Effect of Ultrasound-Assisted Extraction of Carotenoids from Papaya (Carica papaya L. cv. Sweet Mary) Using Vegetable Oils

By-products from fruits and are of great interest for their potential use in the food industry due to their high content of bioactive compounds. Herein, we examined the ultrasound-assisted extraction (UAE) of carotenoid and carotenoid esters from papaya pulp and peel using soybean oil and sunflower oil as alternative green solvents. Response surface methodology (RSM) was established to optimize the UAE process. Three independent variables, ultrasonic amplitude (20–60%), time (10–60 min), and co-solvent percentage (ethanol) (5–20%, v/v), were applied. The highest total carotenoid content in the UAE extracts was obtained from papaya pulp extracts (58.7 ± 1.6 and 56.0 ± 1.5 μg carotenoids/g oil) using soybean oil and sunflower oil, respectively (60% amplitude/ 10 min/ 20% ethanol). On the other hand, the highest carotenoid content (52.0 ± 0.9 μg carotenoids/g oil) was obtained from papaya peel using soybean oil applying the UAE process (20% amplitude/ 77 min/ 20% ethanol); a minor content of 39.3 ± 0.5 μg carotenoids/g oil was obtained from papaya peel using sunflower oil at 60% amplitude/ 60 min/ 5% ethanol. Lycopene was the most abundant carotenoid among all individual carotenoids observed in papaya oil extracts, obtaining the highest yields of this carotenoid when papaya pulp and peel were extracted using soybean oil (94% and 81%, respectively) and sunflower oil (95% and 82%, respectively). Great extraction of xanthophyll esters was detected using 20% of ethanol in the vegetable oil extraction solvent (v/v). High correlations (>0.85) was obtained between total carotenoid content and color determination in the UAE oil extracts. UAE vegetable oil extracts enriched with carotenoids from papaya by-products could be useful to formulate new food ingredients based on emulsions with interesting potential health benefits.     

A new caffeic acid tetramer from the Dracocephalum moldavica L.

A new caffeic acid tetramer compound, named (+) methyl rabdosiin (4), together with seven known caffeic acid multimers (1–3, 5–8) and one caffeic acid monomer (9), were isolated from the aerial parts of Dracocephalum moldavica L. The structures of these compounds were assigned on the basis of 1D and 2D NMR spectroscopic and mass spectrometry analyses. The protective effects of compounds 2–4 against hydrogen peroxide (H₂O₂)-induced apoptosis were evaluated in primary cardiomyocytes of SD neonatal rats in vitro by the MTT method. Three compounds exhibited potent protective activities at 12.5 μg/mL.     

A new alkaloid from Portulaca oleracea L. and its antiacetylcholinesterase activity

A new alkaloid, (10E, 12E)-9-ureidooctadeca-10, 12-dienoic acid, named oleraurea (1) and 10 known compounds, p-hydroxybenzaldehyde (2), p-hydroxybenzoic acid (3), p-hydroxyacetophenone (4), benzamide (5), (E)-p-coumaramide (6), (E)-ferulamide (7), soyalkaloid A (8), β-carboline-3-carboxylic acid (9), 2, 3, 4, 9-tetrahydro-1H-pyrido [3, 4-b] indole-3-carboxylic acid (10), (1S, 3S)-1-methyl-1, 2, 3, 4-tetrahydro-β-carboline-3-carboxylic acid (11) were obtained from Portulaca oleracea L., in which, compounds 4, 5, 8–11 were isolated from the plant for the first time. The structure of the compound 1 was identified using spectroscopic methods including 1D and 2D NMR, HR-ESI-TOF-MS. The compounds 1, 5–11 presented anticholinesterase activities, but the P. oleracea extract (POE) presented very low anticholinesterase activity.     

A new alkylene dihydrofuran glycoside with antioxidation activity from the root bark of Morus alba L.

<正>A new alkylene dihydrofuran glycoside(1) was isolated from the root bark ofMorus alba L.,along with moracin M-3′-O-β-D-glucopyranoside (2),and moracin M-6,3′-di-O-β-D-glucopyranoside(3).Compound 1 was identified as 2-methylene-3-methoxy-2, 5-dihydrofuran-4-O-β-D-glucopyranoside on the basis of chemical and spectroscopic data including 1D and 2D NMR spectral analysis.In addition,the antioxidant activity of 1 was evaluated using the 1,1-diphenyl-2-picrylhydrazyl(DPPH) and 2,2′-azinobis- 3-ethylbenzothiazoline-6-sulphonic acid(ABTS) assay.The IC_(50) values were 2.49 and 0.45 mg/mL,respectively.     

A new flavonoid from the bract of Zea mays L.

<正>A new flavonoid was isolated from the bract of Zea mays L.The structure of the compound was identified as 4',5,7-trihydroxy-3',5'-dimethoxyflavone 7-O-[β-D-apiofuranosyl(1→2)]-β-D-glucopyranoside on the ground of chemical and spectroscopic methods.     

A new sulfated triterpenoid from the bark of Zygophyllum fabago L.

<正>A new sulfated triterpenoid,3β,24-dihydroxyurs-20-ene-24-O-sulphonyl-28-oic acid(fabagoin.1) was isolated from the barks of Zygophyllum fabago L.Its structure was elucidated on the basis of spectroscopic data.     

A new benzofuran derivative from the leaves of Ficus pumila L.

A new benzofuran derivative, pumiloside (1), together with seven known flavonoid glycosides, afzelin (2), astragalin (3), quercitrin (4), isoquercitrin (5), kaempferol 3-O-rutinoside (6), rutin (7) and kaempferol 3-O-sophoroside (8) were isolated from the leaves of Ficus pumila. Their structures were established by spectroscopic data and comparison with the literature values.     

Separation and determination of chalcones from Carthamus tinctorius L. and its medicinal preparation by capillary zone electrophoresis

A new capillary zone electrophoresis (CZE) method was developed for simultaneous assay of four chalcones, hydroxysafflor yellow A, safflor yellow A, safflamin C, and safflamin A, in the Chinese herbal extract from Carthamus tinctorius L. The optimum buffer system was 30 mM borate buffer (Na2B407/HCl, pH 9.00) with 10% (v/v) methanol. The voltage was 15 kV and detection was at 270 nm. Regression equations revealed linear relationships (correlation coefficients: 0.9973, 0.9992, 0.9989, and 0.9996) between the peak area of each compound and its concentration. The within-day relative standard deviations of migration times and peak areas were < 1.53 and 4.14%, respectively. The effects of several CE parameters on the resolution were studied systematically. The contents of four chalcones in Carthamus tinctorius L. were successfully determined with satisfactory repeatability and recovery. The possibilities of using this method for the determination of chalcones in Chinese medicinal preparation was also tested.     

A new benzophenone glycoside from the leaves of Psidium guajava L.

A new benzophenone glycoside,2,6-dihydroxy-4-O-β-D-glucopyranosylbenzophenone(1),was isolated from the leaves of guajava L.Its structure was elucidated by spectral and chemical methods.1 showed significant activities to secretion of NO in mouse peritoneal macrophages in 10μmol/L.     

A new isochroman-4-one derivative from the peel of Musa sapientum L. and its total synthesis

A new isochroman-4-one,7,8-dihydroxy-3-methylisochroman-4-one was isolated from water soluble fraction of Musa sapientum L.Its structure was determined by spectroscopic evidences and its total synthesis has also been reported.The compound showed potent antihypertensive activity.     

A new triterpenoid saponin from the leaves and stems of Panax quinquefolium L.

One new triterpenoid saponin,quinquenoside L_(17)(1),was isolated from the leaves and stems of Panax quinquefolium L.,and its structure was elucidated as 20-O-[(β-D-xylopyranosyl-(1-6)-O-β-D-glucopyranosyl)]-6-O-β-D-glucopyranosyl-dammar-24-ene- 3,6,12,20-tetraol,by the combination analysis of one-dimensional NMR and two-dimensional NMR,mass spectrometry,CD spectrum and chemical evidences.     

Structure elucidation and antibacterial activity of a new coumarinolignoid from Daphne gnidium L.

Phytochemical investigation of the dichloromethane extract from the leaves of Daphne gnidium L. afforded 2‐(4‐hydroxy‐3,5‐dimethoxyphenyl)‐3‐hydroxymethyl‐2,3‐dihydro‐1,4,5‐trioxaphenanthren‐6‐one, and its structure was determined by a combination of spectral methods (1D and 2D ¹H, ¹³C NMR and HRMALDI and EI mass spectrometry). The new compound was found to possess moderate antibacterial activity against Staphylococcus aureus and Bacillus cereus. However, it showed no cytotoxic activity against KB cells. Copyright © 2002 John Wiley & Sons, Ltd.     

A novel tetrahydroquinoline acid and a new racemic benzofuranone from Capparis spinosa L., a case study of absolute configuration determination using quantum methods

A novel tetrahydroquinoline acid (1) and a new racemic benzofuranone (2), were isolated from the stems and fruits of Capparis spinosa L., using different column chromatography. The new benzofuranone was further separated by HPLC via chiral column to yield enantiomers (−)-2a and (+)-2b. The structures are so simple that some characteristics exhibited very close. This caused the difficulty in stereochemistry study. To overcome the difficulties, a comprehensive method is used for their stereochemistry study, such as computations of ¹³C NMR, optical rotation and electronic circular dichroism.     

In vitro and in silico interaction of faba bean (Vicia faba L.) seed extract with xanthine oxidase and evaluation of antioxidant activity as a therapeutic potential

Acetone extract of faba bean (Vicia faba L.) was found to be highest total phenol and flavonoid content among all extracts. Antioxidant activity for inhibition percentage (free radical scavenging activity) had 86.47% for acetone extract, and 97.36% for ascorbic acid respectively. IC₅₀ value of ascorbic acid and acetone extact were found to be 9 μg/mL ± 0.20 and 30 μg/mL ± 0.21. Faba bean seeds had catechin, epicatechin, gallic acid and ellagic acid which on molecular docking study revealed that it binds effectively with xanthine oxidase by binding energy of –7.78, –6.11, –6.39, –5.78 kcal/mol respectively compared to allopurinol drug having binding energy of –4.94 kcal/mol. Gallic acid, ellagic acid, catechin, epicatechin (polyphenols) and allopurinol bind other than catalytic residues (Glu-1261) of xanthine oxidase. In vitro and in silico analysis recommended that mode of enzyme inhibition was mixed type.     

Revised structures of avenacosides A and B and a new sulfated saponin from Avena sativa L.

The revised structures of avenacosides A and B and a new sulfated steroidal saponin isolated from grains of Avena sativa L. were elucidated. Their structures and complete NMR assignments are based on 1D and 2D NMR studies and identified as nuatigenin 3‐O‐{α‐l ‐rhamnopyranosyl‐(1→2)‐[β‐D‐glucopyranosyl‐(1→4)]‐β‐d ‐glucopyranoside}‐26‐O‐β‐d ‐glucopyranoside (1), nuatigenin 3‐O‐{α‐l ‐rhamnopyranosyl‐(1→2)‐[β‐d ‐glucopyranosyl‐(1→3)‐β‐d ‐glucopyranosyl‐(1→4)]‐β‐d ‐glucopyranoside}‐26‐O‐β‐d ‐glucopyranoside (2), and nuatigenin 3‐O‐{α‐l ‐rhamnopyranosyl‐(1→2)‐[β‐d ‐6‐O‐sulfoglucopyranosyl‐(1→4)]‐β‐d ‐glucopyranoside}‐26‐O‐β‐d ‐glucopyranoside (3). Copyright © 2012 John Wiley & Sons, Ltd.     

A Strategy for Identification and Structural Characterization of Compounds from Plantago asiatica L. by Liquid Chromatography-Mass Spectrometry Combined with Ion Mobility Spectrometry

Plantago asiatica L. (PAL) as a medicinal and edible plant is rich in chemical compounds, which makes the systematic and comprehensive characterization of its components challenging. In this study, an integrated strategy based on three-dimensional separation including AB-8 macroporous resin column chromatography, ultra-high performance liquid chromatography–quadrupole time-of-flight mass spectrometry (UHPLC-Q-TOF MS), and ultra-high performance liquid chromatography-mass spectrometry with ion-mobility spectrometry (UHPLC-IM-MS) was established and used to separate and identify the structures of compounds from PAL. The extracts of PAL were firstly separated into three parts by AB-8 macroporous resin and further separated and identified by UHPLC-Q-TOF MS and UHPLC-IM-MS, respectively. Additionally, UHPLC-IM-MS was used to identify isomers and coeluting compounds, so that the product ions appearing at the same retention time (RT)can clearly distinguish where the parent ion belongs by their different drift times. UNIFI software was used for data processing and structure identification. A total of 86 compounds, including triterpenes, iridoids, phenylethanoid glycosides, guanidine derivatives, organic acids, and fatty acids, were identified by using MS information and fragment ion information provided by UHPLC-Q-TOF MS and UHPLC-IM-MS. In particular, a pair of isoforms of plantagoside from PAL were detected and identified by UHPLC-IM-MS combined with the theoretical calculation method for the first time. In conclusion, the AB-8 macroporous resin column chromatography can separate the main compounds of PAL and enrich the trace compounds. Combining UHPLC-IM-MS and UHPLC-Q-TOF MS can obtain not only more fragments but also their unique drift times and RT, which is more conducive to the identification of complex systems, especially isomers. This proposed strategy can provide an effective method to separate and identify chemical components, and distinguish isomers in the complex system of traditional Chinese medicine (TCM).     

A new ocotillol-type ginsenoside from stems and leaves of Panax quinquefolium L. and its anti-oxidative effect on hydrogen peroxide exposed A549 cells

Abstract

A new ocotillol-type ginsenoside, namely 12-one-pseudoginsenoside F₁₁ (12-one-PF₁₁), was isolated from stems and leaves of Panax quinquefolium, whose structure was elucidated 6-O-[α-L-rhamnopyranosyl-(1-2)-β-D-glucopyranosyl]-dammar-12-one-20S,24R-epoxy-3β,6α,25-triol. 12-one-PF₁₁ significantly suppressed hydrogen peroxide induced oxidative stress in human lung carcinoma A549 cells. As compared with model group, 12-one-PF₁₁ improved cell viability of A549 cells in a dose-dependent manner, and significantly decreased the generation of malondialdehyde (MDA) and increased production of superoxide dismutase (SOD) and glutathione (GSH) and protein expression levels of nuclear related factor 2 (Nrf2) and heme oxygenase-1 (HO-1) in A549 cells.     

An efficient high-speed counter-current chromatography method for the preparative separation of sesquiterpenoids from the rhizomes of Cyperus rotundus L. combined with evaluation of the anti-inflammation activity in vitro and molecular docking

Cyperus rotundus L. has been extensively used in ancient medication for the treatment of different disorders worldwide, in which sesquiterpenes are the most representative components. In this study, sesquiterpenes were effectively purified by two-dimensional counter-current chromatography in combination with continuous injection and inner-recycling mode with a solvent system of n-hexane/ethyl acetate/methanol/water (1:0.2:1:0.2, v/v/v/v). For one-dimension separation, continuous injection mode was used with three times injection and the inner-recycling mode was adopted for the separation of two mixtures for two-dimensional separation. Finally, four sesquiterpenoids, including scariodione ( 1 ), cyperenoic acid ( 2 ), scariodione ( 3 ), and α-cyperone ( 4 ), were obtained with purities over 98%. Mass spectrometry and nuclear magnetic resonance were applied to identify their structures. The results from the anti-inflammation effect with zebrafish demonstrated that cyperenoic acid exhibited stronger anti-inflammation activity. Molecular docking results suggested that cyperenoic acid possessed lower binding energies –9.4545 kcal/mol with 1CX2 to form formed hydrogen bond interaction with ARG120. In general, all the obtained findings proved that the strong anti-inflammation capacity of cyperenoic acid can have the potential of being adopted for treating diseases resulting from inflammation.     

A new source of oxygenated monoterpenes with phytotoxic activity: essential oil of Cuminum Cyminum L. from Iran

Abstract

Chemical constitutes and phytotoxic activity of Cuminum cymiunm L. is investigated in the present study. For this means seeds of C. cyminum L. was harvested from Ilkhchi of Iran. The major components of essential oil (EO) with more than 94% were 3-caren-10-al, cuminal, 2-Caren-10-al, γ-Terpinene, (-)-β-Pinene and p-Cymene. This study found that cumin EO displayed meaningful inhibitory impacts on germination indices and the growth of the seedlings of Amaranthus retroflexus, Lactuca sativa, and Acroptilon repens. The germination indices showed severely concentration-dependent responses. In the case of A. retroflexus and L. sativa germination indices were controlled in the 500?ppm and in the A. repens were inhibited in the 1500?ppm of EO concentration. Overall, this study suggests that EO derived from C. cyminum L. looks to be a promising candidate for its utilization as a natural herbicide in large scale.