP-L was composed of (1→4)-linked-α-D-Glcp residues and with branch chain substituted at O-6 position of (1→4,6)-linked-α-D-Glcp. The branch chain consists of →6)-α-D-Galp-(1→, →2)-α-D-Manp-(1→ and ß-D-Glcp-(1→.

Research progress on naturally-occurring and semi-synthetic ocotillol-type ginsenosides in the genus Panax L. (Araliaceae).

Ocotillol (OT)-type ginsenosides, one subtype of ginsenosides, consist of a dammarane skeleton and a tetrahydrofuran ring. Most naturally-occurring OT-type ginsenosides exist in Panax species, particularly in Panax quinquefolius, which may be attributed to the warm and humid climate of its native areas. Till now, merely 28 types of naturally-occurring OT-type ginsenosides have been isolated. In contrast, semi-synthesized OT-type ginsenosides are attracted considerable attentions. These ginsenosides can be obtained through oxidation and cyclization of side chains of dammarane-type ginsenosides, and other methods, which may change their physical and chemical properties and further improve their bioavailabilities. It is also notable that the pharmacological activities of ginsenosides are closely related to the stereoisomers caused by the configuration at C-20. Semi-synthesis of OT-type ginsenosides can facilitate our understanding of the biosynthesis, transformation and metabolism of OT-type ginsenosides in the body. This review will systematically summarize the research progress on naturally-occurring and semi-synthetic OT-type ginsenosides, which provides a theoretical basis for their bioactivity-guided research.

Unique phenolic constituent in Cimicifuga dahurica (Turcz.) Maxim. through Box-Behnken design and response surface methodology.

Cimicifuga dahurica (Turcz.) Maxim. exerts significant antioxidative due to its high phenolic constituent content. In this study, the extraction condition of the phenolic constituents and antioxidant effect was optimized by the Box-Behnken design and response surface methodology. Eleven main bioactive analytes of Cimicifuga dahurica (Turcz.) Maxim. were simultaneously quantified by high-performance capillary electrophoresis with diode-array detector to assess the effect of extraction technology. The optimal extraction parameters were determined as: the concentration of ethanol 56.21%, liquid/solid ratio 14.65:1, and extraction time 1.64 h for 2.67 times. According to the results, a maximal value of total phenolic acids (3.67 mg/g) was obtained. Meanwhile, the influence of different extraction technology on antioxidant activities were evaluated by 1,1-diphenyl-2-picrylhydrazyl, 2,2'-azino-bis-(3-ethylbenzthiazoline-6-sulfonate), ferric reducing antioxidant power and hydroxyl radical scavenging method. The results presented here showed that the content of phenolic acid and antioxidant effect was much higher than the European Pharmacopoeia. Altogether, this method successfully applied response surface methodology to optimize the Cimicifuga dahurica (Turcz.) Maxim. extract with high antioxidant activities.

Antiproliferative Dimeric Aporphinoid Alkaloids from the Roots of Thalictrum cultratum.

Inspired by the intriguing structures and bioactivities of dimeric alkaloids, 11 new thalifaberine-type aporphine-benzylisoquinoline alkaloids, thalicultratines A-K, a tetrahydroprotoberberine-aporphine alkaloid, thalicultratine L, and five known ones were isolated from the roots of Thalictrum cultratum. Their structures were defined on the basis of NMR and HRESIMS data. The antiproliferative activities of compounds 1-17 were evaluated against human leukemia HL-60 and prostate cancer PC-3 cells. Most alkaloids showed potent cytotoxicity against selected cancer cells. Preliminary SARs are discussed. The most active new compound (3), with an IC50 value of 1.06 µM against HL-60 cells, was selected for mechanism of action studies. The results revealed that compound 3 induced apoptosis and arrested the HL-60 cell cycle at the S phase with the loss of mitochondria membrane potential. The nuclear morphological Hoechst 33258 staining assay was also carried out, and the results confirmed apoptosis.

Chemical constituents from rhizome of Anemone amurensis.

Phytochemical investigation of the 70% EtOH extract of the rhizome of Anemone amurensis led to the isolation of two new oleanane-type triterpenoid saponins 1 and 2. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR data, and HR-ESI-MS. Compounds 1 and 2 were tested for cytotoxicities against two human cancer cell lines (A549 and Hep-G2). Compound 2 showed potent cytotoxicity with IC50 values of 38.53 and 66.17 µM, respectively, while compound 1 with IC50 > 100 µM.

Two new triterpenoid saponins from rhizome of Anemone amurensis.

Two new triterpenoid saponins were isolated from the 70% ethanol extract of the rhizome of Anemone amurensis, they are oleanolic acid 28-O-ß-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 4)-ß-d-glucopyranosyl-(1 → 6)-ß-d-glucopyranosyl ester (1) and 23,27-dihydroxy oleanolic acid 3-O-α-l-arabinopyranoside (2). The structures of 1 and 2 were elucidated on the basis of chemical and spectral analysis, including 1D and 2D NMR data and HR-ESI-MS. Compounds 1 and 2 were tested for cytotoxicities against three human cancer cell lines (A549, Hep-G2, and MCF-7). Compound 1 showed potent cytotoxicity with IC50 values of 34.76, 41.17, and 28.92 µM, respectively, while compound 2 with IC50>100 µM.

A new cycloartane nortriterpenoid from stem and leaf of Quercus variabilis.

A new compound 3-acetyloxy-epicycloeucalenol-24-one (1), with 11 known compounds 3α-acetyloxy-4α,14α-dimethyl-9ß,19-cycloergost-24-oic acid (2), 3-epicycloeucalenol (3), 3-epicycloeucalenyl-24-one (4), 3-epicycloeucalenyl acetate (5), 4ß,14α-dimethyl-5α-ergosta-9ß,19-cyclo-24(31)-en-3ß-hydroxy-4α-carboxylic acid (6), cycloeucalenone (7), friedelin (8), epifriedelanol (9), lup-20 (29)-en-3ß,30-diol (10), betulin (11), lupeol (12), was isolated from the stems and leaves of Quercus variabilis Blume. Seven compounds (1-7) showed anti-inflammatory activity.

Reversible inhibition of three important human liver cytochrome p450 enzymes by tiliroside.

Tiliroside, an active flavonoid extensively found in many medicinal plants including Helichrysum italicum, Geranium mexicanum and Helianthemum glomeratum, has been demonstrated to exert multiple biological effects including antiinflammatory, antimicrobial, antioxidant and antitumor activities. Cytochrome P450 (CYP) enzymes play an important role in the Phase I oxidation metabolism of a wide range of xenobiotics and inhibition of CYP isoforms might influence the elimination of drugs and induce serious adverse drug response. The inhibition of seven CYP isoforms (CYP3A4, CYP1A2, CYP2A6, CYP2D6, CYP2C9, CYP2C8 and CYP2E1) by tiliroside was investigated using in vitro human liver microsomal incubation assays. The results showed that tiliroside strongly inhibited the activity of CYP3A4 (IC(50) = 9.0 ± 1.7 µm), CYP2C8 (IC(50) = 12.1 ± 0.9 µm) and CYP2C9 (IC(50) = 10.2 ± 0.9 µm) with other CYP isoforms negligibly influenced. Further kinetic analysis showed that inhibition of these three CYP isoforms by tiliroside is best fit to a competitive way. The K(i) value was calculated to be 5.5 µm, 3.3 µm, 9.4 µm for CYP3A4, CYP2C9 and CYP2C8, respectively. The relatively low K(i) values suggested that tiliroside might induce drug-drug interactions with many clinically used drugs which are mainly metabolized by these three CYP isoforms. Therefore, attention should be given to the probable drug-drug interaction between tiliroside-containing herbs and substrates of CYP3A4, CYP2C9 and CYP2C8.

27-Hydroxyoleanolic acid type triterpenoid saponins from Anemone raddeana rhizome.

Two new 27-hydroxyoleanolic acid type triterpenoid saponins were isolated from the rhizomes of Anemone raddeana Regel. The structures of the two compounds were elucidated as 27-hydroxyoleanolic acid 3-O-beta-D-glucopyranosyl (1 --> 2)-alpha-L-arabinopyranoside (1) and 3-O-alpha-L-rhamnopyranosyl (1 --> 2)[beta-D-glucopyranosyl (1 --> 4)]-alpha-L-arabinopyranosyl-27-hydroxyoleanolic acid 28-O-alpha-L-rhamnopyranosyl (1 --> 4)-beta-D-glucopyranosyl (1 --> 6)-beta-D-glucopyranoside (2) on the basis of chemical and spectral evidence.

[Alpha-linolenic acid and linoleic acid in extract of Portulaca oleracea L. determined by high-performance liquid chromatography].

OBJECTIVE: To determine alpha-linolenic acid and linoleic acid in extract of Portulaca oleracea L. by high performance liquid chromatography (HPLC). METHODS: The determination was done with a Shim-pack CLC-ODS (250 mm x 4.6 mm, 5 microm) and a DIKMA Easyguard C18 (10 mm x 4.6 mm). Elution was employed with the mobile phase of methanol-acetonitrile-0.5% phosphonic acid (60:22:18) at flow rate of 1.1 ml/min. Column temperature was 26 degrees centigrade. Detection wavelength was 210 nm. Injection volume was 25 microl. RESULTS: The standard curves of alpha-linolenic acid and linoleic acid were linear in the range 0.016 2 to 0.194 4 mg/ml and 0.016 9 to 0.203 0 mg/ml, respectively. The regression equations were A=2.915 8 x 10(7) C+12,250.9, r=0.999 9 and A=1.366 4 x 10(7) C-9,759.39, r=0.999 9, respectively. The average recovery rates were 100.5% and 100.8%, respectively. CONCLUSION: The present method (HPLC) may be considered to be reliable and simple for the determination of alpha-linolenic acid and linoleic acid in extract of Portulaca oleracea L.

[Studies on chemical constituents of leaves of Cassia angustifolia].

OBJECTIVE: To study the chemical constituents of the leaves of Cassia angustifolia Vahl. METHODS: Solvents extraction and various chromatographic methods were applied to separate and purify its constituents. The structures were elucidated on the basis of chemical evidence and spectral analysis. RESULTS: Six compounds were obtained and identified as cholesterol (I), kampferol-3-rutinoside (II), calyxanthone (III), 3-methoxy-4-hydroxy-benzoic acid (IV), p-dimethylaminobenzaldehyde (V), 3,4-dihydroxybenzoic acid (VI). CONCLUSION: Six compounds ( I -VI) are obtained from this plant for the first time.

[Study on chemical constituents of rhizome of Anemone raddeana].

AIM: To investigate the chemical constituents of the rhizome of Anemone raddeana Regel, so as to find new active compounds. METHODS: The ethanol extracts of the rhizome of Anemone raddeana were obtained by silica column, HPLC. The structures of the compounds were elucidated by means of physico-chemical method and spectral analysis (IR, FAB-MS, 1HNMR, 13CNMR, DEPT, 1H-1H COSY, HMQC, HMBC). RESULTS: Nine compounds were isolated and identified as 27-hydroxyolean-12(13)-en-28-oic acid-3-0-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside (1), eleutheroside K (2), Oleanolic acid-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D- glucopyranosyl-(1-->4)]-alpha-L-arabinopyranoside (3), betulin (4), betulic acid (5), acetyloleamolic acid (6), evonymitol (7), oleamolic acid (8) and diosgenin (9). CONCLUSION: Compound 1 is a new compound, named raddeanoside 12. Compounds 3-7 were isolated from this plant for the first time.