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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (15 March 2017) | Viewed by 98210

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Prof. Dr. Giancarlo Cravotto

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Department of Drug Science and Technology, University of Turin, Via P. Giuria 9, 10125 Turin, Italy
Interests: green chemistry; process intensification; green extraction; enabling technologies (ultrasound, microwaves, hydrodynamic cavitation, ball milling, flow chemistry); sustainable chemical processes
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Prof. Dr. Francisco J. Barba

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Nutrition and Food Science Area, Preventive Medicine and Public Health, Food Science, Toxicology and Forensic Medicine Department, Faculty of Pharmacy, Universitat de València, Avda. Vicent Andrés Estellés, s/n, 46100 Burjassot, Valencia, Spain
Interests: nutrients; bioactive compounds; food preservation; thermal treatment; innovative processing; high-pressure processing; compressed fluids; pulsed electric fields; ultrasound; microwaves; phytochemical purification; phytochemical analysis; compound isolation; bioaccessibility; bioavailability
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Green production of bioactive naturally occurring compounds is based on a multidisciplinary approach, including non-conventional technologies and complementary expertise. Industrial production requires the development of environmentally benign methods enabling technically feasible and cost-effective processes. The application of highly efficient chemical conversions, including enantioselective transformations, has to be compared with biotechnological methods and heterogeneous enzymatic catalysis. Green extraction and selective isolation from natural sources are also successfully employed. All these strategies promote a process intensification taking advantage from enabling technologies that generate high-energy microenvironments. Green techniques, such as acoustic and hydrodynamic cavitation, microwaves, and ball milling, greatly improve reaction rates and extraction efficiency and provides additional benefits like reduction in cost and waste besides replacement of hazardous chemicals. Not less important is the use of supercritical-CO₂, pulsed electric fields, high-voltage electrical discharges, as well as ultrafiltration and nanofiltration.

Aim of this Special Issue is to highlight the new green challenges in the production of bioactive natural products launched by recent technological advances, new hybrid reactors and bio-based solvents.

Prof. Dr. Giancarlo Cravotto
Dr. Francisco J. Barba
Guest Editors

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Keywords

natural products
green synthesis
green extraction
biotechnological methods
enabling technologies

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Published Papers (11 papers)

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Research

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2075 KiB

Open AccessArticle

Anti-Inflammatory and Antioxidant Properties of Casein Hydrolysate Produced Using High Hydrostatic Pressure Combined with Proteolytic Enzymes

by Fatemeh Bamdad, Seulki Hazel Shin, Joo-Won Suh, Chamila Nimalaratne and Hoon Sunwoo

Molecules 2017, 22(4), 609; https://doi.org/10.3390/molecules22040609 - 10 Apr 2017

Cited by 80 | Viewed by 8205

Abstract

Casein-derived peptides are shown to possess radical scavenging and metal chelating properties. The objective of this study was to evaluate novel anti-inflammatory properties of casein hydrolysates (CH) produced by an eco-friendly process that combines high hydrostatic pressure with enzymatic hydrolysis (HHP-EH). Casein was hydrolysed by different proteases, including flavourzyme (Fla), savinase (Sav), thermolysin (Ther), trypsin (Try), and elastase (Ela) at 0.1, 50, 100, and 200 MPa pressure levels under various enzyme-to-substrate ratios and incubation times. Casein hydrolysates were evaluated for the degree of hydrolysis (DH), molecular weight distribution patterns, and anti-inflammatory properties in chemical and cellular models. Hydrolysates produced using HHP-EH exhibited higher DH values and proportions of smaller peptides compared to atmospheric pressure-enzymatic hydrolysis (AP-EH). Among five enzymes, Fla-digested HHP-EH-CH (HHP-Fla-CH) showed significantly higher antioxidant properties than AP-Fla-CH. The anti-inflammatory properties of HHP-Fla-CH were also observed by significantly reduced nitric oxide and by the suppression of the synthesis of pro-inflammatory cytokines in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells. Liquid chromatography with tandem mass spectrometry (LC-MS/MS) revealed that 59% of the amino acids of the peptides in HHP-Fla-CH were composed of proline, valine, and leucine, indicating the potential anti-inflammatory properties. In conclusion, the HHP-EH method provides a promising technology to produce bioactive peptides from casein in an eco-friendly process. Full article

(This article belongs to the Special Issue Green Production of Bioactive Natural Products)

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5602 KiB

Open AccessArticle

Biosynthesis of Oligomeric Anthocyanins from Grape Skin Extracts

by Jin-Woo Hwang, Sithranga Boopathy Natarajan, Yon-Suk Kim, Eun-Kyung Kim, Jae Woong Lee, Sang-Ho Moon, Byong-Tae Jeon and Pyo-Jam Park

Molecules 2017, 22(3), 497; https://doi.org/10.3390/molecules22030497 - 21 Mar 2017

Cited by 8 | Viewed by 6121

Abstract

We synthesized oligomeric anthocyanins from grape skin-derived monomeric anthocyanins such as anthocyanidin and proanthocyanidin by a fermentation technique using Aspergillus niger, crude enzymes and glucosidase. The biosyntheses of the oligomeric anthocyanins carried out by the conventional method using Aspergillus niger and crude enzymes were confirmed by ESI-MS. The molecular weight of the synthesized anthocyanin oligomers was determined using MALDI-MS. The yield of anthocyanin oligomers using crude enzymes was higher than that of the synthesis using Aspergillus fermentation. Several studies have been demonstrated that oligomeric anthocyanins have higher antioxidant activity than monomeric anthocyanins. Fermentation-based synthesis of oligomeric anthocyanins is an alternative way of producing useful anthocyanins that could support the food industry. Full article

(This article belongs to the Special Issue Green Production of Bioactive Natural Products)

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885 KiB

Open AccessArticle

Valorization of Phosphorus Secondary Raw Materials by Acidithiobacillus ferrooxidans

by Małgorzata Wyciszkiewicz, Agnieszka Saeid, Przemysław Malinowski and Katarzyna Chojnacka

Molecules 2017, 22(3), 473; https://doi.org/10.3390/molecules22030473 - 16 Mar 2017

Cited by 21 | Viewed by 5714

Abstract

This paper presents the possibility of producing phosphorus fertilizers through Acidithiobacillus ferrooxidans utilization in secondary raw materials solubilization. Phosphorus was obtained from the bones of poultry and fish as well as from Morocco phosphorite. Four doses of poultry bones and fish bones were used in the experiment (2, 4, 10 and 20 g/L) and two doses (2 and 4 g/L) of phosphorite were also used. The experimenters measured the final pH, which increased in proportion to the increase in the number of poultry bone doses, whereas in the case of fish bones it decreased in proportion to the increase in the number of fish bone doses. Only in the case of phosphorite, where 10 g/L were used, there was a slight increase in pH during solubilization observed. The highest phosphorus concentration of 1.9% (expressed as P₂O₅) was found for the solubilization performed on fish bones with the highest dose (20 g/L). The formulation obtained in this study meets the necessary requirements for use as a bio-fertilizer because of the relatively low content of P₂O₅ and the low content of toxic elements. The results confirm the utilization of Acidithiobacillus ferrooxidans in the biosolubilization of phosphorus renewable raw materials that can alleviate the problem of the world’s depleting phosphorite deposits. Full article

(This article belongs to the Special Issue Green Production of Bioactive Natural Products)

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2085 KiB

Open AccessArticle

Optimization of Ultrasonic-Assisted Enzymatic Extraction Conditions for Improving Total Phenolic Content, Antioxidant and Antitumor Activities In Vitro from Trapa quadrispinosa Roxb. Residues

by Feng Li, Yi-Dan Mao, Yi-Fan Wang, Aun Raza, Li-Peng Qiu and Xiu-Quan Xu

Molecules 2017, 22(3), 396; https://doi.org/10.3390/molecules22030396 - 6 Mar 2017

Cited by 43 | Viewed by 6734

Abstract

Stems are the important residues of Trapa quadrispinosa Roxb., which are abundant in phenolic compounds. Ultrasonic-assisted enzymatic extraction (UAEE) is confirmed as a novel extraction technology with main advantages of enhancing extraction yield and physiological activities of the extracts from various plants. In this study, UAEE was applied to obtain the highest yield of phenolic content, strongest antioxidant, and antitumor activities and to optimize the extraction conditions using response surface methodology (RSM). The extracts from the stems of T. quadrispinosa were characterized by determination of their antioxidant activities through 2,2-azinobis(3-ethylbenzthiazoline)-6-sulfonic acid (ABTS), 1,1-Diphenyl-2-picrylhydrazxyl (DPPH) radical scavenging, total antioxidant capacity (TAC), ferric reducing antioxidant capacity (FRAC) methods and of their antitumor activity by MTT method. The selected key independent variables were cellulase concentration (X₁: 1.5%–2.5%), extraction time (X₂: 20–30 min) and extraction temperature (X₃: 40–60 °C). The optimal extraction conditions for total phenolic content (TPC) value of the extracts were determined as 1.74% cellulase concentration, 25.5 min ultrasonic extraction time and 49.0 °C ultrasonic temperature. Under these conditions, the highest TPC value of 53.6 ± 2.2 mg Gallic acid equivalent (GAE)/g dry weight (DW) was obtained, which agreed well with the predicted value (52.596 mg GAE/g·DW. Furthermore, the extracts obtained from UAEE presented highest antioxidant activities through ABTS, DPPH, TAC and FRAC methods were of 1.54 ± 0.09 mmol Trolox equivalent (TE)/g·DW; 1.45 ± 0.07 mmol·TE/g·DW; 45.2 ± 2.2 mg·GAE/g·DW; 50.4 ± 2.6 μmol FeSO₄ equivalent/g·DW and lowest IC₅₀ values of 160.4 ± 11.6 μg/mL, 126.1 ± 10.8 μg/mL, and 178.3 ± 13.1 μg/mL against Hela, HepG-2 and U251 tumor cells, respectively. The results indicated that the UAEE was an efficient alternative to improve extraction yield and enhance the antioxidant and antitumor activities of the extracts. The phenolic extracts from the stems of T. quadrispinosa had significant antioxidant and antitumor activities, which could be used as a source of potential antioxidant and antitumor agents. Full article

(This article belongs to the Special Issue Green Production of Bioactive Natural Products)

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462 KiB

Open AccessArticle

Influence of Indole-3-Acetic Acid and Gibberellic Acid on Phenylpropanoid Accumulation in Common Buckwheat (Fagopyrum esculentum Moench) Sprouts

by Chang Ha Park, Hyeon Ji Yeo, Yun Ji Park, Abubaker M. A. Morgan, Mariadhas Valan Arasu, Naif Abdullah Al-Dhabi and Sang Un Park

Molecules 2017, 22(3), 374; https://doi.org/10.3390/molecules22030374 - 28 Feb 2017

Cited by 45 | Viewed by 7213

Abstract

We investigated the effects of natural plant hormones, indole-3-acetic (IAA) acid and gibberellic acid (GA), on the growth parameters and production of flavonoids and other phenolic compounds in common buckwheat sprouts. A total of 17 phenolic compounds were identified using liquid chromatography-mass spectrometry (LC-MS) analysis. Among these, seven compounds (4-hydroxybenzoic acid, catechin, chlorogenic acid, caffeic acid, epicatechin, rutin, and quercetin) were quantified by high-performance liquid chromatography (HPLC) after treating the common buckwheat sprouts with different concentrations of the hormones IAA and GA. At a concentration of 0.5 mg/L, both IAA and GA exhibited the highest levels of growth parameters (shoot length, root length, and fresh weight). The HPLC analysis showed that the treatment of sprouts with IAA at concentrations ranging from 0.1 to 1.0 mg/L produced higher or comparable levels of the total phenolic compounds than the control sprout and enhanced the production of rutin. Similarly, the supplementation with 0.1 and 0.5 mg/L GA increased the content of rutin in buckwheat sprouts. Our results suggested that the treatment with optimal concentrations of IAA and GA enhanced the growth parameters and accumulation of flavonoids and other phenolic compounds in buckwheat sprouts. Full article

(This article belongs to the Special Issue Green Production of Bioactive Natural Products)

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1456 KiB

Open AccessArticle

Hydrophilic Dogwood Extracts as Materials for Reducing the Skin Irritation Potential of Body Wash Cosmetics

by Zofia Nizioł-Łukaszewska, Paweł Osika, Tomasz Wasilewski and Tomasz Bujak

Molecules 2017, 22(2), 320; https://doi.org/10.3390/molecules22020320 - 19 Feb 2017

Cited by 29 | Viewed by 7359

Abstract

A significant problem related to the use of surfactants in body wash cosmetics is their propensity to trigger skin irritations. Only scarce literature exists on the effect of plant extracts on the skin irritation potential. The present study is an attempt to determine the effect of hydrophilic dogwood extracts on the irritant potential of body wash gels. Extractants used in the study were water and mixtures of water with glycerine, water with trimethylglycine (betaine), and water with plant-derived glycol (propanediol). The basic biochemical properties, i.e., the ability to neutralize free radicals, and the content of polyphenols, anthocyanins and flavonoids, were determined. An attempt was undertaken to analyze the impact of the extract added to natural body wash gel formulations on product properties. The skin irritation potential was assessed by determining the zein number and the increase in the pH level of the bovine serum albumin (BSA) solution. The viscosity and foaming ability of the resulting products were evaluated. The studies revealed that an addition of dogwood extract contributes to an improvement in the properties of body wash gels and significantly increases the safety of product use through reducing the skin irritation effect. Full article

(This article belongs to the Special Issue Green Production of Bioactive Natural Products)

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432 KiB

Open AccessArticle

Microbial Glycosylation of Daidzein, Genistein and Biochanin A: Two New Glucosides of Biochanin A

by Sandra Sordon, Jarosław Popłoński, Tomasz Tronina and Ewa Huszcza

Molecules 2017, 22(1), 81; https://doi.org/10.3390/molecules22010081 - 3 Jan 2017

Cited by 41 | Viewed by 8045

Abstract

Biotransformation of daidzein, genistein and biochanin A by three selected filamentous fungi was investigated. As a result of biotransformations, six glycosylation products were obtained. Fungus Beauveria bassiana converted all tested isoflavones to 4″-O-methyl-7-O-glucosyl derivatives, whereas Absidia coerulea and Absidia glauca were able to transform genistein and biochanin A to genistin and sissotrin, respectively. In the culture of Absidia coerulea, in addition to the sissotrin, the product of glucosylation at position 5 was formed. Two of the obtained compounds have not been published so far: 4″-O-methyl-7-O-glucosyl biochanin A and 5-O-glucosyl biochanin A (isosissotrin). Biotransformation products were obtained with 22%–40% isolated yield. Full article

(This article belongs to the Special Issue Green Production of Bioactive Natural Products)

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3540 KiB

Open AccessArticle

Ultrasound-Assisted Extraction, Centrifugation and Ultrafiltration: Multistage Process for Polyphenol Recovery from Purple Sweet Potatoes

by Zhenzhou Zhu, Tian Jiang, Jingren He, Francisco J. Barba, Giancarlo Cravotto and Mohamed Koubaa

Molecules 2016, 21(11), 1584; https://doi.org/10.3390/molecules21111584 - 20 Nov 2016

Cited by 31 | Viewed by 8399

Abstract

This work provides an evaluation of an ultrasound-assisted, combined extraction, centrifugation and ultrafiltration process for the optimal recovery of polyphenols. A purple sweet potato (PSP) extract has been obtained using ultrasonic circulating extraction equipment at a power of 840 W, a frequency of 59 kHz and using water as solvent. Extract ultrafiltration, using polyethersulfone (PES), was carried out for the recovery of polyphenol, protein and anthocyanin. Pre-treatment, via the centrifugation of purple sweet potato extract at 2500 rpm over 6 min, led to better polyphenol recovery, with satisfactory protein removal (reused for future purposes), than PSP extract filtration without centrifugation. Results showed that anthocyanin was efficiently recovered (99%) from permeate. The exponential model fit well with the experimental ultrafiltration data and led to the calculation of the membrane’s fouling coefficient. The optimization of centrifugation conditions showed that, at a centrifugation speed of 4000 rpm (1195× g) and duration of 7.74 min, the optimized polyphenol recovery and fouling coefficient were 34.5% and 29.5 m⁻¹, respectively. The removal of proteins in the centrifugation process means that most of the anthocyanin content (90%) remained after filtration. No significant differences in the intensities of the HPLC-DAD-ESI-MS² peaks were found in the samples taken before and after centrifugation for the main anthocyanins; peonidin-3-feruloylsophoroside-5-glucoside, peonidin-3-caffeoyl-p-hydroxybenzoylsophoroside-5-glucoside, and peonidin-3-caffeoyl-feruloyl sophoroside-5-glucoside. This proves that centrifugation is an efficient method for protein removal without anthocyanin loss. This study considers this process an ultrasound-assisted extraction-centrifugation-ultrafiltration for purple sweet potato valorization in “green” technology. Full article

(This article belongs to the Special Issue Green Production of Bioactive Natural Products)

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2192 KiB

Open AccessArticle

Effects of Power Ultrasound on Stability of Cyanidin-3-glucoside Obtained from Blueberry

by Guang-Long Yao, Xing-Hui Ma, Xian-Yin Cao and Jian Chen

Molecules 2016, 21(11), 1564; https://doi.org/10.3390/molecules21111564 - 18 Nov 2016

Cited by 14 | Viewed by 6320

Abstract

Power ultrasound (US) could potentially be used in the food industry in the future. However, the extent of anthocyanin degradation by US requires investigation. Cyanidin-3-glucoside (Cy-3-glu) obtained from blueberry extracts was used as research material to investigate the effect of power ultrasound on food processing of anthocyanin-rich raw materials. The effects of ultrasonic waves on the stability of Cy-3-glu and on the corresponding changes in UV-Vis spectrum and antioxidant activity were investigated, and the mechanisms of anthocyanin degradation induced by ultrasonic waves were discussed. To explore Cy-3-glu degradation in different environments, we kept the Cy-3-glu solution treated with ultrasonic waves in four concentrations (0%, 10%, 20%, and 50%) of ethanol aqueous solutions to simulate water, beer, wine, and liquor storage environment according to the chemical kinetics method. Results show that the basic spectral characteristics of Cy-3-glu did not significantly change after power ultrasound cell crusher application at 30 °C. However, with anthocyanin degradation, the intensity of the peak for Cy-3-glu at 504 nm significantly decreased (p < 0.05). The degradation kinetics of Cy-3-glu by ultrasonic waves (200–500 W frequency) fitted well to first-order reaction kinetics, and the degradation rate constant of Cy-3-glu under power ultrasound was considerably larger than that under thermal degradation (p < 0.05). The sensitivity of the anthocyanins of blueberry to temperature increased with increasing ethanol concentration, and the longest half-life was observed in 20% ethanol aqueous solution. Full article

(This article belongs to the Special Issue Green Production of Bioactive Natural Products)

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Review

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3686 KiB

Open AccessReview

Innovative “Green” and Novel Strategies for the Extraction of Bioactive Added Value Compounds from Citrus Wastes—A Review

by Predrag Putnik, Danijela Bursać Kovačević, Anet Režek Jambrak, Francisco J. Barba, Giancarlo Cravotto, Arianna Binello, Jose Manuel Lorenzo and Avi Shpigelman

Molecules 2017, 22(5), 680; https://doi.org/10.3390/molecules22050680 - 27 Apr 2017

Cited by 249 | Viewed by 18463

Abstract

Citrus is a major processed crop that results in large quantities of wastes and by-products rich in various bioactive compounds such as pectins, water soluble and insoluble antioxidants and essential oils. While some of those wastes are currently valorised by various technologies (yet most are discarded or used for feed), effective, non-toxic and profitable extraction strategies could further significantly promote the valorisation and provide both increased profits and high quality bioactives. The present review will describe and summarize the latest works concerning novel and greener methods for valorisation of citrus by-products. The outcomes and effectiveness of those technologies such as microwaves, ultrasound, pulsed electric fields and high pressure is compared both to conventional valorisation technologies and between the novel technologies themselves in order to highlight the advantages and potential scalability of these so-called “enabling technologies”. In many cases the reported novel technologies can enable a valorisation extraction process that is “greener” compared to the conventional technique due to a lower energy consumption and reduced utilization of toxic solvents. Full article

(This article belongs to the Special Issue Green Production of Bioactive Natural Products)

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1168 KiB

Open AccessReview

Plant Growth Biostimulants, Dietary Feed Supplements and Cosmetics Formulated with Supercritical CO₂ Algal Extracts

by Izabela Michalak, Katarzyna Chojnacka and Agnieszka Saeid

Molecules 2017, 22(1), 66; https://doi.org/10.3390/molecules22010066 - 3 Jan 2017

Cited by 64 | Viewed by 13720

Abstract

The review paper presents the use of algal extracts as safe and solvent-free components of plant growth biostimulants, dietary feed additives and cosmetics. Innovative technology that uses extracts obtained by supercritical CO₂ extraction, as a method of isolation of biologically active compounds from algal biomass, is presented. An important part of the complete technology is the final formulation of the product. This enabled realization of the further step which was assessment of the utilitarian properties of the extract-based products. The extracts were analysed for the presence of biologically active molecules (e.g., plant hormones, polyphenols) which provide useful properties such as antioxidant, antiviral, anti-inflammatory and antibacterial. The bio-products were tested in germination tests and underwent field trials to search for plant growth biostimulatory properties. Tests on animals (laying hens experiments) were conducted to assess pro-health properties of new dietary feed supplement. Another application were cosmetic formulations (dermatological tests). The results of the application tests were very promising, however further studies are required for the registration of the products and successful implementation to the market. Full article

(This article belongs to the Special Issue Green Production of Bioactive Natural Products)

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