Quantification and purification of procyanidin B1 from food byproducts.

The flavan-3-ols of 10 primarily plant food byproducts, including Muscat Hamburg grape seed, hawthorn sarcocarp, litchi pericarp, cocoa bean, peanut skin, lotus seedpod, Xinyang Maojian green tea, Cinnamomi cortex, Sargentodoxa cuneata stem, and Cyperus esculentus, leaves were analyzed. Ultrahigh-performance liquid chromatography-triple quadrupole mass spectrometry was used for the analysis. Cyperus esculentus leaves contained a high amount of procyanidin B1 (198.9 mg/100 g), second only to Muscat Hamburg grape seed (292.9 mg/100 g). Unlike grape seed that contained several procyanidin B isomers with very similar retention times, C. esculentus leaves contained primarily procyanidin B1 with few isomers. Procyanidin B1 was enriched in the ethyl acetate fraction of a 70% methanol extract of C. esculentus leaves and purified at 95% purity by two runs of open column chromatography. Direct chromatography of the plant extract on octadecylsilane and Sephadex LH20 open columns improved the yield of the resultant leaf procyanidin B1 (95% purity) to 0.21‰. The present research demonstrated that the leaves of C. esculentus, byproducts of tigernut, are ideal plant sources for isolating and providing high-purity procyanidin B1. PRACTICAL APPLICATION: Procyanidin B1 has a broad range of health benefits. Cyperus esculentus is cultivated in many countries with nearly 6190 square hectares (hm2 ) in the Spanish Mediterranean region in 2020-2021 and over 16,700 hm2 in China in recent years, primarily for its tubers. The byproducts, the leaves of C. esculentus, contain high levels of procyanidin B1, with few isomers that interfere with its isolation and purification. Thus, the leaves of this plant provide a viable source for preparing high-purity procyanidin B1.

Effects and mechanisms of 6-hydroxykaempferol 3,6-di-O-glucoside-7-O-glucuronide from Safflower on endothelial injury in vitro and on thrombosis in vivo.

Background: The florets of Carthamus tinctorius L. (Safflower) is an important traditional medicine for promoting blood circulation and removing blood stasis. However, its bioactive compounds and mechanism of action need further clarification. Objective: This study aims to investigate the effect and possible mechanism of 6-hydroxykaempferol 3,6-di-O-glucoside-7-O-glucuronide (HGG) from Safflower on endothelial injury in vitro, and to verify its anti-thrombotic activity in vivo. Methods: The endothelial injury on human umbilical vein endothelial cells (HUVECs) was induced by oxygen-glucose deprivation followed by reoxygenation (OGD/R). The effect of HGG on the proliferation of HUVECs under OGD/R was evaluated by MTT, LDH release, Hoechst-33342 staining, and Annexin V-FITC apoptosis assay. RNA-seq, RT-qPCR, Enzyme-linked immunosorbent assay and Western blot experiments were performed to uncover the molecular mechanism. The anti-thrombotic effect of HGG in vivo was evaluated using phenylhydrazine (PHZ)-induced zebrafish thrombosis model. Results: HGG significantly protected OGD/R induced endothelial injury, and decreased HUVECs apoptosis by regulating expressions of hypoxia inducible factor-1 alpha (HIF-1α) and nuclear factor kappa B (NF-κB) at both transcriptome and protein levels. Moreover, HGG reversed the mRNA expression of pro-inflammatory cytokines including IL-1ß, IL-6, and TNF-α, and reduced the release of IL-6 after OGD/R. In addition, HGG exhibited protective effects against PHZ-induced zebrafish thrombosis and improved blood circulation. Conclusion: HGG regulates the expression of HIF-1α and NF-κB, protects OGD/R induced endothelial dysfunction in vitro and has anti-thrombotic activity in PHZ-induced thrombosis in vivo.

Chemical Constituents of Cyperus esculentus Leaves and the Protective Effect against Agricultural Fungicide-Induced Hepatotoxicity.

Cyperus esculentus is cultivated as a crop plant due to its edible and oily tubers (tiger nut). However, little is known about the phytochemicals and bioeffects of the leaves. This study was conducted to identify and quantify the chemical constituents of C. esculentus leaves and evaluate their bioactivities. By liquid chromatography-mass spectrometry, 30 compounds including flavan-3-ols, caffeic acid derivatives, and flavones, were identified from the leaves. The quantitative analysis revealed that gallocatechin (8), procyanidin B1 (15), catechin (16), chlorogenic acid (19), orientin (30), and luteolin 7-O-glucuronide (31) are the major chemical constituents of C. esculentus leaves. The contents of these six chemical constituents in the leaves collected in September in Hohhot, China, reached to 1460.85±7.66, 10178.77±302.65, 1048.35±17.37, 1722.15±26.13, 5318.62±277.16, and 1526.54±11.95 µg, respectively, in one gram of the dried leaves. The leaf extract (CELE) showed strong antioxidant activity in vitro, with compounds 8, 15, and 19 contributing the most. CELE showed significant protection against the agricultural fungicide tebuconazole-induced developmental toxicity and hepatotoxicity in zebrafish.

Identification and bioactivity evaluation of flavan-3-ols in the milk of dairy sheep fed Cynomorium songaricum.

Cynomorium songaricum is a traditional medicine and also a food material that is eaten raw or processed as tea or beverages. As a featured plant in semi-desert grasslands, C. songaricum is also eaten by the cattle and sheep in the area. This research study fed dairy sheep C. songaricum to determine the flavan-3-ols in sheep milk. Catechin (Cat), epicatechin (Epi), procyanidin A1 (A1), procyanidin A2 (A2), and procyanidin B1 (B1) were detected in sheep milk with the concentration being Epi > A2 > Cat > B1 > A1 at 24 h after the administration of C. songaricum. Neither A1 nor A2 were detected in the methanol extract of C. songaricum. Cysteine degradation of the plant revealed that in addition to Epi, A2 was the extending unit of the polymeric flavan-3-ols in C. songaricum, indicating that A2 is released digestively from the polymers and enters the milk. Procyanidin B-1 was converted to A1 on incubation in raw but not heated milk, indicating that the A1 in milk is the enzymatically transformed product of B1. Accelerated oxidation showed that the flavan-3-ols, B1, Cat, and Epi significantly protects the unsaturated triacyglycerols in the milk from oxidation. The flavan-3-ol could slow down the oxidation of glutathione and the latter may play an important role in preventing the milk triglycerides from oxidation. Flavan-3-ols are polyphenols with many health benefits. The present research revealed the antioxidant activities of flavan-3-ols that could be absorbed to sheep milk, adding new evidences for the values of these flavan-3-ols and for the milk.

Combination of Ephedra sinica stems and Terminalia chebula fruits produces new ephedrine derivatives in vivo that diminish the permeability to BBB while retaining airway dilation and hepatoprotective effects.

ETHNOPHARMACOLOGICAL RELEVANCE: The stems of Ephedra sinica and the fruits of Terminalia chebula are combined using in traditional Mongolian medicine formula "Gurigumu-7" for liver diseases. E. sinica stems contains ephedrine with broncho-dilatory activity. However, ephedrine can pass through the blood-brain barrier (BBB) and excite the central nervous system (CNS) to cause insomnia and restlessness. AIM OF THE STUDY: The present study was to investigate the structures and bioactivities of new compounds formed in vivo after co-administration of E. sinica stems and T. chebula fruits. MATERIALS AND METHODS: Pharmacokinetic investigation was carried out in rats. A parallel artificial membrane permeability measurement system was used to determine BBB permeability. Ex vivo experiments using tracheal rings of guinea pig was performed to examine the tracheal relaxation effect. In vivo hepatoprotective tests were carried out in Tg (fabp10a: dsRed) liver transgenic zebrafish. The fluorescent probe, 2,7-dichlorodihydrofluorescein diacetate, was used to measure reactive oxygen species, and UHPLC-MS was used to determine glutathione concentrations after derivatization with N-ethylmaleimide. RESULTS: New ephedrine derivatives (1 and 2) formed in vivo and reached their maximum serum concentrations at 0.5 h after administration of the two herbal drugs. Compounds 1 and 2 showed lower BBB permeability than ephedrine, suggesting that they have less adverse effects on the CNS. Compounds 1 and 2 relaxed the tracheal rings and had strong hepatoprotective effect on transgenic zebrafish with liver specific expression of RFP. Compounds 1 and 2 significantly reduced the level of reactive oxygen species while increasing that of glutathione in thioacetamide-treated zebrafish, which might be the hepatoprotective mechanism. CONCLUSION: These results provided evidences that the chemical constituents in various herbal drugs in a medicinal formula can interact to generate new compounds with fewer side effects and increased or additive bioactivity.

Hydroxysafflor yellows alleviate thrombosis and acetaminophen-induced toxicity in vivo by enhancing blood circulation and poison excretion.

BACKGROUND: Hydroxysafflor yellow A (HSYA) from the flower of Carthamus tinctorius (Safflower) has been reported to have various pharmacological effects. However, little is known about the bioactivities of other chemical constituents in Safflower and the relationship between enhancement of blood circulation and hepatoprotection by HSYA. PURPOSE: The present research was to evaluate the antithrombotic and hepatoprotective activities of HSYA and C, examine their mechanisms of actions, including influence on the excretion velocity of acetaminophen, and the relationship between the antithrombotic, hepatoprotective, and other bioactivities. METHODS: The hepatoprotective activities were examined by acetaminophen (APAP)-induced zebrafish toxicity and carbon tetrachloride (CCl4)-induced mouse liver injury. The concentrations of APAP in zebrafish and APAP that was excreted to the culture media were quantified by UHPLC-MS. The anti-thrombosis effect of HSYA and C were examined by the phenylhydrazine (PHZ)-induced zebrafish thrombosis. RESULTS: HSYA and HSYC showed robust protection on APAP-induced toxicity and PHZ-induced thrombosis. The hepatoprotective effects of HSYA and C were more potent than that of the positive control, acetylcysteine (61.7% and 58.0%, respectively, vs. 56.9% at 100 µM) and their antithrombosis effects were more robust than aspirin (95.1% and 86.2% vs. 52.7% at 100 µM). HSYA and C enhanced blood circulation, rescued APAP-treated zebrafish from morphological abnormalities, and mitigated APAP-induced toxicity in liver development in liver-specific RFP-expressing transgenic zebrafish. HSYC attenuated CCl4-induced mouse liver injury and regulated the levels of HIF-1α, iNOS, TNF-α, α-SMA, and NFκB in liver tissues. HSYA was also protective in a dual thrombotic and liver toxicity zebrafish model. By UHPLC-MS, HSYA accelerated the excretion of APAP. CONCLUSION: HSYA and C are the bioactive constituents of Safflower that are responsible for the herbal drug's traditional use in promoting blood circulation to remove blood stasis. Safflower and its chalcone constituents may protect from damage due to exogenous or disease-induced endogenous toxins by enhancing the excretion velocity of toxins.

In vivo hepatoprotective activity and the underlying mechanism of chebulinic acid from Terminalia chebula fruit.

BACKGROUND: The fruit of Terminalia chebula Retz. is one of the most widely used herbal drug in Traditional medicine prescriptions including those for liver diseases. In the screening of bioactive constituents that have potential hepatoprotective activity, chebulinic acid (CA) which is a major chemical constituent of T. chebula fruit showed potent activity. PURPOSE: This work was conducted to investigate the hepatoprotective activity and mechanisms of CA. METHODS: The hepatoprotective effect of CA was examined on hepatotoxic models of cells, zebrafish larvae and mice caused by tert-butyl hydrogen peroxide (t-BHP), acetaminophen (APAP) and CCl4, respectively. RESULTS: Pretreatment with CA could prevent t-BHP-induced damage in L-02 hepatocytes by blocking the production of ROS, reducing LDH levels and enhancing HO-1 and NQO1 expression via MAPK/Nrf2 signaling pathway. In animal experiments, CA significantly protected mice from CCl4-induced liver injury, as demonstrated by reduced ALT, AST and MDA levels, enhanced SOD activity, improved liver histopathological changes, and the activation of the Nrf2/HO-1 signaling pathway. CA metabolized to chebulic acid isomers with DPPH radical scavenging activity. In a transgenic zebrafish line with liver specific expression of DsRed RFP, CA diminished the hepatotoxicity induced by 10 mM APAP. CONCLUSION: Experiments in cell and two animal models demonstrated consistent results and comprehensively expounded the hepatoprotective effects of CA.

Protective effect of triterpenes of Ganoderma lucidum on lipopolysaccharide-induced inflammatory responses and acute liver injury.

Ganoderma lucidum is a popular medicinal mushroom, which has been used as therapeutic for centuries in traditional Chinese medicine. Although G. lucidum showed strong protective effects in prevention or treatment of a variety of inflammatory diseases, the mechanisms underlying the anti-inflammatory properties of triterpenes of G. lucidum remain undefined. In the current study, we demonstrated that ethanol extract and triterpenes of G. lucidum specifically suppressed LPS-mediated inflammatory responses. Notably, ganodermanontriol inhibited the expressions and interactions of TLR4 and MyD88, NF-κB translocation to nucleus and its DNA binding activity, phosphorylation of p38, ErK1/2 and JNK. In vivo, we showed that ganodermanontriol effectively prevented LPS/D-Galactosamine-induced liver injury by reducing TNF-α and IL-6 production, and decrease of ALT/AST release. Collectively, our results revealed a novel role in inhibition of inflammatory diseases for triterpenes that may act through potential inhibition of TLR4-MyD88-mediated NF-κB and MAPK signaling pathways.

Comparison of Antioxidant Constituents of Agriophyllum squarrosum Seed with Conventional Crop Seeds.

Twelve chemical constituents were identified from the Agriophyllum squarrosum seed (ASS). ASS contained large amounts of flavonoids, which were more concentrated in the seed coat. ASS-coat (1 g) contained 335.7 µg flavonoids of rutin equivalent, which was similar to the flavonoid content in soybean (351.2 µg/g), and greater than that in millet, wheat, rice, peanut, and corn. By LC-MS analysis, the major constituents in ASS were 3-O-[α-L-rhamnopyranosyl-(1→6)-ß-D- glucopyranosyl]-7- O-(ß-D-glucopyranosyl)-quercetin (1), rutin (4), quercetin-3-O-ß-D- apiosyl(1→2)-[α-L-rhamnosyl(l→6)]-ß-D-glucoside (2), isorhamnetin-3-O-rutinoside (5), and allantoin (3), compared with isoflavonoids-genistin (16), daidzin (14), and glycitin (18) in soybean. Among constituents in ASS, compounds 1, 2, 4, protocatechuic acid (8), isoquercitrin (11), and luteolin-6-C-glucoside (12) potently scavenged DPPH radicals and intracellular ROS; strongly protected against peroxyl radical-induced DNA scission; and upregulated Nrf2, phosphorylated p38, phosphorylated JNK, and Bcl-2 in HepG2 cells. These results indicate that ASS is rich in antioxidant constituents that can enrich the varieties of food flavonoids, with significant beneficial implications for those who suffer from oxidative stress-related conditions. PRACTICAL APPLICATION: This study found that A. squarrosum seed contains large amounts of antioxidative flavonoids and compared its chemical constituents with those of conventional foods. These results should increase the interest in planting the sand-fixing A. squarrosum on a large scale, thus preventing desertification and providing valuable foods.

Identification and Enrichment of α-Glucosidase-Inhibiting Dihydrostilbene and Flavonoids from Glycyrrhiza uralensis Leaves.

To exploit Glycyrrhiza uralensis resources, we examined the bioactive constituents of G. uralensis leaves. Seven chemical components were isolated by repeat column chromatography, and using spectroscopic methods, their structures were determined to be a novel prenylated dihydrostilbene, α,α'-dihydro-3,5,3',4'-tetrahydroxy-2,5'-diprenylstilbene (1); a methylated flavonoid, quercetin-3-Me ether (4); and 5 prenylated flavonoids: 5'-prenylquercetin (3), 8-[(E)-3-hydroxymethyl-2-butenyl]eriodictyol (7), 6-prenyleriodictyol (5), 5'-prenyleriodictyol (6), and 6-prenylquercetin-3-Me ether (2). Compounds 1-7 and their unprenylated counterparts, glycosides, and other related compounds (8-13) were quantitatively analyzed. Using a macroporous resin column, most of these compounds could be enriched in the 40% to 60% ethanol-eluted fractions. Compounds 1-7 showed strong radical scavenging activity toward DPPH, and most of them demonstrated greater inhibitory activity against α-glucosidase than their unprenylated counterparts.

Analysis of aristolochic acids, aristololactams and their analogues using liquid chromatography tandem mass spectrometry.

More than 80 aristolochic acids (AAs) and aristololactams (ALs) have been found in plants of the Aristolochiaceae family, but relatively few have been fully studied. The present study aimed at developing and validating a liquid chromatography tandem mass spectrometry (LC/MS(n)) for the analysis of these compounds. We characterized the fragmentation behaviors of 31 AAs, ALs, and their analogues via high performance liquid chromatography coupled with electrospray ionization mass spectrometry. We summarized their fragmentation rules and used these rules to identify the constituents contained in Aristolochia contorta, Ar. debilis, Ar. manshurensis, Ar. fangchi, Ar. cinnabarina, and Ar. mollissima. The AAs and ALs showed very different MS behaviors. In MS(1) of AAs, the characteristic pseudomolecular ions were [M + NH4](+), [M + H](+), and [M + H - H2O](+). However, only [M + H](+) was found in the MS(1) of ALs, which was simpler than that of AAs. Distinct MS(n)fragmentation patterns were found for AAs and ALs, showing the same skeleton among the different substituent groups. The distribution of the 31 constituents in the 6 species of Aristolochia genus was reported for the first time. 25 Analogues of AAs and ALs were detected in this genus. A hierarchical schemes and a calculating formula of the molecular formula of these nitrophenanthrene carboxylic acids and their lactams were proposed. In conclusion, this method could be applied to identification of similar unknown constituents in other plants.

Hepato-protective effects and chemical constituents of a bioactive fraction of the traditional compound medicine-Gurigumu-7.

BACKGROUND: Gurigumu-7 is an important traditional Mongolian medicine frequently used for liver diseases. However, the pharmacological effects and the bioactive constituents are not well understood. METHOD: This research was to use CCl4-induced liver damage in mice to investigate the hepatoprotective effects of Gurigumu-7 and the methanol eluted fraction from a DIAION column of an extract of Gurigumu-7 (MF). The chemical constituents of MF were analyzed by UPLC-MS. RESULTS: Pretreated orally with MF (66, 132 and 264 mg/kg) once a day for 4 days dose-dependently suppressed CCl4-induced mice liver histopathological changes and serum aminotransferase activities (alanine transaminase: 1144.0 ± 787.2 v.s. 2461.8 ± 1072.7 U/L, p < 0.05; aspartate transaminase: 1173 ± 785.3 v.s. 2506.6 ± 1140.7 U/L, p < 0.01). MF treated group demonstrated increased levels of SOD (108.19 ± 30.32 v.s. 75.75 ± 5.37 U/mg protein, p < 0.01) but decreased levels of malonyldialdehyde (7.68 ± 1.95 v.s. 44.32 ± 16.68 nmol/mg protein, p < 0.01) compared to the CCl4 control group. More than 30 chemical constituents were quantified, and MF was found to be rich in ellagic acid (297.97 mg/g), luteolin and its glucosides (35.10 mg/g), apigenin and its glucosides (>30 mg/g), ursolic acid (14.91 mg/g), bidenoside C (8.75 mg/g), and proanthocyanidins (15.64 mg/g in proanthocyanidin A2 equivalent). CONCLUSION: The methanol eluted fraction (MF) from a DIAION column of an extract of the Mongolian medicine-Gurigumu-7 was found to be more hepatoprotective than Gurigumu-7. The results suggested that MF is a promising bioactive fraction for the development of new hepatoprotective medicine with better formulation and quality control properties.

Quantification of Bile Acids in Traditional Animal Medicines and Their Preparations Using Ultra High-Performance Liquid Chromatography-Mass Spectrometry in the Multiple Reaction Monitoring Mode.

An ultra-high-performance liquid chromatograph-triple quadrupole mass spectrometry has been established and validated for the simultaneous quantification of 15 bile acids in four traditional animal medicines and their preparations. The separations of bile acids were performed on an Agilent ZORBAX Eclipse XDB-C18 column (50 × 2.1 mm; 1.8 µm) with methanol-0.1% formic acid as the mobile phase. Glycyrrhetinic acid was added as internal standard owing to its similar physiochemical properties with the bile acids. Using this condition, detected in the multiple reaction monitoring mode, the 15 bile acids, including three groups of isomers, were well quantified individually. Method validation showed that the linear regression relationship (r(2), 0.9993 - 0.9999), precisions (intra-day RSD, 0.96 - 4.31%; inter-day, 1.73 - 4.43%), and recovery (95.3 - 120.9%) were all satisfactory. The analysis results showed that bear bile and bezoar (Niu Huang) as well as their formulations contained large amounts of most of the 15 bile acids. In addition, this research revealed for the first time the presences of bile acids in animal waste medication used in traditional medicine from two clinics, Hei-Bing-Pian (discharges of wild boar) and Trogopterus Dung. The established method could be used for the quantification of other bile- or animal waste-based crude drugs and their formulated products.

Comparison of pharmacokinetic profiles of Terminalia phenolics after intragastric administration of the aqueous extracts of the fruit of Terminalia chebula and a Mongolian compound medicine-Gurigumu-7.

ETHNOPHARMACOLOGICAL RELEVANCE: The dried fruit of Terminalia chebula (fructus chebulae) is an important Traditional Medicine used for intestinal and hepatic detoxification. Gurigumu-7 which is made of fructus chebulae and 6 other traditional medicines is one of the most frequently used compound Mongolian and Tibet medicines for liver diseases. Terminalia phenolics are considered as the bioactive constituents of fructus chebulae and consequently of Gurigumu-7. AIM OF THE STUDY: To compare the pharmacokinetic profiles of Terminalia phenolics after intragastric administration of the aqueous extracts of fructus chebulae and Gurigumu-7 and to evaluate the possible influence of intestinal bacterial metabolism on these pharmacokinetic profiles. MATERIALS AND METHODS: An ultra performance liquid chromatography with triple quadrupole mass spectrometry method was established and validated for simultaneously determining the pharmacokinetic profiles of seven Terminalia phenolics after intragastric administration of pure compounds, fructus chebulae extract, and Gurigumu-7 extract. In vitro rat fecal lysates experiments were carried out to explore the metabolic discrepancy between fructus chebulae and Gurigumu-7. RESULTS: Seven Terminalia phenolics were detected in rat plasma after intragastric administration of the aqueous extracts of fructus chebulae and Gurigumu-7. Administration of Gurigumu-7 could promote the absorption and increase the Cmax and AUC values of these phenolic constituents compared to fructus chebulae administration. The fecal lysates studies showed that the Terminalia phenolics in Gurigumu-7 were less rapidly bio-transformed than those in fructus chebulae. This may be a contributing factor to the pharmacokinetic discrepancy between the phenolics in fructus chebulae and Gurigumu-7. CONCLUSION: Administration of Gurigumu-7 could increase the absorption of Terminalia phenolics through slowing down the intestinal bacteria metabolism. These results provide, in part, an in vivo rationale for the formulation of the traditional Mongolia / Tibet medicine, Gurigumu-7.

Simultaneous quantification of ten constituents of Xanthoceras sorbifolia Bunge using UHPLC-MS methods and evaluation of their radical scavenging, DNA scission protective, and α-glucosidase inhibitory activities.

The present study was designed to investigate the bioactive constituents of Xanthoceras sorbifolia in terms of amounts and their antioxidant, DNA scission protection, and α-glucosidase inhibitory activities. Simultaneous quantification of 10 X. sorbifolia constituents was carried out by a newly established ultra-high performance liquid chromatography-quadrupole mass spectrometry method (UHPLC-MS). The antioxidant activities were evaluated by measuring DPPH radical scavenging and DNA scission protective activities. The α-glucosidase inhibitory activities were investigated by using an assay with α-glucosidase from Bacillus Stearothermophilus and disaccharidases from mouse intestine. We found that the wood of X. sorbifolia was rich in phenolic compounds with the contents of catechin, epicatechin, myricetin, and dihydromyricetin being 0.12-0.19, 1.94-2.16, 0.77-0.91, and 6.76-7.89 mg·g(-1), respectively. The four constituents strongly scavenged DPPH radicals (with EC50 being 4.2, 3.8 and 5.7 µg·mL(-1), respectively) and remarkably protected peroxyl radical-induced DNA strand scission (92.10%, 94.66%, 75.44% and 89.95% of protection, respectively, at a concentration of 10 µmol·L(-1)). A dimeric flavan 3-ol, epigallocatechin-(4ß→8, 2ß→O-7)-epicatechin potently inhibited α-glucosidase with an IC50 value being as low as 1.2 µg·mL(-1). The established UHPLC-MS method could serve as a quality control tool for X. sorbifolia. In conclusion, the high contents of antioxidant and α-glucosidase inhibitory constituents in X. sorbifolia support its use as complementation of other therapeutic agents for metabolic disorders, such as diabetes and hypertension.

Hepatitis C virus inhibitory hydrolysable tannins from the fruits of Terminalia chebula.

Two new hydrolysable tannins, chebumeinin A (1) and chebumeinin B (2), together with eight known related compounds (3-10), were isolated from the fruits of Terminalia chebula. The new compounds were structurally determined by analysis of their spectroscopic data and the known compounds characterized by comparing their spectroscopic data with literature values. All isolates were evaluated by an HCV protease inhibition assay, and some compounds were found to be potently active.

Structures and antioxidant and intestinal disaccharidase inhibitory activities of A-type proanthocyanidins from peanut skin.

Nine compounds including a new A-type proanthocyanidin trimer, epicatechin-(2ß→O→7,4ß→8)-[catechin-(6→4ß)]-epicatechin (8), and a known trimer, epicatechin-(4ß→8)-epicatechin-(2ß→O→7,4ß→8)-catechin (9), being reported for peanut skin for the first time, were isolated and purified. Their structures were determined by spectroscopic methods and by degradation reactions with L-cysteine in acidic conditions. The DPPH radical scavenging activity and the inhibitory activity on maltase and sucrase of the isolated compounds were investigated. All compounds showed strong DPPH scavenging activities (EC50 < 20 µg/mL). Compound 8 showed the strongest inhibitory activity on maltase with an IC50 value of 0.088 mg/mL, while compound 9 exhibited the strongest inhibition on sucrase with an IC50 value of 0.091 mg/mL.

Chemical constituents and pharmacologic actions of Cynomorium plants.

The stem of Cynomorium songaricum is a traditional Chinese medicine reputed to have tonic effects. C. coccineum growing in northern Africa and the Mediterranean region is regarded in Arabian medical practice as the "treasure of drugs". The major constituents of Cynomorium plants have been revealed to be phenolic compounds, steroids, triterpenes, etc. Pharmacologic studies showed that the Cynomorium plants had antioxidant, immunity-improving, anti-diabetic, neuroprotective, and other bioactivities. Some chemical constituents in Cynomorium plants are unstable, implying that the chemical components of the herbal medicines produced under different conditions may be variable. This review covers the literature published until December, 2011 and describes the pharmacologic effects and secondary metabolites of Cynomorium species.

Flavan-3-ol-cysteine and acetylcysteine conjugates from edible reagents and the stems of Cynomorium songaricum as potent antioxidants.

Flavan-3-ol derivatives, including 3 cysteine conjugates and 3 acetylcysteine conjugates, were prepared using Cynomorium songaricum and edible reagents. The structures were determined, based on NMR and MS spectra. All compounds had stronger radical-scavenging activity than catechin and epicatechin. Moreover, the cysteine conjugates were active against α-glucosidase, whereas catechin and epicatechin were not. Two acetylcysteine flavan-3-ol conjugates, 4ß-(L-acetylcysteinyl)-epicatechin 3-O-gallate and 4ß-(L-acetylcysteinyl)-epiafzelechin, are novel compounds with better logP values than their cysteine counterparts. These conjugates can be prepared from purified flavan-3-ol polymers or directly from herbal material.

The simultaneous quantification of Ganoderma acids and alcohols using ultra high-performance liquid chromatography-mass spectrometry in dynamic selected reaction monitoring mode.

Ultra-high-performance liquid chromatography-triple quadrupole mass spectrometry with dynamic selected reaction monitoring mode was developed to simultaneously quantify Ganoderma acids and alcohols. Cholic acid and hydrocortisone, whose physiochemical properties are similar to triterpene acids and alcohols, respectively, were added as internal standards before sample treatment. The method could be applied to the quantification of triterpenes in single fungus and traditional Chinese medicine preparations. This method also detected 5 triterpenes in the Coriolus genus for the first time.