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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.

Aberrant destruction of the articular extracellular matrix (ECM) has been considered to be one of the pathological features of osteoarthritis (OA) which results in chondrocyte changes and articular cartilage degeneration. The MAPK signaling pathway serves a key role by releasing cartilage-degrading enzymes from OA chondrocytes. However, the use of MAPK inhibitors for OA is hindered by their potential long-term toxicity. Vicenin 3 is one of the major components of the Jian-Gu injection which is effective in the clinical treatment of OA. However, its potential impact on OA remain poorly understood. Therefore, the present study aimed to assess the effects of vicenin 3 on interleukin (IL)-1β-treated SW1353 chondrocytes, which mimic the microenvironment of OA. These chondrocytes were pretreated with vicenin 3 (0, 5 and 20 µM) for 1 h and subsequently stimulated with IL-1β (10 ng/ml) for 24 h. Nitric oxide (NO) production was measured using the Griess reaction, whereas the production of prostaglandin E2 (PGE2), matrix metalloproteinases (MMPs), A disintegrin-like and metalloproteinase with thrombospondin motifs (ADAMTSs), collagen type II and aggrecan were measured using ELISA. The mRNA expression of MMPs and ADAMTSs were measured using reverse transcription-quantitative PCR. The protein expression levels of MAPK were measured using western blotting. Vicenin 3 was found to significantly inhibit IL-1β-induced production of NO and PGE. Increments in the expression levels of MMP-1, MMP-3, MMP-13, ADAMTS-4 and ADAMTS-5 induced by IL-1β, in addition to the IL-1β-induced degradation of collagen type II and aggrecan, were all reversed by vicenin 3 treatment. Furthermore, vicenin 3 suppressed IL-1β-stimulated MAPK activation, an effect that was similar to that exerted by SB203580, a well-known p38 MAPK inhibitor. In conclusion, vicenin 3 may confer therapeutic potential similar to that of the p38 MAPK inhibitor for the treatment of OA.

Ellagitannins (ETs) are plant polyphenols with various health benefits. Recent studies have indicated that the biological activities of ETs are attributable to their degradation products, including ellagic acid and its gut microflora metabolites, such as urolithins. Insect tea produced in the Guangxi region, China, is made from the frass of moth larvae that feed on the ET-rich leaves of Platycarya strobilacea. Chromatographic separation of the Guangxi insect tea showed that the major phenolic constituents are ellagic acid, brevifolin carboxylic acid, gallic acid, brevifolin, and polymeric polyphenols. Chemical investigation of the feed of the larvae, the fresh leaves of P. strobilacea, showed that the major polyphenols are ETs including pedunculagin, casuarictin, strictinin, and a new ET named platycaryanin E. The new ET was confirmed as a dimer of strictinin having a tergalloyl group. The insect tea and the leaves of P. strobilacea contained polymeric polyphenols, both of which were shown to be composed of ETs and proanthocyanidins by acid hydrolysis and thiol degradation. This study clarified that Guangxi insect tea contains ET metabolites produced in the digestive tract of moth larvae, and the metabolites probably have higher bioavailabilities than the original large-molecular ETs of the leaves of P. strobilacea., Molecules, 26(14), art. no. 4134; 2021

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.

Three new compounds (6S,9S)-6′-galloyl-roseoside (1), purpurogallin ethyl carboxylate (2), and tibetana A (3) were isolated from 80% methanol extract of the leaves of Castanopsis tibetana Hance. Their structures were elucidated based on comprehensive spectroscopic methods and chemical data, including optical rotation, UV, MS, 1 D and 2 D NMR spectra. Compounds 1 and 3 were evaluated for their α-glucosidase inhibitory activity, pancreatic lipase inhibitory activity, and tyrosinase inhibitory activity.

Utilizing the distinct HMBC crossed-peak patterns of lower-field range (LFR; 11.80‒14.20 ppm) hydroxyl singlets, presented NMR methodology characterizes flavonoid metabolomes both qualitatively and quantitatively. It enables simultaneous classification of the structural types of 5-OH flavonoids and biogenetically related 2’-OH chalcones, as well as quantification of individual metabolites from (1)H NMR spectra, even in complex mixtures. Initially, metabolite-specific LFR 1D (1)H and 2D HMBC patterns were established via literature mining and experimental data interpretation, demonstrating that LFR HMBC patterns encode the different structural types of 5-OH flavonoids/2’-OH chalcones. Taking advantage of the simplistic multiplicity of the H,H-uncoupled LFR 5-/2’-OH singlets, individual metabolites could subsequently be quantified by peak fitting quantitative (1)H NMR (PF-qHNMR). Metabolomic analysis of enriched fractions from three medicinal licorice (Glycyrrhiza) species established proof-of-concept for distinguishing three major structural types and eight subtypes in biomedical applications. The method identified fifteen G. uralensis (GU) phenols from the six possible subtypes of 5,7-diOH (iso)flav(an)ones with 6-, 8-, and non-prenyl substitution, including the new 6-prenyl-licoisoflavanone (1) and two previously unknown compounds (4 and 7). Relative (100%) qNMR established quantitative metabolome patterns suitable for species discrimination and plant metabolite studies. Absolute qNMR with combined external and internal (solvent) calibration (ECIC) identified and quantified 158 GU metabolites. HMBC-supported qHNMR analysis of flavonoid metabolomes (“flavonomics”) empowers the exploration of structure-abundance-activity relationships of designated bioactivity. Its ability to identify and quantify numerous metabolites simultaneously and without identical reference materials opens new avenues for natural product discovery and botanical quality control and can be adopted to other flavonoid- and chalcone containing taxa.

Deep eutectic solvents (DESs) are emerging as new extraction solvents for the extraction of bioactive compounds from natural plants. In this work, a total of thirteen choline chloride-based DESs were synthesized and evaluated for the simultaneous extraction of five bioactive flavone di-C-glycosides from Premna fulva Craib. DES-F, which was composed of choline chloride and 1,3-propanediol, showed the best extraction efficiency for the flavone di-C-glycosides, exceeding that of the conventional industrial solvent (40% ethanol). Subsequently, the extraction parameters for ultrasonic-assisted extraction (liquid-solid ratio, water content (%) in the selected DES, and extraction time) were optimized using response surface methodology. Furthermore, the microstructural alterations in the samples after extraction were evaluated using scanning electron microscopy. In addition, we further verified the recovery of flavone di-C-glycosides from the DESs using macroporous resins and evaluated the reusability of the DESs as solvents. The results indicated that DES-F was an efficient and sustainable solvent for the extraction of bioactive flavone di-C-glycosides from Premna fulva Craib. Therefore, this novel strategy may represent a sustainable approach for the extraction of bioactive products and could make phytochemistry more attractive and environmentally friendly.

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.

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.

A series of novel structurally simple analogues based on nitidine was designed and synthesized in search of potent anticancer agents. The antitumor activity against human cancer cell lines (HepG2, A549, NCI-H460, and CNE1) was performed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay in vitro. The results showed that some of them had good anticancer activities, especially derivatives with a [(dimethylamino)ethyl]amino side chain in the C-6 position. Planar conjugated compounds 15a, 15b, and 15c, with IC50 values of 1.20 &mu, M, 1.87 &mu, M, and 1.19 &mu, M against CNE1 cells, respectively, were more active than nitidine chloride. Compound 15b and compound 15c with IC50 values of 1.19 &mu, M and 1.37 &mu, M against HepG2 cells and A549 cells demonstrated superior activities to nitidine. Besides, compound 5e which had a phenanthridinone core displayed extraordinary cytotoxicity against all test cells, particularly against CNE1 cells with the IC50 value of 1.13 &mu, M.

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

A new C25 terpene consisting of C15 and C10 terpenes, sarcaglabrin A, and two new sesquiterpene dimers, sarcaglabrins B and C, were isolated from the aerial parts of a medicinal plant Sarcandra glabra used in Guangxi Zhuang Autonomous Region, China. Their structures were elucidated on the basis of detailed spectroscopic analyses including calculation of the ECD spectrum. Sarcaglabrin A was assigned as a conjugate of lindenane type sesquiterpene and ocimene type monoterpene, while sarcaglabrins B and C were elucidated to be lindenane sesquiterpene dimers. Their cytotoxicity against human cancer cell lines were evaluated.

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.

Three new nor-clerodane diterpenoids, crotoeurins A-C (1-3), together with four known ones were isolated from the twigs and leaves of Croton euryphyllus. Among them, crotoeurin A (1) is a new nor-clerodane diterpenoid dimer with a unique cyclobutane ring via a [2+2] cycloaddition. Their structures were elucidated by spectroscopic analyses and the stereochemistry of 1 was confirmed by single-crystal X-ray diffraction analysis. Compounds 1-3 exhibited neurite outgrowth-promoting activity on NGF-mediated PC12 cells at concentration of 10 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

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.

Fordiae Cauliflorae Radix (FC, the root of Fordia cauliflora Hemsl) and Millettiae Pulchrae Radix [MP, the root of Millettia pulchra (Benth.) Kurz var. laxior (Dunn) Z. Wei], which go under the same local name of “Daluosan”, have long been used in Southern China for the treatment of stroke, paralysis, dementia in children, Alzheimer’s disease and other diseases. The same local name and similar functions always confuse users. To further utilize these two ethnodrugs and identify them unambiguously, an HPLC-DAD-ESI-IT-TOF-MSn method was developed to separate and characterize the flavonoids in FC and MP. A total of 41 flavonoids were detected, of which six compounds were identified by comparing their retention time and MS data with those of the reference standards, and the others were tentatively identified based on their tandem mass spectrometry data obtained in the positive ion detection mode. Nineteen of these characterized compounds are reported from these two plants for the first time.

An environmentally friendly, efficient method for transforming alkynes into substituted benzenes catalyzed by p-toluenesulfonic acid monohydrate ( p-TsOH·H 2O) under solvent-free conditions has been developed, which conforms to the principles of "green" chemistry and overcomes the shortcomings of previous methods for the synthesis of substituted benzenes. The reaction is quite general and provides good to excellent yields.

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.

Siamenoside I is the sweetest mogroside that has several kinds of bioactivities, and it is also a constituent of Siraitiae Fructus, a fruit and herb in China. Hitherto the metabolism of siamenoside I in human or animals remains unclear. To reveal its metabolic pathways, a high-performance liquid chromatography-electrospray ionization-ion trap-time of flight-multistage mass spectrometry (HPLC-ESI-IT-TOF-MS(n)) method was used to profile and identify its metabolites in rats. Altogether, 86 new metabolites were identified or tentatively identified, and 23 of them were also new metabolites of mogrosides. In rats, siamenoside I was found to undergo deglycosylation, hydroxylation, dehydrogenation, deoxygenation, isomerization, and glycosylation reactions. Among them, deoxygenation, pentahydroxylation, and didehydrogenation were novel metabolic reactions of mogrosides. The distributions of siamenoside I and its 86 metabolites in rat organs were firstly reported, and they were mainly distributed to intestine, stomach, kidney, and brain. The most widely distributed metabolite was mogroside IIIE. In addition, eight metabolites were bioactive according to literature. These findings would help to understand the metabolism and effective forms of siamenoside I and other mogrosides in vivo.

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．

Triterpene hexahydroxydiphenoyl (HHDP) esters have only been isolated from Castanopsis species, and the distribution of these esters in nature is of chemotaxonomical interest. In this study, the chemical constituents of the leaves of Castanopsis fissa were examined in detail to identify and isolate potential HHDP esters. Together with 53 known compounds, 3,4-di-O-galloyl-1-O-purpurogallin carbonyl quinic acid (1) and 3,24-(S)-HHDP-2α,3β,23,24-tetrahydroxytaraxastan-28,20β-olide (2) were isolated and their structures were elucidated by spectroscopic and chemical methods. The polyphenols of the leaves were mainly composed of galloyl quinic acids, triterpenes HHDP esters, ellagitannins and flavonol glycosides. In particular, the isolation yields of 1,3,4-trigalloyl quinic acid and compound 2 were 1.53% and 0.27%, respectively, from the fresh leaves. The presence of lipid soluble HHDP esters of oleanane-type triterpenes as one of the major metabolites is an important chemotaxonomical discovery. Lipase inhibition activities and ORAC values of the major constituents were compared. The triterpene HHDP ester showed moderate lipase inhibition activity and myricitrin gave the largest ORAC value., Phytochemistry, 72(16), pp.2006-2014; 2011

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

A novel, efficient, and accurate fingerprinting method using high performance liquid chromatography-photodiode array detection has been developed and optimized for the investigation and demonstration of the variance in chemical properties among Siraitia grosvenorii fruits from different origins. The effects of growth stages, cultivated varieties, collection locations, and fruit portions of the herb on chromatographic fingerprints were examined. Eleven compounds were identified on chromatograms by comparing the retention time and UV spectrum of each peak separately with those of external references. The results revealed that chromatographic fingerprints, combining similarity or hierarchical clustering analysis along with reference compounds, could efficiently identify and distinguish S. grosvenorii fruits from different sources, which provided helpful clues for studying the plants' secondary metabolites and benefitted quality control.

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.

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.

Three new nor-clerodane diterpenoids, crotoeurins A-C (1-3), together with four known ones were isolated from the twigs and leaves of Croton euryphyllus. Among them, crotoeurin A (1) is a new nor-clerodane diterpenoid dimer with a unique cyclobutane ring via a [2+2] cycloaddition. Their structures were elucidated by spectroscopic analyses and the stereochemistry of 1 was confirmed by single-crystal X-ray diffraction analysis. Compounds 1-3 exhibited neurite outgrowth-promoting activity on NGF-mediated PC12 cells at concentration of 10 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

Mogroside V, a cucurbitane-type saponin, is not only the major bioactive constituent of traditional Chinese medicine Siraitiae Fructus, but also a widely used sweetener. To clarify its biotransformation process and identify its effective forms in vivo, we studied its metabolism in a human intestinal bacteria incubation system, a rat hepatic 9000g supernatant (S9) incubation system, and rats. Meanwhile, the distribution of mogroside V and its metabolites was also reported firstly. Seventy-seven new metabolites, including 52 oxidation products formed by mono- to tetra- hydroxylation/dehydrogenation, were identified with the aid of HPLC in tandem with ESI ion trap (IT) TOF multistage mass spectrometry (HPLC-ESI-IT-TOF-MS(n)). Specifically, 14 metabolites were identified in human intestinal bacteria incubation system, 4 in hepatic S9 incubation system, 58 in faeces, 29 in urine, 14 in plasma, 34 in heart, 33 in liver, 39 in spleen, 39 in lungs, 42 in kidneys, 45 in stomach, and 51 in small intestine. The metabolic pathways of mogroside V were proposed and the identified metabolic reactions were deglycosylation, hydroxylation, dehydrogenation, isomerization, glucosylation, and methylation. Mogroside V and its metabolites were distributed unevenly in the organs of treated rats. Seven bioactive metabolites of mogroside V were identified, among which mogroside IIE was abundant in heart, liver, spleen and lung, suggesting that it may contribute to the bioactivities of mogroside V. Mogroside V was mainly excreted in urine, whereas its metabolites were mainly excreted in faeces. To our knowledge, this is the first report that a plant constituent can be biotransformed into more than 65 metabolites in vivo. These findings will improve understanding of the in vivo metabolism, distribution, and effective forms of mogroside V and congeneric molecules.

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.

In this study, we report three novel naturally occurring compounds, blapsins A (1) and B (2), and blapsamide (3) from the ethanol extract of the stink beetle, Blaps japanensis. The structures of these compounds were determined using spectroscopic methods. Compound 3 is a phenolic compound bearing a formamido group in the structure. Functional studies revealed that compounds 1 and 2 potently inhibited 14-3-3 protein-protein interactions (PPIs) with IC50 values of 9.2 and 10.0 mu M as determined by an ELISA assay, and 2.0 and 2.5 mu M in an FP assay, respectively. These compounds represent the first example of natural small-molecule 14-3-3 inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

A novel 18,19-seco-ursane saponin, aculeoside I ( 1 ), in addition to four known saponins were isolated from the leaves of Ilex aculeolata Nakai and identified by using spectroscopic and chemical methods. The structure of the new saponin was established as 3,19-dihydroxyl-16,21-epoxy-18,19-seco-13(18)-urs-ene-28-oic-acid-19-O- f - l -rhamnopyranosyl-(1 M 2)- f - l -arabinopyranoside.

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.

Mogroside IIE is a bitter triterpenoid saponin which is the main component of unripe Luo Han Guo fruit and a precursor of the commercially available sweetener mogroside V. In this study, we developed an enzymatic glycosyl transfer method, by which bitter mogroside IIE could be converted into a sweet triterpenoid saponin mixture. The reactant concentration, temperature, pH and buffer system were studied. New saponins with the α-glucose group were isolated from the resulting mixtures, and the structures of three components of the extract were determined. The structure-taste relationships of these derivatives were also studied together with those of the natural mogrosides. The number and stereoconfiguration of glucose groups present in the mogroside molecules were found to be the main factor to determine the sweet or bitter taste of a compound. The antioxidant and food safety properties were initially evaluated by their radical scavenging ability and via 7 day mice survival tests, respectively. The results showed that the sweet triterpenoid saponin mixture has the same favorable physiological and safety characteristics as the natural mogrosides.

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.

Monomeric ellagitannin named carlesiin A (I) and its macrocyclic dimer are isolated from leaves of Castanopsis carlesii.

A new cardenolide tupichinolide (1) and a new steroidal saponin tupichinin A (2), together with seven known compounds, were isolated from the rhizomes of Tupistra chinensis. Their structures were established using spectroscopic analysis and chemical methods. Compound 1 was the first cardenolide isolated from Tupistra chinensis and exhibited potent cytotoxicity against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480. (C) 2012 Elsevier B.V. All rights reserved.

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

The microstructure of the eutectic SnBi/Cu interface was investigated by transmission electron microscopy (TEM). In-situ and ex-situ thermal aging were conducted to study the nucleation and growth of Cu 3 Sn and Cu 6 Sn 5 on both polycrystalline and single crystalline Cu substrates. The growth kinetic analysis showed that although the growth of total IMCs (Cu 3 Sn + Cu 6 Sn 5 ) was similar on single and polycrystalline Cu substrates, the Cu 3 Sn grew faster on polycrystalline Cu substrate than that on single crystal Cu substrate, while Cu 6 Sn 5 grew slowly on polycrystalline Cu during thermal aging.

Transmission electron microscope observations and precise diffraction analyses were performed on the interfacial reaction between In-48Sn and Cu at the temperature range from 160°C to 250°C for up to 90 minutes. The results indicated that two different morphologies formed between In-48Sn and Cu at the temperature below 200°C: small-grain Cu 2 (In,Sn) at the Cu side and large-grain Cu 2 (In,Sn) at the solder side. If the soldering temperature is above 200°C, the Cu 6 (In,Sn) 5 phase is the first phase formed at the solder/Cu interface. However, the subsequent solid-state diffusion of In and Sn atoms through the initial Cu 6 (In,Sn) 5 layer drove the formation of Cu 9 (In,Sn) 4 phase between Cu 6 (In,Sn) 5 and Cu substrate.

The interfacial reaction between eutectic SnBi and Cu was studied by TEM after the sample was reflowed and aged in solid state, respectively. The microstructural evolution at the SnBi/Cu interface during reflowed and solid-state aged process was analyzed. The results show that there are two layers of intermetallic compounds (IMCs), Cu3Sn and Cu6Sn5, located at the interface between solder and Cu after the sample was reflowed. The segregation of Bi at the interface between Cu3Sn and Cu was observed. Furthermore, the segregation of Bi induced the formation of voids at Cu3Sn/Cu interface during solid-state aging process.

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.

Four new triterpenoid saponins, godosides A-D (1-4), along with eight known saponins, have been isolated from the fresh aerial parts of Ilex godajam. Structure elucidation of 1-4 was based on NMR, MS, IR and chemical analyses.

In a phytochemical and chemotaxonomical investigation of Castanopsis species (Fagaceae), new monomeric and dimeric ellagitannins, named carlesiins A (1) and B (2), were isolated from fresh leaves of Castanopsis carlesii along with 55 known compounds. Carlesiin A was identified as 1-O-galloyl-4,6-(S)- tergalloyl-ß-D-glucose. Carlesiin B is a macrocyclic ellagitannin dimer with a symmetrical structure composed of two tergalloyl and two glucopyranose moieties. Their structures were elucidated based on spectroscopic and chemical evidence., HETEROCYCLES, 86(1), pp.381-389; 2012