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50-99-7 Usage

Description

Different sources of media describe the Description of 50-99-7 differently. You can refer to the following data:
1. D(+)-glucose ,a short form of dextrorotatory glucose, is a stereoisomer of glucose molecule, which is biologically active and whose bottom chiral carbon has its hydroxyl group (OH) located spatially to the right. Its molecule can exist in an open-chain (acyclic) and ring (cyclic) form and has two isomers α- and β-. It is the main source of energy in the form of ATP for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. In animals, it arises from the breakdown of glycogen in a process known as glycogenolysis. D-(+)-Glucose has been used as a standard for the estimation of total sugar in hydrolyzed starch by phenol-sulfuric acid method. It has also been used in the preparation of the liquid media for culturing some yeast cells. In addition, it is used therapeutically in fluid and nutrient replacement, such as glucose syrup and glucose powder. It can be obtained by enzymatic cleavage of starch, so there are multiple sources like sugar cane, sugar beet, corn (corn syrup), potatoes and wheat. Today, large-scale starch hydrolysis is used to produce glucose.
2. D-(+)-Glucose is a monosaccharide that occurs in nature and is used by organisms as an energy source. D-(+)-Glucose is the more common enantiomer of L-(–)-glucose (Item No. 20829). Anhydrous Dextrose is the anhydrous form of D-glucose, a natural monosaccharide and carbohydrate. Dextrose serves to replenish lost nutrients and electrolytes. The agent provides metabolic energy and is the primary ingredient in oral rehydration salts (ORS) and is used in intravenous (IV) fluids to provide nutrients to patients under intensive care who are unable to receive them by the oral route. Solutions containing dextrose restore blood glucose levels and provide calories and may aid in minimizing liver glycogen depletion and exerts a protein-sparing action. Dextrose anhydrous also plays a role in the production of proteins and in lipid metabolism. Watery odorless colorless liquid. Denser than water and soluble in water. Hence sinks in and mixes with water. (USCG, 1999) Aldehydo-D-glucose is the open chain form of D-glucose. It is a D-glucose and an aldehydo-glucose. It is an enantiomer of an aldehydo-L-glucose.
3. D(+)-Glucose?is one of the most important biological compounds found in nature. It is a main product in photosynthesis and is oxidized in cellular respiration. D(+)-Glucose?polymerizes to form several important classes of biomolecules including cellulose, starch, and glycogen. It also combines with other compounds to produce common sugars such as sucrose and lactose. The form of D(+)-Glucose?displayed above is D-D(+)-Glucose. The “D” designation indicates the configuration of the molecule. The “D” configuration specifies that the hydroxyl group on the number 5 carbon is on the right side of the molecule. The mirror image of D-D(+)-Glucose?produces another form of D(+)-Glucose?called L-D(+)-Glucose.D(+)-Glucose?is the most common form of a large class of molecules called carbohydrates. Carbohydrates are the predominant type of organic compounds found in organisms and include sugar, starches, and fats. Carbohydrates, as the name implies, derive their name from D(+)-Glucose,C6H12O6, which was considered a hydrate of carbon with the general formula of Cn(H2O)n, where n is a positive integer. Although the idea of water bonded to carbon to form a hydrate of carbon was wrong, the term carbohydrate persisted. Carbohydrates consist of carbon, hydrogen, and oxygen atoms, with the carbon atoms generally forming long unbranched chains. Carbohydrates are also known as saccharides derived from the Latin word for sugar, saccharon.

References

1. http://www.sigmaaldrich.com/catalog/product/sigma/g8270?lang=en®ion=CA 2. https://pubchem.ncbi.nlm.nih.gov/compound/D-glucose#section=Top 3. http://www.hmdb.ca/metabolites/HMDB00122 4. http://www.biology-online.org/dictionary/D-glucose 5. http://www3.hhu.de/biodidaktik/zucker/sugar/glukose.html

Chemical Properties

White or almost white, crystalline powder.

Originator

Dextrose,Wockhardt Ltd.,India

History

D(+)-Glucose?is the most important and predominant monosaccharide found in nature. It was isolated from raisins by Andreas Sigismund Marggraf (1709–1782) in 1747, and in 1838, Jean-Baptiste-André Dumas (1800–1884) adopted the name glucose from the Greek word glycos meaning sweet. Emil Fischer (1852–1919) determined the structure of glucose in the late 19th century. Glucose also goes by the names dextrose (from its ability to rotate polarized light to the right), grape sugar, and blood sugar. The term blood sugar indicates that glucose is the primary sugar dissolved in blood. Glucose’s abundant hydroxyl groups enable extensive hydrogen bonding, and so glucose is highly soluble in water.

Uses

Different sources of media describe the Uses of 50-99-7 differently. You can refer to the following data:
1. Glucose is the primary fuel for biological respiration. During digestion, complex sugarsand starches are broken down into glucose (as well as fructose and galactose) in the small intestine.Glucose then moves into the bloodstream and is transported to the liver where glucoseis metabolized through a series of biochemical reactions, collectively referred to as glycolysis.Glycolysis, the breakdown of glucose, occurs in most organisms. In glycolysis, the final productis pyruvate. The fate of pyruvate depends on the type of organism and cellular conditions.In animals, pyruvate is oxidized under aerobic conditions producing carbon dioxide. Underanaerobic conditions in animals, lactate is produced. This occurs in the muscle of humansand other animals. During strenuous conditions the accumulation of lactate causes musclefatigue and soreness. Certain microorganisms, such as yeast, under anaerobic conditions convertpyruvate to carbonic dioxide and ethanol. This is the basis of the production of alcohol.Glycolysis also results in the production of various intermediates used in the synthesis of otherbiomolecules. Depending on the organism, glycolysis takes various forms, with numerousproducts and intermediates possible.
2. glucose has moisture-binding properties and provides the skin with a soothing effect. It is a sugar that is generally obtained by the hydrolysis of starch.
3. Glucose is a corn sweetener that is commercially made from starch by the action of heat and acids or enzymes, resulting in the complete hydrolysis of the cornstarch. There are two types of refined commercially available: hydrate, which contains 9% by weight water of crystallization and is the most often used, and anhydrous glucose, which contains less than 0.5% water. is a reducing sugar and produces a high-temperature browning effect in baked goods. It is used in ice cream, bakery products, and confections. It is also termed corn sugar.
4. Dextrose(D-glucose), a simple sugar (monosaccharide), is an important carbohydrate in biology
5. Labelled D-Glucose is a simple sugar that is present in plants. A monosaccharide that may exist in open chain or cyclic conformation if in solution. It plays a vital role in photosynthesis and fuels the energy required for cellular respiration. D-Glucose is used in various metabolic processes including enzymic synthesis of cyclohexyl-α and β-D-glucosides. Can also be used as a diagnostic tool in detection of type 2 diabetes mellitus and potentially Huntington's disease through analysis of blood-glucose in type 1 diabetes mellitus.
6. A primary source of energy for living organisms
7. D(+)-Glucose anhydrous for biochemistry Reag. Ph Eur. CAS 50-99-7, molar mass 180.16?g/mol.

Definition

Different sources of media describe the Definition of 50-99-7 differently. You can refer to the following data:
1. Naturally occurring GLUCOSE belongs to the stereochemical series D and is dextrorotatory, indicated by the symbol (+). Thus the term dextrose is used to indicate D-(+)-glucose. As other stereochemical forms of glucose have no significance in biological systems the term ‘glucose’ is often used interchangeably with dextrose in biology.
2. ChEBI: The open chain form of D-glucose.

Manufacturing Process

D-Glucose is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement.Dehydration of Dextrose Monohydrate.1. Dehydration with Fluid-bed DryerDextrose monohydrate was brought in a horizontal-placed turbo-dryer (VOMM, Mailand, Italy). The dehydration occurred at a temperature of between 90° to 150°C in a stream of air of 5 Normalised m3/kg (i.e volume of gas at 0°C and 1 mbar) dextrose and a rotation speed of 1200 min-1.Dehydration of Glucose Syrup (Dextrose Content 96%).A glucose syrup (C*SWEET D 02763 Cerestar) (dry substance ca. 70%) was sprayed at a flow rate of 7 kg/h at 70°C into a Niro FSD pilot plant spray dryer. For powdering ca. 9 kg coarsely milled dried product at a ratio liquid/solid of 1:2 was added. The atomising conditions were as follows:The drying chamber was operated at:The fluid bed was adjusted to:

Biotechnological Production

The D-configuration of D-isoascorbic acid at C5 allows a short biosynthetic pathway from D-glucose, i.e., its 1,5-glucopyranoside, which is oxidized to D-glucono-1,5-lactone by glucose oxidase followed by oxidation at C2 by D-gluconolactone oxidase. The immediate oxidation product of D-glucono-1,5-lactone by gluconolactone oxidase already has reducing activity on, e.g., 2,6-dichlorphenolindophenol. It is rather stable at pH 4. Upon pH shift, this compound spontaneously converts to D-isoascorbic acid. The unidentified immediate oxidation product could be 2-keto-D-glucono-1,5-lactone, which rearranges via a reversible transesterification reaction to the 1,4-lactone followed by an irreversible enolization to D-isoascorbic acid. The formation of 2-keto-D-gluconic acid as the result of 2-keto-D-glucono-1,5-lactone hydrolysis was not reported. The oxidation of the 1,4-lactone by D-gluconolactone oxidase might also occur to some extent, since D-glucono-1,5-lactone shows a tendency to slowly rearrange to the 1,4-lactone at pH[4and the D-gluconolactone oxidase of Penicillium cyaneofulvum accepts both D-glucono-1,5-lactone and the corresponding 1,4-lactone . This reaction would directly deliver the keto-isomer of D-isoascorbic acid. The sequence of the reactions from D-glucose to D-isoascorbic acid, first oxidation at C1, then oxidation at C2 (C1, C2), is similar to the naturally evolved Asc biosynthesis from L-galactose or L-gulose. Oxidation of D-gluconolactone at C2 is also afforded by pyranose-2-oxidase from Polyporus obtusus. In this reaction both D-isoascorbic acid and 2-keto- D-gluconic acid were obtained in a roughly 1:1 ratio. Obviously, following the natural C1, C2 oxidation sequence, transesterification and (iso)ascorbic acid formation are preferred over hydrolysis and 2-keto sugar acid formation or are at least possible to a significant extent. If the sequence of oxidation reactions is reversed (C2, C1), i.e., D-glucopyranose is first oxidized by pyranose-2-oxidase to D-glucosone followed by glucose oxidase treatment, 2-keto-D-gluconate was reported as the only oxidation product. Though not explicitly reported, it is safe to assume that the later oxidation occurs with 2-keto-D-gluco-1,5-pyranose and delivers as the immediate reaction product 2-keto-D-glucono-1,5-lactone, which hydrolyzes affording 2-keto-D-gluconate. It is unclear why the spontaneous follow-up reaction of 2-keto-D-glucono-1,5-lactone delivers, at least to some extent, D-isoascorbic acid if obtained according to the C1, C2 reaction sequence, but only 2-keto-D-gluconate if obtained by the C2, C1 oxidation sequence.

General Description

Watery odorless colorless liquid. Denser than water and soluble in water. Hence sinks in and mixes with water.

Air & Water Reactions

Water soluble.

Reactivity Profile

A weak reducing agent.

Health Hazard

No toxicity

Biochem/physiol Actions

Glycogen phosphorylase, muscle associated (PYGM), is an important contributor to glycogenolysis. Down regulation of PYGM gene is observed in schizophrenia. Mutation in PYGM leads to McArdle disease, a glycogen storage disorder. The PYGM gene is significantly associated with energy production.

Safety Profile

Mildly toxic by ingest ion. An experimental teratogen. Experi mental reproductive effects. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. Potentially explosive reaction with potassium nitrate + sodium peroxide when heated in a sealed container. Uxtures with alkali release carbon monoxide when heated. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Crystallise -D-glucose from hot glacial acetic acid or pyridine. Traces of solvent are removed by drying in a vacuum oven at 75o for >3hours. [Gottfried Adv Carbohydr Chem 5 127 1950, Kjaer & Lindberg Acta Chem Scand 1 3 1713 1959, Whistler & Miller Methods in Carbohydrate Chemistry I 1301962, Academic Press, Beilstein 1 IV 4306.] [For equilibrium forms see Angyal Adv Carbohydr Chem 42 15 1984, Angyal & Pickles Aust J Chem 25 1711 1972.]

Check Digit Verification of cas no

The CAS Registry Mumber 50-99-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 0 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 50-99:
(4*5)+(3*0)+(2*9)+(1*9)=47
47 % 10 = 7
So 50-99-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5+,6+/m0/s1

50-99-7 Well-known Company Product Price

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  • Alfa Aesar

  • (A16828)  D-(+)-Glucose, anhydrous, 99%   

  • 50-99-7

  • 500g

  • 245.0CNY

  • Detail
  • Alfa Aesar

  • (A16828)  D-(+)-Glucose, anhydrous, 99%   

  • 50-99-7

  • 2500g

  • 714.0CNY

  • Detail
  • Alfa Aesar

  • (A16828)  D-(+)-Glucose, anhydrous, 99%   

  • 50-99-7

  • 10000g

  • 2295.0CNY

  • Detail
  • Supelco

  • (47829)  D-(+)Glucose  analytical standard

  • 50-99-7

  • 000000000000047829

  • 376.74CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1000)  D-(+)-Glucose  pharmaceutical secondary standard; traceable to USP and PhEur

  • 50-99-7

  • PHR1000-1G

  • 732.19CNY

  • Detail
  • USP

  • (1181302)  Dextrose  United States Pharmacopeia (USP) Reference Standard

  • 50-99-7

  • 1181302-500MG

  • 4,662.45CNY

  • Detail
  • Sigma-Aldrich

  • (G5767)  D-(+)-Glucose  ACS reagent

  • 50-99-7

  • G5767-25G

  • 325.26CNY

  • Detail
  • Sigma-Aldrich

  • (G5767)  D-(+)-Glucose  ACS reagent

  • 50-99-7

  • G5767-500G

  • 457.47CNY

  • Detail
  • Sigma-Aldrich

  • (G5767)  D-(+)-Glucose  ACS reagent

  • 50-99-7

  • G5767-5KG

  • 2,182.05CNY

  • Detail
  • Sigma-Aldrich

  • (16325)  D-(+)-Glucose  meets analytical specification of Ph. Eur., BP, anhydrous

  • 50-99-7

  • 16325-1KG

  • 627.12CNY

  • Detail
  • Sigma-Aldrich

  • (49152)  D-(+)-Glucose  tested according to Ph.Eur., anhydrous

  • 50-99-7

  • 49152-1KG

  • 1,434.42CNY

  • Detail
  • Supelco

  • (47249)  D-(+)-Glucose  analytical standard

  • 50-99-7

  • 000000000000047249

  • 312.39CNY

  • Detail

50-99-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name aldehydo-D-glucose

1.2 Other means of identification

Product number -
Other names D-(+)-Glucose

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Processing Aids and Additives
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:50-99-7 SDS

50-99-7Synthetic route

cellulose

cellulose

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With lithium chloride In N,N-dimethyl-formamide at 120℃; for 8h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent;99%
With hydrogenchloride; water for 3h; Reactivity; Ionic liquid;94%
Tonsil Supreme 110F, impregnated gallium sulphate In water at 20 - 110℃; for 0.35h; Product distribution / selectivity;75%
1,2-O-benzylidene-α-D-glucofuranose
22154-74-1

1,2-O-benzylidene-α-D-glucofuranose

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With ammonium formate; palladium on activated charcoal In methanol for 0.666667h; Product distribution; Heating; at various types of sugars;97%
Cellobiose
13360-52-6

Cellobiose

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With water at 120℃; for 1h; Autoclave;96%
With sulfuric acid In water at 130℃; for 6h; pH=4; Kinetics; Catalytic behavior; pH-value; Temperature; Inert atmosphere; Sealed tube;91.1%
With phosphotungstic acid hydrate; water at 160℃; for 0.5h; Reagent/catalyst; Temperature;37.6%
ptaquiloside
87625-62-5

ptaquiloside

A

D-glucose
50-99-7

D-glucose

B

C14H18O2
87701-34-6

C14H18O2

Conditions
ConditionsYield
With sodium carbonate In water at 25℃; for 0.333333h; pH:8-11;A n/a
B 95%
With glycosidase Inert atmosphere; Enzymatic reaction;
amylose

amylose

amylopectin

amylopectin

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With water at 150℃; for 3h; Autoclave;95%
cellulose

cellulose

A

5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

B

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With hydrogenchloride; water for 4h; Reactivity; Ionic liquid;A 6%
B 93%
With carbon based mesoporous Sibunit-4-ox In water for 5h;A n/a
B 45%
With water; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride at 160℃; for 2.66667h; Product distribution / selectivity;A 7%
B 32%
(2S,3R)-3,7-dimethyl-6-octene-1,2,3-triol 2-O-β-D-glucopyranoside

(2S,3R)-3,7-dimethyl-6-octene-1,2,3-triol 2-O-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

(2S,3R)-3,7-dimethyl-6-octene-1,2,3-triol
90988-60-6

(2S,3R)-3,7-dimethyl-6-octene-1,2,3-triol

Conditions
ConditionsYield
With β-glucosidase In water at 37℃; for 96h; Enzymatic reaction;A n/a
B 93%
protogenkwanin-4'-glucoside
78983-46-7

protogenkwanin-4'-glucoside

A

D-glucose
50-99-7

D-glucose

B

protogenkwanin
74996-29-5

protogenkwanin

Conditions
ConditionsYield
With cellulase from Aspergillus niger at 40℃; for 144h; pH=4.6;A n/a
B 92%
cellobiose
528-50-7

cellobiose

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
In water at 249℃; for 0.0166667h; Product distribution; Kinetics; Thermodynamic data; activation energy; various pH (3-5.7), temperatures (180-249 deg C), and times (0.3-15 min);90%
With recombinant C,N-terminal 6xHis-tagged rabbit cecum umbgl3B β-glucosidase; water at 28℃; for 0.25h; pH=6; aq. phosphate buffer;
With Bgl1T β-D-glucoside glucohydrolase; calcium chloride at 37℃; for 0.25h; pH=7; aq. phosphate buffer; Enzymatic reaction;
cellulose

cellulose

A

D-glucose
50-99-7

D-glucose

B

levulinic acid
123-76-2

levulinic acid

Conditions
ConditionsYield
With dodecatungstophosphoric acid hydrate; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride In water at 139.84℃; for 5h; Reagent/catalyst;A 89%
B n/a
With water at 150℃; for 12h; Autoclave;A 12%
B 42%
With 1-(3-sulfopropyl)pyridinium phosphotungstate; water at 150℃; under 15001.5 Torr; for 5h; Autoclave; Inert atmosphere;A 32.9%
B 18.1%
12β-O-acetyl-3-O-(β-D-glucopyranosyl-(1→4)-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-D-oleandronyl)-11α-O-tigloyltenacigenin B

12β-O-acetyl-3-O-(β-D-glucopyranosyl-(1→4)-6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-D-oleandronyl)-11α-O-tigloyltenacigenin B

A

D-glucose
50-99-7

D-glucose

B

12β-O-acetyl-3-O-(6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-D-oleandronyl)-11α-O-tigloyltenacigenin B

12β-O-acetyl-3-O-(6-deoxy-3-O-methyl-β-D-allopyranosyl-(1→4)-D-oleandronyl)-11α-O-tigloyltenacigenin B

Conditions
ConditionsYield
With cellulase In aq. acetate buffer at 37℃; for 168h; pH=5; Enzymatic reaction;A 88%
B 4 mg
(3S,4R,5S,7R,9S)-megastigma-6,7-diene-3,4,5,9-tetrol 4-O-β-D-glucopyranoside

(3S,4R,5S,7R,9S)-megastigma-6,7-diene-3,4,5,9-tetrol 4-O-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

crotalionol A

crotalionol A

Conditions
ConditionsYield
With hesperidinase; emulsin; water at 37℃; for 24h;A 86%
B 72%
megastigman-7-en-3,6-epoxy-5,9-diol 9-O-β-D-glucopyranoside
1374460-70-4

megastigman-7-en-3,6-epoxy-5,9-diol 9-O-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

crotalionol C

crotalionol C

Conditions
ConditionsYield
With hesperidinase; emulsin; water at 37℃; for 24h;A 67%
B 86%
Sucrose
57-50-1

Sucrose

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With water at 79.84℃; for 2h;85.9%
With water; acetone in Gegenwart eines sauren Kationenaustauschers;
With potassium phosphate buffer; rat intestinal α-glucosidase; 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one In dimethyl sulfoxide at 37℃; for 0.25h; pH=6.3; Enzyme kinetics;
(3R,4R,5S,6S,7E,9R)-megastigman-7-ene-3,4,9-triol 9-O-β-D-glucopyranoside
1232683-60-1

(3R,4R,5S,6S,7E,9R)-megastigman-7-ene-3,4,9-triol 9-O-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

(3R,4R,5S,6S,7E,9R)-megastigman-7-ene-3,4,9-triol

(3R,4R,5S,6S,7E,9R)-megastigman-7-ene-3,4,9-triol

Conditions
ConditionsYield
With hesperidinase; emulsin; water at 37℃; for 18h; Enzymatic reaction;A 85%
B 76%
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
582-52-5

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With K 10 clay In methanol; water at 75℃; for 72h;83%
2,3,4,5,6-penta-O-benzyl aldehydo D-glucose
78699-85-1

2,3,4,5,6-penta-O-benzyl aldehydo D-glucose

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In methanol for 120h; Ambient temperature;83%
alpha-D-glucopyranose
492-62-6

alpha-D-glucopyranose

1-amino-2-propene
107-11-9

1-amino-2-propene

A

D-glucose
50-99-7

D-glucose

B

1-(allylamino)-1-deoxy-β-D-glucopyranose

1-(allylamino)-1-deoxy-β-D-glucopyranose

Conditions
ConditionsYield
In ethanol at 53℃; for 1h; Temperature; Time; Inert atmosphere;A n/a
B 81.4%
starch

starch

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With H3N*2H(1+)*TeW6O21(2-); water at 130℃; for 4h; Autoclave;78.4%
With Arthrobacter sp. DL001 α-D-glucoside glucohydrolase; water at 30℃; for 0.5h; pH=5.5; citrate-phosphate buffer; Enzymatic reaction;
(3S,4R,5S,7R,9R)-megastigma-6,7-diene-3,4,5,9-tetrol 4-O-β-D-glucopyranoside

(3S,4R,5S,7R,9R)-megastigma-6,7-diene-3,4,5,9-tetrol 4-O-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

crotalionol B

crotalionol B

Conditions
ConditionsYield
With hesperidinase; emulsin; water at 37℃; for 24h;A 50%
B 74%
(2S)-naringenin 5-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside
1160434-44-5

(2S)-naringenin 5-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With hydrogenchloride; water at 80℃; for 1h;A n/a
B 73%
(2R)-naringenin 5-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside

(2R)-naringenin 5-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

Conditions
ConditionsYield
With hydrogenchloride; water at 80℃; for 1h;A n/a
B 73%
microcrystalline cellulose

microcrystalline cellulose

A

5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

B

formic acid
64-18-6

formic acid

C

D-glucose
50-99-7

D-glucose

D

levulinic acid
123-76-2

levulinic acid

Conditions
ConditionsYield
With graphene oxide (GO) In water at 199.84℃; for 1h; Temperature; Microwave irradiation; Green chemistry;A n/a
B n/a
C 73%
D n/a
chalconaringenin 2'-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside

chalconaringenin 2'-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

2',4',6',4-tetrahydroxydihydrochalcone
25515-46-2, 73692-50-9

2',4',6',4-tetrahydroxydihydrochalcone

Conditions
ConditionsYield
With hydrogenchloride; water at 80℃; for 1h;A n/a
B 72%
D-glucose
50-99-7

D-glucose

D-sorbitol
50-70-4

D-sorbitol

Conditions
ConditionsYield
With hydrogen In water at 120℃; under 15001.5 Torr; for 1h;100%
With hydrogen; ruthenium embedded in mesoporous carbon In water at 120℃; under 15001.5 Torr; for 2h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Autoclave;99.3%
With hydrogen at 120℃; under 22502.3 Torr; for 2h; high pressure reactor;94.43%
D-glucose
50-99-7

D-glucose

3,4-di-O-formyl-D-erythrose

3,4-di-O-formyl-D-erythrose

Conditions
ConditionsYield
With lead(IV) acetate In acetic acid at 16 - 28℃; for 0.75h; oxidative cleavage;100%
D-glucose
50-99-7

D-glucose

O-(4-methoxybenzyl)-hydroxylamine HCl

O-(4-methoxybenzyl)-hydroxylamine HCl

(2S,3R,4R,5R)-2,3,4,5,6-Pentahydroxy-hexanal O-(4-methoxy-benzyl)-oxime
365278-77-9

(2S,3R,4R,5R)-2,3,4,5,6-Pentahydroxy-hexanal O-(4-methoxy-benzyl)-oxime

Conditions
ConditionsYield
In acetate buffer at 20℃; for 2.16667h; pH=4;100%
D-glucose
50-99-7

D-glucose

7-hydroxy-8-hydroxyaminomethylcoumarin
365278-56-4

7-hydroxy-8-hydroxyaminomethylcoumarin

C16H19NO9

C16H19NO9

Conditions
ConditionsYield
In phosphate buffer at 20℃; pH=6.5;100%
D-glucose
50-99-7

D-glucose

N-(3-methoxybenzyl)hydroxylamine hydrochloride

N-(3-methoxybenzyl)hydroxylamine hydrochloride

C14H21NO7

C14H21NO7

Conditions
ConditionsYield
In phosphate buffer at 20℃; pH=6.5;100%
D-glucose
50-99-7

D-glucose

8-aminooxymethyl-7-hydroxycoumarin

8-aminooxymethyl-7-hydroxycoumarin

2,3,4,5,6-pentahydroxy-hexanal O-(7-hydroxy-2-oxo-2H-chromen-8-ylmethyl)-oxime

2,3,4,5,6-pentahydroxy-hexanal O-(7-hydroxy-2-oxo-2H-chromen-8-ylmethyl)-oxime

Conditions
ConditionsYield
In acetate buffer at 20℃; for 2.16667h; pH=4;100%
D-glucose
50-99-7

D-glucose

ethanamine hydrochloride
557-66-4

ethanamine hydrochloride

N-ethyl-D-gluconamide

N-ethyl-D-gluconamide

Conditions
ConditionsYield
With iodine; potassium carbonate In methanol at 20℃; for 6h;100%
D-glucose
50-99-7

D-glucose

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With manganese(II) sulfate; rubidium sulfate; sulfuric acid; magnesium sulfate In water at 40℃; for 0.166667h; Temperature; Reagent/catalyst;100%
With cesium sulfate; sulfuric acid; water; magnesium sulfate; 2Co(2+)*2O4S(2-) at 145℃;
With sulfuric acid In water at 33℃; for 72h; pH=3.9; Kinetics; Reagent/catalyst; Temperature; Microbiological reaction;
2-[2-(vinyloxy)ethoxymethyl]oxirane
16801-19-7

2-[2-(vinyloxy)ethoxymethyl]oxirane

D-glucose
50-99-7

D-glucose

1,2,3,5,6-penta-O-{1-[2-(glycidyloxy)ethoxy]ethyl}-D-glucopyranose

1,2,3,5,6-penta-O-{1-[2-(glycidyloxy)ethoxy]ethyl}-D-glucopyranose

Conditions
ConditionsYield
With trifluoroacetic acid at 100 - 110℃; for 1h; Temperature;100%
D-glucose
50-99-7

D-glucose

3-dibutylaminopropylamine
102-83-0

3-dibutylaminopropylamine

C17H36N2O5

C17H36N2O5

Conditions
ConditionsYield
In methanol; water at 65℃; for 0.166667h; Schiff Reaction; Inert atmosphere;100%
In neat (no solvent) at 25℃; for 24h; Kinetics; Solvent;
methanol
67-56-1

methanol

D-glucose
50-99-7

D-glucose

Methyl formate
107-31-3

Methyl formate

Conditions
ConditionsYield
With H8[PMo7V5O40]; oxygen at 90℃; under 15001.5 Torr; for 24h; Autoclave;100%
With H8[PMo7V5O40]; oxygen at 90℃; under 15001.5 Torr; for 24h; Autoclave;
D-glucose
50-99-7

D-glucose

gluconic acid
526-95-4

gluconic acid

Conditions
ConditionsYield
With sodium carbonate In water at 30℃; for 40h; Wavelength; Irradiation;99%
With oxygen; sodium carbonate In water at 24.84℃; under 750.075 Torr; for 2h; pH=< 9; Catalytic behavior; Reagent/catalyst;99%
With 5% Pd/C; water; oxygen; sodium carbonate at 20℃; under 760.051 Torr; for 2h; Reagent/catalyst;98%
Conditions
ConditionsYield
With sodium acetate at 100℃; for 0.333333h;99%
D-glucose
50-99-7

D-glucose

butyryl chloride
141-75-3

butyryl chloride

[(2R,3R,4S,5R)-3,4,5,6-tetra(butanoyloxy)tetrahydropyran-2-yl]methyl butanoate
125161-50-4

[(2R,3R,4S,5R)-3,4,5,6-tetra(butanoyloxy)tetrahydropyran-2-yl]methyl butanoate

Conditions
ConditionsYield
Stage #1: D-glucose; butyryl chloride In dichloromethane at 15℃; for 0.5h;
Stage #2: With pyridine In dichloromethane at 15℃; for 15.5h;
98%
Stage #1: D-glucose; butyryl chloride In dichloromethane at 15℃; for 0.5h;
Stage #2: With pyridine In dichloromethane at 15℃; for 16h;
98.46%
Stage #1: D-glucose; butyryl chloride In dichloromethane at 15℃; for 0.5h;
Stage #2: With pyridine In dichloromethane at 15℃; for 16h;
98.46%
D-glucose
50-99-7

D-glucose

acetic anhydride
108-24-7

acetic anhydride

β-D-glucose pentaacetate
604-69-3

β-D-glucose pentaacetate

Conditions
ConditionsYield
Stage #1: acetic anhydride With sodium acetate for 0.333333h; Reflux;
Stage #2: D-glucose for 0.25h; Reflux;
98%
With sodium acetate at 90℃; for 4h; Inert atmosphere;85%
With sodium thiocyanide
4,5-Dichloro-1,2-phenylenediamine
5348-42-5

4,5-Dichloro-1,2-phenylenediamine

D-glucose
50-99-7

D-glucose

(1'S,2'R,3'R,4'R)-1H-2-[(1,2,3,4,5-pentahydroxy)pentyl]-5,6-dichlorobenzimidazole
108757-42-2

(1'S,2'R,3'R,4'R)-1H-2-[(1,2,3,4,5-pentahydroxy)pentyl]-5,6-dichlorobenzimidazole

Conditions
ConditionsYield
With air; iodine; acetic acid at 20℃; for 3h;98%
D-glucose
50-99-7

D-glucose

2,3-Diaminonaphthalene
771-97-1

2,3-Diaminonaphthalene

(1'S,2'R,3'R,4'R)-2-[1',2',3',4',5'-pentahydroxypentyl]-1H-naphthimidazole
1027103-22-5

(1'S,2'R,3'R,4'R)-2-[1',2',3',4',5'-pentahydroxypentyl]-1H-naphthimidazole

Conditions
ConditionsYield
With air; iodine; acetic acid at 20℃; for 6h;98%
With iodine; acetic acid at 20℃; for 6h;
D-glucose
50-99-7

D-glucose

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

(1'S,2'R,3'R,4'R)-2-[1',2',3',4',5'-pentahydroxypentyl]-1H-benzimidazole
7147-74-2

(1'S,2'R,3'R,4'R)-2-[1',2',3',4',5'-pentahydroxypentyl]-1H-benzimidazole

Conditions
ConditionsYield
With air; iodine; acetic acid at 20℃; for 8h;98%
carbonic acid bis(1-isopropylhydrazide) dihydrochloride

carbonic acid bis(1-isopropylhydrazide) dihydrochloride

D-glucose
50-99-7

D-glucose

1'S,2'R,3'R,4'R-2,4-diisopropyl-6-(1',2',3',4',5'-pentahydroxypentyl)-1,2,4,5-tetrazinan-3-one

1'S,2'R,3'R,4'R-2,4-diisopropyl-6-(1',2',3',4',5'-pentahydroxypentyl)-1,2,4,5-tetrazinan-3-one

Conditions
ConditionsYield
With sodium acetate In water at 20℃;98%
D-glucose
50-99-7

D-glucose

5,7-dihydroxy-4-phenyl-2H-1-benzopyran-2-one
7758-73-8

5,7-dihydroxy-4-phenyl-2H-1-benzopyran-2-one

6-(C-β-D-Glucosyl)-4-phenyl-5,7-dihydroxycoumarin

6-(C-β-D-Glucosyl)-4-phenyl-5,7-dihydroxycoumarin

Conditions
ConditionsYield
With E. coli whole cells harboring coumarin C-glucosyltransferase from Morus alba (MaCGT) at 30℃; for 24h; Enzymatic reaction;98%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

D-glucose
50-99-7

D-glucose

2,3,4,5,6-pentakis-O-(trimethylsilyl)-D-glucose
6736-97-6

2,3,4,5,6-pentakis-O-(trimethylsilyl)-D-glucose

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 0 - 20℃;97%
D-glucose
50-99-7

D-glucose

5-amino-1-(6-phenyl-pyridazin-3-yl)-1H-pyrazole-4-carboxylic acid hydrazide
1649475-06-8

5-amino-1-(6-phenyl-pyridazin-3-yl)-1H-pyrazole-4-carboxylic acid hydrazide

5-amino-1-(6-phenyl-pyridazin-3-yl)-1H-pyrazole-4-carboxylic acid (2,3,4,5,6-pentahydroxy-hexylidine)hydrazide

5-amino-1-(6-phenyl-pyridazin-3-yl)-1H-pyrazole-4-carboxylic acid (2,3,4,5,6-pentahydroxy-hexylidine)hydrazide

Conditions
ConditionsYield
With acetic acid In N,N-dimethyl-formamide at 80℃; for 1h;96.93%
D-glucose
50-99-7

D-glucose

acetyl chloride
75-36-5

acetyl chloride

α-D-glucopyranose peracetylate
604-68-2

α-D-glucopyranose peracetylate

Conditions
ConditionsYield
With triethylamine In chloroform at 0 - 10℃; for 2h; Concentration;96.8%
With pyridine; chloroform
D-glucose
50-99-7

D-glucose

5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

Conditions
ConditionsYield
With sodium chloride In water at 180℃; for 8h; Catalytic behavior; Reagent/catalyst; Solvent;96%
With chromium chloride; 1-butyl-3-methylimidazolium chloride In toluene at 100℃; for 4h;91%
With aluminium(III) triflate; methanesulfonic acid In dimethyl sulfoxide at 120℃; for 6h; Reagent/catalyst;90%

50-99-7Relevant articles and documents

A new secoiridoid glycoside and a new sesquiterpenoid glycoside from Valeriana jatamansi with neuroprotective activity

Tan, Yu-Zhu,Yong, Yan,Dong, Yan-Hong,Wang, Ru-Jing,Li, Hong-Xiang,Zhang, Hai,Guo, Da-Le,Zhang, Shi-Jin,Dong, Xiao-Ping,Xie, Xiao-Fang

, p. 177 - 180 (2016)

A new secoiridoid glycoside, isopatrinioside (1) and a new sesquiterpenoid glycoside, valeriananoid F (2), together with nine known compounds, were isolated from the roots of Valeriana jatamansi. Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 was an unusual monocyclic iridoid glycoside ring-opened between C-1 and C-2 produced by the cleavage of the pyran ring. Of the eleven isolates, compounds 1 and 4 exhibited moderate neuroprotective effects against CoCl2-induced neuronal cell death in PC12 cells.

A new triterpene glycoside from fruit of Phytolacca americana

Getiya,Gabelaya,Mshvildadze,Pichette,Lavoie,Dekanosidze

, p. 764 - 766 (2011)

Glycosides H and I, the structures of which were established by modern physicochemical analytical methods (PMR, 13C NMR, COSY, TOCSY, HMBC, MS) and acid-base hydrolysis, were isolated from the purified total saponins from fruit of Phytolacca americana containing at least 10 triterpene glycosides by rechromatography of enriched fractions over a column of silica gel. Glycoside H was a bidesmoside of phytolaccageninic acid, which was isolated earlier from cell culture of Phytolacca acinosa. Glycoside I was 3-O-(β-D-xylopyranosyl- (1 → 3)-β-D-galactopyranosyl-(1 → 3-β-D-xylopyranosyl)-28-O- β-D-glucopyranosyl phytolaccagenin, which was isolated by us for the first time.

Substrate control through per-O-methylation of cyclodextrin acids

Fenger, Thomas H.,Bols, Mikael

, p. 7769 - 7771 (2010)

Per-O-methylated cyclodextrins containing a single 2-O-(2-acetate), 2-O-(3-propanoate) or a 6-carboxylate were investigated for glycosidase activity on p-nitrophenyl glycosides. The former two compounds displayed enzyme catalysis giving rate accelerations of 500-1000, while the latter compound gave marginal catalysis. These results show that per-O-methylated cyclodextrins direct substrate binding from the secondary face leading to better catalysis. The Royal Society of Chemistry.

Polysciosides J and K, two new oleanane-type triterpenoid saponins from the leaves of Polyscias fruticosa (L.) harms. cultivating in An Giang Province, Viet Nam

Do, Van Mai,Tran, Cong Luan,Nguyen, Tan Phat

, p. 1250 - 1255 (2020)

For the first time, the phytochemical constituents of the leaves of Polyscias fruticosa (L.) Harms. cultivating in An Giang Province, Viet Nam were investigated and led to purify two new oleanane-type triterpenoid saponins, named polyscioside J (1) and polyscioside K (2) together with two known saponins, ladyginoside A (3) and chikusetsusaponin IVa (4) using variously chromatographic methods. Saponin (4) was reported for the first time from this species. Their structures were verified by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments and compared with previous literatures.

A membrane-bound trehalase from Chironomus riparius larvae: Purification and sensitivity to inhibition

Forcella, Matilde,Cardona, Francesca,Goti, Andrea,Parmeggiani, Camilla,Cipolla, Laura,Gregori, Maria,Schirone, Raffaella,Fusi, Paola,Parenti, Paolo

, p. 1186 - 1195 (2010)

A preparation of a membrane-bound trehalase from the larvae of the midge Chironomus riparius (Diptera: Chironomidae) was obtained by detergent solubilization, ion-exchange chromatography and concanavalin A affinity chromatography. Trehalase was purified 1080-fold to a specific activity of 75 U mg-1. The initial rate of trehalase activity followed Henri-Michaelis-Menten kinetics with a Km of 0.48 ± 0.04 mM. Catalytic efficiency was maximal at pH 6.5. The activity was highly inhibited by mono-and bicyclic iminosugar alkaloids such as (in order of potency) casuarine (IC50 = 0.25 ± 0.03 μM), deoxynojirimycin (IC50 = 2.83 ± 0.34 μM) and castanospermine (IC50 = 12.7 ± 1.4 μM). Increasing substrate concentration reduced the inhibition. However, in the presence of deoxynojirimycin, Lineweaver-Burk plots were curvilinear upward. Linear plots were obtained with porcine trehalase. Here, we propose that deoxynojirimycin inhibits the activity of trehalase from C. riparius according to a ligand exclusion model. Inhibition was further characterized by measuring enzyme activity in the presence of a series of casuarine and deoxynojirimycin derivatives. For comparison, inhibition studies were also performed with porcine trehalase. Results indicate substantial differences between midge trehalase and mammalian trehalase suggesting that, in principle, inhibitors against insect pests having trehalase as biochemical targets can be developed.

New grayanol diterpenoid and new phenolic glucoside from the flowers of Pieris formosa

Wang, Wei-Guang,Li, Hong-Mei,Li, Hai-Zhou,Wu, Zhao-Yuan,Li, Rong-Tao

, p. 70 - 75 (2010)

A new grayanol diterpenoid, grayanotoxin XXII (1), and a new phenolic glucoside, benzyl 2-hydroxy-4-O-[-xylopyranosyl(1″→6′)-β- glucopyranosyl]-benzoate (2), were isolated from the flowers of Pieris formosa. Their structures were determined on the basis of spectroscopic analysis and chemical methods.

Three new phenol compounds from Iris dichotoma PALL

Huang, Long,Ma, Wenhui,Liu, Yanze,Peng, Yong,Xiao, Peigen

, p. 1033 - 1036 (2012)

Three new phenolic compounds, irisdichototins D, E, and F (1 - 3, resp.) were isolated from the stems of Iris dichotoma. The structures of the new compounds were elucidated by spectroscopic analyses, including 2D-NMR techniques.

New dammarane-type triterpenoid glycosides from Gynostemma burmanicum

Nguyen Phuong, Thao,Nguyen Tien, Dat,Pham, Thanh Binh,Pham, Thanh Ky,Than, Thi Kieu My

, p. 217 - 224 (2020)

The chemical composition of Gynostemma burmanicum King ex Chakrav. was investigated for the first time in this study. Nine dammarane glycosides (1?9) were isolated from the EtOH extract of the aerial parts of G. burmanicum. Their structures were elucidate

Isolation and Some Properties of Sorbitol Oxidase from Streptomyces sp. H-7775

Hiraga, Kazumi,Kitazawa, Mitsunori,Kaneko, Norihisa,Oda, Kohei

, p. 1699 - 1704 (1997)

A sorbitol oxidase (SOX) was found in the cell-free extract of a strain isolated from soil. The strain was classified and designated as Streptomyces sp. H-7775. SOX is constitutively expressed in the cell. The molecular weight of SOX that purified from the cell-free extract was 45,000. The optimum pH and the Km for sorbitol were 6.5-7.5 and 0.26 mM, respectively. The prosthetic group was a covalently bound FAD. SOX catalyzed oxidation of D-sorbitol to glucose and hydrogen peroxide without any requirements of exogenous cofactors. SOX did not react with glucose, a reaction product of D-sorbitol. This feature is useful in its application for diagnosis.

A grayanotox-9(11)-ene derivative from Rhododendron brachycarpum and its structural assignment via a protocol combining NMR and DP4 plus application

Tuan, Nguyen Quoc,Oh, Joonseok,Park, Hyun Bong,Ferreira, Daneel,Choe, Sanggil,Lee, Juseon,Na, MinKyun

, p. 45 - 50 (2017)

A growing body of evidence points to the useful roles of computational approaches in the structural characterization of natural products. Rhododendron brachycarpum has been traditionally used for the control of diabetes, hepatitis, hypertension, and rheumatoid arthritis and classified as an endangered species in Korea. A grayanotox-9(11)-ene derivative along with five known diterpenoids, were isolated from the MeOH extract of R.?brachycarpum. Extensive 1D and 2D NMR experiments were conducted to establish the 2D structure and relative configuration of the grayanotox-9(11)-ene derivative. Comparison of simulated and experimental ECD spectra resulted in an inconclusive outcome to assign its absolute configuration. Alternatively, gauge-including atomic orbitals (GIAO) NMR chemical shift calculations, with support by the advanced statistical method DP4 plus, and acid hydrolysis were employed to establish its absolute configuration. This work exemplifies how NMR analysis, combined with quantum mechanics calculations, is a viable approach to accomplish structural assignment of minor abundance molecules in lieu of X-ray crystallography or chiroptical approaches.

Cordycepamides A?E and cordyglycoside A, new alkaloidal and glycoside metabolites from the entomopathogenic fungus Cordyceps sp.

Fan, Wenwen,Li, Erwei,Liu, Xingzhong,Ren, Jinwei,Wang, Wenzhao,Zhang, Yongjie

, (2020)

Five new alkaloidal metabolites cordycepamides A?E (1?5), and one glycoside metabolite cordyglycoside A (6), together with six known compounds (7?12) were isolated from the entomopathogenic fungus Cordyceps sp. (LB1.18060004) from unidentified insect collected in Baoshan City, Yunnan Province, People's Republic of China. The structures were characterized by NMR and HRESIMS spectroscopic analyses. Cordycepamides A and B (1 and 2) were mixtures of two isomers in 5:4 ratio by integration of 1H NMR spectra. In additional, the structure of cordycepamide A (1) was further confirmed by X-ray crystallography as a pair of enantiomers. Absolute configurations of sugar moiety of cordyglycoside A (6) was confirmed by the acid hydrolysis and subsequent HPLC analysis. The isolated metabolites were evaluated for antimicrobial, cytotoxicity, and the DPPH scavenging assay, only 4 showed modest antioxidant effects in the DPPH scavenging assay (IC50 = 51.42 ± 3.08 μM).

Three new sulfated triterpenoids from the roots of Gypsophila pacifica

Luo, Jian-Guang,Nie, Wei,Kong, Ling-Yi

, p. 529 - 533 (2011)

Three new sulfated triterpenoids (1-3), along with one known compound (4), were isolated from the roots of Gypsophila pacifica Kom. The structures of the new compounds were established as 3β-O-sulfate gypsogenin 28-O-β-d-glucopyranosyl ester (1), 3β-O-sulfate gypsogenin (2), and 3β-O-sulfate quillaic acid (3) on the basis of 1D, 2D NMR, and HR-ESI-MS methods.

Structural characterization of cholestane rhamnosides from ornithogalum saundersiae bulbs and their cytotoxic activity against cultured tumor cells

Iguchi, Tomoki,Kuroda, Minpei,Naito, Rei,Watanabe, Tomoyuki,Matsuo, Yukiko,Yokosuka, Akihito,Mimaki, Yoshihiro

, (2017)

Previous phytochemical studies of the bulbs of Ornithogalum saundersiae, an ornamental perennial plant native to South Africa, resulted in the isolation of 29 new cholestane glycosides, some of which were structurally unique and showed potent cytotoxic activity against cultured tumor cell lines. Therefore, we aimed to perform further phytochemical examinations of methanolic extracts obtained from Ornithogalum saundersiae bulbs, isolating 12 new cholestane rhamnosides (1-12) and seven known compounds (13-19). The structures of the new compounds (1-12) were identified via NMR-based structural characterization methods, and through a sequence of chemical transformations followed by spectroscopic and chromatographic analysis. The cytotoxic activity of the isolated compounds (1-19) and the derivatives (1a and 6a) against HL-60 human promyelocytic leukemia cells and A549 human lung adenocarcinoma cells was evaluated. Compounds 10-12, 16, and 17 showed cytotoxicity against both HL-60 and A549 cells. Compound 11 showed potent cytotoxicity with an IC50 value of 0.16 μM against HL-60 cells and induced apoptotic cell death via a mitochondrion-independent pathway.

New Glycosides of Eriodictyol from Dracocephalum palmatum

Olennikov,Chirikova,Kim, Eungyoung,Kim, Sang Woo,Zul’fugarov

, (2018)

Two new glycosides of eriodictyol were isolated from the aerial part of Dracocephalum palmatum and identified using UV, NMR, and CD spectroscopy and mass spectrometry as (S)-eriodictyol-7-O-(6′′-O-malonyl)-β-Dglucopyranoside (pyracanthoside-6′′ -O-malonat

Medicinal flowers. XXXX.1) Structures of dihydroisocoumarin glycosides and inhibitory effects on aldose reducatase from the flowers of Hydrangea macrophylla var. thunbergii

Liu, Jiang,Nakamura, Seikou,Zhuang, Yan,Yoshikawa, Masayuki,Hussein, Ghazi Mohamed Eisa,Matsuo, Kyohei,Matsuda, Hisashi

, p. 655 - 661 (2013)

Six dihydroisocoumarin glycosides, florahydrosides I and II, thunberginol G 8-O-β-D-glucopyranoside, thunberginol C 8-O-β-D-glucopyranoside, 4-hydroxythunberginol G 3′-O-β-D-glucopyranoside, and thunberginol D 3′-O-β-D-glucopyranoside, have been isolated from the flowers of Hydrangea macrophylla SERINGE var. thunbergii MAKINO (Saxifragaceae) together with 20 known compounds. The chemical structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. Among the constituents, acylated quinic acid analog, neochlorogenic acid, was shown to substantially inhibit aldose reductase [IC50=5.6 μM]. In addition, the inhibitory effects on aldose reductase of several caffeoylquinic acid analogs were examined for structure-activity relationship study. As the results, 4,5-O-trans-p-dicaffeoyl-D-quinic acid was found to exhibit a potent inhibitory effect [IC50=0.29 μM].

The bioassay-guided isolation of antifungal saponins from Hosta plantaginea leaves

Wang, Meng-Yue,Peng, Ying,Peng, Chong-Sheng,Qu, Jiang-Yuan,Li, Xiao-Bo

, p. 501 - 509 (2018)

Four new steroidal saponins hostaside Ⅰ (1), hostaside Ⅱ (2), hostaside Ⅲ (3), and hostaside Ⅳ (4), together with five known steroidal saponins (5–9), were isolated by the bioassay-guided fractionation from the leaves of Hosta plantaginea (Lam.) Aschers, a worldwide well-known ornamental plant. Hostasides Ⅰ and Ⅱ showed significant antifungal activities, and they could inhibit the growth of Candida albicans and Fusarium oxysporium with MIC values as low as 4?μg/ml.

Isolation, identification and antioxidative capacity of water-soluble phenylpropanoid compounds from Rhodiola crenulata

Chen, Danjun,Fan, Junting,Wang, Peng,Zhu, Lanying,Jin, Yang,Peng, Yan,Du, Shuhu

, p. 2126 - 2133 (2012)

Six water-soluble phenylpropanoid compounds obtained from Rhodiola crenulata (R. crenulata) were fractionated by high-speed counter-current chromatography (HSCCC), and purified by semi-preparative high-performance liquid chromatography (Semi-prep HPLC). The purities of the six compounds were all above 98.0% and their structures were identified by spectroscopic methods. Among them, a new compound, 2-(4-hydroxyphenyl)-ethyl-O-β-d-glucopyranosyl-6-O- β-d-glucopyranoside (1), together with two known phenylpropanoids, p-hydroxyphenacyl-β-d-glucopyranoside (3) and picein (4) were isolated from R. crenulata for the first time. Meanwhile, the contents of six isolated ingredients from the crude extract of R. crenulata had been simultaneously detected, with satisfactory results. Furthermore, the antioxidant activities of the six compounds were accessed by measuring the radical scavenging activity against 2,2-diphenyl-1-picrylhydrazy (DPPH), and four compounds exhibited potent antioxidative activity.

Four new cytotoxic oligosaccharidic derivatives of 12-oleanene from Lysimachia heterogenea Klatt

Huang, Xin-an,Liang, Yong-ju,Cai, Xiao-ling,Feng, Xiao-quan,Zhang, Chuan-hai,Fu, Li-wu,Deng, Wen-di

, p. 6515 - 6518 (2009)

Cytotoxicity-guided phytochemical analysis on the extract of Lysimachia heterogenea Klatt led to the isolation of 3β,16β-12-oleanene-3,16,23,28-tetrol (1) and its four new oligosaccharidic derivatives heterogenosides A, B, C, and D (2-5). Their structural

Two new sesquiterpenoid glycosides from the stems of Zanthoxylum armatum DC

Liu, Ya-Lin,Gao, Liang-Liang,Song, Tong-Tong,Guo, Tao,Chang, Jun

, p. 3036 - 3041 (2020)

Two new sesquiterpenoid glycosides as dihydrophaseic acid 4′-O-[6″-O-(4″′-hydroxy-3″′, 5″′-dimethoxy) benzoyl)]-β-D-glucopyranoside (1) and dihydrophaseic acid 4′-O-[6″-O-(3″′-methoxy- 4″′-hydroxy) benzoyl)]-β-D-glucopyranoside (2), were isolated from the stems of Zanthoxylum armatum in the study. The compound 1 and 2 showed moderate scavenging activity in DPPH free radical assay with IC50 values of 241 and 264 μM, respectively.

Depolymerization of cellulosic feedstocks using magnetically separable functionalized graphene oxide

Verma, Deepak,Tiwari, Rashmi,Sinha, Anil Kumar

, p. 13265 - 13272 (2013)

Hydrolysis of cellulose into saccharides using a magnetically separable functionalized graphene is reported for potential applications in the environmentally benign saccharification of cellulose. Crystalline pure cellulose is hydrolyzed by graphene bearing -SO3H, -COOH and -OH functional groups in combination with iron nanoparticles. We observed nearly complete hydrolysis of cellulose into glucose and small (4-5 unit size) oligomers using low (1:1) catalyst to cellulose ratio. The apparent activation energy for the hydrolysis of cellulose into glucose using these catalysts is estimated to be 12 kJ mol-1, several times smaller than that for sulfuric acid under optimal conditions (170 kJ mol-1). The catalyst can be readily magnetically separated from the saccharide solution after the reaction for reuse in the reaction without loss of activity. Nearly complete hydrolysis of sugarcane bagasse into water soluble saccharides with repeated recycling was also possible. The catalytic performance of the graphene-based catalyst is attributed to the ability of the water soluble nanostructured material with a large concentration of polar groups (-OH, -COOH) which readily adsorb cellulose, while providing a large concentration of acidic functionality to hydrolyze the cellulose.

New ecdysteroid and ecdysteroid glycosides from the roots of Serratula chinensis

Zhang, Zi-Yue,Yang, Wei-Qun,Fan, Chun-Lin,Zhao, Hui-Nan,Huang, Xiao-Jun,Wang, Ying,Ye, Wen-Cai

, p. 208 - 214 (2017)

Three new ecdysteroid glycosides (1–3) and one new ecdysteroid (4), were isolated from the roots of Serratula chinensis. Their structures were established on the basis of extensive spectroscopic analysis and chemical methods.

Complete assignments of 1H and 13C NMR spectroscopic data for three new stigmastane glycosides from Vernonia cumingiana

Suo, Maorong,Yang, Junshan

, p. 179 - 183 (2009)

Three new steroidal saponins, Vernoniosides S1 (1), Vernoniosides S2 (2) and Vernoniosides S3 (3) were isolated from the stem of Vernonia cumingian. Their chemical structures were elucidated on the basis of MS, NMR spectroscopic and chemical analysis. Com

Use of electrospray ionization ion-trap tandem mass spectrometry and principal component analysis to directly distinguish monosaccharides

Xia, Bing,Zhou, Yan,Liu, Xin,Xiao, Juan,Liu, Qing,Gu, Yucheng,Ding, Lisheng

, p. 1259 - 1264 (2012)

RATIONALE Carbohydrates are good source of drugs and play important roles in metabolism processes and cellular interactions in organisms. Distinguishing monosaccharide isomers in saccharide derivates is an important and elementary work in investigating saccharides. It is important to develop a fast, simple and direct method for this purpose, which is described in this study. METHODS Stock solutions of monosaccharide with a concentration of 400 μM and sodium chloride at a concentration of 10 μM were made in water/methanol (50:50, v/v). The samples were subjected to electrospray ionization ion-trap tandem mass spectrometry (ESI-MS) and the detected [2M + Na - H2O]+ ions were further investigated by tandem mass spectrometry (MS/MS), followed by applying principal component analysis (PCA) on the obtained MS/MS data sets. RESULTS The MS/MS spectra of the [2M + Na - H2O]+ ions at m/z 365 for hexoses and m/z 305 for pentoses yielded unambiguous fragment patterns, while rhamnose can be directly identified by its ESI-MS [M + Na] + ion at m/z 187. PCA showed clustering of MS/MS data of identical monosaccharide samples obtained from different experiments. By using this method, the monosaccharide in daucosterol hydrolysate was successfully identified. CONCLUSIONS A new strategy was developed for differentiation of the monosaccharides using ESI-MS/MS and PCA. In MS/MS spectra, the [2M + Na - H 2O]+ ions yielded unambiguous distinction. PCA of the archived MS/MS data sets was applied to demonstrate the spatial resolution of the studied samples. This method presented a simple and reliable way for distinguishing monosaccharides by ESI-MS/MS. Copyright

Flavonoids and terpenoids with PTP-1B inhibitory properties from the infusion of salvia amarissima ortega

González-Andrade, Martín,Mata, Rachel,Pérez-Vásquez, Araceli,Rangel-Grimaldo, Manuel,Rivero-Cruz, Isabel,Salinas-Arellano, Eric,Torres-Colin, Rafael

, (2020)

An infusion prepared from the aerial parts of Salvia amarissima Ortega inhibited the enzyme protein tyrosine phosphatase 1B (PTP-1B) (IC50~88 and 33 μg/mL, respectively). Phytochemical analysis of the infusion yielded amarisolide (1), 5,6,40-trihydroxy-7,30-dimethoxyflavone (2), 6-hydroxyluteolin (3), rutin (4), rosmarinic acid (5), isoquercitrin (6), pedalitin (7) and a new neo-clerodane type diterpenoid glucoside, named amarisolide G (8a,b). Compound 8a,b is a new natural product, and 2–6 are reported for the first time for the species. All compounds were tested for their inhibitory activity against PTP-1B; their IC50 values ranged from 62.0 to 514.2 μM. The activity was compared to that of ursolic acid (IC50 = 29.14 μM). The most active compound was pedalitin (7). Docking analysis predicted that compound 7 has higher affinity for the allosteric site of the enzyme. Gas chromatography coupled to mass spectrometry analyses of the essential oils prepared from dried and fresh materials revealed that germacrene D (15) and β-selinene (16), followed by β-caryophyllene (13) and spathulenol (17) were their major components. An ultra-high performance liquid chromatography coupled to mass spectrometry method was developed and validated to quantify amarisolide (1) in the ethyl acetate soluble fraction of the infusion of S. amarissima.

A new megastigmane diglycoside from litsea glutinosa (Lour.) C. B. Rob.

Wang, Yun-Song,Liao, Zhen,Li, Yan,Huang, Rong,Zhang, Hong-Bing,Yang, Jing-Hua

, p. 2234 - 2238 (2011)

Phytochemical study on the leaves and twigs of afforded the new megastigmane diglycoside (6S, 7E, 9R)-6, 9-dihydroxy-4, 7-megastigmadien-3-one- 9-O-[α-L-arabinofuranosyl-(l→6)]-β-D-glucopyranoside (1), along with glycosides (6S, 7E, 9R)-roseoside (2), (7'R, 8'R)-3, 5'-dimethoxy-9, 9'-dihydroxy-4, 7'-epoxylignan 4'-β-D-glucopyranoside (3), (7'R, 8'S)-dihydrodehydrodiconifenyl alcohol 9'-O-β-D-xylopyranoside (4) and pinoresinol 3-O-β-D-glucopyranoside (5). Their structures were established on the basis of extensive spectroscopic and chemical methods. Compounds 2-5 were reported for the first time in this species. Compound 1 was evaluated for cytotoxic activities against human tumor cell lines (myeloid leukemia HL-60, hepatocellular carcinoma SMMC-7721, lung cancer A-549, breast cancer MCF-7 and colon cancer SW480 cells), for which it was proved to be inactive (IC 50 > 40 μM).

Two new glycosides from Dianella ensifolia (L.) DC

Fan, Miao-Yin,Liu, Bing-Rui,Yang, Fan,Zhang, Pu-Zhao

, p. 18 - 20 (2021/11/11)

The Dianella genus includes approximately 20 species in all over the world. So far, only the chemical constituents of the lipophilic extract from Dianella ensifolia have been investigated. However, there have been no reports of its aqueous extract. In thi

Iridoid glucosides from the leaves of Vitex negundo var. cannabifolia

Huo, Huixia,Li, Jun,Li, Manman,Liang, Naiyun,Ma, Jiale,Song, Yuelin,Sun, Jing,Tu, Pengfei,Wang, Rongye,Zhao, Yunfang,Zheng, Jiao

, p. 56 - 62 (2021/11/30)

Five new iridoid glucosides, cannabifolisides A–E (1 – 5), together with nine analogues (6 – 14), were isolated from the leaves of Vitex negundo var. cannabifolia. Their structures were elucidated by spectroscopic data (NMR, UV, IR, and MS) analyses and comparison of their spectroscopic and physical data with the literature values. The protective effect of isolated compounds on human gastric epithelial cells were evaluated by measuring the enhanced cell viability of GES-1 cell insulted by TCA. Among these, compounds 4, 6, 8, 10, 12, and 14 remarkably increased the cell viability in a concentration-depend manner.

Long-chain fatty acid acylated derivatives of isoflavone glycosides from the rhizomes of Iris domestica

Li, Jiayuan,Liu, Yanfei,Ni, Gang,Wang, Renzhong,Yu, Dequan

, (2021/11/01)

Six undescribed long-chain fatty acid esters of isoflavone glycosides were obtained from the rhizomes of Iris domestica (L.). Their structures were elucidated by comprehensive spectroscopic data, alkaline hydrolysis, and acid hydrolysis. This is the first report of the long-chain (C14–C18) fatty acid derivatives of isoflavone glycosides from natural products. Belamcandnoate B and D exhibited moderate cytotoxic activities against HCT-116, HepG2, and BGC823 cell lines with IC50 values of 1.69–6.86 μM. Belamcandnoate B and E exhibited 72.27 and 58.98% inhibitory activities, respectively, against Fe2+/cysteine-induced liver microsomal lipid peroxidation at a concentration of 10 μM.

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