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Catechins: From Biosynthesis to Health Benefits

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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 (30 November 2021) | Viewed by 23793

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Special Issue Editors

Prof. Dr. Saverio Bettuzzi

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Guest Editor

Department of Medicine and Surgery, University of Parma, Via Volturno 39, 43125 Parma, Italy
Interests: clusterin; catechins; polyphenols; chemoprevention; prostate cancer; cell growth control; polyamines
Special Issues, Collections and Topics in MDPI journals

Dr. Mohamed Ali Ibrahim

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Co-Guest Editor

National Center for Natural Products Research (NCNPR), School of Pharmacy, The University of Mississippi, University, MS 38677, USA
Interests: drug discovery; natural products chemistry; organic synthesis; pharmacokinetics; anticancer drug leads; CB2 drug leads
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Catechins are a family of natural polyphenols that can be found in fruits, vegetables and, most remarkably, in green tea. The number of scientific publications on catechins is constantly increasing, indicating an increasing attention from the scientific community in these compounds. What strikes scientists is the wide range of potential health benefits, which have been demonstrated in many fields, and the many potential technological applications that are open to implementation. In this Special Issue entitled “Catechins: From Biosynthesis to Health Benefits”, we will collect scientific contributions addressing their biosynthesis, metabolism, biological effects, and promising results in the prevention of many diseases, as well as the potential for applications and innovation in various fields related to human health and nutrition.

Prof. Dr. Saverio Bettuzzi

Dr. Mohamed A. Ibrahim
Guest Editors

Manuscript Submission Information

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Keywords

catechins
green tea extract
EGCG
technological applications
bioavailability
health benefits
cell signaling pathways
chemoprevention
clinical trials
dietary supplement

Published Papers (5 papers)

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Research

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9 pages, 876 KiB

Open AccessArticle

Plasma-Induced Oxidation Products of (–)-Epigallocatechin Gallate with Digestive Enzymes Inhibitory Effects

by Gyeong Han Jeong and Tae Hoon Kim

Molecules 2021, 26(19), 5799; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26195799 - 24 Sep 2021

Cited by 2 | Viewed by 1819

Abstract

(−)-Epigallocatechin gallate (EGCG), the chief dietary constituent in green tea (Camellia sinensis), is relatively unstable under oxidative conditions. This study evaluated the use of non-thermal dielectric barrier discharge (DBD) plasma to improve the anti-digestive enzyme capacities of EGCG oxidation products. Pure EGCG was dissolved in an aqueous solution and irradiated with DBD plasma for 20, 40, and 60 min. The reactant, irradiated for 60 min, exhibited improved inhibitory properties against α-glucosidase and α-amylase compared with the parent EGCG. The chemical structures of these oxidation products 1–3 from the EGCG, irradiated with the plasma for 60 min, were characterized using spectroscopic methods. Among the oxidation products, EGCG quinone dimer A (1) showed the most potent inhibitory effects toward α-glucosidase and α-amylase with IC₅₀ values of 15.9 ± 0.3 and 18.7 ± 0.3 μM, respectively. These values were significantly higher than that of the positive control, acarbose. Compound 1, which was the most active, was the most abundant in the plasma-irradiated reactant for 60 min according to quantitative high-performance liquid chromatography analysis. These results suggest that the increased biological capacity of EGCG can be attributed to the structural changes to EGCG in H₂O, induced by cold plasma irradiation. Full article

(This article belongs to the Special Issue Catechins: From Biosynthesis to Health Benefits)

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24 pages, 4822 KiB

Open AccessArticle

Structure–Activity Relationships of the Antimalarial Agent Artemisinin 10. Synthesis and Antimalarial Activity of Enantiomers of rac-5β-Hydroxy-d-Secoartemisinin and Analogs: Implications Regarding the Mechanism of Action

by Mohamed Jahan, Francisco Leon, Frank R. Fronczek, Khaled M. Elokely, John Rimoldi, Shabana I. Khan and Mitchell A. Avery

Molecules 2021, 26(14), 4163; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26144163 - 08 Jul 2021

Cited by 4 | Viewed by 3750

Abstract

An efficient synthesis of rac-6-desmethyl-5β–hydroxy-d-secoartemisinin 2, a tricyclic analog of R-(+)-artemisinin 1, was accomplished and the racemate was resolved into the (+)-2b and (−)-2a enantiomers via their Mosher Ester diastereomers. Antimalarial activity resided with only the artemisinin-like enantiomer R-(−)-2a. Several new compounds 9–16, 19a, 19b, 22 and 29 were synthesized from rac-2 but the C-5 secondary hydroxyl group was surprisingly unreactive. For example, the formation of carbamates and Mitsunobu reactions were unsuccessful. In order to assess the unusual reactivity of 2, a single crystal X-ray crystallographic analysis revealed a close intramolecular hydrogen bond from the C-5 alcohol to the oxepane ether oxygen (O-11). All products were tested in vitro against the W-2 and D-6 strains of Plasmodium falciparum. Several of the analogs had moderate activity in comparison to the natural product 1. Iron (II) bromide-promoted rearrangement of 2 gave, in 50% yield, the ring-contracted tetrahydrofuran 22, while the 5-ketone 15 provided a monocyclic methyl ketone 29 (50%). Neither 22 nor 29 possessed in vitro antimalarial activity. These results have implications in regard to the antimalarial mechanism of action of artemisinin. Full article

(This article belongs to the Special Issue Catechins: From Biosynthesis to Health Benefits)

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14 pages, 2662 KiB

Open AccessArticle

Preventive Effects of Green Tea Extract against Obesity Development in Zebrafish

by Liqing Zang, Yasuhito Shimada, Hiroko Nakayama, Hirotaka Katsuzaki, Youngil Kim, Djong-Chi Chu, Lekh Raj Juneja, Junya Kuroyanagi and Norihiro Nishimura

Molecules 2021, 26(9), 2627; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26092627 - 30 Apr 2021

Cited by 10 | Viewed by 3266

Abstract

Various natural products (NPs) have been used to treat obesity and related diseases. However, the best way to fight obesity is preventive, with accurate body weight management through exercise, diet, or bioactive NPs to avoid obesity development. We demonstrated that green tea extract (GTE) is an anti-obesity NP using a zebrafish obesity model. Based on a hypothesis that GTE can prevent obesity, the objective of this study was to assess GTE’s ability to attenuate obesity development. Juvenile zebrafish were pretreated with GTE for seven days before obesity induction via a high-fat diet; adult zebrafish were pretreated with GTE for two weeks before obesity induction by overfeeding. As a preventive intervention, GTE significantly decreased visceral adipose tissue accumulation in juveniles and ameliorated visceral adiposity and plasma triglyceride levels in adult zebrafish obesity models. RNA sequencing analysis was performed using liver tissues from adult obese zebrafish, with or without GTE administration, to investigate the underlying molecular mechanism. Transcriptome analysis revealed that preventive GTE treatment affects several pathways associated with anti-obesity regulation, including activation of STAT and downregulation of CEBP signaling pathways. In conclusion, GTE could be used as a preventive agent against obesity. Full article

(This article belongs to the Special Issue Catechins: From Biosynthesis to Health Benefits)

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21 pages, 2114 KiB

Open AccessArticle

Full-Spectrum Analysis of Bioactive Compounds in Rosemary (Rosmarinus officinalis L.) as Influenced by Different Extraction Methods

by Yashaswini Sharma, Ravikishore Velamuri, John Fagan and Jim Schaefer

Molecules 2020, 25(20), 4599; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25204599 - 09 Oct 2020

Cited by 41 | Viewed by 4877

Abstract

Rosmarinus officinalis is a potent antioxidant herb rich in polyphenols. Ultra-high-performance liquid chromatography, coupled with electrospray ionization and quadrupole-time of flight mass spectrometry (UHPLC-ESI-QTOF-MS), enables an exhaustive, full-spectrum analysis of the molecular constituents of natural products. The study aimed to develop a rapid UHPLC method to contribute new insights into the phytochemical composition of rosemary and to assess the performance of nine different procedures for extraction. These include fresh tissue homogenization, fresh and dry leaf decoction, and their respective fermentation, Soxhlet extraction, and sonication using water and methanol. Different extraction methods were found to recover quite different groups of polyphenols within 11 min during 20 min of analysis. Soxhlet extraction, yielded very high concentrations of rosmarinic acid (33,491.33 ± 86.29 µg/g), luteolin-7-O-glucoside (209.95 ± 8.78 µg/g), carnosic acid (2915.40 ± 33.23 µg/g), carnosol (22,000.67 ± 77.39 µg/g), and ursolic acid (5144.27 ± 28.68 µg/g). UHPLC-ESI-QTOF-MS enabled the detection of more than 50 polyphenols, including phenolic acids, flavonoids, and terpenoids in the various extracts. Of these, sagerinic acid ([M − H]⁻m/z 719.16), salvianolic acid A ([M − H]⁻m/z 493.11) and B ([M − H]⁻m/z 717.15), and a pentacyclic triterpenoid corosolic acid ([M − H]⁻m/z 471.34) were detected for the first time in rosemary. Soxhlet extraction was found to be the most efficient method, followed by dry leaf decoction. The UHPLC-ESI-QTOF-MS methodology for the analysis proved to be very efficient in the identification and characterization of targeted and untargeted bioactive molecules in the rosemary. Full article

(This article belongs to the Special Issue Catechins: From Biosynthesis to Health Benefits)

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Review

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15 pages, 1306 KiB

Open AccessReview

Beneficial Effects of Green Tea Catechins on Female Reproductive Disorders: A Review

by Datu Agasi Mohd Kamal, Norizam Salamt, Siti Sarah Mohamad Zaid and Mohd Helmy Mokhtar

Molecules 2021, 26(9), 2675; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26092675 - 03 May 2021

Cited by 24 | Viewed by 9353

Abstract

Tea is one of the most widely consumed beverages worldwide after water, and green tea accounts for 20% of the total tea consumption. The health benefits of green tea are attributed to its natural antioxidants, namely, catechins, which are phenolic compounds with diverse beneficial effects on human health. The beneficial effects of green tea and its major bioactive component, (−)-epigallocatechin-3-gallate (EGCG), on health include high antioxidative, osteoprotective, neuroprotective, anti-cancer, anti-hyperlipidemia and anti-diabetic effects. However, the review of green tea’s benefits on female reproductive disorders, including polycystic ovary syndrome (PCOS), endometriosis and dysmenorrhea, remains scarce. Thus, this review summarises current knowledge on the beneficial effects of green tea catechins on selected female reproductive disorders. Green tea or its derivative, EGCG, improves endometriosis mainly through anti-angiogenic, anti-fibrotic, anti-proliferative and proapoptotic mechanisms. Moreover, green tea enhances ovulation and reduces cyst formation in PCOS while improving generalised hyperalgesia, and reduces plasma corticosterone levels and uterine contractility in dysmenorrhea. However, information on clinical trials is inadequate for translating excellent findings on green tea benefits in animal endometriosis models. Thus, future clinical intervention studies are needed to provide clear evidence of the green tea benefits with regard to these diseases. Full article

(This article belongs to the Special Issue Catechins: From Biosynthesis to Health Benefits)

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