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Aims: The ripe fruit of Siraitia grosvenorii (Swingle) C. Jeffrey (Cucurbitaceae) is used in Traditional Chinese Medicine (TCM) for treatment of diabetes. The ripe fruit is very edible, nutritious and of high sweet taste, while the unripe fruit which is usually very bitter and not edible, has not been widely studied. Therefore, the aim of this study is to evaluate the antidiabetic activity of the unripe fruit of S. grosvenorii and to compare it with that of the ripe fruit as well as to determine their possible mechanism of action. Methodology: The method of streptozotocin-nicotinamide induced diabetic animal model in mice was employed and mice with blood glucose greater than 9.0 mmol/l were selected for treatment with unripe fruit extract (UFE) and ripe fruit extract (RFE) for 24 days. Alpha-glucosidase and alpha amylase enzymes inhibitory assays for determination of possible mechanism of action, were performed. Results: The RFE exhibited better efficacy in antidiabetic activity than the UFE, though the later displayed better potency in activity. The RFE, UFE (300 mg/kg) and glibenclamide exhibited significant (P

Passiflora edulis Sims (passion fruit) seeds are often discarded as byproducts during juice processing. In fact, the seeds are of considerable commercial value in the food and cosmetics industry because of their rich polyphenols, especially piceatannol. In this study, high-speed countercurrent chromatography (HSCCC) was applied for the separation of stilbene polyphenols from passion fruit seeds. The n-hexane-ethyl acetate-methanol-water (1:2:1:2.8, v/v) was found to be the optimum two-phase solvent for the preparation of two major stilbenes, scirpusin B (8) and piceatannol (9) with purities of 90.2% and 94.8%, respectively. In addition, a continuous semipreparative HPLC was applied to further purify the HSCCC fractions containing minor stilbenes and obtain four new piceatannol derivatives (1-4) along with three known ones (5-7). The structures of these new compounds were determined using spectroscopic methods, including NMR, high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), and circular dichroism (CD). The isolated compounds were evaluated for α-glucosidase inhibitory activities in vitro. The result suggested that all of them exhibited more significant activity than acarbose, and passiflorinol B (2) had the strongest activity, with a IC50 value of 1.7 μM.

Polyphenols, widely distributed in the genus Melastoma plants, possess extensive cellular protective effects such as anti-inflammatory, anti-tyrosinase, and anti-obesity, which makes it a potential anti-inflammatory drug or enzyme inhibitor. Therefore, the aim of this study is to screen for the anti-inflammatory and enzyme inhibitory activities of compounds from title plant. Using silica gel, MCI, ODS C18, and Sephadex LH-20 column chromatography, as well as semipreparative HPLC, the extract of Melastoma normale roots was separated. Four new ellagitannins, Whiskey tannin C (1), 1-O-(4-methoxygalloyl)-6-O-galloyl-2,3-O-(S)-hexahydroxydiphenoyl-β-d-glucose (2), 1-O-galloyl-6-O-(3-methoxygalloyl)-2,3-O-(S)-hexahydroxydiphenoyl-β-d-glucose (3), and 1-O-galloyl-6-O-vanilloyl-2,3-O-(S)-hexahydroxydiphenoyl-β-d-glucose (4), along with eight known polyphenols were firstly obtained from this plant. The structures of all isolates were elucidated by HRMS, NMR, and CD analyses. Using lipopolysaccharide (LPS)-stimulated RAW2 64.7 cells, we investigated the anti-inflammatory activities of compounds 1–4, unfortunately, none of them exhibit inhibit nitric oxide (NO) production, their IC50 values are all &gt, 50 μM. Anti-tyrosinase activity assays was done by tyrosinase inhibition activity screening model. Compound 1 showed weak tyrosinase inhibitory activity with IC50 values of 426.02 ± 11.31 μM. Compounds 2–4 displayed moderate tyrosinase inhibitory activities with IC50 values in the range of 124.74 ± 3.12–241.41 ± 6.23 μM. The structure–activity relationships indicate that hydroxylation at C-3′, C-4′, and C-3 in the flavones were key to their anti-tyrosinase activities. The successful isolation and structure identification of ellagitannin provide materials for the screening of anti-inflammatory drugs and enzyme inhibitors, and also contribute to the development and utilization of M. normale.

A series of novel derivatives based on mogrol were designed and synthesized in attempt to improve anti-lung cancer activity. The cytotoxicity against human lung cancer cells including A549 and NCI-H460 were performed by Cell Counting Kit-8 (CCK8) assay in vitro. The screening result showed that compound 8f exhibited the strongest activity with an IC50 value of 4.47 μM against A549 cell, and could induce the cell apoptosis in a dose-dependent manner and arrest cell cycle at G0/G1 phase. Besides, compound 8f displayed anti-proliferation effect on A549 cell through inhibiting phosphorylation of signal transducer and activator of transcription 3 (STAT3). Furthermore, compared with morgol, compound 10a significantly improved the cytotoxicity against NCI-H460 with the IC50 value of 17.13 μM. The research stimulated the development of potential therapeutic agent for lung cancer from the natural mogrol.

Soil microbes may be critical players in determining the allelopathic potential of some plants. Low levels of plant community biodiversity in Eucalyptus plantations have been attributed to the allelopathic potential of these tree species. The role of soil microbes in the allelopathic effect of leaf leachates of the hybrid tree Eucalyptus grandis × E. urophylla, was tested in Petri dish assays with Brassica chinensis as a receiver plant. Soils were collected from either a local garden (soil A) or a Eucalyptus plantation (soil B) and half of each soil was sterilized to remove microbes. These soils were then treated with E. grandis × E. urophylla leachates for 0–72 h. Seed germination of B. chinensis was significantly inhibited in soils treated with leaf leachates relative to untreated soils. The inhibitory effect of the leaf leachates was more pronounced in sterilized soils. Total phenolic content was obvious lower in nonsterile leachate-treated soils than in sterile soils. Biomass of B. chinensis was negatively correlated with the total phenolic content in soils. Our findings suggest that soil microbes can alleviate the allelopathic potential of Eucalyptus and thereby its negative impact on plant growth.

In the course of a phytochemical and chemotaxonomical investigation for the Castanopsis (Fagaceae) species, fifteen compounds, including two triterpene hexahydroxydiphenoyl esters (1 and 2), seven gallotannins (3–9), three flavonoids (10–12), and three other compounds (13–15) were isolated from the leaves of Castanopsis fargesii Franch. Their structures were elucidated by means of spectroscopic methods and in comparison with published data. All these compounds were obtained from this species for the first time. Moreover, ethyl glucopyranoside (15) was firstly isolated from the genus Castanopsis. 6-O-Galloyl-β- d -glucose (3) and 3,4′,5,7-tetrahydroxyflavone (11) have not been reported from any species in Fagaceae family. The chemotaxonomic significance of these compounds was summarized.

Background Tomato fruit (Lycopersicon esculentum Mill.) has been suggested to be useful for the prevention of diabetes. Esculeoside A is the main saponin compounds in tomatoes. This study investigated the hypoglycemic effects and the underlying mechanism of esculeoside A in C57BLKS/Leprdb (db/db) mice. Methods Wild-type C57BLKS (db/dm) mice were used in the db/dm mouse group and db/db mice were randomly divided into 2 groups: untreated and treated db/db mouse groups. Esculeoside A (100 mg/kg) was administered by gavage for 56 days to the treated db/db mouse group. Distilled water was administered to the db/dm mouse group and the untreated db/db mouse group. The blood and liver biochemical parameters and the expression of liver insulin signaling-related proteins were examined. Results The results showed that esculeoside A reduced the fasting blood glucose (FBG) levels and improved the glucose tolerance. Further investigation revealed that hepatic protein expressions of total AMP-activated protein kinase (T-AMPK), phosphorylated AMP-activated protein kinase (p-AMPK), insulin receptor substrate-1 (IRS-1), and glucokinase (GCK) were significantly upregulated after esculeoside A treatment. In contrast, the hepatic protein expression of phosphoenolpyruvate carboxykinase (PEPCK) was significantly downregulated by esculeoside A treatment. Conclusion These findings suggested that esculeoside A has a potential of alleviating the metabolic abnormalities in db/db mice via regulation of AMPK/IRS-1 pathway. Our findings supported a possible application of esculeoside A as a functional supplement for diabetes treatment.

The aim of this study was to characterize hydrolyzable tannins in Polygonaceous plants, as only a few plants have previously been reported to contain ellagitannins. From Persicaria chinensis, a new hydrolyzable tannin called persicarianin was isolated and characterized to be 3-O-galloyl-4,6-(S)-dehydrohexahydroxydiphenoyl-d-glucose. Interestingly, acid hydrolysis of this compound afforded ellagic acid, despite the absence of a hexahydroxydiphenoyl group. From the rhizome of Polygonum runcinatum var. sinense, a large amount of granatin A, along with minor ellagitannins, helioscpoinin A, davicratinic acids B and C, and a new ellagitannin called polygonanin A, were isolated. Based on 2D nuclear magnetic resonance (NMR) spectroscopic examination, the structure of polygonanin A was determined to be 1,6-(S)-hexahydroxydiphenoyl-2,4-hydroxychebuloyl-β-d-glucopyranose. These are the second and third hydrolyzable tannins isolated from Polygonaceous plants. In addition, oligomeric proanthocyanidins of Persicaria capitatum and P. chinensis were characterized by thiol degradation. These results suggested that some Polygonaceous plants are the source of hydrolyzable tannins not only proanthocyanidins., Molecules, 26(2), art.no.337; 2021

Six new limonoids, munropins A−F (1–6), were isolated from the aerial parts of a Chinese medicinal plant, Munronia pinnata (Meliaceae). The structures of 1–6 were assigned by detailed analyses of their spectroscopic data. Munropins A (1) and B (2) are limonoids possessing a prieurianin skeleton with α,β-unsaturated γ-lactam moieties at C-17. Munropins C (3), D (4), and E (5) are also prieurianin type limonoids with an α,β-unsaturated γ-lactone moiety, an acetyl group, and an acetoxyacetyl group at C-17, respectively. Munropin F (6) was assigned as a nimbolinin type limonoid with a γ-hydroxy-α,β-unsaturated γ-lactone moiety.

In the course of a phytochemical and chemotaxonomical investigation of Castanopsis species (Fagaceae), three new phenolic compounds, (3R,1'S)-[1'-(6″-O-galloyl-β-d-gluco-pyranosyl)oxyethyl]-3-hydroxy-dihydrofuran-2(3H)-one (1), (2R,3S)-2-[2'-(galloyl)oxyethyl]-dihydroxybutanoic acid (2), and (3S,4S)-3-hydroxymethyl-3,4-dihydro-5,6,7-trihydroxy-4-(4'-hydroxy-3'-methoxyphenyl)-1H-[2]-benzopyran-1-one (3) were isolated from the fresh leaves of Castanopsis fargesii. In addition, a known phenolic glycoside, gentisic acid 5-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside (4) was also isolated and identified. Their structures were elucidated by means of spectroscopic methods including one- and two-dimensional NMR techniques.

Hydrodistillation of the fresh leaves of E.grandis×E.urophylla hybrids and pure species E.grandis, E.urophylla, E.pellita, E.camaldulensis, E. dunni, and E.saligna collected from the trees grown in Guangxi Huangmian Forest (China), afforded essential oils in yields varying from 0.24±0.15% to 5.36±0.28%, according to the species. Analysis by GC (FID) and GC/MS allowed the identification of 67 compounds, representing 82.55% to 91.03% of the total oil composition. The dominant compounds were 1,8-cineole in E.saligna, E.urophylla, E.grandis×E.urophylla, E.grandis, E.pellita and E. dunni (67.48, 57.12, 48.21, 23.64, 20.34, 20.22%), p-Cymene in E.camaldulensis,E. dunni and E.grandis(21.32, 14.74, 13.38%), α-pinene in E.grandis and E.grandis×E.urophylla (21.77, 15.55%), α-terpinene in E. dunni and E.grandis (17.96, 9.35%), α-terpineol in E.pellita and E.saligna (19.24,11.54%), respectively. Hierarchical Cluster Analysis separated the characterized essential oils into two groups, each constituting a chemotype. E.grandis×E.urophylla and E.urophylla were classified in the same group, while E.grandis in the other.

In this study, four new lignan glucosides, named difengpiosides A-D (1-4), were isolated from the stem barks of Illicium difengpi, together with seven known compounds 5-11. Their structures were identified on the basis of spectroscopic analyses (1D and 2D NMR, HRESIMS, CD) and a comparison with literature data. All the compounds were evaluated for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells.

A high-performance liquid chromatographic method (HPLC) with evaporative light scattering detection (ELSD) has been developed for fingerprint analysis of Flos Lonicerae. The samples were separated with an Agilent C18 column using acetonitrile (A) and 0.1% formic acid solution under gradient conditions (0→10 min：11.5%→15% A, 10→12 min：15% →22% A, 12→18min：22%→33% A; 18→30min: 33%→45% A) as the mobile phase at a flow rate of 0.8ml min−1 within 30 min. The ELSD conditions were optimized at nebulizer-gas flow rate 2.7 L min−1 and drift tube temperature 105°C. Precision experiments showed relative standard deviation (R.S.D.) of peak area and retention time were better than 2.5%, inter-day and intra-day variabilities showed that R.S.D. was ranged from 0.66% to 4.17%. Accuracy validation showed that average recovery was between 95.33% and 104.10%. The method was validated to achieve the satisfactory precision and recovery. Relative retention time and relative peak area were used to identify the common peaks for fingerprint analysis. There are nine common peaks in the fingerprint. The quality of sixteen batches of Flos Lonicerae samples was evaluated by hierarchical clustering analysis, which classfied all bacthes into two clusters. Furthermore, the contents of important medicinal compounds (chlorogenic acid, macranthoidin B and dipsacoside B) in different batches of Flos Lonicerae samples were determined simultaneously using the developed HPLC-ELSD method. The developed analytical procedure was proved to be a reliable and rapid method for the quality control of Flos Lonicerae.

In the course of a chemotaxonomical study of Castanopsis species (Fagaceae), detailed investigation of the leaves of C. sclerophylla led to isolation of three new phenolic compounds together with 62 known compounds. The structures of the new compounds were elucidated as 2-O-galloyl-O-4,6-(S)-valoneoyl-d-glucose (1), 6-O-galloyl-1-O-vanilloyl-β-d-glucose (2), and 4″-O-galloylchestanin (3) by means of spectroscopic analyses and enzymatic hydrolysis with tannase. Comparison with other Castanopsis species indicated that C. sclerophylla characteristically accumulates chlorogenic acid and a dimeric ellagitannin, rugosin E. Triterpene hexahydroxydiphenoyl esters, which are major constituents of C. cuspidata var. sieboldii, C. hystrix, and C. fissa were not detected., Phytochemistry Letters, 5(1), pp.158-161; 2012

Esculeoside A, the tomato saponins from Lycopersicon esculentum MILL, may be metabolized into various steroidal hormones such as pregnane derivatives that are expected to exhibit various bioactivities in the body, such as anti-osteoporosis, antimenopausal disorder and anti-tumor actions. In order to enrich large amount of esculeoside A for further scientific research, we firstly developed a high performance liquid chromatography (HPLC) with evaporative light scattering detection (ELSD) method for its quantification, and used it to examined the content of esculeoside A in different cultivated varieties of tomato fruits and tomato extract. Statistical analysis of the obtained data demonstrated that our method was simple, and has achieved desired linearity, precision and accuracy. Then we have explored the feasibility of using pectinase as a means for assisting esculeoside A extraction from fresh tomato fruits, and several factors such as the enzyme concentration, pH value of enzyme solution, temperature, incubation time which influenced on extraction were investigated. Moreover, in our previous study, the adsorption characteristics on several types of macroporous resins have been compared. Among them, D-101 resin showed the best separation behaviors on esculeoside A. So in the present paper, in order to get the best parameters for D101 adsorption, the adsorption kinetic curve, the appropriate ethanol concentration for elution and breakthrough volume were analyzed．

In the course of a chemotaxonomical study of Chinese Castanopsis species, two previously unknown flavan-3-ols, named sclerophynins A and B, were isolated from the leaves of C. sclerophylla, together with five related known compounds. On the basis of spectroscopic analysis, the new compounds were characterized to be (4S,8R,9S)-4-(3,4-dihydroxyphenyl)-8-(3,4,5-trihydroxyphenyl)- 3,4,9,10-tetrahydro-5,9-dihydroxy-2H,8H-benzo[1,2-b:3,4-b']dipyran-2- one and (4S,7S,8R)-4,8-bis(3,4-dihydroxyphenyl)-3,4,6,7-tetrahydro-5-glucopyranosyloxy- 7-hydroxy-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one, respectively., HETEROCYCLES, 83(10), pp.2321-2328; 2011

Three new pregnane glycosides, 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl-(20R)-pregn-5-ene-3β,20-diol (1), 3-O-α-L-arabinopyranosyl-(20R)-pregn-5-ene-3β,20-diol-20-O-β-D-glucopyranoside (2), 3-O-α-L-arabinopyranosyl-(20R)-pregn-5-ene-3β,20-diol-20-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (3) were isolated along with four known compounds, 4-7, from the leaves and stems of Brucea javanica. Their structures were determined by detailed analyses of 1D- and 2D-NMR spectroscopic data. All of the compounds isolated from Brucea javanica were tested for the antifeedant activities against the larva of Pieris rapae. Compounds 1, 3, and 5 showed significant antifeedant activities after 72 h incubation.

Compensatory growth is a phase of accelerated growth apparent when favourable conditions are restored after a period of growth depression. To investigate if F-2 common 'all-fish' growth hormone gene transgenic common carp (Cyprinus carpio) could mount compensatory growth, a 9 week study at 29 degrees C was performed. The control group was fed to satiation twice a day throughout the experiment. The other two groups were deprived of feed for 1 or 2 weeks, respectively, and then fed to satiation during the re-feeding period. At the end of the experiment, the live masses of fish in the deprived groups were still significantly lower than those of the controls. During the re-feeding period, size-adjusted mean specific growth rates and mean feed intakes were significantly higher in the deprived fish than in the controls, indicating a partial compensatory growth response in these fish. No significant differences were found in food conversion efficiency between the deprived and control fish during re-feeding, suggesting that hyperphagia was the mechanism responsible for increased growth rates. The proximate composition of the deprived fish at the end of the experiment was similar to that of the control fish. This study is, to our knowledge, the first to report that fast-growing transgenic fish can achieve partial compensation of growth following starvation. (c) 2007 The Authors Journal compilation (c) 2007 The Fisheries Society of the British Isles.

The growth and energy budget for F-2 'all-fish' growth hormone gene transgenic common carp Cyprinus carpio of two body sizes were investigated at 29.2 degrees C for 21 days. Specific growth rate, feed intake, feed efficiency, digestibility coefficients of dry matter and protein, gross energy intake (I-E), and the proportion of I-E utilized for heat production (H-E) were significantly higher in the transgenics than in the controls. The proportion of I-E directed to waste products [faecal energy (F-E) and excretory energy loss (Z(E) + U-E) where Z(E) is through the gills and U-E through the kidney], and the proportion of metabolizable energy (M-E) for recovered energy (R-E) were significantly lower in the transgenics than in the controls. The average energy budget equation of transgenic fish was as follows: 100 I-E = 19.3 F-E + 6.0 (Z(E) + U-E) + 45.2 H-E + 29.5 R-E or 100 M-E = 60.5 H-E + 39.5 R-E. The average energy budget equation of the controls was: 100 I-E = 25.2 F-E + 7.4 (Z(E) + U-E) + 35.5 H-E + 31.9 R-E or 100 M-E = 52.7 H-E + 47.3 R-E. These findings indicate that the high growth rate of 'all-fish' transgenic common carp relative to their non-transgenic counterparts was due to their increased feed intake, reduced lose of waste productions and improved feed efficiency. The benefit of the increased energy intake by transgenic fish, however, was diminished by their increased metabolism.

Studies on the constituents of the unripe fruits of Siraitia grosvenori led to the isolation of three new cucurbitane triterpene glycosides, 11-oxomogroside III (10), 11-dehydroxymogroside III (11), and 11-oxomogroside IV A (12). Their structures were determined on the basis of detailed analyses of 1D, 2D-NMR spectroscopic methods. All of the compounds isolated from the unripe fruits of S. grosvenori were tested for cytotoxic activities against tumor cells, HCT-116 and SMMC-7721.

Keywords: C. nudiflora; phenols; HP-20 macroporous resin Abstract: Objective To study the technological parameters of the purification process of phenols from Callicarpa nudiflora (C. nudiflora ) with HP-20 macroporous resin.Methods The kinetic adsorption and desorption experiments were carried out on HP-20 macroporous resin (HP-20) to optimize the separation process of phenols. Additionally, the effects of four parameters including adsorption flow rate, elute flow rate, volume of 10% ethanol and 50% ethanol solution for elution were explored by a L4/3 orthogonal experiment. Finally, content of phenols in samples before and after being treated by HP-20 were compared. Results The results showed that a good separation and purification of crude total phenols extract from C. nudiflora was achieved using HP-20. The optimum conditions were found to be: initial concentration of 50 mg·mL -1 , absorb flow rate of 1 mL·min -1 , elute flow rate of 3 mL·min -1 , 5 BV of 10% ethanol solution for prewash and 10 BV of 50% ethanol solution for desorption solvent. Conclusion The content of phenols is above 40% in C. nudiflora after being treated by HP-20, indicating that HP-20 could be successfully applied to enrich and purify phenols in C. nudiflora.

From the unripe fruits of Lo Han Kuo (Siraitia grosvenori), a Chinese medicinal plant, two new cucurbitane triterpene glycosides, 20-hydroxy-11-oxomogroside IA(1) (1) and 11-oxomogroside IIE (2), were isolated along with five known cucurbitane glycosides, 11-oxomogroside IA(1) (3), mogroside IIE (4), mogroside III (5), mogroside IVA (6), and mogroside V (7), and two flavonoid glycosides, kaempferol 7-O-alpha-L-rhamnopyranoside (8) and kaempferol 3,7-di-O-alpha-L-rhamnopyranoside (9). Their structures were determined on the basis of detailed analyses of 1D, 2D-NMR spectroscopic methods and by comparing with literature values. This paper describes the first investigation of unripe bitter Lo Han Kuo fruits.

A new daphnane diterpenoid, venenatin (1), along with six known compounds, was isolated from the aerial parts of Excoecaria venenata. The structure of 1 was elucidated on the basis of extensive spectroscopic analysis. Compound 1 exhibited growth inhibitory effect on human leukaemia HL-60 cell line with IC50 value of 28.10 μM.

A new triterpenoid saponin, 3-O-β-D-xylopyranosyl spathodic acid (1), was isolated from the EtOH extract of the root of Croton lachnocarpus Benth., together with four known compounds. These compounds were characterised on the basis of their spectral data and compatible with values in the literature. Compound 1 was the first triterpenoid glucoside isolated from the genus Croton. The known compound myriaboric acid (2) showed cytotoxic activity against human hepatocellular carcinoma SMMC-7721 cell line with an IC50 value of 42.2 μM.

The chemotaxonomical study of Castanopsis species leads to the isolation of two previously unknown flavanols.

From the unripe fruits of Lo Han Kuo (Siraitia grosvenori), a Chinese medicinal plant, two new cucurbitane triterpene glycosides, 20-hydroxy-11-oxomogroside IA(1) (1) and 11-oxomogroside IIE (2), were isolated along with five known cucurbitane glycosides, 11-oxomogroside IA(1) (3), mogroside IIE (4), mogroside III (5), mogroside IVA (6), and mogroside V (7), and two flavonoid glycosides, kaempferol 7-O-alpha-L-rhamnopyranoside (8) and kaempferol 3,7-di-O-alpha-L-rhamnopyranoside (9). Their structures were determined on the basis of detailed analyses of 1D, 2D-NMR spectroscopic methods and by comparing with literature values. This paper describes the first investigation of unripe bitter Lo Han Kuo fruits.