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113558-15-9

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113558-15-9 Usage

Uses

Baohuoside I is an inhibitor of cell growth and also is a down-regulator of durvivin and cyclin D1 expression. Used in the treatment of esophageal cancer. Anti-cancer agent.

Definition

ChEBI: A glycosyloxyflavone that is 3,5,7-trihydroxy-4'-methoxy-8-prenylflavone in which the hydroxy group at position 3 has been converted to its alpha-L-rhamnopyranoside.

Check Digit Verification of cas no

The CAS Registry Mumber 113558-15-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,3,5,5 and 8 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 113558-15:
(8*1)+(7*1)+(6*3)+(5*5)+(4*5)+(3*8)+(2*1)+(1*5)=109
109 % 10 = 9
So 113558-15-9 is a valid CAS Registry Number.
InChI:InChI=1/C27H30O10/c1-12(2)5-10-16-17(28)11-18(29)19-21(31)26(37-27-23(33)22(32)20(30)13(3)35-27)24(36-25(16)19)14-6-8-15(34-4)9-7-14/h5-9,11,13,20,22-23,27-30,32-33H,10H2,1-4H3/t13-,20-,22+,23+,27-/m0/s1

113558-15-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name icariside II

1.2 Other means of identification

Product number -
Other names 2h44

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:113558-15-9 SDS

113558-15-9Synthetic route

icariin
489-32-7

icariin

icariside II
113558-15-9

icariside II

Conditions
ConditionsYield
With Cunninghamella blakesleana In methanol for 120h; Microbiological reaction; regioselective reaction;95.1%
With cellulase In dimethyl sulfoxide at 37℃; pH=5.7; Enzymatic reaction;84%
With β-glucanase; sodium acetate In aq. buffer at 50℃; for 5h; Enzymatic reaction;79%
C15H24N2O17P2

C15H24N2O17P2

icaritin
118525-40-9

icaritin

icariside II
113558-15-9

icariside II

Conditions
ConditionsYield
With recombinant rhamnosyl transferase from Epimedium pseudowushanense; UDP-rhamnose synthase from Epimedium pseudowushanense; nicotinamide adenine dinucleotide; NADPH In dimethyl sulfoxide at 30℃; for 12h; pH=7.4; Enzymatic reaction; regioselective reaction;87%
icariin

icariin

icariside II
113558-15-9

icariside II

Conditions
ConditionsYield
With hydrogenchloride; sodium acetate In ethanol; water at 50℃; for 5h; pH=5; Enzymatic reaction;79%
icariin

icariin

icariside II
113558-15-9

icariside II

Conditions
ConditionsYield
With emulsin
epimedium koreanum Nakai, leaves; 1-butanol-ether-hexane-methanol extract of

epimedium koreanum Nakai, leaves; 1-butanol-ether-hexane-methanol extract of

A

icaritin
118525-40-9

icaritin

B

icariside II
113558-15-9

icariside II

C

3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin
56725-99-6

3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin

Conditions
ConditionsYield
With hydrogenchloride; methanol; water at 80℃; for 8h; Product distribution / selectivity; Heating / reflux;
With sodium methylate In pyridine at 80℃; for 8h; Product distribution / selectivity; Heating / reflux;
With acetic acid; β-glucuronidase; naringinase; hesperidinase; β-galactosidase; cellulase; amyloglucosidase at 37℃; for 48h; pH=4.5; Product distribution / selectivity;
Stage #1: epimedium koreanum Nakai, leaves; 1-butanol-ether-hexane-methanol extract of With water at 121℃; for 0.5h;
Stage #2: at 30℃; for 120h; Product distribution / selectivity;
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
518-82-1

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

icariin
489-32-7

icariin

A

anthraglycoside B
23313-21-5

anthraglycoside B

B

icariside II
113558-15-9

icariside II

Conditions
ConditionsYield
With glycosyltransferase from Carthamus tinctorius (L.) (Honghua) recombinant; UDP; Cleland's reagent In aq. buffer at 30℃; for 12h; pH=7.4; Enzymatic reaction; regiospecific reaction;A 26 %Chromat.
B 24 %Chromat.
icariin

icariin

icariside II
113558-15-9

icariside II

Conditions
ConditionsYield
With GH1 thermostable putative β-glucosidase IagBgl1 from Ignisphaera aggregans at 90℃; for 1.5h; pH=6.5; Temperature; Concentration; pH-value; Enzymatic reaction;
icariside II
113558-15-9

icariside II

icaritin
118525-40-9

icaritin

Conditions
ConditionsYield
With sulfuric acid In ethanol; water at 50℃; for 5h;82%
With sulfuric acid In ethanol; water at 50℃; for 5h;82%
With sulfuric acid In ethanol; water at 50℃; for 5h;82%
1 ,6-dibromohexane
629-03-8

1 ,6-dibromohexane

icariside II
113558-15-9

icariside II

7-((6-bromohexyl)oxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one

7-((6-bromohexyl)oxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux; Inert atmosphere;63%
icariside II
113558-15-9

icariside II

2-bromoethanol
540-51-2

2-bromoethanol

5-hydroxy-7-(2-hydroxyethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one
827320-51-4

5-hydroxy-7-(2-hydroxyethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone for 8h; Reflux;55%
With potassium carbonate In acetone Reflux; Inert atmosphere;30%
UDP-glucose
133-89-1

UDP-glucose

icariside II
113558-15-9

icariside II

icariin
489-32-7

icariin

Conditions
ConditionsYield
With 7-O-glucosyltransferase from Epimedium pseudowushanense In dimethyl sulfoxide at 30℃; for 12h; pH=7.4; Kinetics; Catalytic behavior; Reagent/catalyst; Temperature; pH-value; Green chemistry; Enzymatic reaction; regiospecific reaction;32.8%
icariside II
113558-15-9

icariside II

2-bromoethanol
540-51-2

2-bromoethanol

5-hydroxy-3,7-bis(2-hydroxyethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
1067198-74-6

5-hydroxy-3,7-bis(2-hydroxyethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone for 8h; Reflux;20.2%
icariside II
113558-15-9

icariside II

7-O-β-D-[2-(N-acetylamino)-2-deoxyglucopyranosyl]baohuoside

7-O-β-D-[2-(N-acetylamino)-2-deoxyglucopyranosyl]baohuoside

Conditions
ConditionsYield
With 7-O-glucosyltransferase from Epimedium pseudowushanense In dimethyl sulfoxide at 30℃; for 12h; pH=7.4; Kinetics; Green chemistry; Enzymatic reaction;19.7%
β-dimethylaminoethyl chloride hydrochloride

β-dimethylaminoethyl chloride hydrochloride

icariside II
113558-15-9

icariside II

7-(2-dimethylaminoethoxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one

7-(2-dimethylaminoethoxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux; Inert atmosphere;16.7%
UDP-xylose
3616-06-6

UDP-xylose

icariside II
113558-15-9

icariside II

7-O-β-D-xylosylbaohuoside

7-O-β-D-xylosylbaohuoside

Conditions
ConditionsYield
With 7-O-glucosyltransferase from Epimedium pseudowushanense In dimethyl sulfoxide at 30℃; for 12h; pH=7.4; Kinetics; Green chemistry; Enzymatic reaction;6%
icaritin
118525-40-9

icaritin

icariside II
113558-15-9

icariside II

3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin
56725-99-6

3-hydroxy-7-O-β-glucose-8-prenyl-4'-methoxychrysin

rhamnose

rhamnose

Conditions
ConditionsYield
With methanol In chloroform Purification / work up; Column chromatography;
icariside II
113558-15-9

icariside II

(((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromene-3-yl)oxy)methyl)phosphonic acid

(((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromene-3-yl)oxy)methyl)phosphonic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / ethanol; water / 5 h / 50 °C
2: caesium carbonate / acetone / Inert atmosphere; Reflux
3: 2,6-dimethylpyridine; trimethylsilyl bromide / dichloromethane / 20 °C / Inert atmosphere
View Scheme
icariside II
113558-15-9

icariside II

(((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromen-3-yl)oxy)methyl)phosphonate disodium

(((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromen-3-yl)oxy)methyl)phosphonate disodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sulfuric acid / ethanol; water / 5 h / 50 °C
2: caesium carbonate / acetone / Inert atmosphere; Reflux
3: 2,6-dimethylpyridine; trimethylsilyl bromide / dichloromethane / 20 °C / Inert atmosphere
4: sodium methylate / methanol / 0.5 h / 20 °C / Cooling with ice
View Scheme
icariside II
113558-15-9

icariside II

6(((5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4Η-chromene-3,7-diyl)bis(oxy))bis(methyl))bis(phosphonic acid diethyl ester)

6(((5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4Η-chromene-3,7-diyl)bis(oxy))bis(methyl))bis(phosphonic acid diethyl ester)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / ethanol; water / 5 h / 50 °C
2: caesium carbonate / acetone / Inert atmosphere; Reflux
View Scheme
icariside II
113558-15-9

icariside II

(((5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)oxo-4Η-chromene-3,7-diyl)bis(oxy))bis(methylene))bisphosphonate sodium

(((5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)oxo-4Η-chromene-3,7-diyl)bis(oxy))bis(methylene))bisphosphonate sodium

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sulfuric acid / ethanol; water / 5 h / 50 °C
2: caesium carbonate / acetone / Inert atmosphere; Reflux
3: 2,6-dimethylpyridine; trimethylsilyl bromide / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere
4: sodium hydroxide / methanol / 0.5 h
View Scheme
icariside II
113558-15-9

icariside II

(((5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromene-3,7-diyl)bis(oxy))bis(methylene))bisphosphonic acid

(((5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromene-3,7-diyl)bis(oxy))bis(methylene))bisphosphonic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / ethanol; water / 5 h / 50 °C
2: caesium carbonate / acetone / Inert atmosphere; Reflux
3: 2,6-dimethylpyridine; trimethylsilyl bromide / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere
View Scheme
icariside II
113558-15-9

icariside II

(2S)-2-((((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en1-yl)-4-oxo-4H-chromen-3-yl)oxy)(ethoxy)phosphoryl)amino)-3-methylbutanoate

(2S)-2-((((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en1-yl)-4-oxo-4H-chromen-3-yl)oxy)(ethoxy)phosphoryl)amino)-3-methylbutanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / ethanol; water / 5 h / 50 °C
2: triethylamine; dmap / dichloromethane / 49 h / 0 - 20 °C
View Scheme
icariside II
113558-15-9

icariside II

2-((((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl)oxy)(ethoxy)phosphoryl)amino)acetic acid ethyl ester

2-((((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl)oxy)(ethoxy)phosphoryl)amino)acetic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / ethanol; water / 5 h / 50 °C
2: triethylamine; dmap / dichloromethane / 49 h / 0 - 20 °C
View Scheme
icariside II
113558-15-9

icariside II

(((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromen-3-yl)oxy)methyl)phosphonate diethyl ester

(((5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-ene-1-yl)-4-oxo-4H-chromen-3-yl)oxy)methyl)phosphonate diethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / ethanol; water / 5 h / 50 °C
2: caesium carbonate / acetone / Inert atmosphere; Reflux
View Scheme
icariside II
113558-15-9

icariside II

5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-((6-morpholin4-yl)hexyloxy)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one

5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-((6-morpholin4-yl)hexyloxy)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / Reflux; Inert atmosphere
2: tetrahydrofuran / Reflux; Inert atmosphere
View Scheme
N-(2-bromoethyl)morpholine
89583-07-3

N-(2-bromoethyl)morpholine

icariside II
113558-15-9

icariside II

5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(2-morpholinoethoxy)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one

5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(2-morpholinoethoxy)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromene-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux; Inert atmosphere;100 mg
Reaxys ID: 31529750

Reaxys ID: 31529750

icariside II
113558-15-9

icariside II

Reaxys ID: 31529749

Reaxys ID: 31529749

icariside II
113558-15-9

icariside II

3,7-bis(2-(dimethylamino)ethoxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

3,7-bis(2-(dimethylamino)ethoxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / ethanol; water / 5 h / 50 °C
2: potassium carbonate / acetone / Reflux; Inert atmosphere
View Scheme
icariside II
113558-15-9

icariside II

5-hydroxy-3,7-bis(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

5-hydroxy-3,7-bis(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / ethanol; water / 5 h / 50 °C
2: potassium carbonate / acetone / Reflux; Inert atmosphere
View Scheme

113558-15-9Related news

baohuoside I (cas 113558-15-9) production through enzyme hydrolysis and parameter optimization by using response surface and subset selection08/22/2019

A rapid and efficient baohuoside I preparation method was established. A uniform design coupled with subset selection was employed to determine pH, reaction time, and temperature parameters, as well as dextranase hydrolysis efficiency. Hydrolysis parameters were optimized using response surface ...detailed

Construction of a novel catalysis system for clean and efficient preparation of baohuoside I (cas 113558-15-9) from Icariin based on biphase enzymatic hydrolysis08/21/2019

Baohuoside I has better in vivo bioactivities than Icariin. Its preparation methods, such as acid hydrolysis, are of low efficiency, with undesirable byproducts. The objective of this study was to establish a novel catalysis system for its clean and efficient preparation via biphase enzymatic hy...detailed

113558-15-9Relevant articles and documents

Regio-selective deglycosylation of icariin by cell suspension cultures of Glycyrrhiza uralensis and Morus alba

Zhang, De-Wu,Tao, Xiao-Yu,Chen, Ri-Dao,Yu, Li-Yan,Dai, Jun-Gui

, p. 656 - 661 (2015)

Biotransformations of icariin (1) by cell suspension cultures of Glycyrrhiza uralensis and Morus alba yielded two new metabolites, icaruralins A and B (2 and 3), and one known metabolite, baohuoside I (4). Their structures were determined on the basis of extensive spectroscopic analysis. This is the first report that the cell suspension cultures of G. uralensis and M. alba possess deglycosylation functionality.

Characterization of a novel thermostable glucose-tolerant GH1 β-glucosidase from the hyperthermophile Ignisphaera aggregans and its application in the efficient production of baohuoside I from icariin and total epimedium flavonoids

Jiang, Jianchun,Wei, Min,Xie, Jingcong,Xu, Hao,Yang, Jing,Zhang, Ning,Zhao, Jian

, (2020)

The minor flavonoid baohuoside I from Herba epimedii has better bioactivities than its precursor compounds icariin and other major epimedium flavonoids. In this study, a novel β-glucosidase gene (Igag_0940) was cloned and expressed to improve the conversion efficiency in the process of baohuoside I production. For the first time, the recombinant IagBgl1 was purified and then identified uniquely as a trimer in GH 1 family protein from Archaea. The maximum activity of recombinant IagBgl1 was exhibited at 95 °C, pH 6.5, and it retained more than 70% after incubation at 90 °C for 4 h. IagBgl1 had a high catalytic activity towards icariin with a Kcat/Km ratio of 488.19 mM?1·s?1. Under optimized conditions (65 °C, pH 6.5, 0.8 U/mL enzyme, and 90 min), 10 g/L icariin was transformed into 7.564 g/L baohuoside I with a molar conversion of 99.48%. Meanwhile, 2.434 g/L baohuoside I was obtained from 10 g/L total epimedium flavonoids by a two-step conversion system built with IagBgl1 and two other thermostable enzymes. This is the first report of enzymatic conversion for producing baohuoside I by thermostable enzymes.

Baohuoside i production through enzyme hydrolysis and parameter optimization by using response surface and subset selection

Yang, Qianxu,Wang, Li,Zhang, Liangxiao,Xiao, Hongbin

, p. 132 - 138 (2013)

A rapid and efficient baohuoside I preparation method was established. A uniform design coupled with subset selection was employed to determine pH, reaction time, and temperature parameters, as well as dextranase hydrolysis efficiency. Hydrolysis parameters were optimized using response surface and subset selection. Our results showed that pH plays an important role in the hydrolysis reaction within a relatively narrow range (pH 4-7). Temperature was the secondary factor, which was positively correlated with conversion rate. A 3-h reaction time was sufficient. Finally, a relatively good hydrolysis parameters were found, and their effectiveness was verified.

Biotransformation of major flavonoid glycosides in herb epimedii by the fungus Cunninghamella blakesleana

Xin, XiuLan,Fan, Guang-Jun,Sun, Zheng,Zhang, Ning,Li, Ye,Lan, Rong,Chen, Liang,Dong, PeiPei

, p. 141 - 146 (2015)

Biotransformation of icariin (1), epimedin C (2), epimedoside A (3), epimedin A (4) and epimidin B (5), five major components of E. koreanum, were performed by using Cunninghamella blakesleana. And they could be metabolized efficiently to icariside II (1a), 2″-O-rhamnosylikarisoside II (2a), epimedoside b (3a), baohuoside VII (4a) and sagittatoside B (5a) with high yields of 95.1%, 97.7%, 93.7%, 95.8% and 96.4%, respectively. And these transformed products as major forms of herb epimedii in vivo exhibited the more significant anti-osteoporosis activities. Our method could be applied for enriching these rare flavonoids in herb epimedii, for further development of anti-osteoporosis medicines or functional foods.

ANALOGS OF THE NATURAL PRODUCT ICARIIN

-

Paragraph 00168; 00182, (2020/03/02)

Provided herein are analogs of the natural product icariin represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof. The analogs can be used to modulate (e.g., inhibit, such as by competitive inhibition) PDE5 and thereby treat a wide range of PDE5- mediated diseases, including cardiovascular, gastrointestinal, pulmonary, musculoskeletal, neurological and reproductive diseases. Also provided herein are compositions and methods including compounds of Structural Formula (I).

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