Structural requirements of flavonoids for inhibition of antigen-Induced degranulation, TNF-α and IL-4 production from RBL-2H3 cells

Mastuda, Hisashi; Morikawa, Toshio; Ueda, Kazuho; Managi, Hiromi; Yoshikawa, Masayuki

doi:10.1016/s0968-0896(02)00227-4

Cited by 164 publications

(125 citation statements)

References 12 publications

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“…The potency of melleolide H was nearly one order of magnitude weaker than melleolide J. Again, the potency of the reference substance quercetin was one order of magnitude stronger than melleolide J. Quercetin had an IC 50 of 6.7 µM, a value in accordance with the literature [24]. The biological effects are summarised in ▶ Table 1.…”

Section: Resultssupporting

confidence: 78%

Untitled

2017

PMIO

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IntroductionDuring our investigations of biologically active fungi, Armillaria ostoyae (Romagn.) Herink [1], a basidiomycete belonging to the family Physalacriaceae, came into focus, as it affected degranulation in RBL-2H3 cells. The species is commonly known as edible mushroom, but it also occurs as a devastating pathogen of various tree species causing serious economic losses in forestry all over the world [2]. The mechanisms of host infection as well as hostpathogen interactions have been studied intensively [3][4][5][6][7]. In addition, Armillaria mushrooms attract a wider interest, for instance, as the worldʼs biggest living organism [8] or as a producer of bioluminescence [9]. A broad variety of antibacterial and cytotoxic sesquiterpene aryl esters were isolated from the genus Armillaria, especially Armillaria mellea [10][11][12][13][14][15][16][17][18][19][20], but also Armillaria novae-zelandiae [21] and Armillaria tabescens [22]. In this manuscript, degranulation inhibiting effects of extracts from fruiting bodies and cultivated mycelium as well as bioactivity-guided isolation of compounds from the mycelium of A. ostoyae are described. Degranulation is the process in which cells release secretory products stored in secretory granules by exocytosis. It is an important feature of many immune cells, e.g., for release of mediators [23]. Inhibition of degranulation can result in the blocking of inflammatory or allergic reactions.

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Section: Resultssupporting

confidence: 78%

Untitled

2017

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“…The reaction mixture was neutralized with Dowex HCR W2 (H ϩ form) and the resin was removed by filtration. Evaporation of the solvent from the filtrate under reduced pressure yielded a crude product, whose most part was subjected to ordinary-phase silica gel column chro- 21) with some modifications. Briefly, RBL-2H3 cells were dispensed into 48-well plates at a concentration of 4ϫ104 cells/well using Eagle's minimum essential medium (MEM, Sigma) containing fetal calf serum (10%), penicillin (100 units/ml), streptomycin (100 mg/ ml), and 0.45 mg/ml of anti-DNP IgE, and these were incubated overnight at 37°C in 5% CO 2 for sensitization of the cells.…”

Section: Methodsmentioning

confidence: 99%

“…In the course of our studies on antiallergic constituents from natural medicines, [21][22][23][24][25][26][27][28][29][30][31][32] we previously reported that some triterpenes and oleanane-type triterpene oligoglycosides showed inhibitory effects on histamine release from rat exudate cells induced by an antigen-antibody reaction 33,34) and on b-hexosaminidase release induced by dinitrophenylated bovine serum albumin (DNP-BSA) from RBL-2H3 cells sensitized with anti-DNP immunoglobulin E (IgE). 8,14) As a continuation of this study, we examined the effects of acylated oleanane-type triterpene saponins, sasanquasaponins, on the release of b-hexosaminidase from RBL-2H3 cells.…”

Section: Inhibitory Effects Of Saponin Constituents (1-6) On the Relementioning

confidence: 99%

Medicinal Flowers. XXXI. Acylated Oleanane-Type Triterpene Saponins, Sasanquasaponins I-V, with Antiallergic Activity from the Flower Buds of Camellia sasanqua

et al. 2010

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A Theaceae plant, Camellia (C.) sasanqua THUNB. (Japanese name "sazanka"), which is native to Japan, has been widely cultivated as an ornamental plant in Japanese garden. The flower buds of this plant are used for the similar purpose to those of C. japonica (Japanese name "tsubaki"), which has been used for the treatment of blood vomiting and bleeding due to internal and external injury, and also as antiinflamatory, tonic, and stomachic in Japanese folk medicine. As chemical constituents of this medicinal flower, several hydrolyzable tannins, 2) acylated anthocyanins, 3) and purin alkaloids 4) were reported. However, the pharmacological activities of the flower buds of this plant have not yet characterized. Recently, we have reported the isolation and structure elucidation of triterpene saponins from the flower buds of C. japonica L. (camelliosides A-D), 5,6) C. sinensis L. (chakasaponins I-VI, floratheasaponins A-J), [7][8][9][10][11][12] and C. oleifera ABEL (yuchasaponins A-D).13) Furthermore, those saponins were found to exhibit antiallergic, antidiabetic, antiobestic, gastroprotective, and platelet aggregation activities, etc. 5-13)As a continuation of our studies on bioactive constituents of the flower buds of Camellia species, we found that the methanolic extract and its 1-butanol-soluble fraction from the flower buds of C. sasanqua inhibited an immediate allergic reaction by monitoring the release of b-hexosaminidase from rat basophile leukemia (RBL-2H3) cells. 14) From the 1-butanol-soluble fraction, we have isolated new acylated oleanane-type triterpene saponins termed sasanquasaponins I (1), II (2), III (3), IV (4), and V (5), together with a known saponin, primulagenin15) In addition, we examined the inhibitory effects of sasanquasaponins (1-5) and 6 on the release of b-hexosaminidase from RBL-2H3 cells. In this paper, we describe the isolation and structure elucidaMedicinal Flowers. XXXI. Yamashina-ku, Kyoto 607-8412, Japan: and b Pharmaceutical Research and Technology Institute, Kinki University; 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan. Received August 9, 2010; accepted September 13, 2010; published online September 14, 2010 The methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia sasanqua THUNB. were found to show inhibitory activities on the release of b-hexosaminidase from rat basophile leukemia (RBL-2H3) cells. From the 1-butanol-soluble fraction, five new acylated oleanane-type triterpene saponins, sasanquasaponins I-V, were isolated together with a known saponin and their chemical structures were elucidated on the basis of chemical and physicochemical evidence. The principal saponin constituents, sasanquasaponins I-III, with an acyl group at the 22-position of the aglycon part showed the inhibitory effects on the release of b-hexosaminidase and some structure-activity relationships were reported.

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“…Stimulation was stopped by placing the cells on ice. After centrifugation, the amount of -hexosaminidase activity released from the cells in the supernatant was measured according to the method of Shibata et al 30) and Matsuda et al 31) with some modifications. Fifty microliters of supernatant and 50 ml of 1 mM 4-nitrophenyl N-acetyl--D-glucosaminide (in a 0.1 M sodium citrate buffer at pH 4.5) were mixed in a 96-well plate, and then incubated at 37 C for 2 h. The reaction was stopped by adding 200 ml of a 0.1 M sodium bicarbonate buffer (pH 10.0), and the -hexosaminidase activity in the supernatant was quantified by measuring the absorbance with a microplate reader having a 405-nm filter.…”

Section: Methodsmentioning

confidence: 99%