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1.
Biosci Biotechnol Biochem ; 83(12): 2288-2297, 2019 Dec.
Article in English | MEDLINE | ID: mdl-31327308

ABSTRACT

We investigated the content of phenolic compounds and antioxidant capacity of two batches of non-heated and heated leaves of the yacon cultivar "Andes no yuki", grown in Japan. Lyophilized yacon leaves heated at 160°C for 20 min and 100°C for 60 min had a 1.96 to 9.69-times higher total phenolic content than that of the non-heated leaves. Heated leaves exhibited a 1.98 to 4.07-times higher antioxidant capacity than that of the non-heated leaves in three different free radical scavenging assays. Heated leaves were more efficient at attenuating the superoxide anion radical production in human granulocytic cells than the non-heated leaves. High-performance liquid chromatography analysis revealed that, in the heated leaves, the caffeic acid content was 2.13 to 3.64-times higher and the chlorogenic acid content was slightly lower than those in the non-heated leaves. Hence, heat processing may affect the active constituent contents in yacon leaves, potentiating its antioxidant capacity.Abbreviations: ABTS+: 2,2'-azinobis(2-ethylbenzothiazoline-6-sulfonic acid) cation; DPPH: 1,1-diphenyl-2-picrylhydrazyl, HPLC: high-performance liquid chromatography; NBT: nitroblue tetrazolium; O2-: superoxide anion; PMA: phorbol 12-myristate 13-acetate; PMS: phenazine methosulfate; TEAC: Trolox equivalent antioxidant capacity.


Subject(s)
Antioxidants/pharmacology , Asteraceae/chemistry , Hot Temperature , Phenols/analysis , Plant Leaves/chemistry , Caffeic Acids/analysis , Chlorogenic Acid/analysis , Chromatography, High Pressure Liquid , Free Radical Scavengers/pharmacology , HL-60 Cells , Humans , Plant Extracts/pharmacology , Superoxides/metabolism
2.
Yakugaku Zasshi ; 139(3): 381-384, 2019.
Article in Japanese | MEDLINE | ID: mdl-30828014

ABSTRACT

Approximately 20% of diabetic patients develop diabetic cataracts. As lens proteins are known to be only slightly metabolized during the lifetime, cataracts are difficult to recover from once they have progressed. Therefore, the daily intake of natural compounds would be an important strategy for the prevention of diabetic cataracts. Aphanothece sacrum Okada (Asa) is a freshwater blue-green algae endemic to Japan. It has been eaten since the Edo period in Kyushu. In this study, the inhibitory effects of Asa on the pathogenesis of diabetic cataracts were evaluated. Furthermore, the inhibitory effects of Asa on the formation of Nε-(carboxymethyl) lysine (CML), an oxidation-dependent advanced glycation end-product, were also measured. After 3-month administration, the CML contents in the lens were measured by liquid chromatography tandem mass spectrometry using an internal standard of CML or lysine. Asa significantly inhibited the progression of cataractogenesis and accumulation of CML in diabetic lens compared with the normal diet group. These results suggested that daily intake of Asa reduces oxidative stress and prevents the pathogenesis of cataracts.


Subject(s)
Cataract/etiology , Cataract/prevention & control , Cyanobacteria , Diabetes Mellitus, Experimental/complications , Diabetes Mellitus, Type 1/complications , Oxidative Stress , Animals , Cataract/metabolism , Disease Models, Animal , Glycation End Products, Advanced/analysis , Glycation End Products, Advanced/metabolism , Lens, Crystalline/metabolism , Lysine/analogs & derivatives , Lysine/analysis , Lysine/metabolism , Male , Mice, Inbred Strains , Streptozocin , Tandem Mass Spectrometry
3.
J Nutr Sci Vitaminol (Tokyo) ; 63(4): 263-268, 2017.
Article in English | MEDLINE | ID: mdl-28978874

ABSTRACT

Aphanothece sacrum (Sur.) Okada is a species of cyanobacteria found in Japan. Although it has been used in local cuisine in Kyushu, Japan, for 250 y, little is known about its beneficial effect as food. The daily intake of health beneficial phytochemicals is believed to be useful for preventing lifestyle-related diseases, such as diabetic cataracts. In this study, the inhibitory effect of freeze-dried A. sacrum (Asa) on the formation of diabetic cataracts (DCs) was evaluated. Type 1 diabetes was induced in mice using streptozotocin (STZ). The mice were divided into two groups: one was fed a normal diet (DM-control group) and the other was fed a diet containing 1% Asa (DM-Asa group). During the study, changes in blood glucose levels and the amount of food and water consumed were measured. After 3 mo, the amount of Nε-(carboxymethyl)lysine (CML), an oxidative stress marker, in the lens was measured using liquid chromatography-tandem mass spectrometry (LC-MS/MS). Although the blood glucose levels (p=0.91) and food consumption did not significantly change in any group, the oral administration of Asa tended to suppress CML accumulation (p=0.15) and significantly inhibited the progression of cataractogenesis in the diabetic lens compared with that reported for the normal diet (p=0.009). These results suggested that the daily intake of A. sacrum prevents the pathogenesis of cataracts, and indicated that may reduce the number of DC patients.


Subject(s)
Cataract/etiology , Cataract/prevention & control , Cyanobacteria , Diabetes Mellitus, Experimental/complications , Diet , Animals , Biomarkers/analysis , Cyanobacteria/chemistry , Diabetes Mellitus, Experimental/diet therapy , Freeze Drying , Lens, Crystalline/chemistry , Lysine/analogs & derivatives , Lysine/analysis , Male , Mice , Oxidative Stress
4.
J Food Sci ; 80(11): C2420-9, 2015 Nov.
Article in English | MEDLINE | ID: mdl-26457985

ABSTRACT

UNLABELLED: Yacon (Smallanthus sonchifolius), a native Andean plant, has been cultivated as a crop and locally used as a traditional folk medicine for the people suffering from diabetes and digestive/renal disorders. However, the medicinal properties of this plant and its processed foods have not been completely established. This study investigates the potent antioxidative effects of herbal tea leaves from yacon in different free radical models and a ferric reducing model. A hot-water extract exhibited the highest yield of total polyphenol and scavenging effect on 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical among four extracts prepared with hot water, methanol, ethanol, and ethylacetate. In addition, a higher reducing power of the hot-water extract was similarly demonstrated among these extracts. Varying concentrations of the hot-water extract resulted in different scavenging activities in four synthetic free radical models: DPPH radical (EC50 28.1 µg/mL), 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) cation radical (EC50 23.7 µg/mL), galvinoxyl radical (EC50 3.06 µg/mL), and chlorpromazine cation radical (EC50 475 µg/mL). The yacon tea-leaf extract further demonstrated superoxide anion (O2(-)) radical scavenging effects in the phenazine methosulfate-NADH-nitroblue tetrazolium (EC50 64.5 µg/mL) and xanthine oxidase assay systems (EC50 20.7 µg/mL). Subsequently, incubating human neutrophilic cells in the presence of the tea-leaf extract could suppress the cellular O2(-) radical generation (IC50 65.7 µg/mL) in a phorbol 12-myristate 13-acetate-activated cell model. These results support yacon tea leaves may be a good source of natural antioxidants for preventing O2(-) radical-mediated disorders. PRACTICAL APPLICATION: Yacon has been considered to be a potent alternative food source for patients who require a dietary cure in regional area, while the leaf part has been provided and consumed as an herbal tea in local markets. We demonstrated here potent antioxidative effects of the tea leaves from yacon in different free radical assays, reducing power assay, and cellular superoxide anion radical generation assay. Results support yacon tea leaves may be a good source of natural antioxidants for preventing O2(-) radical-mediated disorders.


Subject(s)
Antioxidants/pharmacology , Asteraceae/chemistry , Plant Extracts/pharmacology , Superoxides/metabolism , Teas, Herbal/analysis , Antioxidants/analysis , Benzhydryl Compounds/metabolism , Benzothiazoles/metabolism , Biphenyl Compounds/metabolism , Chlorpromazine/metabolism , Free Radicals/metabolism , Humans , Phenols/analysis , Phenols/pharmacology , Picrates/metabolism , Plant Extracts/chemistry , Plant Leaves/chemistry , Sulfonic Acids/metabolism
5.
Chem Pharm Bull (Tokyo) ; 63(8): 641-8, 2015.
Article in English | MEDLINE | ID: mdl-26235171

ABSTRACT

Four new resin glycosides, named calysolins XIV (1), XV (2), XVI (3), and XVII (4) were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM.. et SCHULT. (Convolvulaceae). Their structures were determined based on spectroscopic and chemical evidence, and consisted of two different types: those (1) with a macrolactone structure and those (2-4) with a non-macrolactone structure. Their sugar moieties were partially acylated by specific organic acids, including tiglic, 2S-methylbutyric, and 2S,3S-nilic acids. Additionally, evaluation of the antiviral activity of 1-4 revealed effects against the herpes simplex virus type 1.


Subject(s)
Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Calystegia/chemistry , Glycosides/chemistry , Glycosides/pharmacology , Herpesvirus 1, Human/drug effects , Antiviral Agents/isolation & purification , Glycosides/isolation & purification , Herpes Simplex/drug therapy , Humans
6.
Chem Pharm Bull (Tokyo) ; 62(8): 839-44, 2014.
Article in English | MEDLINE | ID: mdl-25087638

ABSTRACT

Four new resin glycosides having macrolactone structures (jalapins), named calysolins X (1)-XIII (4), were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae). Their structures were determined on the basis of spectroscopic data as well as chemical evidence. The sugar moieties of 1-4 were partially acylated by some organic acids, including tiglic acid, 2S-methylbutyric acid, and 2S,3S-nilic acid. Additionally, the antiviral activity of 1-4 toward herpes simplex virus type 1 was evaluated. All the compounds showed antiviral activity.


Subject(s)
Antiviral Agents/chemistry , Calystegia/chemistry , Glycosides/chemistry , Herpesvirus 1, Human/drug effects , Lactones/chemistry , Resins, Plant/chemistry , Antiviral Agents/isolation & purification , Antiviral Agents/pharmacology , Glycosides/isolation & purification , Glycosides/pharmacology , Herpes Simplex/drug therapy , Humans , Lactones/isolation & purification , Lactones/pharmacology
7.
Chem Pharm Bull (Tokyo) ; 62(1): 97-105, 2014.
Article in English | MEDLINE | ID: mdl-24390499

ABSTRACT

Five new resin glycosides having macrolactone structures (jalapins), named calysolins V-IX (1-5), were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae). Their structures were determined on the basis of spectroscopic data as well as chemical evidence. The isolated compounds could be classified into two macrolactone types-one having a 22-membered ring (1-4) and the other with a 27-membered ring (5). The sugar moieties of 1-5 were found to exist in partially acylated forms comprising 2S-methylbutyric acid and tiglic acid. Compounds 4 and 5 are the first representatives of the calysolic acid C as the component glycosidic acid. Additionally, the antiviral activity of 1-5, together with calysolins I-IV and soldanelline B, which are previously isolated jalapins from this plant, toward herpes simplex virus type 1 was evaluated. All the compounds showed antiviral activity.


Subject(s)
Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Calystegia/chemistry , Glycosides/chemistry , Glycosides/pharmacology , Herpesvirus 1, Human/drug effects , Lactones/chemistry , Lactones/pharmacology , Resins, Plant/chemistry , Resins, Plant/pharmacology
8.
J Nat Prod ; 74(11): 2414-9, 2011 Nov 28.
Article in English | MEDLINE | ID: mdl-21992192

ABSTRACT

Four new resin glycosides having intramolecular cyclic ester structures (jalapins), named calysolins I-IV (1-4), were isolated from the methanol extract of leaves, stems, and roots of Calystegia soldanella , along with one known jalapin (5) derivative. The structures of 1-4 were determined on the basis of spectroscopic data and chemical evidence. They fall into two types, one having a 22-membered ring (1 and 4) and the other with a 27-membered ring (2 and 3). The sugar moieties of 1-4 were partially acylated by some organic acids. Compound 4 is the first example of a hexaglycoside of jalapin.


Subject(s)
Calystegia/chemistry , Glycosides/isolation & purification , Resins, Plant/isolation & purification , Carbohydrate Sequence , Glycosides/analysis , Glycosides/chemistry , Molecular Structure , Plant Leaves/chemistry , Plant Roots/chemistry , Plant Stems/chemistry , Resins, Plant/analysis , Resins, Plant/chemistry
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