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D-Glucuronic acid, derived from the oxidation of glucose, is a carboxylic acid with a structural similarity to glucose. Its sixth carbon is oxidized to a carboxylic acid, resulting in the chemical formula C6H10O7. The salts and esters of D-glucuronic acid are referred to as glucuronates, and the anion C6H9O7represents the glucuronate ion. D-Glucuronic acid is a white solid and plays a crucial role in various biological processes, including the synthesis of glycosaminoglycans and detoxification of certain drugs and toxins.

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  • 6556-12-3 Structure
  • Basic information

    1. Product Name: D-GLUCURONIC ACID
    2. Synonyms: GLUCURONIC ACID;D-GLCA;D-GLUCURONIC ACID;Glycuronic acid ;D-GLUCURONIC ACID FREE ACID F & D &;Glucosiduronic Acid;Glucuronic Aci;(2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid
    3. CAS NO:6556-12-3
    4. Molecular Formula: C6H10O7
    5. Molecular Weight: 194.14
    6. EINECS: 229-486-4
    7. Product Categories: 13C & 2H Sugars;Biochemistry;Glucose;Sugars;Carbohydrates & Derivatives;Carbohydrate LibraryEnzyme Inhibitors by Enzyme;Glucuronidase, betaGlycobiology;InhibitorsAnalytical Enzymes;D to;Inhibitors and Substrates;Metabolic Libraries;Metabolomics;Related Products;β-Glucuronidase
    8. Mol File: 6556-12-3.mol
  • Chemical Properties

    1. Melting Point: 159-161 °C(lit.)
    2. Boiling Point: 250.56°C (rough estimate)
    3. Flash Point: 211.1 °C
    4. Appearance: White to off-white/Crystalline Powder
    5. Density: 1.4301 (rough estimate)
    6. Vapor Pressure: 5.45E-08mmHg at 25°C
    7. Refractive Index: 36 ° (C=6, H2O)
    8. Storage Temp.: Refrigerator (+4°C)
    9. Solubility: H2O: soluble100mg/mL, clear to slightly hazy
    10. PKA: pKa 3.18(H2O t=20.0) (Uncertain)
    11. Water Solubility: Soluble in water.
    12. Merck: 14,4465
    13. BRN: 1727083
    14. CAS DataBase Reference: D-GLUCURONIC ACID(CAS DataBase Reference)
    15. NIST Chemistry Reference: D-GLUCURONIC ACID(6556-12-3)
    16. EPA Substance Registry System: D-GLUCURONIC ACID(6556-12-3)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 37/39-26-36
    4. WGK Germany: 3
    5. RTECS: LZ8836600
    6. TSCA: Yes
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 6556-12-3(Hazardous Substances Data)

6556-12-3 Usage

Uses

1. Pharmaceutical Industry:
D-Glucuronic acid is used as a pharmaceutical intermediate for the synthesis of various drugs and serves as a key component in the development of quality control standards for pharmaceutical laboratories and manufacturers.
2. Chemical Research:
It is utilized in chemical research as a building block for the synthesis of complex molecules and the study of its properties and reactions.
3. Detoxification Process:
D-Glucuronic acid is involved in the detoxification of certain drugs and toxins by conjugating with them to form glucuronides, which are more water-soluble and can be excreted from the body.
4. Glycosaminoglycan Synthesis:
D-Glucuronic acid is a basic building block of hyaluronic acid and chondroitin sulfate, which are essential components of mammalian connective tissue, such as cartilage.
5. Vitamin C Synthesis:
It serves as a precursor to vitamin C, which is the chief detoxifying agent in plants and animals.
6. Plant Cell Wall Polysaccharides:
D-Glucuronic acid is a major component of plant cell wall polysaccharides, such as arabinoxylan and pectin, which are essential for plant structure and function.
7. Glycosidic Combination:
D-Glucuronic acid usually occurs in a "paired" form as a glycosidic combination with phenols and alcohols, playing a role in the detoxification of poisonous hydroxyl-containing substances in the liver.
8. Urinary Excretion:
The glucuronides present in normal urine are those of phenol, cresol, and indoxyl. After the ingestion of poisons such as morphine, chloral hydrate, camphor, or turpentine, glucuronides formed with the poison or its hydroxylated derivatives appear in the urine, aiding in their elimination from the body.

Biological Functions

Proteoglycans Glucuronic acid is common in carbohydrate chains of proteoglycans. It is part of mucous animal secretions (such as saliva), cell glycocalyx and intercellular matrix (for instance hyaluronan)) Glucuronidation of toxic substances In the animal body, glucuronic acid is often linked to the xenobiotic metabolism of substances such as drugs, pollutants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids, and bile acids. These linkages involve glycosidic bonds, and this linkage process is known as glucuronidation. Glucuronidation occurs mainly in the liver, although the enzyme responsible for its catalysis, UDP-glucuronyltransferase, has been found in all major body organs, e.g., intestine, kidneys, brain, adrenal gland, spleen, and thymus.UseDetermination of urinary steroids and of steroid conjugates in blood. Contained in some commercially available brands of Kombucha as an antioxidant & organic acid In all plants and mammals - other than guinea pigs and primatesglucuronic acid is a precursor of ascorbic acid , also known as vitamin c.ConformationUnlike its C5 epimer iduronic acid, which may occur in a number of conformations, glucuronic acid occurs in predominantly the 4C1 conformation.GlucuronidasesGlucuronidases are those enzymes that hydrolyze the glycosidic bond between glucuronic acid and some other compound.

Biochem/physiol Actions

In humans, glucuronic acid conjugation with steroidal compounds and drugs is an important step in phase II metabolic reactions. This influences the biotransformation process of the compound.

Purification Methods

Crystallise the acid from EtOH or EtOAc, wash it with MeOH and dry it in vacuo to give the “ ” form. Heating converts it to the lactone (see below). The sodium salt monohydrate [207300-70-7] M 234.1 has m ~136-138o(dec) [] D 20 +21o (c 2, H2O after 2hours). [Sutter & Reichstein Helv Chim Acta 21 1210 1938, Beilstein 3 H 886, 3 IV 1997.]

Check Digit Verification of cas no

The CAS Registry Mumber 6556-12-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,5,5 and 6 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 6556-12:
(6*6)+(5*5)+(4*5)+(3*6)+(2*1)+(1*2)=103
103 % 10 = 3
So 6556-12-3 is a valid CAS Registry Number.
InChI:InChI=1/C7H12O6/c1-2(8)6-4(10)3(9)5(11)7(12)13-6/h3-7,9-12H,1H3/t3-,4-,5+,6+,7+/m0/s1

6556-12-3 Well-known Company Product Price

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  • Alfa Aesar

  • (L14350)  D-Glucuronic acid, 98+%   

  • 6556-12-3

  • 5g

  • 271.0CNY

  • Detail
  • Alfa Aesar

  • (L14350)  D-Glucuronic acid, 98+%   

  • 6556-12-3

  • 25g

  • 1013.0CNY

  • Detail
  • USP

  • (1294319)  D-Glucuronic acid  United States Pharmacopeia (USP) Reference Standard

  • 6556-12-3

  • 1294319-50MG

  • 4,662.45CNY

  • Detail

6556-12-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name aldehydo-D-glucuronic acid

1.2 Other means of identification

Product number -
Other names D-Glucuronic Acid

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:6556-12-3 SDS

6556-12-3Synthetic route

apigenin 7-O-[β-D-glucuronopyranosyl-(1->2)]-O-β-D-glucuronopyranoside

apigenin 7-O-[β-D-glucuronopyranosyl-(1->2)]-O-β-D-glucuronopyranoside

A

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

B

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
520-36-5

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

Conditions
ConditionsYield
Acid hydrolysis;A n/a
B 52%
methyl-alpha-D-glucopyranoside
97-30-3

methyl-alpha-D-glucopyranoside

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With sulfuric acid; water; sodium sulfate under 8090.6 Torr; Electrolysis.anschl. Erwaermen mit wss. H2SO4;
With platinum on activated charcoal; water; sodium hydrogencarbonate unter Einleiten von Luft und anschl. Behandeln mit wss. H2SO4;
With water; nitric acid; sodium nitrite anschl. Erwaermen mir wss. H2SO4;
With chloroform; dinitrogen tetraoxide anschl. mit wss. H2SO4;
With tetrachloromethane; dinitrogen tetraoxide anschl. mit wss. Methanol und dann mit wss. H2SO4;
D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With barium dihydroxide; water
With alkaline solution; water
(-)-Menthol glucuronide
79466-08-3

(-)-Menthol glucuronide

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With sulfuric acid; water anschl. Erwaermen mit BaCO3, dann mit wss.-aethanol. H2SO4;
C55H90O23

C55H90O23

A

L-Rhamnose
3615-41-6

L-Rhamnose

B

D-glucose
50-99-7

D-glucose

C

D-Galactose
59-23-4

D-Galactose

D

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

E

Protoprimulagenin A
2611-08-7, 53342-82-8

Protoprimulagenin A

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;
echinocystic acid 3-O-β-D-glucuronopyranoside

echinocystic acid 3-O-β-D-glucuronopyranoside

A

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

B

echinocystic acid
510-30-5

echinocystic acid

Conditions
ConditionsYield
With hydrogenchloride for 2h;
foetidissimoside A

foetidissimoside A

A

D-xylose
58-86-6

D-xylose

B

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

C

C41H66O12

C41H66O12

Conditions
ConditionsYield
With β-glucuronidase; sodium acetate; acetic acid at 39℃; for 48h;
C47H76O20

C47H76O20

A

L-arabinose
5328-37-0

L-arabinose

B

D-glucose
50-99-7

D-glucose

C

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

D

A1-barrigenol
15448-03-0

A1-barrigenol

Conditions
ConditionsYield
With hydrogenchloride; silver carbonate In methanol for 2h;
C47H76O21

C47H76O21

A

L-arabinose
5328-37-0

L-arabinose

B

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

C

A1-barrigenol
15448-03-0

A1-barrigenol

Conditions
ConditionsYield
With hydrogenchloride; silver carbonate In methanol for 2h;
A1-barrigenol 3-O-β-D-glucopyranosyl-(1 - 2)-<β-D-galactopyranosyl-(1 - 3)>-β-D-glucopyranosiduronic acid

A1-barrigenol 3-O-β-D-glucopyranosyl-(1 - 2)-<β-D-galactopyranosyl-(1 - 3)>-β-D-glucopyranosiduronic acid

A

D-Mannose
3458-28-4

D-Mannose

B

D-glucose
50-99-7

D-glucose

C

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

D

A1-barrigenol
15448-03-0

A1-barrigenol

Conditions
ConditionsYield
With sulfuric acid In ethanol for 2h;
C53H86O25

C53H86O25

A

L-arabinose
5328-37-0

L-arabinose

B

D-glucose
50-99-7

D-glucose

C

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

D

A1-barrigenol
15448-03-0

A1-barrigenol

Conditions
ConditionsYield
With hydrogenchloride; silver carbonate In methanol for 2h;
calcium salt of/the/ O1,O2-isopropylidene-α-D-glucofuranuronic acid

calcium salt of/the/ O1,O2-isopropylidene-α-D-glucofuranuronic acid

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With water; oxalic acid
D-glucaric acid-1->4-lactone hydrate

D-glucaric acid-1->4-lactone hydrate

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With sodium amalgam; water
d-saccharolactonic acid

d-saccharolactonic acid

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With sodium amalgam; water
euxanthinic acid

euxanthinic acid

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With water at 120 - 125℃;
With sulfuric acid at 135℃; im Autoklaven;
mentholglucuronic acid

mentholglucuronic acid

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With sulfuric acid
O1-<(Ξ)-bornyl>-β-D-glucopyranuronic acid

O1-<(Ξ)-bornyl>-β-D-glucopyranuronic acid

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With sulfuric acid; water
D-glucose
50-99-7

D-glucose

copper (II)-hydroxide

copper (II)-hydroxide

aqueous NaOH-solution

aqueous NaOH-solution

A

LACTIC ACID
849585-22-4

LACTIC ACID

B

tartronic acid
80-69-3

tartronic acid

C

gluconic acid
526-95-4

gluconic acid

D

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
Produkt 5: Acetaldehyd;
D-glucose
50-99-7

D-glucose

water
7732-18-5

water

A

gluconic acid
526-95-4

gluconic acid

B

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

C

Glyoxal
131543-46-9

Glyoxal

Conditions
ConditionsYield
bei der Einwirkung von γ-Strahlen unter Durchleiten von Sauerstoff.Irradiation;
3-O-{β-D-apiofuranosyl-(1->4)-[α-L-arabinopyranosyl-(1->2)]-β-D-glucuronopyranosyl}oleanolic acid

3-O-{β-D-apiofuranosyl-(1->4)-[α-L-arabinopyranosyl-(1->2)]-β-D-glucuronopyranosyl}oleanolic acid

B

D-Galactose
59-23-4

D-Galactose

C

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 100℃; for 1h;
3-O-{α-L-ramnopyranosyl-(1->4)-[α-L-arabinopyranosyl-(1->2)]-β-D-glucuronopyranosyl}oleanolic acid

3-O-{α-L-ramnopyranosyl-(1->4)-[α-L-arabinopyranosyl-(1->2)]-β-D-glucuronopyranosyl}oleanolic acid

A

L-arabinose
5328-37-0

L-arabinose

B

L-Rhamnose
3615-41-6

L-Rhamnose

C

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 100℃; for 1h;
3-O-[β-D-apiofuranosyl-(1->4)-β-D-glucuronopyranosyl]oleanolic acid 28-O-β-D-glucopyranosyl ester

3-O-[β-D-apiofuranosyl-(1->4)-β-D-glucuronopyranosyl]oleanolic acid 28-O-β-D-glucopyranosyl ester

B

D-glucose
50-99-7

D-glucose

C

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 100℃; for 1h;
3-O-{α-L-rhamnopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)]-β-D-glucuronopyranosyl}oleanolic acid

3-O-{α-L-rhamnopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)]-β-D-glucuronopyranosyl}oleanolic acid

A

L-Rhamnose
3615-41-6

L-Rhamnose

B

D-Galactose
59-23-4

D-Galactose

C

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 100℃; for 1h;
3-O-{β-D-apiofuranosyl-(1->4)-[α-L-arabinopyranosyl-(1->2)]-β-D-glucuronopyranosyl}oleanolic acid 28-O-β-D-glucopyranosyl ester

3-O-{β-D-apiofuranosyl-(1->4)-[α-L-arabinopyranosyl-(1->2)]-β-D-glucuronopyranosyl}oleanolic acid 28-O-β-D-glucopyranosyl ester

B

L-arabinose
5328-37-0

L-arabinose

C

D-glucose
50-99-7

D-glucose

D

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 100℃; for 1h;
3-O-{α-L-rhamnopyranosyl-(1->4)-[α-L-arabinopyranosyl-(1->2)]-β-D-glucuronopyranosyl}oleanolic acid 28-O-β-D-glucopyranosyl ester

3-O-{α-L-rhamnopyranosyl-(1->4)-[α-L-arabinopyranosyl-(1->2)]-β-D-glucuronopyranosyl}oleanolic acid 28-O-β-D-glucopyranosyl ester

A

L-arabinose
5328-37-0

L-arabinose

B

L-Rhamnose
3615-41-6

L-Rhamnose

C

D-glucose
50-99-7

D-glucose

D

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 100℃; for 1h;
3-O-{α-L-rhamnopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)]-β-D-glucuronopyranosyl}oleanolic acid 28-O-β-D-glucopyranosyl ester

3-O-{α-L-rhamnopyranosyl-(1->4)-[β-D-galactopyranosyl-(1->2)]-β-D-glucuronopyranosyl}oleanolic acid 28-O-β-D-glucopyranosyl ester

A

L-Rhamnose
3615-41-6

L-Rhamnose

B

D-glucose
50-99-7

D-glucose

C

D-Galactose
59-23-4

D-Galactose

D

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 100℃; for 1h;
D-Glucose
2280-44-6

D-Glucose

A

gluconic acid
526-95-4

gluconic acid

B

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

C

D-glucaric acid
87-73-0

D-glucaric acid

D

glucose dialdehyde
3056-44-8

glucose dialdehyde

Conditions
ConditionsYield
With sodium hydroxide; oxygen In water at 60℃; pH=9;
desacyl yuchasaponin A

desacyl yuchasaponin A

A

L-Rhamnose
3615-41-6

L-Rhamnose

B

D-glucose
50-99-7

D-glucose

C

D-Galactose
59-23-4

D-Galactose

D

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

E

R1-barrigenol
15399-43-6

R1-barrigenol

Conditions
ConditionsYield
With sulfuric acid; water In 1,4-dioxane for 2h; Reflux;
C54H88O26

C54H88O26

A

L-Rhamnose
3615-41-6

L-Rhamnose

B

D-Galactose
59-23-4

D-Galactose

C

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

D

R1-barrigenol
15399-43-6

R1-barrigenol

Conditions
ConditionsYield
With sulfuric acid; water In 1,4-dioxane for 2h; Reflux;
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

2,3-Diaminonaphthalene
771-97-1

2,3-Diaminonaphthalene

(1'S,2'R,3'R,4'R)-2-[4'-carboxy-1',2',3',4'-tetrahydroxypentyl]-1H-naphthimidazole
1027103-31-6

(1'S,2'R,3'R,4'R)-2-[4'-carboxy-1',2',3',4'-tetrahydroxypentyl]-1H-naphthimidazole

Conditions
ConditionsYield
With air; iodine; acetic acid at 20℃; for 6h;97%
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

tegaserod
1044642-88-7

tegaserod

3-(5-methoxy-1H-indol-3-ylmethylene)-N-pentylcarbazimidamide glucuronate

3-(5-methoxy-1H-indol-3-ylmethylene)-N-pentylcarbazimidamide glucuronate

Conditions
ConditionsYield
In methanol at 20 - 55℃;94.7%
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

acetic anhydride
108-24-7

acetic anhydride

2,3,4-tri-O-acetyl-β-D-glucopyranurono-6,1-lactone
82970-25-0

2,3,4-tri-O-acetyl-β-D-glucopyranurono-6,1-lactone

Conditions
ConditionsYield
With iodine at 115℃; for 0.166667h; microwave irradiation;92%
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

3-azidopropyl (β-D-galactopyranosyl)-(1→4)-O-2-deoxy-2-acetamido-β-D-glucopyranoside
1246842-76-1

3-azidopropyl (β-D-galactopyranosyl)-(1→4)-O-2-deoxy-2-acetamido-β-D-glucopyranoside

3-azidopropyl β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside

3-azidopropyl β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside

Conditions
ConditionsYield
With Bifidobacterium longum UDP-sugar pyrophosphorylase; human β1−3-glucuronyltransferase; recombinant Arabidopsis thaliana glucuronokinase; UTP; ATP; manganese(ll) chloride In aq. buffer at 37℃; pH=8; Enzymatic reaction;92%
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

3-azidopropyl β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)-[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)]-α-D-mannopyranoside

3-azidopropyl β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)-[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)]-α-D-mannopyranoside

3-azidopropyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside

3-azidopropyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside

Conditions
ConditionsYield
With Bifidobacterium longum UDP-sugar pyrophosphorylase; human β1−3-glucuronyltransferase; recombinant Arabidopsis thaliana glucuronokinase; UTP; ATP; manganese(ll) chloride In aq. buffer at 37℃; pH=8; Enzymatic reaction;91%
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

3-azidopropyl β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-β-D-mannopyranoside

3-azidopropyl β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-β-D-mannopyranoside

3-azidopropyl β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-D-mannopyranoside

3-azidopropyl β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-D-mannopyranoside

Conditions
ConditionsYield
With Bifidobacterium longum UDP-sugar pyrophosphorylase; human β1−3-glucuronyltransferase; recombinant Arabidopsis thaliana glucuronokinase; UTP; ATP; manganese(ll) chloride In aq. buffer at 37℃; pH=8; Enzymatic reaction;91%
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

3-azidopropyl β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside

3-azidopropyl β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside

3-azidopropyl β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside

3-azidopropyl β-D-glucopyranosyluronic-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)[β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→6)]-α-D-mannopyranoside

Conditions
ConditionsYield
With Bifidobacterium longum UDP-sugar pyrophosphorylase; human β1−3-glucuronyltransferase; recombinant Arabidopsis thaliana glucuronokinase; UTP; ATP; manganese(ll) chloride In aq. buffer at 37℃; pH=8; Enzymatic reaction;90%
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

acetamido cetyl dimethyl ammonium hydroxide

acetamido cetyl dimethyl ammonium hydroxide

acetamido cetyl dimethyl ammonium glucuronate

acetamido cetyl dimethyl ammonium glucuronate

Conditions
ConditionsYield
In methanol at 20℃; for 1.5h;86%
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

ethyl β-D-galactopyranosyl-(1→4)-2-deoxy-2-trifluoroacetamido-1-thio-β-D-glucopyranoside

ethyl β-D-galactopyranosyl-(1→4)-2-deoxy-2-trifluoroacetamido-1-thio-β-D-glucopyranoside

ethyl β-D-glucopyranosyluronate-(1→3)-β-D-galactopyranosyl-(1→4)-2-deoxy-2-trifluoroacetamido-1-thio-β-D-glucopyranoside

ethyl β-D-glucopyranosyluronate-(1→3)-β-D-galactopyranosyl-(1→4)-2-deoxy-2-trifluoroacetamido-1-thio-β-D-glucopyranoside

Conditions
ConditionsYield
With Bifidobacterium longum UDP-sugar pyrophosphorylase; human β1−3-glucuronyltransferase; recombinant Arabidopsis thaliana glucuronokinase; UTP; ATP; manganese(ll) chloride In aq. buffer at 37℃; pH=8; Enzymatic reaction;82%
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

benzyl bromide
100-39-0

benzyl bromide

benzyl α,β-D-glucuronate

benzyl α,β-D-glucuronate

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 18h; Inert atmosphere;72.6%
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

hexan-1-amine
111-26-2

hexan-1-amine

1-(N-hexyl)glucaric acid monoamide
1115231-03-2

1-(N-hexyl)glucaric acid monoamide

Conditions
ConditionsYield
With iodine; potassium carbonate In methanol at 20℃; for 12h;61%
octanol
111-87-5

octanol

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

n-octyl β-D-glucofuranosidurono-6,3-lactone

n-octyl β-D-glucofuranosidurono-6,3-lactone

Conditions
ConditionsYield
With iron(III) chloride In tetrahydrofuran at 20℃; for 24h;50%
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

10-Undecen-1-ol
112-43-6

10-Undecen-1-ol

(3R,3aR,5R,6R,6aR)-3,6-Dihydroxy-5-undec-10-enyloxy-tetrahydro-furo[3,2-b]furan-2-one

(3R,3aR,5R,6R,6aR)-3,6-Dihydroxy-5-undec-10-enyloxy-tetrahydro-furo[3,2-b]furan-2-one

Conditions
ConditionsYield
With iron(III) chloride In tetrahydrofuran at 20℃; for 72h;50%
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

formic acid
64-18-6

formic acid

Conditions
ConditionsYield
With phosphovanadomolybdic acid; oxygen In water at 150℃; under 15001.5 Torr; for 3h;34.6%
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

glycolic Acid
79-14-1

glycolic Acid

Conditions
ConditionsYield
With phosphomolybdic acid; oxygen In water at 150℃; under 15001.5 Torr; for 1h; Autoclave;25.3%
chloromethyldimethylsilane
3144-74-9

chloromethyldimethylsilane

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

D-glucuronic acid TMS
19126-97-7

D-glucuronic acid TMS

Conditions
ConditionsYield
With pyridine; hexane; formamide
isoniazid
54-85-3

isoniazid

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

6-isonicotinoylhydrazono-6-deoxy-L-gulonic acid-(N'-isonicotinoyl-hydrazide)
111617-78-8

6-isonicotinoylhydrazono-6-deoxy-L-gulonic acid-(N'-isonicotinoyl-hydrazide)

Conditions
ConditionsYield
With acetic acid
isoniazid
54-85-3

isoniazid

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

6-isonicotinoylhydrazono-6-deoxy-L-gulonic acid
25019-85-6

6-isonicotinoylhydrazono-6-deoxy-L-gulonic acid

Conditions
ConditionsYield
With water
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

1,3-dihydroxynaphthalene
132-86-5

1,3-dihydroxynaphthalene

9-methoxy-14-(3-methoxy-2-oxo-2H-pyran-6-yl)-dibenzo[a,j]xanthen-5-one
103820-48-0

9-methoxy-14-(3-methoxy-2-oxo-2H-pyran-6-yl)-dibenzo[a,j]xanthen-5-one

Conditions
ConditionsYield
With hydrogenchloride Behandeln des Reaktionsprodukts mit Diazomethan in Aether;
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

thiobenzoylhydrazine
20605-40-7

thiobenzoylhydrazine

(S)-((2R)-3c,4c-dihydroxy-5-oxo-tetrahydro-[2r]furyl)-hydroxy-acetaldehyde-thiobenzoylhydrazone

(S)-((2R)-3c,4c-dihydroxy-5-oxo-tetrahydro-[2r]furyl)-hydroxy-acetaldehyde-thiobenzoylhydrazone

Conditions
ConditionsYield
With hydrogenchloride
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

2-phenylnaphthalene-1,3-diol
13148-15-7

2-phenylnaphthalene-1,3-diol

4-[(2,4-dihydroxy-3-phenyl-[1]naphthyl)-[2]furyl-methylene]-3-hydroxy-2-phenyl-4H-naphthalen-1-one

4-[(2,4-dihydroxy-3-phenyl-[1]naphthyl)-[2]furyl-methylene]-3-hydroxy-2-phenyl-4H-naphthalen-1-one

Conditions
ConditionsYield
With acetic acid; zinc(II) chloride
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

4-nitrobenzenesulfonohydrazide
2937-05-5

4-nitrobenzenesulfonohydrazide

(S)-((2R)-3c,4c-dihydroxy-5-oxo-tetrahydro-[2r]furyl)-hydroxy-acetaldehyde-(4-nitro-benzenesulfonylhydrazone)

(S)-((2R)-3c,4c-dihydroxy-5-oxo-tetrahydro-[2r]furyl)-hydroxy-acetaldehyde-(4-nitro-benzenesulfonylhydrazone)

Conditions
ConditionsYield
With acetonitrile
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

potassium cyanide
151-50-8

potassium cyanide

D-glycero-D-gulo-heptaric acid
527-03-7, 93780-20-2

D-glycero-D-gulo-heptaric acid

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

2,3,4-trihydroxy-2-methyl-glutaric acid
469-44-3

2,3,4-trihydroxy-2-methyl-glutaric acid

Conditions
ConditionsYield
With water; methyllithium; calcium carbonate
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

2,3-dihydroxy-2-cyclopenten-1-one
80-72-8

2,3-dihydroxy-2-cyclopenten-1-one

Conditions
ConditionsYield
With sulfuric acid at 150℃;
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

D-glucurono-6,3-lactone
32449-92-6

D-glucurono-6,3-lactone

Conditions
ConditionsYield
untersucht wurde das Lactonisierungsgleichgewicht in wss. Loesungen vom pH 7 - 8.5;
D-Glucuronic acid
6556-12-3

D-Glucuronic acid

p-toluidine
106-49-0

p-toluidine

1-p-toluidino-1-deoxy-β-D-glucopyranuronic acid
96933-51-6

1-p-toluidino-1-deoxy-β-D-glucopyranuronic acid

D-Glucuronic acid
6556-12-3

D-Glucuronic acid

p-toluidine
106-49-0

p-toluidine

6-p-toluidino-D-lyxo-6-deoxy-[5]hexulosonic acid
109068-38-4

6-p-toluidino-D-lyxo-6-deoxy-[5]hexulosonic acid

6556-12-3Relevant articles and documents

Colorimetric detection of glucose by a hybrid nanomaterial based on amplified peroxidase-like activity of ferrosoferric oxide modified with gold-platinum heterodimer

Bai, Zhenyu,Feng, Xiaoyang,Fu, Hao,Hu, Xueping,Li, Ping,Song, Xingliang

, p. 239 - 249 (2021/12/30)

The colorimetric detection of glucose using hybrid nanostructures is a rapidly growing research hotspot. In this work, we established a simple route for the synthesis of a class of multi-metal hybrid nanostructure materials and investigated their peroxidase-like performance for the colorimetric detection of glucose. The hybrid nanomaterial (Fe3O4@Au-Pt) incorporated ferrosoferric oxide nanoparticles (Fe3O4NPs) and heterodimers composed of gold (Au) and platinum (Pt), which presents excellent morphology and structure. On the basis of our research, we constructed an easy and sensitive colorimetric sensor for the detection of glucose and hydrogen peroxide (H2O2), and the results indicated that the Fe3O4@Au-Pt hybrid nanomaterial possessed preferable peroxidase-like activity in comparison with other nanozyme materials and showing prominent selectivity for glucose detection. For H2O2, the sensor has a linear range of 0.05-120 μM and a relatively low limit of detection (LOD) of 0.018 μM. For glucose, the linear range is 0.05-140 μM with an LOD of 0.025 μM. It is envisioned that these hydrophilic hybrid nanostructures will be widely applied in sensing target analytes, biomedical diagnosis, and therapeutic applications in the future by taking advantage of their specific structure and excellent catalytic performance.

Comparative study on the structural characterization and α-glucosidase inhibitory activity of polysaccharide fractions extracted from Sargassum fusiforme at different pH conditions

Jia, Rui-Bo,Li, Zhao-Rong,Lin, Lianzhu,Luo, Donghui,Ou, Zhi-Rong,Zhao, Mouming,Zheng, Qianwen

, p. 602 - 610 (2021/11/30)

Sargassum fusiforme polysaccharides (SFPs), including SFP-3-40, SFP-3-60, SFP-3-80, SFP-7-40, SFP-7-60, SFP-7-80, SFP-10-40, SFP-10-60, and SFP-10-80, were extracted at different pH (3, 7, and 10), and then precipitated with graded precipitation of 40%, 60% and 80% (v/v) ethanol solution, respectively. Their physicochemical properties and α-glucosidase inhibitory activity were determined. Results showed that SFPs significantly differed in the contents of total sugar, protein, uronic acid, sulfate, the zeta potential, and molecular weight distribution. SFPs, including SFP-10-40, SFP-10-60, and SFP-10-80, had bigger absolute zeta potential value and higher respective average molecular weight in the same ethanol concentration precipitate. All samples were mainly composed of fucose, glucuronic acid, and mannose with different molar ratios. The extraction pH and precipitation ethanol solution concentration caused little changes in functional groups, but significantly altered surface morphology of SFPs. Congo red test revealed that all polysaccharides were not helical polysaccharides. Rheological measurements indicated that SFPs were pseudoplastic fluids and showed elastic behavior of the gel. Except SFP-3-40 and SFP-3-60, all other samples had a stronger α-glucosidase inhibitory activity than that of acarbose. The inhibition type of SFPs against α-glucosidase varied owing to different extraction pH and precipitation ethyl concentration. This study shows that extraction pH can significantly affect the structure and hypoglycemic activity of SFPs and provide a data support for the scientific use of Sargassum fusiforme in industrial production.

Application of bacterial directed enzyme prodrug therapy as a targeted chemotherapy approach in a mouse model of breast cancer

Bahrami, Ahmad Reza,Hosseini-Giv, Niloufar,Matin, Maryam M.

, (2021/08/03)

Cancer is the second leading cause of death in the world. Some of the usual cancer treatments include surgery, chemotherapy, and radiotherapy. However, due to low efficacy and side effects of these treatments, novel targeted therapeutic methods are needed. One of the common drawbacks of cancer chemotherapy is off-target toxicity. In order to overcome this problem, many investigations have been conducted. One of the new targeted therapy methods known as bacterial directed enzyme-prodrug therapy (BDEPT) employs bacteria as enzyme carriers to convert a pro-drug to a drug specifically within the tumor site. In the present study, we used Escherichia coli DH5α carrying luxCDABE gene cluster and overexpressing β-glucuronidase for luminescent emission and enzyme expression, respectively. Enzyme expression can lead to the conversion of glycyrrhizic acid as a prodrug to glycyrrhetinic acid, a potent anti-cancer agent. DH5α-lux/βG was characterized and its stability was also evaluated. Bacteria colonization in the tumor site was measured by tissue homogenate preparation and colony counting method. Histopathological studies on the liver, spleen, and tumor were also conducted. According to the results, co-treatment of 4T1, a highly metastatic mouse breast cancer cell line, with GL and DH5α-lux/βG could significantly decrease the IC50 values. Moreover, increased number of bacteria could lead to a dramatic drop in IC50 value. Specific colonization of DH5α-lux/βG was observed in the tumor site compared with other tissues (p 0.0001). Moreover, the biocompatibility evaluation proved that DH5α-lux/βG had no adverse effects on normal tissues. Furthermore, concurrent usage of GL and bacteria in the treatment of induced 4T1 tumors in BALB/c mice significantly delayed tumor growth (p0.001) during 16 days of investigation. Based on these findings, BDEPT might be useful for targeted breast cancer therapy, although further investigations are required to confirm this.

Triterpenoid saponins from the leaves and stems of Pericampylus glaucus and their insulin mimetic activities

Lee, Hee-Ju,Cho, Hyo-Moon,Park, Eun-Jin,Lee, Ba-Wool,Nghiem, Duc-Trong,Pham, Ha-Thanh-Tung,Pan, Cheol-Ho,Oh, Won-Keun

, (2021/11/01)

During an attempt to discover insulin mimetics, thirteen new triterpenoid saponins (1–13), including three phytolaccagenic acids (1, 2, and 12) and ten serjanic acids (3–11 and 13), as aglycones were isolated from a 70% ethanol extract of leaves and stems from Pericampylus glaucus. The chemical structures of compounds 1–13 were determined through spectroscopic data analysis, including NMR, IR, and HRESIMS. All isolated compounds (1–13) were evaluated using 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose (2-NBDG) as a fluorescent-tagged glucose probe to determine their stimulatory effects on glucose uptake in differentiated 3 T3-L1 adipocyte cells. Consequently, four compounds (4, 7, 11, and 12) exhibited stimulatory effects on glucose uptake.

A novel acid polysaccharide from Boletus edulis: extraction, characteristics and antitumor activities in vitro

Meng, Ting,Yu, Sha-sha,Ji, Hai-yu,Xu, Xiao-meng,Liu, An-jun

, p. 13 - 24 (2021/02/01)

A novel cold-water-soluble polysaccharide (BEP), with a molecular weight of 6.0 × 106?Da, was isolated from Boletus edulis. BEP consists of galactose, glucose, xylose, mannose, glucuronic, and galacturonic acid in a ratio of 0.34:0.28:0.28:2.57:1.00:0.44. The IR results showed that BEP was an acid polysaccharide, containing α-type and β-type glucoside bonds. MTT assay showed BEP could inhibit cell proliferation significantly. Morphological observation demonstrated that BEP-treated MDA-MB-231 and Ca761 cells exhibited typical apoptotic morphological features. Flow cytometry analysis revealed that BEP caused mitochondrial membrane potential collapse. Annexin V-FITC/PI staining indicated that BEP induced apoptosis of MDA-MB-231 and Ca761 cells through cell block in S phase and G0/G1 phase, respectively. Western blot results showed that BEP could increase the Bax/Bcl-2 ratios, promote the release of cytochrome C, and activate the expression of caspase-3 and caspase-9 in MDA-MB-231 and Ca761 cells. In conclusion, our results demonstrated that BEP could inhibit the proliferation of breast cancer cells and induce apoptosis through mitochondrial pathways.

Triterpene glycosides and phenylpropane derivatives from Staurogyne concinnula possessing anti-angiogenic activity

Vo, Thanh-Hoa,Lin, Yu-Chi,Liaw, Chia-Ching,Pan, Wen-Pin,Cheng, Jing-Jy,Lee, Ching-Kuo,Kuo, Yao-Haur

, (2021/02/03)

After anti-angiogenic activity screening, the potential n-butanol layer partitioned from the ethanol extract of Staurogyne concinnula was conducted. Further purification by Diaion HP20 column and preparative HPLC chromatography, four undescribed triterpen

Chemical constituents from shells of Xanthoceras sorbifolium

Chen, Gang,Xie, Yumeng,Zhou, Di,Yang, Yanqiu,Liu, Jingyu,Hou, Yue,Cheng, Maosheng,Liu, Yang,Li, Ning

, (2020/02/11)

Three undescribed triterpenes and four previously unreported saponins, along with two known ones, were isolated from shells of Xanthoceras sorbifolium (Sapindaceae). Their structures were elucidated by the interpretation of 1D and 2D NMR data. The nitric oxide (NO) assay revealed that 28-O-isobutyryl-21-O-angeloyl-R1-barrigenol and 3-O-β-D-6-O-methylglucuronopyranosyl-21,22-di-O-angeloyl-R1-barrigenol possessed stronger inhibitory effects on LPS-induced NO overproduction (IC50 = 18.5 ± 1.2 and 28.2 ± 1.8 μM, respectively) than the positive drug minocycline (IC50 = 30.1 ± 1.3 μM) in activated BV2 cells. Western blot, RT-qPCR, and docking experiments further validated that the regulation of iNOS and IL-1β expressions was involved in the anti-neuroinflammatory effects of these two compounds.

Quantitative Determination of Pt- Catalyzed d -Glucose Oxidation Products Using 2D NMR

Armstrong,Hirayama,Knight,Hutchings

, p. 325 - 335 (2019/01/04)

Quantitative correlative 1H-13C NMR has long been discussed as a potential method for quantifying the components of complex reaction mixtures. Here, we show that quantitative HMBC NMR can be applied to understand the complexity of the catalytic oxidation of glucose to glucaric acid, which is a promising bio-derived precursor to adipic acid, under aqueous aerobic conditions. It is shown through 2D NMR analysis that the product streams of this increasingly studied reaction contain lactone and dilactone derivatives of acid products, including glucaric acid, which are not observable/quantifiable using traditional chromatographic techniques. At 98% glucose conversion, total C6 lactone yield reaches 44%. Furthermore, a study of catalyst stability shows that all Pt catalysts undergo product-mediated chemical leaching. Through catalyst development studies, it is shown that sequestration of leached Pt can be achieved through use of carbon supports.

New olean-15-ene type gymnemic acids from Gymnema sylvestre (Retz.)R.Br. and their antihyperglycemic activity through α-glucosidase inhibition

Alkefai, Naila Hassan Ali,Amin, Saima,Sharma, Manju,Ahamad, Javed,Mir, Showkat R.

, p. 83 - 89 (2019/05/24)

A mixture of gymnemic acids was precipitated from the water extract of leaves of Gymnema sylvestre (Retz.)R.Br. ex Sm. (Asclepiadaceae)by acidification with 2 N H2SO4. The chromatographic separation of the mixture afforded five new gymnemic acids (1-5). The compounds were characterized as Δ15 oleanane glycosides on the basis of extensive spectral data analysis. The compounds (1-5)showed dose dependent inhibition of α-glucosidase, which was found to be comparable to acarbose (IC50 95 μg/ml). Maximum inhibition was achieved with compound 4 (IC50 57 μg/ml)followed by 3 (IC50 62 μg/ml), 1 (IC50 80 μg/ml), 2 (IC50 120 μg/ml)and 5 (IC50 128 μg/ml). The results revealed that the overall pattern of hydroxyl and acyl substitutions of compounds affected their inhibitory activity. In oral sucrose tolerance test, pre-treatment with crude gymnemic acid mixture and isolated compounds 1 and 4 at a dose of 10 mg/Kg b.w. significantly blunted the effect of sucrose challenge in mice. Based on these results, the antihyperglycemic effect of G. sylvestre can be, at least partly, attributed to the inhibition of α-glucosidase by its gymnemic acids. The current study provides relatively more direct evidence explaining the effectiveness of G. sylvestre against hyperglycemia.

Saponins from the roots of Chenopodium bonus-henricus L.

Kokanova-Nedialkova, Zlatina,Nedialkov, Paraskev T.,Momekov, Georgi

, p. 2024 - 2031 (2018/06/12)

Two new glycosides of phytolaccagenin and 2β-hydroxyoleanoic acid, namely bonushenricoside A (3) and bonushenricoside B (5) together with four known saponins, respectively compounds 3-O-L-α-arabinopyranosyl-bayogenin-28-O-β-glucopyranosyl ester (1), 3-O-β-glucuronopyranosyl-2β-hydroxygypsogenin-28-O-β-glucopyranosyl ester (2), 3-O-β-glucuronopyranosyl-bayogenin-28-O-β-glucopyranosyl ester (4) and 3-O-β-glucuronopyranosyl-medicagenic acid-28-β-xylopyranosyl(1→4)-α-rhamnopyranosyl(1→2)-α-arabinopyranosyl ester (6) were isolated from the roots of Chenopodium bonus-henricus L. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, IR and HRMS). The MeOH extract and compounds were tested for cytotoxic activity on five leukemic cell lines (HL-60, SKW-3, Jurkat E6-1, BV-173 and K-562). In addition, the ability of metanolic extract and saponins to modulate the interleukin-2 production in PHA/PMA stimulated Jurkat E6-1 cells was investigated as well.

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