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Androsin Sale

(Synonyms: 草夹竹桃苷) 目录号 : GC35342

A phenol glucoside with diverse biological activities

Androsin Chemical Structure

Cas No.:531-28-2

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产品描述

Androsin is a phenol glucoside that has been found in P. kurroa and has diverse biological activities.1,2,3 It is active against the bacteria S. aureus, S. epidermidis, P. aeruginosa, E. cloacae, K. pneumoniae, and E. coli (MICs = 0.6, 0.68, 0.97, 0.85, 1, and 1.08 mg/ml, respectively) and the fungi C. albicans, C. tropicalis, and C. glabrata (MICs = 1.85, 1.7, and 1.65 mg/ml, respectively).3 Androsin (10 mg/kg) inhibits bronchial obstruction in a guinea pig model of asthma induced by ovalbumin or platelet-activating factor (PAF).2

1.Stuppner, H., and Wagner, H.Minor iridoid and phenol glycosides of Picrorhiza kurrooaPlanta Med.55(5)467-469(1988) 2.Dorsch, W., Stuppner, H., Wagner, H., et al.Antiasthmatic effects of Picrorhiza kurroa: Androsin prevents allergen- and PAF-induced bronchial obstruction in guinea pigsInt. Arch. Allergy Appl. Immunol.95(2-3)128-133(1991) 3.Zajdel, S.M., Graikou, K., Sotiroudis, G., et al.Two new iridoids from selected Penstemon species - antimicrobial activityNat. Prod. Res.27(24)2263-2271(2013)

Chemical Properties

Cas No. 531-28-2 SDF
别名 草夹竹桃苷
Canonical SMILES CC(C1=CC=C(O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)C(OC)=C1)=O
分子式 C15H20O8 分子量 328.31
溶解度 Soluble in DMSO 储存条件 4°C, protect from light
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1 mg 5 mg 10 mg
1 mM 3.0459 mL 15.2295 mL 30.459 mL
5 mM 0.6092 mL 3.0459 mL 6.0918 mL
10 mM 0.3046 mL 1.523 mL 3.0459 mL
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Research Update

Antiasthmatic effects of Picrorhiza kurroa: Androsin prevents allergen- and PAF-induced bronchial obstruction in guinea pigs

Int Arch Allergy Appl Immunol 1991;95(2-3):128-33.PMID:1718906DOI:10.1159/000235416.

In the Ayurvedic medicine, Picrorhiza kurroa Royle ex Benth. is used for the treatment of liver and lung diseases. Using different chemical and pharmacological methods, we could identify the phenol glycoside Androsin as active compound preventing allergen and platelet-activating factor induced bronchial obstruction in guinea pigs in vivo (10 mg/kg p.o.; 1 h prior to the inhalation challenge). Histamine release from human polymorphonuclear leukocytes in vitro was inhibited by other compounds yet to be identified.

Phenolic glycosides from Pyrola japonica

Chem Pharm Bull (Tokyo) 2004 Jun;52(6):714-7.PMID:15187393DOI:10.1248/cpb.52.714.

Five new phenolic glycosides, 2-beta-D-glucopyranosyloxy-5-hydroxyphenylacetic acid methyl ester (4), 4-hydroxy-2-[3-hydroxy-3-methylbutyl]-5-methylphenyl beta-D-glucopyranoside (5), 4-hydroxy-2-[(E)-4-hydroxy-3-methyl-2-butenyl]-5-methylphenyl beta-D-glucopyranoside (7), 4-hydroxy-2-[(2E,6Z)-8-beta-D-glucopyranosyloxy-3,7-dimethylocta-2,6-dien-1-yl]-5-methylphenyl beta-D-glucopyranoside (8), and 2,7-dimethyl-1,4-dihydronaphthalene-5,8-diol 5-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranoside (10), were isolated from the whole plants of Pyrola japonica (Pyrolaceae), together with Androsin, (-)-syringaresinol glucoside, homoarbutin, pirolatin, hyperin, monotropein and chimaphilin.

Minor Iridoid and Phenol Glycosides of Picrorhiza kurrooa

Planta Med 1989 Oct;55(5):467-9.PMID:17262460DOI:10.1055/s-2006-962066.

From the roots of PICRORHIZA KURROOA a new iridoid glycoside, 6-feruloylcatalpol has been isolated, along with veronicoside and minecoside and two phenol glucosides, picein and Androsin.

Antioxidative phenylethanoid and phenolic glycosides from Picrorhiza scrophulariiflora

Chem Pharm Bull (Tokyo) 2004 May;52(5):615-7.PMID:15133218DOI:10.1248/cpb.52.615.

One new phenylenthanoid glycoside, scroside D (2), was isolated from the roots of Picrorhiza scrophulariiflora (Scrophulariaceae), together with nine known phenylethanoid and phenolic glycosides: 2-(3,4-dihydroxyphenyl)-ethyl-O-beta-D-glucopyranoside (1), 2-(3-hydroxy-4-methoxyphenyl)-ethyl-O-beta-D-glucopyranosyl (1-->3)-beta-D-glucopyranoside (3), scroside B (4), hemiphroside A (5), plantainoside D (6), scroside A (7), Androsin (8), piceoside (9), and 6-O-feruloyl-beta-D-glucopyranoside (10). The structures of these compounds were elucidated using spectroscopic methods. The antioxidative activities of these isolated compounds were evaluated based on their scavenging effects on hydroxyl radicals and superoxide anion radicals, respectively. Compounds 1, 2, and 6 showed potent antioxidative effects as those of ascorbic acid and the structure-activity relationship is discussed.

Counter-current chromatographic method for preparative scale isolation of picrosides from traditional Chinese medicine Picrorhiza scrophulariiflora

J Sep Sci 2011 Aug;34(15):1910-6.PMID:21721121DOI:10.1002/jssc.201100025.

Apocynin, Androsin, together with picroside I, II and III from crude extracts of Picrorhiza scrophulariiflora were isolated by means of high-speed counter-current chromatography (CCC) combining elution-extrusion (EE) and cycling-elution (CE) approach. The EECCC took full advantages of the liquid nature of the stationary phase for a complete sample recovery and extended the solute hydrophobicity window, while CECCC showed its unique advantage in achieving effective separation of special compounds through preventing stationary phase loss. In the present work, the biphasic liquid system composed of n-hexane/ethyl acetate/methanol/water (1:2:1:2, v/v/v/v) was used for separation of apocynin and Androsin, ethyl acetate/n-butanol/water/formic acid (4:1:5:0.005, v/v/v/v) for picroside I, II and III. However, due to the extremely similar K values (K1 /K2 ≈1.2), picroside I and III were always eluted together by several biphasic solvent systems. In this case, the CECCC exhibited great superiority and baseline separated in the sixth cycle using ethyl acetate/water (1:1, v/v) as biphasic liquid system. Each fraction was analyzed by UPLC-UV and ESI-MS analysis, and identified by comparing with the data of reference substances. Compared with classical elution, the combination of EE and CE approach exhibits strong separation efficiency and great potential to be a high-throughput separation technique in the case of complex samples.