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Eight new complex flavanones with a novel linkage, cryptoyunnanones A-H (1-8), together with four known α-pyrones, were isolated from the leaves and twigs of Cryptocarya yunnanensis. The structures of 1-8 including their absolute configurations were characterized by spectroscopic data analysis and single-crystal X-ray crystallography. Plausible biosynthetic pathways for the formation of compounds 1-8 were proposed. Compounds 1-4 exhibited cytotoxicity against HCT-116, MDA-MB-231, and PC-3 cancer cells with IC50 values from 6.4 to 9.1 μM.

Five new α-pyrone derivatives, cryptoyunnanes A − E (1 − 5), together with four known analogues, were isolated from the leaves and twigs of Cryptocarya yunnanensis. Their structures including absol...

In the aim to evaluate the functional food property of Cinnamomum bejolghota, seven new lignans and neolignans, bejolghotins A-G (1-4 and 9-11), along with 14 known ones (5-8 and 12-21), were isolated and their structures including absolute configurations were elucidated by extensive spectroscopic data and electronic circular dichroism (ECD) analyses. All of the isolates were tested for antioxidant and human cancer cell proliferation inhibitory activities. Twenty compounds showed comparable antioxidant activity to the positive controls, and three significantly inhibited the growth of three cancer cell lines HCT-116, A549, and MDA-MB-231 with IC50 values of 0.78-2.93 μM, which confirmed its health benefits.

Two biphenyl-type neolignans with a rare dibenzofuran skeleton, including a new one piyunneolignan A (1) and a known one piperneolignan D (2), together with a new sesquiterpenoid piyunin A (3), were isolated from the leaves and twigs of Piper yunnanense. Their structures were established on the basis of comprehensive spectroscopic data analysis and electronic circular dichroism (ECD) calculation. Piyunneolignan A (1) featured a rare C-2-C-2'/C-3-O-C-3' linkage. Compounds 1-3 were evaluated for their antimicrobial and cytotoxic activities against a panel of bacteria, fungi, and human cancer cell lines, respectively.

Two new spiroketal derivatives with an unprecedented amino group, 2'-aminodechloromaldoxin (1) and 2'-aminodechlorogeodoxin (2), along with one known analogue dechloromaldoxin (3), were isolated from the plant endophytic fungus Pestalotiopsis flavidula. Their structures were elucidated on the basis of extensive spectroscopic analysis. The purification was cytotoxicity-guided which indicated the extract, fractions and compounds were evaluated in vitro for anti-proliferative activity against a panel of human cancer cell lines. The results showed compounds 1 and 2 with moderate cytotoxicity while 3 was inactive, which suggested -NH2 group might play a very important role for their cytotoxicity. This is the first study for P. flavidula and the first time to report the spiroketal derivatives as alkaloids from the Pestalotiopsis genus.

Five undescribed cycloartane triterpenoids, including two cycloartane trinor-triterpenoids, were isolated from a 70% ethanol extract of the whole plant of Actaea vaginata (Ranunculaceae), together with thirteen known cycloartane triterpenoids. Their structures were determined by spectroscopic techniques and quantum chemical calculations for intramolecular noncovalent interactions with reduced density gradient method. All compounds were evaluated for their anti-inflammatory effects by a lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production model in RAW264.7 macrophage cells, and some showed potent inhibitory effects with IC 50 values ranging from 5.0 to 24.4 μ M. Further mechanism studies showed that one compound dose-dependently suppressed LPS-induced NO production and pro-inflammatory cytokines secretion, and decreased the expression of iNOS, through inhibiting NF- κ B activation.

Phytochemical investigation on the twigs and leaves of Trichilia sinensis led to the isolation of two previously undescribed limonoids (i.e., trichiliasinenoids D and E, 1 and 2), two previously undescribed phenolic acids (3 and 4), and one previously undescribed natural phenolic acid dimer (5), together with 11 known compounds (6-16). Their structures were elucidated by extensive spectroscopic analysis (IR, UV, HRESIMS, 1D and 2D NMR) and chemical techniques. The potential anti-inflammatory activities of all the compounds were evaluated in lipopolysaccharide-stimulated RAW 264.7 cells. Among these isolates, compounds 1, 2, 6, and 11-13 expressed weak NO inhibition. The antibacterial activities of all the compounds against bacteria were also tested in vitro. Compound 16 exhibited moderate antibacterial activities against Escherichia Coli.

Eleven previously uncharacterized steroids, along with three analogs were isolated from Aglaia lawii leaves. Their structures were definitely characterized by the methods of NMR, MS, IR, ECD and X-ray crystallography study. Among these unreported compounds, 3-epi-dyscusin C, 3-epi-lansisterone E and (Z)-2α-hydroxyaglawone were C-21 pregnane steroids incorporating a highly oxygenated ring A, while others were Δ5-3β-hydroxy-7-ketosteroids bearing different ring D and C-17 aliphatic chains. All isolates were evaluated for nitric oxide (NO) inhibitory activities. 3-Epi-dyscusin C, 3-epi-lansisterone E, (Z)-2α-hydroxyaglawone and 17(20)E-dyscusin B showed significant anti-inflammatory activities with IC50 values of NO inhibition less than 10 μM (in the range from 4.47 ± 0.36 to 7.67 ± 0.46 μM).

Four previously undescribed steroids, identified as (3S,7S,8S,9S,10R,13S,14S,16S,17R,20S)-7α-methoxy-ergosta-5,24(28)-dien-3β,16β,20-triol (1), ergosta-5,24(28)-dien-3β,7α,16β-triol (2), ergosta-5,25-dien-3β,7α,16β,20-tetrol (3) and 7α,16β,24α-trihydroxy-varninasterol (4), as well as five known analogues (5–9), were isolated from the leaves and twigs of Dysoxylum pallens Hiern (Meliaceae). Their structures were elucidated based on extensive spectroscopic analysis such as HR-ESI-MS, 1D and 2D NMR, UV, and IR. The absolute configuration of compound 1 was determined by X-ray diffraction analysis. Selected compounds were evaluated for their cytotoxic activities. Compounds 1, 2, and 8 exhibited moderate cytotoxic activity against HL-60, Hela, and HepG2 tumor cell lines with IC50 ranged from 11.09 to 17.51 μM.

The aim of this study was to evaluate the role of bamboo shoot fiber (BSF) in regulating insulin sensitivity in mice. Two BSFs were obtained from D. hamiltonii and D. latiforus. C57BL/6 mice were fed a low-fat diet or a high-fat diet with 10% fiber as cellulose (HFC), or two BSFs (HFDH or HFDL) for 13 weeks. Compared with the HFC group, HFDH and HFDL groups exhibited considerably less body weight gain, lower levels of fasting glucose and insulin, and lower values of glucose areas under the curve during glucose and insulin tolerance tests. BSF groups also had lower glucoses stimulated insulin concentrations. In addition, more phosphorylation of Akt in insulin target tissues was associated with higher protein expression levels of PGC-1α and phosphorylated AMPK and p38 in BSF fed mice. These results indicated that BSF improved insulin sensitivity in high-fat diet-fed mice through enhancing insulin signaling and activating PGC-1α.

Ethnopharmacological relevance Salvia plebeia R. Brown, a traditional Chinese medicinal herb, has been used to treat inflammatory diseases such as cough, hepatitis, and diarrhea for a long history. Aim of the study The aim of the present study was to isolate and identify potential anti-inflammatory agents from the herb of S. plebeia, which may have contributed to its folk pharmacological use in the treatment of inflammatory diseases. Material and methods The aerial parts of S. plebeia were extracted with 95% ethanol and separated by silica gel, RP-C18, Sephadex LH-20, and HPLC. The structures of the isolated compounds were elucidated by extensive spectroscopic analysis (MS, NMR, and X-ray). Anti-inflammatory activities of all compounds were evaluated by the model of LPS-induced up-regulated of NO in Raw264.7 macrophages. The expression levels of cytokine (TNF-α) and proteins (iNOS and COX-2) were assessed by ELISA kit and Western blotting analysis, respectively. Furthermore, the influences of salviplenoid A (1) on NF-κB and MAPK signaling pathways were determined by Western blotting analysis and immunofluorescence assay. Results Six new (1−6, salviplenoids A–F) and ten known (7–16) sesquiterpenoids were isolated from the herb of S. plebeia. The absolute configurations of compounds 1, 2, and 7 were determined by X-ray diffraction. The new eudesmane-type sesquiterpenoid, salviplenoid A (1), significantly decreased the release of NO and TNF-α and the expression of proteins iNOS and COX-2. In addition, the biochemical mechanistic study indicated that 1 regulated the NF-κB dependent transcriptional activity through inhibiting the nuclear translocation of p50/p65 dimer and decreasing the phosphorylation of IκB and Erk1/2. Conclusions Among all sesquiterpenoids isolated from S. plebeian, the new salviplenoid A (1) exhibited the most potent anti-inflammatory activity in LPS-induced Raw264.7 cells via inhibition of NF-κB and Erk1/2 signaling pathways.

Four new limonoids, named as trichiconlide G (1), 2-hydroxyltrijugin F (2), 23-oxo-21-hydroxyltrijugin F (3), 21-oxo-23-hydroxyltrijugin F (4), along with sixteen known analogues (5–20) were isolated from the leaves and twigs of Trichilia connaroides. Their structures and absolute configurations were determined by spectroscopic analyses, X-ray diffraction analysis, and TD-DFT-ECD calculations. Trichiconlide G (1) is one rare naturally occurring 1,2-seco phragmalin-type limonoid bearing a C-7/28 δ-lactone ring. Additionally, 2-hydroxyltrijugin F (2), 23-oxo-21-hydroxyltrijugin F (3), and 21-oxo-23-hydroxyltrijugin F (4) are three naturally occurring limonoids with a rare C-16/8 δ-lactone ring. All isolates were evaluated for their cytotoxic and anti-inflammatory activities. None of compounds exhibited cytotoxicity against five human cancer cell lines A-549, HepG2, 5-8F, Siha, and SCC-4 at the concentration of 40 μM. Compounds 16 and 17 showed moderate anti-inflammatory activity with IC50 values of 28.45 ± 2.51 and 22.66 ± 2.01 μM, respectively.

Trichiliasinenoids A–C (1–3), three new limonoids with an unprecedented C-29-C-7 connecting carbon skeleton formed by migration of C-7 from C-6 to C-29 of a mexicanolide-type limonoid precursor were isolated from the leaves and twigs of Trichilia sinensis. Their structures were assigned by spectroscopic analysis, and the absolute configurations were determined by X-ray crystallography (1) and ECD calculation (2 and 3). A possible biosynthetic pathway of 1 was also proposed. Compound 2 exhibited moderate cytotoxicity against HL-60 cells and weak cytotoxicity against SMMC-7721cells.

Two new prenylated acetophenone derivatives racemates, meliviticines A ( 1 ) and B ( 2 ) with unprecedented rearranged skeletons, were isolated from Melicope viticina . Subsequent chiral resolution led to the separation of two pairs of enantiomers, (±)-meliviticines A ( 1a / 1b ) and (±)-meliviticines B ( 2a / 2b ). Their structures including absolute configurations were elucidated by extensive spectroscopic data, electronic circular dichroism analysis, and X-ray crystallography. A plausible biosynthetic pathway of 1 and 2 , involving ring cleavage and rearrangement of the prenylated acetophenone backbone was proposed. All the isolates showed moderate antimicrobial activities with MIC values of 25–50 μ g/mL against several bacterial and fungal strains.

Three new arylalkenyl α,β-unsaturated δ-lactones, cryptobrachytones A–C (1–3), together with one known analogue kurzilactone (4), were isolated from the leaves and twigs of Cryptocarya brachythyrsa. Their structures were elucidated based on extensive spectroscopic data and electronic circular dichroism (ECD) analysis. All the isolates were evaluated in vitro for anti-proliferative activity against a panel of five human cancer cell lines and one human normal cell, respectively, and the results showed 1, 2 and 4 possessing significant selective cytotoxicity toward the human cancer cell lines with IC50 values from 5.41 to 15.43 μM. This is the first study for C. brachythyrsa.

Curcumenol was firstly revealed as a pair of hemiacetal–ketone tautomers in solutions by using temperature variation 1H-NMR experiments, 2D NMR, and chemical methods. Quantum chemical calculation allowed the explanation of its spectroscopic behavior. An antioxidative SAR study on its derivatives verified the tautomeric bio-significance. Curcumenol also remarkably enhanced myogenic differentiation and mitochondrial function.

Eight new prenylated coumarins (1a/1b, 2a/2b, and 3–6) including two pairs of enantiomers (1a/1b and 2a/2b), a new phenolic acid derivative, methyl (E)-3,4-bis(4-hydroxyphenyl)-4-oxobut-2-enoate (7), and 33 known compounds (8–40) were isolated from the stems of Toddalia asiatica. Their structures were established from spectroscopic data and by chemical methods. The absolute configurations of two pairs of enantiomers (1a/1b and 2a/2b) were determined by X-ray diffraction analysis together with ECD and specific optical rotation calculations. The inhibitory effects of selected compounds against phosphodiesterase-4 (PDE4) were evaluated, and compounds 12, 19, 21–23, 26, 34, and 35 exhibited PDE4 inhibition activities with IC50 values less than 10 μM.

Choosing a suitable solvent system for a counter-current chromatography separation presents a challenge for many researchers. In this study we introduce a quick method of separating a target compound from the bark of Zanthoxylum myriacanthum var. pubescens by counter-current chromatography. This method relies on the thin-layer chromatography based generally useful estimation of solvent systems. This paper will present how to quickly choose a suitable solvent system with a thin-layer chromatography based generally useful estimation of solvent systems working chart. O-Methyltembamide (1) was enriched by counter-current chromatography using n-hexane/ethyl acetate/methanol/water (6:4:6:4) as the solvent system. Further purification was achieved by high-performance liquid chromatography with purities of 98.2% from Z. myriacanthum var. pubescens bark. This article is protected by copyright. All rights reserved

Five new compounds, namely fimbricalyxoids A–D (1–4) and 13-O-methylfimbricalyx B (5), together with five known compounds (6–10) were isolated from the leaves and stems of Strophioblachia fimbricalyx. Fimbricalyxoid A (1), a cleistanthane diterpenoid, possesses a rare 3,20-oxybridge, while fimbricalyxoids C–D (3–4) are the first seco-ring-A pentanorditerpenoids. Their structures and absolute configuration were established based on NMR and MS data and ECD calculation (1). Compounds 1, 6, and 7 exhibited cytotoxicity against five human tumor cell lines with IC50 values in the range of 1.4–8.2 μM.

Two new vilasinin limonoids, walsuronoids DnE ( 1 n 2 ), along with three known compounds ( 3 n 5 ) were isolated and identified from the leaves ofn Walsura robusta . Their structures were established based on extensive spectroscopic analysis. Compoundsn 1 n 2 nshowed potent cytotoxic activity against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cancer cell lines, with IC 50 nvalues ranging from 2.7 to 4.5nmM. The absolute configuration ofn 3 nwas determined to be (24 R , 25 S )-cycloartane-3b,24,25,26-tetrol for the first time by using X-ray diffraction analysis.

Twelve previously undescribed mexicanolide-type limonoids, including two pairs of isomers, together with seven known analogues were isolated from the twigs and leaves of Cipadessa baccifera. Their structures were determined by extensive spectroscopic methods and electronic circular dichroism (ECD) calculations. Structural variations mainly occurred at the attachment of C-3 and the carbon residues linked to C-17. 21-deoxo-23-oxofebrifugin A and 3-O-detigloyl-3-O-isobutyryl-21-deoxo-23-oxofebrifugin A are two rare naturally occurring mexicanolide-type limonoids bearing an α,β-unsaturated-γ-lactone motif at C-17. Moreover, cipaferen R is the first degraded tetranortriterpenoid derivative featuring an unique acetyl group at C-17. Some isolated compounds were evaluated for nematicidal, antifungal, cytotoxic (against five human cancer cell lines), and acetylcholinesterase inhibitory activities. No nematicidal and antifungal activities were observed, yet 3-O-detigloyl-3-O-isobutyrylfebrifugin A, febrifugin A, febrifugin, and khaysin T exhibited moderate cytotoxic activity against the tested cells with IC50 values ranging from 18.56 ± 0.27 to 38.00 ± 0.85 μM, and 3-O-detigloyl-3-O-isobutyrylfebrifugin A, granatumin E, khaysin T, and 2′S-cipadesin A showed moderate inhibitory activities against acetylcholinesterase (AChE) at 50 μM.

Eight previously undescribed diterpenoids, euphoroyleans A−H, including two cembranes, three ingenanes, two ent-atisanes, and one ent-kaurane, along with 22 known analogues were isolated from the whole plants of Euphorbia royleana. The structures of euphoroyleans A−H, including the absolute configurations, were elucidated by extensive spectroscopic analyses, chemical transformation, and single crystal X-ray diffractions. All the isolates were screened for their chemoreversal abilities on P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) cancer cell line HepG2/DOX, and eight compounds exhibited significant activities. Among them, ingol-3,7,12-triacetate-8-benzoate, the most active MDR modulator with no obvious cytotoxicity, could enhance the efficacy of anticancer drug DOX to ca. 105 folds at 10 μM, being stronger than the positive drug verapamil. Mechanistic study revealed that ingol-3,7,12-triacetate-8-benzoate could inhibit the transport activity of P-gp rather than its expression, and the possible recognition mechanism between compounds and P-gp was predicted by molecular docking.

Chemical investigation of Lansium domesticum has led to the isolation of two undescribed compounds, namely 17(20)E-dyscusin B (1) and 17(20)Z-dyscusin B (2), as well as three known ones (3 – 5). Structural elucidation was accomplished by the analysis of NMR, MS and IR data. Compounds 1 and 2 were a pair of Δ17(20) geometric isomers of pregnane steroids and showed the significant nitric oxide (NO) inhibitory activities.

Chemical investigation of the aerial parts of Mikania micrantha led to the isolation of eight sesquiterpenoids and ten diterpenoids, including five cadinane sesquiterpenoids (1−5), three bisabolene sesquiterpenoids (6 − 8), nine ent-kaurane diterpenoids (9–17), and an abietane diterpenoid (18). Among them, 1 − 3 are new and feature a rare lactone or furan ring derived from C-6 isopropyl group side chain. Compound 18 was isolated from genus Mikania for the first time, and was also the first example of abietane-type diterpenoids from this plant. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HRESIMS, and ECD). All compounds were examined for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 macrophage cells, and compound 18 exhibited pronounced inhibition on NO production (IC50 = 11.04 µM), being comparable to the positive control, quercetin (IC50 = 11.15 µM).

Four highly rearranged labdane-type diterpenoids, maximumins A–D (1–4) possessing different new carbon skeletons, together with a biosynthetically related known analog 5 were isolated from Amomum maximum. The structures of new compounds with absolute configurations were characterized by spectroscopic and computational approaches. The plausible biogenetic pathways for 1–4 were proposed. These compounds showed moderate to weak activities against nuclear factor kappa B (NF-κB).

Mulberry Diels-Alder-type adducts (MDAAs) are a group of structurally unique natural products biosynthetically derived from the intermolecular [4 + 2] cycloaddition of a dehydroprenylphenol and a chalcone. In the current study, ten MDAAs, including an undescribed one, inethermulberrofuran C, were isolated from the root bark of Morus alba. The anti-Alzheimer's disease (anti-AD) properties of these isolates were systematically screened for a series of potential targets (Aβ self-aggregation, tau aggregation, and ChEs) as well as the anti-neuroinflammatory and neuroprotective activities. Four compounds, mulberrofuran C, mulberrofuran K, mulberrofuran G, and isomulberrofuran G, turned out to be potent multi-targeted agents for AD. Among them, mulberrofuran K with a good blood-brain barrier (BBB) permeability (8.7 ± 0.3 × 10−6 cm/s) was selected as a promising candidate for further mechanism study in glutamate-induced HT22 cell model, which showed its neuroprotective ability on up-regulation of the glutathione (GSH) level and suppression of the reactive oxygen species (ROS) production.

Background & objectives: Diabetes is a metabolic disorder and it can affect many organs and different types of antioxidant enzymes through increased production of reactive oxygen species (ROS). A few essential oils have been reported to have antioxidant and antidiabetic effects. The objective of our present study is to explore the anti-diabetic potential of Maqian essential oil (MQEO). Aim: The aim of this study was to evaluate the hepatoprotective and antioxidant effect of MQEO in streptozotocin (STZ)-induced diabetes in mice. Method: Diabetes was induced in male ICR mice with a single intraperitoneal injection of STZ (200 mg/kg body weight). MQEO was administered orally for 7 days. At the end of experiment liver was weighed and enzymatic and non-enzymatic oxidative stress parameters were measured, and part of liver was examined by hematoxylin/eosin staining. Results: MQEO treatment resulted in significantly decreased MDA level and increased antioxidant enzymes including superoxide dismutase, catalase, glutathione peroxidase and glutathione-Stransferase in STZ-diabetic mice. Histology examination showed severe pathology changes in diabetic mice including congestion of sinusoids and focal necrosis in liver and MQEO restored tissue architecture almost as in the normal control mice. Conclusion: MQEO has pronounced antioxidant effect and could reverse liver damages in STZ-induced diabetic mice. It could be useful for controlling diabetic complications.

Two new rearranged limonoids, trichiliton I (1) and 12-deacetoxyltrijugin A (2) along with four previously reported compounds (3-6) were isolated from the roots of Trichilia connaroides. Their structures were established on the basis of extensive spectroscopic analysis including HR-ESI-MS and 1D and 2D NMR. The new compounds 1 and 2 exhibited weak inhibitory effects on lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 cells in a dose-dependent manner.n

This study reports the essential oils chemical composition and antioxidant and antimicrobial potentials of the leaves of Phrynium pubinerve Blume and Thysanolaena latifolia (Roxb. ex Hornem.) Honda, which are used as natural packaging materials by ethnic groups in Xishuangbanna, southwest China. GCeMS analysis identified 46 and 21 components, representing 88.6% and 93.4% of the essential oils of P. pubinerve and T. latifolia, respectively. The major constituents for P. pubinerve were (Z)-3-hexen-1-ol (17.31%), (E)-2-hexenal (9.01%) and 1-hexanol (8.61%). The major constituents for T. latifolia were (Z)3-hexen-1-ol (28.79%), phytol (12.30) and (E)-b-ionone (9.54%). Both the essential oils and ethanol extracts showed antioxidant activity in DPPH test (IC50 values ¼ 192.47e706.07 mg/ml), ABTS assay (IC50 values ¼ 35.54e134.97 mg/ml) and FRAP assays. The essential oils showed considerable antimicrobial activity against pathogenic bacteria and spoilage organisms, with MIC and MBC values in the ranges of 64 e3072 mg/ml and 64e4096 mg/ml, respectively. The bioactivities of these two plant species validate the traditional use of these two plants, suggesting that both could be new sources of natural antioxidant and antimicrobial agents for the packaging, medical and functional food industries.

Twelve compounds were isolated from the roots of Aglaia odorata. Their structures were established on the basis of NMR and MS data as rocaglaol (1), rocaglamide (2), eichlerialactone (3), sapelins A (4), isofouquierone (5), eichlerianic acid (6), shoreic acid (7), agladupol E (8), 3-epimeliantriol (9), cleomiscosins B (10), 2β,3β-dihydroxy-5α-pregnane-16-one (11) and β-D-glucopyranos-1-yl N-methylpyrrole-2-carboxylate (12). Among them, compounds 1 and 2 showed significant cytotoxicity against human cancer cell (HL-60, SMMC-7721, A-549, MCF-7 and SW480) with IC50 values of 0.007-0.095 μM, while compounds 3-5 and 10 and 11 showed moderate to no cytotoxicity (IC50 0.43 to values >40 μM). Compound 6 showed only weak cytotoxicity (IC50 6.87 to >40 μM) and its epmier 7 was completely inactivite (IC50>40 μM) in the assay. However, potent synergistic effect was observed when the molar ratio of 6 to 7 is between 4:1 and 1:1.

Four new diterpenoids, named aspidoptoids A&ndash, D (1&ndash, 4), together with two known analogues (5&ndash, 6) were isolated from Aspidopterys obcordata vine. Aspidoptoids A&ndash, B (1&ndash, 2) are the first examples of phenylethylene-bearing 20-nor-diterpenoids of which aspidoptoid B (2) possesses a rare 3,10-oxybridge. Their structures and absolute configuration were determined by extensive spectroscopic analyses (IR, HRESIMS, 1D and 2D NMR) and electronic circular dichroism (ECD) calculation. In addition, all the isolates were evaluated for their cytotoxic activities and inhibitory effects on the nitric oxide (NO) production.

Ethnopharmacological relevance: Magian (Zanthoxylum myriacanthum var. pubescens Huang) is widely consumed as an indigenous remedy for digestive disorders, detoxification, detumescence and analgesia by the ethnic groups in Xishuangbanna, SW China. A related species, Huajiao (Zanthoxylum schinifolium Sieb. et Zucc.), has similar uses in traditional Chinese medicine. We aimed to scientifically validate the traditional uses by investigating and comparing the chemical composition, antimicrobial and anti-inflammatory activities of the essential oils of Magian and Huajiao. Materials and methods: Essential oils were collected from the fruits of Magian and Huajiao by simultaneous distillation extraction and identified by gas chromatography-mass spectrometry (GC-MS) analysis. To assess antimicrobial activity, the minimum inhibitory and bactericidal concentrations (MIC and MBC) against 7 microbial strains, including 5 food-borne pathogens, were evaluated by serial dilution with a standardized microdilution broth methodology. For anti-inflammatory activity, the cell viability and nitric oxide (NO) production were determined on lipopolysaccharide (LPS)-stimulated RAW 264.7 cells by MTS assay and the Griess reagent system, respectively. Results: The essential oil from Magian is rich in limonene (67.06%) and has strong antimicrobial activity against the tested pathogens and spoilage organisms, with MIC ranging from 64 to1024 mu g/ml and MBC ranging from 64 to 2048 mu g/ml. It also showed anti-inflammatory activity by significantly inhibiting nitric oxide (NO) production induced by LPS in RAW 264.7 cells at 0.04 parts per thousand without effects on cell viability. Furthermore, it showed relatively stronger antimicrobial and anti-inflammatory activities than the essential oil from Huajiao. Conclusions: Our findings not only justify the use of Magian as an indigenous remedy for digestive disorders, detoxification, detumescence and analgesia, but also suggest that it could be promoted as a preferred substitute for Huajiao. (C) 2014 Elsevier Ireland Ltd. All rights reserved.

Nine new cedrelone limonoids, namely, walsuranolide B (1), 11β-hydroxy-23-O-methylwalsuranolide (2), yunnanolide A (3), yunnanol A (4), 11β-hydroxyisowalsuranolide (5), 11β-hydroxy-1,2-dihydroisowalsuranolide (6), 1α,11β-dihydroxy-1,2-dihydroisowalsuranolide (7), 11β-hydroxy-1α-methoxy-1,2-dihydroisowalsuranolide (8), and yunnanolide B (9), together with a new cycloartane triterpenoid, (24S*,25R*)-cycloartane-3β,24,25,26-tetrol (10), were isolated from the leaves and twigs of Walsura yunnanensis. Their structures were elucidated on the basis of spectroscopic analysis and by comparison with literature data. Compounds 3 and 5 exhibited potent cytotoxicity against five human tumor cell lines with IC50 values in the range 2.2-4.2 μM.

Two new limonoids, namely 14,15-didehydroruageanin A (1) and 3-O-methyl- butyrylseneganolide A (2), were isolated from the fruits of Khaya ivorensis along with six known limonoids: seneganolide A (3), 1,3-dideacetylkhivorin (4), 7-deacetylkhivorin (5), 3-deacetylkhivorin (6), 1-deacetylkhivorin (7), and 3-deacetyl-7-oxokhivorin (8). All the compounds were evaluated for their cytotoxicity against five tumor cell lines.

Two new compounds, the 6-oxo oleanane-type triterpenoid uncarilic acid, and its 5,6-secotriterpenoid derivative, secouncarilic acid, were isolated from the hooks and stems of Uucaria sessilifructus together with seven known ursane-type triterpenoids. Uncarilic acid is the second 6-oxo oleanane-type triterpenoid ever reported, while secouncarilic acid is the first oleanane-type 5,6-secotriterpenoid. A plausible biosynthetic pathway from uncarilic acid to secouncarilic acid was also postulated. The inhibitory activities of all the nine compounds against LPS-induced nitric oxide production in RAW264.7 macrophages were evaluated.

Five selaginellin derivatives (1 and 3–6) including a new one, selaginellin T (1), and a new triarylbenzophenone analog, selagibenzophenone A (2), were isolated from the whole plants of Selaginella pulvinata. Their structures were determined by 1D- and 2D-NMR and HR-ESI-MS data. Selagibenzophenone A (2) is the first example of naturally occurring triarylbenzophenone. The results of the phosphodiesterase-4 (PDE4) inhibitory screening assays showed that compounds 1−6 exhibited potent activities with the IC50 values in the range of 1.04−9.35 μM.

Phytochemical investigation of Strychnos nitida has led to the isolation of three new racemic pyridocarbazole alkaloids, (±)-stritidas A-C (1–3) and three known monoterpenoid indole alkaloids (4–6). Compounds 2 and 3 represent the first examples of pyridocarbazole alkaloids featuring an N-2-hydroxyethyl moiety. Their structures were determined by combined spectroscopic data (MS, UV, IR and NMR) and chemical methods.

Bioassay-guided isolation of the stems of Gelsemium elegans has led to the isolation of two new Gelsemium alkaloids, 21-(2-oxopropyl)-koumine (1) and 11-methoxygelselegine (2), and two known alkaloids, koumine (3) and gelselegine (4). The structures of 1-2 were determined by spectroscopic (for both) and single-crystal X-ray diffraction (for 1) analysis. All compounds isolated were evaluated for their potential as immunosuppressive agents and the data suggested that Gelsemium alkaloids of different structural types possibly have potential as immunosuppressive agents. (C) 2012 Elsevier B.V. All rights reserved.

The young leaves of seven Ficus species including F. virens var. sublanceolata, F. auriculata, F. vasculosa, F. callosa, F. virens var. verins, F. racemosa and F. oligodon are traditionally consumed by local people in Xishuangbanna. The dry young leaves were studied for their total phenolic and flavonoid contents. The 90% ethanolic extracts of the young leaves were screened for potential antioxidant capacity by employing different in vitro assays including ABTS + and DPPH radical scavenging capacities, ferric reducing power and lipid peroxidation inhibition properties. Extracts from F. virens var. sublanceolata and F. auriculata showed higher antioxidant activity in all the systems than other species. We concluded that these two species are promising sources of natural dietary antioxidants. According to our statistical analysis, the total phenolic and flavonoid contents appear to be responsible, at least in part, for the extracts’ excellent antioxidant capacity and all the extracts exhibited dose-dependent antioxidant activity.

Nine new alkaloids of the koumine (1–4), humantenine (5–7), and yohimbane (8, 9) types as well as 12 known analogues were isolated from the leaves and vine stems of Gelsemium elegans. Compound 1 is the first N-4-demethyl alkaloid of the koumine type, compound 7 is the first nor-humantenine alkaloid, and compounds 8 and 9 are the first N-1-oxide and the first seco-E-ring alkaloids, respectively, of the yohimbane type. Compounds 1 and 7 exhibited moderate cytotoxicity against five human tumor cell lines with IC50 values in the range 4.6–9.3 μM.

Ten cedrelone limonoids were isolated from the leaves of Trichilia americana. These compounds include americanolides A-D (1-4), 1,2-dihydrodeacetylhirtin (5), 1 alpha-hydroxy-1,2-dihydrodeacetylhirtin (6), 1ahydroxy-1,2-dihydrohirtin (7), 1 alpha-methoxy-1,2-dihydrodeacetylhirtin (8), 11 beta-hydroxy-12 alpha-propanoyloxycedrelone (9), and 1 alpha,11 beta-dihydroxy-1,2-dihydrocedrelone (10), as well as two previously reported compounds, deacetylhirtin (11) and hirtin (12). Their structures were characterized on the basis of spectroscopic studies, and the assignment of the absolute configuration of americanolide A (1) was supported by single-crystal X-ray diffraction studies. The cytotoxic activities of all isolated compounds were also evaluated against five human tumour cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW-480) using an MTS assay. Compounds 11 and 12 showed significant cytotoxicity with IC50 values ranging from 0.1 to 0.5 mu M, and compounds 5, 6, 7, 8, 9, and 10 exhibited potent or selective cytotoxic activity with IC50 values ranging from 1.0 to 39.6 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

Dysoxylentin A (1), the first 21-nortriterpenoid bearing a 2-(propan-2-ylidenyl)furan-3(2H)-one functional group was isolated from the stem of Dysoxylum lenticellatum. Its structure was elucidated by extensive spectroscopic analysis. A plausible biosynthetic pathway was postulated. Dysoxylentin A exhibited selective cytotoxicity against HL-60 tumor cell line. (C) 2011 Elsevier Ltd. All rights reserved.

Cratoxylum formosum ssp. pruniflorum is a valuable species distributed in Yunnan and Guangxi Provinces of China. Thirteen compounds have been isolated from the bark of C. formosum ssp. pruniflorum. Their structures were identified on the basis of spectroscopic analysis and chemical evidence: epifriedelinol (2), vismiaquinone B (3), 3,8-dihydroxy-1,2,4trimethoxyxanthone (5), methyl-2,6-dihydroxy-3,4-dimethylbenzoate (6), 1,7-dihydroxy-4-methoxyxanthone (7), 11-hydroxy5-methoxy-2,2,9-trimethyl-2H-naphtho[1,2-b]pyran-7,12-dione (8), physcion (9), 1,8-dihydroxy-2-methoxyxanthone (10), vismione B (11), neriifolone C (12), and 1,7-dihydroxyxanthone (13). Compounds 1 and 4 were identified by direct comparison with authentic samples as -sitosterol and friedelin, respectively. Among them, compounds 1, 2–6, 10, 11, and 13 were isolated from C. formosum ssp. pruniflorum for the first time. The air-dried and powdered bark of Cratoxylum formosum ssp. pruniflorum (7.0 kg) were extracted with 95% aqueous ethanol and filtered at room temperature. The filtrate was concentrated and extracted with petroleum ether, then extracted by ethyl acetate. The petroleum ether extract (100 g) was subjected to silica gel column chromatography eluted with a petroleum ether–EtOAc (90:10 40:60) gradient system to furnish six fractions, G1–G6. All fractions were collected and combined by monitoring with TLC. Fraction G2 (21 g) was further chromatographed over RP-18 (MeOH–H2O 70:30 100:0) to provide subfractions G2a–G2c. Subfraction G2a was further chromatographed over silica gel using acetone–petroleum ether (10%) to give compounds 1 (7 mg) and 2 (20 mg). Then, in the same way, G2b and G2c were further separated to give compounds 3 (15 mg), 4 (17 mg), 5 (12 mg), 6 (10 mg), and 7 (10 mg). Subfraction G4 was treated in the same way to give compound 11 (11 mg). The ethyl acetate (250 g) extract was subjected to silica gel column chromatography eluted with a methanol–chloroform (100:1 5:1) gradient system to furnish five fractions, F1–F5. All fractions were collected and combined by monitoring with TLC. Fraction F3 was further chromatographed over RP-18 (MeOH–H2O 60:40 100:0) to provide subfractions F3a–F3b. The F3a part was further purified by Sephadex LH-20 (MeOH) to obtain compounds 6 (7 mg), 7 (13 mg), and 12 (15 mg). Then, in the same way, F3b was further separated to give compounds 8 (14 mg), 9 (13 mg), 10 (17 mg), and 13 (13 mg). Epifriedelinol (2), colorless amorphous powder, C30H52O. ESI-MS m/z 429 [M + H]+. The MS and NMR spectral data were consistent with those reported 1 . Vismiaquinone B (3), yellow amorphous powder, C21H20O6. ESI-MS m/z 369 [M + H] +. The MS and NMR spectral data were consistent with those reported 2 . 3,8-Dihydroxy-1,2,4-trimethoxyxanthone (5), yellow amorphous powder, C16H14O7. ESI-MS m/z 319 [M + H]+. The MS and NMR spectral data were consistent with those reported 3 . Methyl 2,6-dihydroxy-3,4-dimethylbenzoate (6), colorless amorphous powder, C10H12O4. ESI-MS m/z 197 [M + H] +. The MS and NMR spectral data were consistent with those reported 4 . 7-Dihydroxy-4-methoxyxanthone (7), yellow amorphous powder, C14H10O5. ESI-MS m/z 259 [M + H]+. The MS and NMR spectral data were consistent with those reported 5 . 11-Hydroxy-5-methoxy-2,2,9-trimethyl-2H-naphtho[1,2-b]pyran-7,12-dione (8), yellow amorphous powder, C21H18O5. ESI-MS m/z 351 [M + H] +. The MS and NMR spectral data were consistent with those reported 6 . Physcion (9), yellow amorphous powder, C16H12O5. ESI-MS m/z 285 [M + H]+. The MS and NMR spectral data were consistent with those reported 7 .

A new prenylated xanthone, named bannaxanthone I (1), has been isolated from the leaves of Garcinia xipshuanbannaensis, along with five other known compounds, bannaxanthone E (2), mangostinone (3), tovophyllin A (4), garcinone E (5), and γ-mangostin (6). The structure of the new compound was elucidated on the basis of high-resolution fast atom bombardment mass spectra (HRFABMS), 1D-and 2D-NMR experiments, including heteronuclear multiple bond connectivity (HMBC), heteronuclear single quantum coherence (HSQC) and 1H–1H-COSY (correlated spectroscopy, COSY).

Three new norlimonoids, toonaciliatins A (1), F (6), and G (7), four new limonoids, toonaciliatins B-E (2-5), and five known compounds, 5alpha,6beta,8alpha-trihydroxy-28-norisotoonafolin (8), toonaciliatins H (9) and I (10), febrifugin (11), and khayasin T (12), were isolated from the leaves and stems of Toona ciliata. Compounds 1-3 have an unusual 1-en-3-one system with a 1,11-oxygen bridge, limonoids 11 and 12 have a mexicanolide-type structural frame, and others are typical A,B-seco- (4, 5, 9, and 10) or B-seco-29-nor- (3, 6, 7, and 8) limonoids. Toonaciliatins H (9) and I (10) were obtained for the first time as natural products. The structures were established by extensive spectroscopic methods, particularly 1D and 2D NMR techniques.

Three new alkaloids, gelsebanine (1), 14alpha-hydroxyelegansamine (2), and 14alpha-hydroxygelsamydine (3), and a new extraction artifact , gelsebamine (4), together with 12 known alkaloids, were isolated from the stems and leaves of Gelsemium elegans. The structures of 1-4 were determined by spectroscopic methods, especially 2D NMR techniques. Compounds 1-4 were evaluated for cytotoxic activity against four tumor cell lines, and gelsebamine (4) selectively inhibited the A-549 human lung adenocarcinoma cell line.

Sacha Inchi oil was studied for its physicochemical characteristics, chemical composition, radical scavenging activity and storage stability. The fatty acid composition was studied by gas chromatography–flame ionization (GC–FID) and the analysis showed that the oil is highly enriched in α–linolenic (43.5%) and linoleic (39.6%) acids. The tocopherol content in the oil analyzed by high performance liquid chromatography/ultraviolet– visible detector (HPLC/UV–VIS) was also high (161.87 mg.100 g -1 ). Both DPPH and ABTS assays detected relatively high radical scavenging activity. After twelve months of storage, the oil showed relatively good storage stability. The results will help guide further investigation of the health benefits of Sacha Inchi oil for the population and the development of better edible oil products and nutraceuticals.

Eleganoside A (1) and odoratanone A (15), a triterpenoid trisaccharide glycoside and a nortriterpenoid, together with twelve known compounds (2–13) and a mixture of cerebrosides (14) were isolated from Gelsemium elegans and Aglaia odorata. Their structures were elucidated by extensive spectroscopic and spectrometric analysis. Eleganoside A (1) features a 3- O-α-L-rhamnopyranosyl (1→4)-β-D-glucopyranosyl (1→4)-β-D-glucopyranoside of a peculiar 3,16-dihydroxyl-lanosta-8,24-dien-26-oic acid triterpenoid skeleton, and odoratanone A (15) is a 29-norcycloartane-type triterpenoid bearing an unusual five-membered methyl acetal ring. Anti-acetylcholinesterase/butyrylcholinesterase (AChE/BChE) assay indicated that at 50 μM, ethyl caffeate (5) was promising as a dual inhibitor of AChE and BChE, and paeonol (3) and 24-hydroperoxy-24-vinylcholesterol (9) exhibited BChE-selective inhibition.