Icariside II
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Icariside II
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CAS No:
113558-15-9
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Formula:
C27H30O10
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Chemical Name:
Icariside II
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Synonyms:
4H-1-Benzopyran-4-one,3-[(6-deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-;4H-1-Benzopyran-4-one,3-[(6-deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-;3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one;Icariside II;Baohuoside I;Baohuoside 1;Icariin II;Baohuside I
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CAS No:
Description
Baohuoside I, a flavonoid isolated from Epimedium koreanum Nakai, acts as an inhibitor of CXCR4, downregulates CXCR4 expression, induces apoptosis and shows anti-tumor activity.
Icariside II is a glycosyloxyflavone that is 3,5,7-trihydroxy-4'-methoxy-8-prenylflavone in which the hydroxy group at position 3 has been converted into its alpha-L-rhamnopyranoside. It has a role as a plant metabolite, an anti-inflammatory agent, an antineoplastic agent and an apoptosis inducer. It derives from an alpha-L-rhamnopyranose.
Characteristics
155
3.5
1.5±0.1 g/cm3
202-203 °C
759.4ºC at 760mmHg
253.9±26.4 °C
1.666
3.07E-24mmHg at 25°C
Icariside II Use and Manufacturing
Mycelia of C. blakesleeana from agar slants (2cmIcariin(10 g, 14.8 mmol) and β-glucanase(10 g) was added to 500 mLSodium acetate and Hydrochloric acid Buffer solution (Et0H / H20 (V / V) = 30/70, ? H = 5.0) The reaction mixture was stirred at 50 ° C for 5 hours, And concentrated under reduced pressure. The residue was added with water (2000 mL) and stirred for 30 minutes. Ethyl acetate was added (50 mL' 3) and the combined organic layers were washed with saturated sodium chloride solution (30 mL) and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure and the residue was recrystallized from ethyl acetate to give the title compound as a yellow solid (6 g, 79percent).Icariin (10g)And beta-glucanase (10 g)Add 500 mL of sodium acetate and hydrochloric acid in a buffer solution (pH= 5.0, EtOH / H2O = 30/70, V / V), The reaction mixture was stirred at 50 ° C for 5 hours and concentrated under reduced pressure.The residue was added to 2000 mL of water and stirred for 30 minutes, Ethyl acetate (50 mL x 3) was added, The organic phases were combined, washed with saturated sodium chloride solution (30 mL) and dried over anhydrous sodium sulfate.The organic phase was concentrated under reduced pressure and the residue was recrystallized from ethyl acetate.The title compound was obtained as a yellow solid (6 g, yield 79percent, HPLC: 98percent).On the culture day 10, 300mg of 1 in 1.2mlDMF was added into 25 flasks with cellcultures. After additional 4 days of incubation, the cell cultures were filtered under avacuum and the filtrate was extracted withEtOAc. The EtOAc extract was evaporatedunder reduced pressure to yield 2.1 g ofresidue, which was subjected to CC overSephadex LH-20 (CHCl3–MeOH 1:1, v/v) to obtain six fractions (Fr.1-Fr.6). Fraction 4(42.5mg) was further separated by reversephasesemi-preparative HPLC eluting withCH3OH–H2O (80:20) at 3ml/min to afford4 (17.8mg, ca. 5.9percent; tR 10.1min).
Computed Properties
Molecular Weight:514.5
XLogP3:3.5
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:6
Exact Mass:514.18389715
Monoisotopic Mass:514.18389715
Topological Polar Surface Area:155
Heavy Atom Count:37
Complexity:874
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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