Markhasphingolipid A,new phytosphingolipid from the leaves of Markhamia stipulata var. canaense V.S. Dang

Abstract

From the leaves of Markhamia stipulata var. canaense V.S. Dang, one new phytosphingolipid, named markhasphingolipid A (6) together with five known compounds, 4’,7-O-dimethylapigenin (1), narigenin (2), tectoquinone (3), mollic acid (4), 1-hexadecanoyl-sn-glycerol (5) were classified by various chromatographic methods. Their structures were designated by IR, UV, HR-ESI-MS, HR-ESI-MS/MS and NMR experiments. All compounds were recognized for the first time from this species. The cytotoxicity of all n-hexane fractions and isolated compounds (5 & 6) against three human cancer cell lines (HeLa, HepG2, and MCF-7) were evaluated by SRB assay. All n-hexane fractions expressed cytotoxic effect on three tested cancer cell lines (at the concentration of 100?μg/mL, percent of cytotoxicity ranged from 55.81% to 95.83%) as well as compound 5 (IC₅₀ ranged from 48.51 to 63.30?μM) whereas fraction H.I and compound 6 did not show activity.

     

α-Tetralone glycosides from the green walnut husks of Juglans mandshurica Maxim. and their cytotoxic activities

Abstract

Five new α-tetralone glycosides, juglanbiosides A-E (1–5), together with an α-tetralone derivative (15) and nine known 1,4-naphthoquinones (6–14) were isolated from the 95% EtOH extract of green walnut husks of Juglans mandshurica Maxim. Their structures were elucidated by comprehensive spectroscopic methods (¹H, ¹³C NMR, DEPT, HSQC, HMBC, CD, HR-ESI-MS). In vitro cytotoxicities of all the isolated compounds were evaluated against BGC-823, HCT-15 and K562 cancer cell lines.

     

Isolation and characterization of flavonoids from the roots of medicinal plant Tadehagi triquetrum (L.) H.Ohashi

Abstract

Three flavonoid compounds were isolated from the roots of medicinal plant Tadehagi triquetrum (L.) H.Ohashi, also known as Desmodium triquetrum (Fabaceae). On the basis of the chemical and spectral analysis, the compounds were identified as baicalein (Flavone), naringin and neohesperidin (Flavonone). To the best of our knowledge and based on the literature survey all three compounds were first time reported from this medicinal plant.

     

Isolation,characterization, and xanthine oxidase inhibitory activities of flavonoids from the leaves of Perilla frutescens

Abstract

Phytochemical investigation of the water extract from the leaves of Perilla frutescens (Lamiaceae) led to the isolation of a new flavanone, a new chalcone, and a new aurone, namely, (2S)-5,7-dimethoxy-8,4'-dihydroxyflavanone (1), 2',4'-dimethoxy-4,5',6'-trihydroxychalcone (2), and (Z)-4,6-dimethoxy-7,4'-dihydroxyaurone (3), respectively. The structures were unambiguously elucidated on the basis of spectroscopic data. And the absolute configuration of 1 was determined by analysis of electronic circular dichroism spectrum. The isolated compounds were evaluated for their inhibitory effects on xanthine oxidase in vitro. Among them, 2 showed more potent activity than the positive control allopurinol, a well-known XO inhibitor clinically used for treatment of gout. Lineweaver-Burk transformation of the inhibition kinetics data demonstrated that it was a mixed-type inhibitor.

     

Prenylated isoflavones with potential antiproliferative activities from Mappianthus iodoides

Abstract

A phytochemical investigation on the stems of Mappianthus iodoides led to the isolation of a new naturally occurring prenylated isoflavone, mappianthone A (1), together with seven known analogues (2?8). The structure of 1 was elucidated by extensive spectroscopic methods and the known compounds were identified by comparison with data reported in the literature. All isolated compounds were evaluated for their antiproliferative activities against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 in vitro. Compounds 1?8 showed significant antiproliferative effects against several human cancer cell lines with IC₅₀ values ranging from 0.16 to 12.68?μM.

     

Isolation and identification of new prenylated acetophenone derivatives from Acronychia oligophlebia

Three new prenylated acetophenone derivatives, acronyculatin P (1), acronyculatin Q (2), and acronyculatin R (3) were isolated from the leaves of Acronychia oligophlebia. Their structures were identified by extensive analyses of spectroscopic data (IR, UV, ESI-HRMS, 1D and 2D NMR) and comparison with the literatures. In addition, the cytotoxic activity against MCF-7 cells of the compounds were evaluated by the MTT assay and the IC₅₀ values were 56.8, 40.4 and 69.1?μM, respectively.     

Neuroprotective terpenoids from the leaves of Viburnum odoratissimum

Abstract

As a part of our ongoing search for neuroprotective compounds from natural products, two new iridoid glycosides, vibsansuspenside A-B (1-2), along with five known terpenoids (3-7), were isolated from the dry leaves of Viburnum odoratissimum. Their chemical structures were well determined by means of NMR spectroscopic data as well as HRESIMS analysis. All compounds were detected for their neuroprotective effects against H₂O₂-induced damage in human dopaminergic neuroblastoma cells (SH-SY5Y). Among them, compound 3 displayed the most potent neuroprotective ability, and further investigation by Annexin V/PI and Western blot analysis demonstrated that compound 3 could protect SH-SY5Y cells from oxidative damage through inhibiting cell apoptosis.

     

Two new triterpenoids from Gardenia jasminoides fruits

A new cycloartane triterpenoid, named gardenolic acid C (1), a new ursane triterpenoid, named 3β,16β,21β,23,24-pentahydroxy urs-12,18,20-trien-28-oic acid γ-lactone (2), together with three know triterpenoids, gardenolic acid A (3), gardenolic acid B (4), and 3α,16β,23,24-tetrahydroxy-28-nor-ursane-12,17,19,21-tetraen (5) were isolated from the fruits of Gardenia jasminoides Ellis. The structures of these compounds were elucidated by analyses of spectroscopic data. All isolates were evaluated for their neuroprotective effects in vitro.

     

A rare diketopiperazine glycoside from marine-sourced Streptomyces sp. ZZ446

Abstract

Two diketopiperazines were isolated from a culture of the marine-derived actinomycete Streptomyces sp. ZZ446. Their structures were elucidated as maculosin (1) and maculosin-O-α-L-rhamnopyranoside (2) based on their NMR and HRESIMS data, specific rotation, and chemical degradation. Maculosin-O-α-L-rhamnopyranoside (2) is a new diketopiperazine glycoside, a structural class not reported previously from the natural sources. Both compounds showed antimicrobial activity against methicillin-resistant Staphylococcus aureus, Escherichia coli, and Candida albicans with MIC values in a range from 26.0 to 37.0?μg/mL.

     

The natural phenolic compounds and their antioxidant and anticholinesterase potential of herb Leiotulus dasyanthus (K. Koch) Pimenov & Ostr.

Abstract

The presented work reports anticholinesterase and antioxidant activities of extracts, fractions from aerial parts, fruits, flowers, roots and isolated compounds of roots from Leiotulus dasyanthus (bergapten, pimpinellin, umbelliferone, quercetin, rutin and kaempferol). Phenolic contents, antioxidant activities of samples were carried out by Folin-Ciocalteu, DPPH, TBA methods. Anticholinesterase activity was evaluated by Ellman’s method. The highest and lowest total phenolic content were detected in root MeOH extract (88.6?mg GAE g^?1 DW) and aerial part (51.83?mg GAE g^?1 DW), respectively. The highest antioxidant activity among isolated secondary metabolites got coumarins umbelliferone, bergapten and pimpinellin. Pimpinellin (66.55%) and umbelliferone (61.09%) demonstrated strong inhibition towards acetylcholinesterase and butyrylcholinesterase, respectively. Dichloromethane fraction of root demonstrated significant inhibition against AChE (49.66%) and BuChE (92.21%) at 20 µg/mL. Dichloromethane fractions of roots had a notableness antioxidant and anticholinesterase activities. The further studies on roots will be important for development use of this plant for pharmaceutical and food research needs.

     

Phytochemical,antimicrobial and antiquorum-sensing studies of pulicaria undulata L.: a revision on the structure of 1β,2α,3β,19α,23-pentahydroxy-urs-12-en-28-oic acid

Abstract

Phytochemical study of the aerial part of Pulicaria undulata L. led to the isolation of nine compounds. The structure of 1β,2α,3β,19α,23-pentahydroxy-urs-12-en-28-oic acid (4) was revised and confirmation of the stereochemical configuration of the hydroxyl groups was established using NOESY and selective decoupling experiments. The other compounds were identified as 1,2-dehydro-1,10α-dihydropseudoivalin (1), axillarin (2), grandifloric acid-15-β-glucoside (3), myrianthic acid (5), caffeic acid (6), quercetin (7), paniculoside IV (8) and caffeic anhydride (9). The structures were characterized by 1?D, 2?D NMR spectroscopy and confirmed with HRMS. Antimicrobial and antiquorum-sensing activities of the different extracts and isolated compounds of the plant were investigated. Generally, the phenolic rather than the terpenoidal compounds exhibited remarkable antimicrobial and antiquorum-sensing activity.

     

Quassinoids from seeds of Brucea Javanica and their anticomplement activities

Abstract

An investigation on seeds of Brucea javanica led to the acquisition of a new quassinoid, 20-hydroxyyadanzigan (1), along with five known quassinoids (2–6). The structure of the new compound was elucidated on the basis of extensive spectral analysis. All of the compounds were assayed for their anticomplement activities through classical and alternative pathways. Compounds 1–6 exhibited potent anticomplement activity with CH₅₀ and AP₅₀ values of 0.032–0.075?mg/mL and 0.061–0.118?mg/mL, respectively. Moreover, the structure-activity relationships of these compounds are discussed.

     

A new 5α,8α-epidioxysterol with immunosuppressive activity from the South China Sea soft coral Sinularia sp.

Abstract

A new 5α,8α-epidioxysterol, namely yalongsterol A (1), along with two known related steroids 5α,8α-epidioxy-24-methyl-cholesta-6,24(28)-dien-3β-ol (2) and (22E,24S)-5α,8α-epidioxy-24-methyl-cholesta-6,22-dien-3β-ol (3), were isolated from the South China Sea soft coral Sinularia sp. Their structures were established by extensive spectroscopic analyses and comparisons of the spectral data with those reported in the literature. In bioassay, compounds 1–3 showed moderate immunosuppressive activities against T and/or B lymphocyte cells with IC₅₀ values ranging from 19.30 to 59.49 μM, and low cytotoxicity on murine splenocytes with CC₅₀ values ranging from 40.88 to 62.29 μM.

     

In vitro and in silico study of Aloe vera leaf extract against human breast cancer

Abstract

Aloe vera leaf contains some bioactive compounds that have a strong binding affinity toward estrogen receptor as compared to standard drug tamoxifen. In this study, we have found that the IC₅₀ of Aloe vera leaf extract against breast cancer cell line (MCF-7) is 23?µg/mL which is much lower than the IC₅₀ (332?µg/mL) of Aloe vera leaf extract against non-cancerous cell line (NIH-3T3). We have also calculated the total concentration of phenolic acid (385.662?µg/mL), flavonoids (160.402?µg/mL) and alkaloids (276.754?µg/mL) in Aloe vera leaf extract. The free radical scavenging activity of Aloe vera leaf extract is 67% to 89% (at 50 to 300?µg/ml). Our virtual molecular docking study suggests that bioactive compounds like Aloe-emodin (?8.8?Kcal/mol), 7-hydroxy-2,5 dimethylchromone (?7.5?Kcal/mol), Beta-sitosterol (?7.3?Kcal/mol) etc. have a greater binding affinity toward estrogen alpha receptor as compared to standard drug Tamoxifen (?6.4?Kcal/mol).

     

New cytotoxic flavonoids from aerial parts of Platycladus orientalis L.

Abstract

Investigation of Platycladus orientalis yielded five flavonoids, including aglycone flavone 1 (apigenin), flavone glycoside 2 (apigenin 7-O-β-D-glucopyranoside), new gernaylated flavone glycoside 3 (apigenin 8-gernayl-4′-O-α-gluco pyranoside) and two new pernylated flavonoid glycosides 4 & 5 (apigenin 8-pernyl-4′-glucopyranosyl-7-O-α-glucopyranoside and apigenin 5-pernyl-7-glucopyranosyl-4′-O-β-D-glucopyranoside). Their structures were elucidated on the basis of spectroscopic evidence. The cytotoxicity of compounds 1–5 were tested against Lung adenocarcinoma (A549), human hepatocellular liver carcinoma (HepG2), human breast carcinoma (MCF-7) cell lines and mouse fibroblast cell line NIH/3T3 as normal cells. This assay gave spot on structure activity relationship which, showed that cytotoxicity of compounds (1) and (2) against three cell lines was weak as IC₅₀?>?15. Compounds (4) and (5) had moderate cytotoxic and no toxic effect on normal cell. Compound (3) showed high cytotoxic activity against tested three cell lines with no toxic effect of normal cells.

     

Four lignans from Portulaca oleracea L. and its antioxidant activities

Abstract

A new lignan, named oleralignan (1) and three known componds (+)-syringaresinol (2), (+)-lirioresinol A (3) and monomethyl 3,3′,4,4′-tetrahydroxy-δ-truxinate (4) were isolated from the P. oleracea for the first time. The compound (1) were identified by 1D, 2D NMR spectroscopic methods and high resolution electrospray ionization time-of-flight mass spectrometry. In addition, it was found that the four lignans presented the scavenging activities in 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical quenching assay more than that of hydroxyl anisole (BHA).

     

The antioxidant compounds isolated from the fruits of chinese wild raspberry Rubus Chingii Hu

Abstract

Raspberry, the fruit of Rubus Chingji Hu, is a widely distributed economic staple food in China. It has long been used as a traditional medicine in mainland China to treat kidney enuresis, nocturnal emission and premature ejaculation in clinic. In this paper, six known compounds (1?–?6) were purified from the fruits of Rubus chingji. Their structures were elucidated as (16α)-16,17-dihydroxy-ent-kauran-2-one17-O-β-D-glucopyranoside (1), (16R) -16,17-dihydroxy-ent-kaurane-2-one (2), 3,3′-di-O-methylellagic acid 4-(5′′-acetyl)-α-L-arabinofuranoside (3), quercilicoside A (4), esculetine (5) and ethyl-β-D-glucoside (6). All the compounds were isolated from Rubus Chingji Hu for the first time. Compounds 3 and 5 shown distinctive free radical scavenging activities in DPPH and FRAP assays. In addition, no cytotoxicity was observed for compounds 3 and 5 against different cancer cells, suggesting that they might be useful as potential antioxidant agents against various reactive oxygen species.

     

Synthesis and structure anti-inflammatory activity relationships studies of andrographolide derivatives

Abstract

Andrographolide is a main bioactive diterpene lactone in A. paniculata with anti-inflammatory activity. In this study, a series of andrographolide derivatives were synthesized and evaluated for their structure-anti-inflammatory activity relationships in vivo. Among all compounds, isoandrographolide and 14-deoxyandrographolide showed stronger anti-inflammatory activity than andrographolide. The results indicated that the introduction of tetrahydrofuran ring and cyclic olefinic bond plays an important role in enhancing the anti-inflammatory activity of andrographolide derivatives. Isoandrographolide and 14-deoxyandrographolide are potent inhibitor of inflammation.

     

Protective effect of Epicatechin on APAP-induced acute liver injury of mice through anti-inflammation and apoptosis inhibition

Abstract

Epicatechin (EC) is the most effective compound in Euonymus alatus (Thunb.)Sieb, and possesses a series of benefits, including anti-inflammatory, antioxidant, antiobesity and anticancer effects. In this study, we investigated the protective effects of EC in Acetaminophen(N-acetyl-p-aminophenol, APAP)-induced acute liver injury in C57BL/6J mice and explored the possible mechanisms involved in these effects.

     

A immunosuppressive triterpenoid saponin from the stems of Epigynum griffithianum

Abstract

Chemical investigation of the stems of Epigunum griffithianum led to the isolation and identification of a new triterpenoid saponin (1) and two known compounds (epigynosides A (2) and B (3)). These structures were elucidated by means of spectroscopic analysis (1D and 2D NMR, MS, UV, IR) as well as comparison with the reported data. Compound 1 was evaluated in vitro for the immunosuppressive activities on proliferation of mice splenocyte and displayed significant immunosuppressive activities compared to the positive control (dexamethasone) with the concentration at 25?μM.