Phenylpropanoids from Brachybotrys paridiformis maxim. Ex oliv. And their anti-HBV activities (II).

Five undescribed phenylpropanoids, one undescribed phenolic glucoside, and sixteen known compounds were isolated from Brachybotrys paridiformis Maxim. Ex Oliv. The undescribed compounds were named brachoside B-C, brach acid A-B, brachnan A, and brachin D, respectively. Additionally, the anti-hepatitis B virus activities of all isolated compounds were studied. Among them, brachnan A, brach acid A, globoidnan A, 3-carboxy-6,7-dihydroxy-1-(3',4'-dihydroxy-phenyl)-naphthalene, and 3,4-dihydroxybenzaldehyde showed significant anti-hepatitis B virus activities.

The evaluation of hepatoprotective effects of flavonoids from Scorzonera austriaca Wild against CCl4-induced acute liver injury in vitro and in vivo.

Scorzonera austriaca Wild is a traditional herbal medicine; however, little is known with regard to the effect of flavonoids from S. austriaca (FSA) on liver injury induced by Carbon tetrachloride (CCl4), especially the mechanism remains unknown. Therefore, our paper was designed to investigate the hepatoprotective effect of FSA against CCl4-induced acute liver injury in vitro and in vivo, with focus on its potential mechanism. The purity of FSA prepared by using polyporous resin column chromatography could reach 94.5%, and seven flavonoid compounds in FSA were identified by using LC-ESI-MS analysis. In vivo results showed that FSA markedly decreased the levels of aspartate aminotransferase (AST), alanine aminotransferase (ALT), lactate dehydrogenase (LDH) and malonaldehyde (MDA) and increased the contents of superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px). Furthermore, in vivo and in vitro results confirmed that FSA could inhibit inflammatory response, as evidenced by decreasing the levels of tumor necrosis factor alpha (TNF-α) and interleukin-6 (IL-6) through inactivating toll-like receptor-4/nuclear factor-κB (TLR4/NF-κB) signaling pathway. FSA activated autophagy by increasing the ratio of LC3B-II/I and decreasing the protein level of p62 so as to exert its hepatoprotective effect. In general, these evidences suggested that FSA is likely to serve as a potential material for the drugs against chemical hepatic injury.

New Triterpenoid Saponins from the Herb Hylomecon japonica.

Background: Hylomecon japonica, a plant of the Papaveraceae family which is well-known for the alkaloids they produce, is a perennial plant widely distributed in the northeast, central and east regions of China. Although a variety of chemical constituents, including alkaloids, flavonoids, and megastigmoids, have been isolated from H. japonica, the investigation of saponins in H. japonica has not been reported until now. Methods: Various separation techniques, including polyporous resin column chromatography, silica gel column chromatography and hemi-preparative HPLC were applied to the isolation of triterpenoid saponins, and chemical methods such as acid hydrolysis and spectroscopic methods including HRESIMS and NMR were applied to their structure elucidation, and the XTT reduction method was used to assay cytotoxicity. Results: Two new triterpenoid saponins, named hylomeconoside A (1) and B (2) which were identified as 3-O-ß-d-galactopyranosyl-(1→2)-ß-d-glucuronopyranosyl-gypsogenin-28-O-ß-d-xylopyranosyl-(1→3)-ß-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-ß-d-quinovopyranoside (1) and 3-O-ß-d-galactopyranosyl-(1→2)-ß-d-glucuronopyranosyl-gypsogenin-28-O-ß-d-xylopyranosyl-(1→3)-ß-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside (2), and two known triterpenoid saponins identified as dubioside C (3) and lucyoside P (4) on the basis of spectroscopic and chemical evidence, were isolated from H. japonica. Compound 1 exhibited moderate cytotoxicity on MGC-803 and HL-60 cells, with IC50 values of 43.8 and 32.4 µg·mL-1, respectively. Conclusions: Compounds 1 and 2 are new saponins, and 1 is considered to be one of the antitumor principles in this plant. This is the first time that triterpenoid saponins have been isolated from plants of the Papaveraceae family.

Preparative Separation and Purification of the Total Flavonoids in Scorzonera austriaca with Macroporous Resins.

The use of macroporous resins for the separation and purification of total flavonoids to obtain high-purity total flavonoids from Scorzonera austriaca was studied. The optimal conditions for separation and purification of total flavonoids in S. austriaca with macroporous resins were as follows: D4020 resin columns were loaded with crude flavonoid extract solution, and after reaching adsorptive saturation, the columns were eluted successively with 5 bed volumes (BV) of water, 5 BV of 5% (v/v) aqueous ethanol and 5 BV of 30% (v/v) aqueous ethanol at an elute flow rate of 2 BV·h(-1). Total flavonoids were obtained from the 30% aqueous ethanol eluate by vacuum distillation recovery. The content of flavonoid compounds in the total flavonoids was 93.5%, which represents an improvement by about 150%. In addition, five flavonoid compounds in the product were identified as 2″-O-ß-d-xylopyranosyl isoorientin, 6-C-α-l-arabipyranosyl orientin, orientin, isoorientin and vitexin by LC-ESI-MS analysis and internal standard methods. The results in this study could represent a method for the large-scale production of total flavonoids from S. austriaca.

A caryophyllane-type sesquiterpene, caryophyllenol A from Valeriana amurensis.

A new caryophyllane derivative, caryophyllenol A, and a new germacrane derivative, isovolvalerenal D, together with 11 known sesquiterpenoids, were isolated from a petroleum ether partition of the roots and rhizomes of Valeriana amurensis. Structure elucidation of caryophyllenol A and isovolvalerenal D was accomplished on the basis of various spectroscopic techniques including HRESIMS and 2D NMR analyses. The structure of caryophyllenol A was further confirmed by X-ray crystallography and using quantum-chemical ECD calculation adopting TDDFT method. Caryophyllenol A and other eight sesquiterpenoids were evaluated for sedative activity with the model of Drosophila melanogaster, and eight of them showed the effect of prolonging the total sleeping time (TST) of D. melanogaster, displaying significant sedative action.

Isolation and identification of the phenolic compounds from the roots of Sanguisorba officinalis L. and their antioxidant activities.

Four phenolic compounds were isolated from the roots of Sanguisorba officinalis L. by silica gel column chromatography and preparative HPLC. On the basis of chemical and spectroscopic methods, their structures were identified as methyl 4-O-ß-D-glucopyranosy-5-hydroxy-3-methoxylbenzoate (1), 3,3',4'-tri-O-methylellagic acid (2), fisetinidol-(4α-8)-catechin (3), and (+)-catechin (4). Compound 1 is a new phenolic glycoside and compounds 2 and 3 were isolated from the Sanguisorba genus for the first time. Compounds 1­4 were also assayed for their antioxidant activities using the DPPH free radical assay.

Terpene glycosides from the roots of Sanguisorba officinalis L. and their hemostatic activities.

Guided by a hemostasis bioassay, seven terpene glycosides were isolated from the roots of Sanguisorba officinalis L. by silica gel column chromatography and preparative HPLC. On the grounds of chemical and spectroscopic methods, their structures were identified as citronellol-1-O-α-L-arabinofuranosyl-(1→6)-ß-D-glucopyranoside (1), geraniol-1-O-α-L-arabinofuranosyl-(1→6)-ß-D-glucopyranoside (2), geraniol-1-O-α-Larabinopyranosyl-(1→6)-ß-D-glucopyranoside (3), 3ß-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-ß-D-glucopyranoside (4), 3ß-[(α-L-arabinopyranosyl)-oxy]-19α-hydroxyurs-12-en-28-oic acid 28-ß-D-glucopyranoside (ziyu-glycoside I, 5), 3ß,19α-hydroxyolean-12-en-28-oic acid 28-ß-D-glucopyranoside (6) and 3ß,19α-dihydroxyurs-12-en-28-oic acid 28-ß-D-glucopyranoside (7). Compound 1 is a new mono-terpene glycoside and compounds 2, 3 and 5 were isolated from the Sanguisorba genus for the first time. Compounds 1­7 were assayed for their hemostatic activities with a Goat Anti-Human α2-plasmin inhibitor ELISA kit, and ziyu-glycoside I (5) showed the strongest hemostatic activity among the seven terpene glycosides. This is the first report that ziyu-glycoside Ι has strong hemostatic activity.

Structures of four new triterpenoid saponins from the leaves of Oplopanax elatus Nakai.

AIM: Isolation and structural elucidation of the triterpenoid saponins of Oplopanax elatus Nakai. METHODS: Solvent extraction and column chromatography were used to isolate the triterpenoid saponins, physico-chemical constants and spectroscopic analysis were employed for structural elucidation. RESULTS: Four newtriterpenoid saponins named cirenshenoside S (1), cirenshenoside T (2), cirenshenoside U (3) and cirenshenoside V (4) were isolated, and their structures were elucidated to be 3-O-beta-D-glucopyranosyl 3beta,23-dihydroxylup-20 (29)-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl (1 --> 4)-beta-D-glucopyranosyl (1 --> 6)-beta-D-glucopyranoside (1), 3-O-beta-D-glucopyranosyl hederagenin 28-O-alpha-L-rhamnopyranosyl (1 --> 4)-beta-D-glucopyranosyl (1 --> 6)-beta-D-glucopyranoside (2), 3-O-beta-D-glucopyranosyl 3beta-hydroxyolean-9(11),12-dien-28-oic acid 28-O-alpha-L-rhamnopyranosyl (1 --> 4)-beta-D-glucopyranosyl (1 --> 6)-beta-D-glucopyranoside (3) and 3alpha-hydroxyolean-12-dien-23,28-dioic acid 28-O-alpha-L-rhamnopyranosyl (1 --> 4 )-beta-D-glucopyranosyl (1 --> 6)-beta-D-glucopyranoside (4), respectively. CONCLUSION: Compounds 1-4 are new triterpenoid saponins and isolated from the leaves of Oplopanax elatus Nakai for the first time.