One new and seven known triterpene glycosides from the aerial parts of Cimicifuga dahurica.

One new triterpene glycoside, asiaticoside I (1), along with seven known ones (2-8), were isolated from the aerial parts of Cimicifuga dahurica (Turcz.) Maxim. The structure of 1 was elucidated on the basis of extensive spectroscopic methods including 1D-NMR, 2D-NMR and MS data. The structures of known compounds were determined by comparison with the literature data. Compound 1 exhibited moderate cell growth inhibitory activities in vitro against HELF, non-small cell lung cancer A549, and pancreatic cancer PANC-1 cell lines, with IC50 values of 62.97, 43.19, and 60.40 µM, respectively.

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.

Two new phenolic acids from the fruits of Forsythia suspense.

Two new phenolic acids forsythiayanoside C (1) and forsythiayanoside D (2), were isolated from the fruits of Forsythia suspense (Thunb.) Vahl. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses, HRESIMS and CD spectrometry. The cytotoxic and antioxidant activities testing showed that compound 2 exhibited free radical scavenging activity.

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.

Three new phenols and one new lignan from Clematis terniflora var. manshurica (Rupr.) Ohwi with their anti-inflammatory activity.

Three undescribed phenols, mandshusica C-E (1-3) and a new lignan, mandshusica F (5), along with six known compounds (4, 6-10) were isolated from the roots and rhizomes of Clematis terniflora var. manshurica (Rupr.) Ohwi. Their structures were elucidated by extensive spectroscopic analysis as well as NMR and ECD calculations. Moreover, the possible biosynthetic pathways of compounds 1-3 were also discussed. All compounds were evaluated for their anti-inflammatory activities in LPS-induced RAW 264.7 cells. Compounds 1, 3, 4 significantly reduced the levels of NO and TNF-α, while compounds 2 and 8 significantly inhibited NO production in LPS-induced RAW264.7 cells.

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.

Two new anti-inflammatory compounds from the roots and rhizomes of Clematis terniflora var. manshurica (Rupr.) Ohwi.

Two new compounds named mandshurica A (1) and mandshurica B (2), together with four known lignans (3-6) were isolated from the roots and rhizomes of Clematis terniflora var. manshurica (Rupr.) Ohwi. The structures of the new compounds were elucidated by HR-ESI-MS, 1D and 2D NMR spectroscopy. Moreover, the anti-inflammatory activity of compounds 1 and 2 were evaluated against lipopolysaccharide-induced mouse macrophage RAW264.7 cells. Compounds 1 and 2 displayed significant inhibitory effect on NO production, and compound 2 exhibited obvious inhibition on the pro-inflammatory cytokines TNF-α. Both new compounds showed potential anti-inflammatory activity.

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→.

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.

A new triterpenoid saponin with nine sugar units from Anemone amurensis (Korsh.) Kom.

A new triterpenoid saponin named Anemonside A (1) was isolated from the rhizome of Anemone amurensis (Korsh.) Kom. Its structure was determined by chemical and spectral analysis, including 1D, 2D NMR data, HRESIMS and hydrolysis reaction. The new saponin contains nine sugar units with two O-linked sugar chains, which is relatively rare in natural products. In addition, the cytotoxic activity of Anemonside A was evaluated by against A549 and HepG2 cell lines with the MTT method and showed no cytotoxic activity with IC50 over 100 µM.

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.