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Biomedical subjects

J Kinjo

Publications and source records attributed to J Kinjo.

At least 37 records · Page 2Linked to original sources
PubMed1998

Preventive effects of saponins from the Pueraria lobata root on in vitro immunological liver injury of rat primary hepatocyte cultures.

Preventive effects of nine saponins obtained from Puerariae Radix (the roots of Pueraria lobata) on in vitro immunological liver injury in primary cultured rat hepatocytes were studied. Although all tested saponins showed hepatoprotective action, the levels of activity of individual saponins differed. Structure-activity relationships for the sapogenol moiety suggested that the hydroxy group at C-29 would reduce the hepatoprotective activity while the hydroxy group at C-21 could enhance the hepatoprotective activity. Furthermore, structure-activity relationships for the sugar moiety suggested that the oxygen-bearing group at C-5" would enhance the hepatoprotective activity, though the configuration of the hydroxy group at C-3" could be less important for hepatoprotective activity.

Animals↗
PubMed1998

Structures of three new oleanene glucuronides isolated from Lathyrus palustris var. pilosus and hepatoprotective activity.

Three new saponins, named palustrosides I, II and III, together with azukisaponins II, V and soyasapogenol B monoglucuronide, were isolated from the aerial parts of Lathylus palustris L. var. pilosus Ledeb. The structures of palustrosides I, II and III were identified as 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosides of soyasapogenol E, abrisapogenol E, and bredemolic acid 28-O-beta-D-glucopyranoside, respectively, by spectroscopic and chemical methods. As part of our studies on hepatoprotective drugs, we also examined the hepatoprotective effects of these saponins towards immunologically induced liver injury in primary cultured rat hepatocytes. The activity of the disaccharide group was greater than that of the trisaccharide group. This information regarding the structure-activity relationships substantiated previously obtained data. Structure-hepatoprotective relationships for the sapogenol moiety suggested that the hydroxyl group at C-30 reduces the hepatoprotective effect. On the other hand, the carbonyl group at C-22 may be equivalent to a hydroxyl group at C-22 in terms of hepatoprotective action. Oleanolic acid-type saponins also exhibited hepatoprotective action.

Animals↗
PubMed1998

Partial hydrolysis of soyasaponin I and the hepatoprotective effects of the hydrolytic products. Study of the structure-hepatoprotective relationship of soyasapogenol B analogs.

As a part of our studies of hepatoprotective drugs, we prepared some soyasapogenol B analogs from soyasaponin I. We examined the hepatoprotective effects of these analogs, using immunologically-induced liver injury, in primary cultured rat hepatocytes. Soyasaponin III and soyasapogenol B monoglucuronide were more effective than soyasaponin I. Both compounds were significantly effective even at 30 microM. The action of soyasapogenol B was almost equal to that of soyasaponin I, although glucuronic acid did not show any activity even at the highest dose (500 microM). When the two compounds were mixed, the hepatoprotective action did not change, compared with soyasapogenol B. Therefore, we concluded that the linkage between glucuronic acid and soyasapogenol B could enhance the hepato-protective activity.

Animals↗
PubMed1998

A new oleanene glucuronide having a branched-chain sugar from Melilotus officinalis.

A new oleanene glucuronide called melilotus-saponin O1 (1) was isolated together with three known ones from the roots of Melilotus officinalis (L.) PALLAS (Leguminosae). The structure of 1 was determined to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1--> 3)]- beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl soyasapogenol B by spectroscopic and chemical methods.

Antiviral Agents↗
PubMed1998

HPLC profile analysis of oleanene-glucuronides in several edible beans.

HPLC analysis and yield of oleanene-glucuronide (OG) was done on some commercially available edible beans: seeds of Glycine max, Glycine max cv. Kuromame, Phaseolus vulgaris cv. Torosuku, Phaseolus vulgaris cv. Toramame, Phaseolus vulgaris cv. Taishokintoki, Phaseolus coccineus cv. Ooshirobana, Phaseolus coccineus cv. Murasakihanamame, Vigna unguiculata cv. Chuguro, Vigna angularis cv. Dainagon, Arachis hypogaea, Pisum sativum, and Vicia faba. All the beans listed above have OG, though in varying the amounts. Furthermore the HPLC profiles of beans belonging to the same genus were very similar except for that of the Vigna genus. There was no great difference of the HPLC profiles with respect to the cultivated varieties. The structures of the major OGs in each type of beans were identified as soyasaponins I (1) and V (2), and phaseoside I (3) (Phaseolus vulgaris and P. coccineus); 1 and soyasaponin II (4) (Glycine max); 1 and 2 (Vigna unguiculata); 1 (Pisum sativum, Arachis hypogaea and Vicia faba). In contrast, those in Dainagon (Vigna angularis cv. Dainagon) were identified as azukisaponins II (5) and VI (6).

Carbohydrate Sequence↗
PubMed1997

Cytotoxic glycosides from Albizia julibrissin.

During the course of a study of leguminous plants, cytotoxicity was demonstrated by the crude saponin fraction of Albizia julibrissin. Following chromatographic purification, the structures of three novel saponins, julibrosides I-III (1-3), inclusive of a cytotoxic principle, were elucidated. A comparison of the cytotoxicity of julibrosides (1-3) and their prosapogenins (4-15) prepared by alkaline hydrolysis clearly indicated that both an alpha-L-arabinofuranosyl-(1-->4)-[beta-D-glucopyranosyl-(1-->3)]-alpha- L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester unit and a monoterpene-quinovopyranosyl moiety are crucial substituents for cytotoxicity among this class of compounds. The hydroxy group at C-16 of aglycon may play an important role in mediating cytotoxicity, and the N-acetyl-glucosamine moiety at C-3 seems to enhance activity because 3 showed the strongest cytotoxicity.

Antineoplastic Agents, Phytogenic↗
PubMed1997

Pharmacological studies on Puerariae flos III: protective effects of kakkalide on ethanol-induced lethality and acute hepatic injury in mice.

Kakkalide, one of the major isoflavonoid components of Puerariae flos, has been investigated for its effect on ethanol-induced intoxication and on hepatic injury, including hyperglycaemia, in mice. Kakkalide reduced mortality associated with administration of ethanol. At doses of 100 and 200 mg kg-1 the effect of kakkalide was significant. The same dose of kakkalide prevented increased serum glutamic oxaloacetic transaminase and glutamic pyruvic transaminase activity. At a dose of 200 mg kg-1 it also counteracted ethanol-induced elevation of glucose levels. These results suggest that kakkalide might be useful for counteracting the effects of alcohol and might be effective for treating hepatic injury.

Acute Disease↗
PubMed1997

Preventive effects of saponins from puerariae radix (the root of Pueraria lobata Ohwi) on in vitro immunological injury of rat primary hepatocyte cultures.

The preventive effects of saponins from Puerariae Radix toward in vitro immunological liver injury using an antiserum against the rat liver plasma membranes on primary cultured rat hepatocytes were studied. Crude saponin from Puerariae Radix inhibited the elevation of alanine aminotransferase (ALT) activity at the dose of 90 micrograms/ml. The inhibition was stronger than that of glycyrrhizin, which was a positive control drug. The representative saponins in this drug, soyasaponin I and kudzusaponin SA3, were also more effective than glycyrrhizin, although their effects were weaker than that of crude saponin at the lower doses (90, 200 micrograms/ml). At 500 micrograms/ml, kudzusaponin SA3 showed antihepatotoxic activity equal to that of crude saponin.

Animals↗
PubMed1997

Oleanene-type triterpene glycosides from puerariae radix. IV. Six new saponins from Pueraria lobata.

From Puerariae Radix, the root of Pueraria lobata (Leguminosae), six new oleanene-type triterpene glycosides, called kudzusaponins A1 (1), A2 (2), Ar (3), SA4 (5), and SB1 (6) were isolated together with kudzusaponin A3 (7), soyasaponins SA3 (8), and I (9). The structures of 1-6 were determined to be 3-O-alpha-L-rhamnopyranosyl- (1-->2)-beta-D-arabinopyranosyl-(1-->2)beta-D-glucuronopyranosy l kudzusapogenol A 22-O-beta-D-xylopyranoside, 3-O-beta- D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl kudzusapogenol A, 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl kudzusapogenol A, 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta- D-glucoronopyranosyl kudzusapogenol A, 3-O-beta-D-glucuronopyranosyl[(1-->2)-beta-D-glucuronopyranosyl soyasapogenol A22-O-alpha-L-arabinopyranoside,and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl- (1-->2)-beta- D-glucuronopyranosyl (beta-fabatriosyl) soyasapogenol B 22-O-alpha-L-arabinopyranoside, respectively.

Carbohydrate Sequence↗
PubMed1996

Triterpene saponins from Abrus cantoniensis (Leguminosae). II. Characterization of six new saponins having a branched-chain sugar.

The chemical structures of abrisaponins So1 (1), So2 (2), D2 (3), D3 (4), F (5) and SB (6), six of twenty-three saponins from Abri Herba, the whole plants of Abrus cantoniensis (Leguminosae), were investigated. They were elucidated to be 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[O-beta-D-glucopyranosyl-(1-->3)]-beta-D-galactopyranosyl-(1 --> 2)-beta-D-glucuronopyranosyl [sequence: see text] (designated as beta-abritetraosyl) sophoradiol (1), 3-O-beta-abritetraosyl sophoradiol 22-O-beta-D-xylopyranoside (2), 3-O-beta-abritetraosyl abrisapogenol D (3), O-beta-abritetraosyl abrisapogenol D 22-O-beta-D-glucopyranoside (4), 3-O-beta-abritetraosyl abrisapogenol F (5) and 3-O-beta-abritetraosyl soyasapogenol B (6), respectively.

Fabaceae↗
PubMed1996

Oleanene-type triterpene glycosides from puerariae radix. III. Three new saponins from Pueraria thomsonii.

From the root of Pueraria thomsonii (Leguminosae), three new oleanane-type triterpene glycosides, named kudzusaponin B1, acetyl-kaikasaponin III and acetyl-soyasaponin I were isolated, together with soyasaponin I (4) and subproside V (5). Their structures were determined to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2) -beta-D-glucuronopyranosyl kudzusapogenol B (1), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2) -beta-D-glucuronopyranosyl sophoradiol 22-O-acetate (2) and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2) -beta-D-glucuronopyranosyl soyasapogenol B 22-O-acetate (3), respectively.

Chromatography, Thin Layer↗
PubMed1995

Triterpenoidal saponins from Dumasia truncata.

Extraction of the aerial parts of Dumasia truncata Sieb et Zucc. afforded two new triterpenoidal saponins, together with four known ones. The structures of the new compounds were elucidated by spectral analysis as 3-O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucuronopyranosy-28-O- beta-D- glucopyransoyl hederagenin and 3-O-beta-D-xylopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl (1-->3)]-beta-D-glucuronopyranosyl oleanic acid.

Carbohydrate Conformation↗
PubMed1995

Oleanene-type triterpene glycosides from Puerariae Radix. II. Isolation of saponins and the application of tandem mass spectrometry to their structure determination.

A continuing study of the ingredients of Puerariae Radix, the roots of Pueraria lobata (WILLD.) OHWI, which is one of the most important crude drugs, has resulted in the first isolation of four new oleanene-type triterpene glycosides, named kudzusaponins SA1, SA2, SA3 and C1 (1-4). Their structures were determined to be 3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl soyasapogenol A (1), 3-O-beta-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl soyasapogenol A 22-O-alpha-L-arabinopyranoside (2), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-D- glucuronopyranosyl kudzusapogenol C 21-O-beta-D-glucopyranoside (4), respectively. The usefulness of tandem mass spectrometry in the structural determination of oleanene-type triterpene bisdesmosides is also discussed.

Carbohydrate Conformation↗
PubMed1995

Five new triterpene glycosides from Wisteria brachybotrys (Leguminosae).

From the vines of Wisteria brachybotrys (Leguminosae), five new oleanene glycosides, called wistariasaponins YC1,2, B3 and A2,3, together with four known ones were isolated. Their structures have been elucidated to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl-(1-->2)-beta-D- glucuronopyranosyl yunganogenin C 21-O-beta-D-glucopyranoside (1), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta -D- glucuronopyranosyl yunganogenin C 21-O-beta-D-glucopyranoside (2), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl-(1-->2)-beta- -D-glucuronopyranosyl wistariasapogenol B 30-O-beta-D-glucopyranoside (3), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl-(1-->2)-beta-D- glucuronopyranosyl wistartiasapogenol A 30-O-beta-D-glucopyranoside (4) and 3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl wistariasapogenol A 30-O-beta-D-glucopyranoside (5), respectively.

Carbohydrate Sequence↗
PubMed1994

Two new triterpenoidal glycosides from Medicago polymorpha L.

Two new triterpenoid glycosides called medicago-saponins P1 (1) and P2 (2) were isolated together with five known glycosides from the aerial parts of Medicago polymorpha L. (Leguminosae). The structures of 1 and 2 were determined to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl caulophyllogenin 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside and the desglucoside of 1.

Carbohydrate Sequence↗
PubMed1994

Five new triterpene glycosides from Russell lupine.

In a continuing study on the ingredients of Lupinus genus, we examined the oligoglycoside constituents of the Russell lupine (L. polyphyllus x L. arboreus hybrid). Five new oleanene glycosides, called Lupinosides PA1-5 (1-5), together with three known ones were isolated. Their structures of 1-5 were determined to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl- (1-->2)-beta-D-glucuronopyranosyl soyasapogenol A 21-O-beta-D- xylopyranoside (1), 3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl soyasapogenol A 21-O-beta-D-xylopyranoside (2), 3- O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta-D -glucuronopyranosyl kudzusapogenol A 21-O-beta-D- xylopyranoside (3), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D- galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl soyasapogenol B 22-O-alpha-L-rhamnopyranoside (4), and 3-O-alpha-L-rhamnopyranosyl-(1-->2)- beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl soyasapogenol B 22-O- beta-D-glucopyranosyl-(1-->4)-alpha-L-rhamnopyranoside (5), respectively.

Carbohydrate Sequence↗
PubMed1993

Synthesis and pharmacokinetics of a dihydropyridine chemical delivery system for the antiimmunodeficiency virus agent dideoxycytidine.

In order to explore the possibility that a dihydropyridine/pyridinium redox chemical delivery system might enhance significantly the brain uptake of the anti-HIV agent dideoxycytidine (DDC), we prepared a DDC derivative which bore the 1,4-dihydro-1-methyl-3-pyridylcarbonyl moiety at both the cytidine exocyclic amino moiety and the sugar 5'-hydroxyl function; namely, 5',4N-bis-[(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl]-2',3'- dideoxycytidine (2). In cell-free extracts of rat brain tissue, compound 2 was readily converted to free DDC by stepwise oxidation and hydrolysis of the dihydropyridyl groups. Time-dependent plasma and brain concentrations of DDC and 2 were determined following iv administration of 2 (49.3 mg/kg) to rats. Compound 2 could be detected in brain, reaching peak concentrations of 7.7 +/- 2.9 nmol/g at 15 min. Low levels of DDC also were detected with a peak concentration of 1.4 +/- 0.5 nmol/g at 240 min after injection. The brain/plasma concentration integral of compound 2 was 0.95 whereas that for DDC in brain as a ratio of combined DDC and compound 2 levels in plasma was 0.24. Despite this, brain concentrations remained low and not significantly different from those achieved following administration of DDC alone.

Animals↗