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4-Hydroxyisoleucine

CAS# 781658-23-9

4-Hydroxyisoleucine

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Chemical structure

4-Hydroxyisoleucine

3D structure

Chemical Properties of 4-Hydroxyisoleucine

Cas No. 781658-23-9 SDF Download SDF
PubChem ID 2773624 Appearance White powder
Formula C6H13NO3 M.Wt 147.17
Type of Compound Miscellaneous Storage Desiccate at -20°C
Synonyms L-4-Hydroxyisoleucine;6001-78-8
Solubility Soluble in water
Chemical Name (2S,3R)-2-amino-4-hydroxy-3-methylpentanoic acid
SMILES CC(C(C)O)C(C(=O)O)N
Standard InChIKey OSCCDBFHNMXNME-DSDZBIDZSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 4-Hydroxyisoleucine

The seeds of Trigonella foenum-graecum L.

Biological Activity of 4-Hydroxyisoleucine

Description4-Hydroxyisoleucine has antidepressant-like, antidyslipidemic, and antihyperglycemic effects. It acts to improve insulin resistance by promoting mitochondrial biogenesis in high fructose diet fed STZ induced diabetic rats, it also has beneficial effects on low-grade inflammation.L-4-Hydroxyisoleucine is a natural product from Trigonella foenum-graecum L.
TargetsTNF-α | AMPK | Akt | GSK-3 | ROS | NF-kB | JNK | ERK | p38MAPK | 5-HT Receptor
In vitro

4-Hydroxyisoleucine ameliorates fatty acid-induced insulin resistance and inflammatory response in skeletal muscle cells.[Pubmed: 25109277]

Mol Cell Endocrinol. 2014 Sep;395(1-2):51-60.

The 4-Hydroxyisoleucine (4-HIL), an unusual amino acid isolated from the seeds of Trigonella foenum-graecum was investigated for its metabolic effects to ameliorate free fatty acid-induced insulin resistance in skeletal muscle cells.
METHODS AND RESULTS:
An incubation of L6 myotubes with palmitate inhibited insulin stimulated-glucose uptake and -translocation of glucose transporter 4 (GLUT4) to the cell surface. Addition of 4-Hydroxyisoleucine strongly prevented this inhibition. We then examined the insulin signaling pathway, where 4-Hydroxyisoleucine effectively inhibited the ability of palmitate to reduce insulin-stimulated phosphorylation of insulin receptor substrate-1 (IRS-1), protein kinase B (PKB/AKT), AKT substrate of 160 kD (AS160) and glycogen synthase kinase 3β (GSK-3β) in L6 myotubes. Moreover, 4-Hydroxyisoleucine presented strong inhibition on palmitate-induced production of reactive oxygen species (ROS) and associated inflammation, as the activation of NF-κB, JNK1/2, ERK1/2 and p38 MAPK was greatly reduced. 4-Hydroxyisoleucine also inhibited inflammation-stimulated IRS-1 serine phosphorylation and restored insulin-stimulated IRS-1 tyrosine phosphorylation in the presence of palmitate, leading to enhanced insulin sensitivity.
CONCLUSIONS:
These findings suggested that 4-Hydroxyisoleucine could inhibit palmitate-induced, ROS-associated inflammation and restored insulin sensitivity through regulating IRS-1 function.

In vivo

4-Hydroxyisoleucine improves insulin resistance by promoting mitochondrial biogenesis and act through AMPK and Akt dependent pathway.[Pubmed: 25454462]

Fitoterapia. 2014 Dec;99:307-17.

4-Hydroxyisoleucine (4-HIL) is an unusual amino acid isolated from fenugreek seeds (Trigonella foenum graecum L). Various studies have shown that it acts as an antidiabetic agent yet its mechanism of action is not clear.
METHODS AND RESULTS:
We therefore investigated the effect 4-Hydroxyisoleucine on the high fructose diet fed streptozotocin induced diabetic rats and L6 myotubes. 4-Hydroxyisoleucine (50 mg/kg) has improved blood lipid profile, glucose tolerance and insulin sensitivity in a diabetic rat model. It has increased the glucose uptake in L6 myotubes in AMPK-dependent manner and upregulated the expression of genes (PGC-1α, PGC-1β, CPT 1 and CPT 2), which have role in mitochondrial biogenesis and energy metabolism in the liver, skeletal muscles as well as in L6 myotubes. Interestingly, it also increased the AMPK and Akt expression along with their phosphorylated forms in the liver and muscle tissues of treated animals.
CONCLUSIONS:
Altogether we concluded that 4-Hydroxyisoleucine acts to improve insulin resistance by promoting mitochondrial biogenesis in high fructose diet fed STZ induced diabetic rats.

4-hydroxyisoleucine an unusual amino acid as antidyslipidemic and antihyperglycemic agent.[Pubmed: 16246556 ]

Bioorg Med Chem Lett. 2006 Jan 15;16(2):293-6.

Trigonella foenum-graecum, commonly known as fenugreek, is an annual herbaceous plant.
METHODS AND RESULTS:
From the seeds of T. foenum-graecum an unusual amino acid, 4-Hydroxyisoleucine 5, has been isolated, which significantly decreased the plasma triglyceride levels by 33% (P<0.002), total cholesterol (TC) by 22% (P<0.02), and free fatty acids by 14%, accompanied by an increase in HDL-C/TC ratio by 39% in the dyslipidemic hamster model.

Protocol of 4-Hydroxyisoleucine

Cell Research

In vitro anti-hyperglycemic activity of 4-hydroxyisoleucine derivatives.[Pubmed: 25636873]

Phytomedicine. 2015 Jan 15;22(1):66-70.

The nonproteinogenic amino acid, 4-Hydroxyisoleucine (1) has been isolated in large quantities from the fenugreek (T. foenum-graecum) seeds.
METHODS AND RESULTS:
Few novel derivatives (3-11 and 13-18) were prepared from the naturally occurring 4-Hydroxyisoleucine (1) and screened for their in vitro glucose uptake stimulatory effect in L-6 skeletal muscle cells.
CONCLUSIONS:
The derivatives 6, 7, 8, 10 and 11 exhibited better glucose uptake stimulatory activity than parent compound, 4-Hydroxyisoleucine at 5 and 10μM concentrations and compounds 7 and 11 enhanced translocation of insulin sensitive glucose transporters-4 in skeletal muscle cells.

Animal Research

Antidepressant-like effect of 4-hydroxyisoleucine from Trigonella foenum graecum L. seeds in mice.[Reference: WebLink]

Biomed. Aging Pathol., 2012, 2(3):121-5.

Trigonella foenum graecum L. (Fabaceae), also known as fenugreek, is one of the oldest medicinal plants, and has a long history of medical use in traditional and modern literature. 4-Hydroxyisoleucine (4-HI) constitutes about is 80% of the total content of free amino acids in Trigonella foenum graecum seeds.
METHODS AND RESULTS:
In present study, we report antidepressant-like effects of 4-HI in animal models of depression. The effects of 4-HI (10, 30 or 100 mg/kg) in Forced swim test, 5-hydroxytryptophan (5-HTP)-induced head twitches, and spontaneous motor activity (SMA) scores were assessed in mice. Oral acute administration of 4-HI showed the dose-dependent reversal in forced swim induced increased immobility behavior in normal and reserpinized mice in dose range of 3 to 30 mg/kg. The SMA scores were not affected by 4-HI in normal or reserpinized mice except for dose of 30 mg/kg, showing central rather than peripheral mechanism of 4-HI. Further, significant increase in number of 5-HTP (precursor of serotonin) induced head twitches was shown by 4-HI.
CONCLUSIONS:
In conclusion, 4-HI showed antidepressant-like effects in animal models of depression by brain serotonin turnover enhancement.

Structure Identification
Microbiologyopen. 2013 Jun;2(3):471-81.

A novel l-isoleucine-4'-dioxygenase and l-isoleucine dihydroxylation cascade in Pantoea ananatis.[Pubmed: 23554367 ]

A unique operon structure has been identified in the genomes of several plant- and insect-associated bacteria. The distinguishing feature of this operon is the presence of tandem hilA and hilB genes encoding dioxygenases belonging to the PF13640 and PF10014 (BsmA) Pfam families, respectively.
METHODS AND RESULTS:
The genes encoding HilA and HilB from Pantoea ananatis AJ13355 were cloned and expressed in Escherichia coli. The culturing of E. coli cells expressing hilA (E. coli-HilA) or both hilA and hilB (E. coli-HilAB) in the presence of l-isoleucine resulted in the conversion of l-isoleucine into two novel biogenic compounds: l-4'-isoleucine and l-4,4'-dihydroxyisoleucine, respectively. In parallel, two novel enzymatic activities were detected in the crude cell lysates of the E. coli-HilA and E. coli-HilAB strains: l-isoleucine, 2-oxoglutarate: oxygen oxidoreductase (4'-hydroxylating) (HilA) and l-4'-hydroxyisoleucine, 2-oxoglutarate: oxygen oxidoreductase (4-hydroxylating) (HilB), respectively. Two hypotheses regarding the physiological significance of C-4(4')-hydroxylation of l-isoleucine in bacteria are also discussed.
CONCLUSIONS:
According to first hypothesis, the l-isoleucine dihydroxylation cascade is involved in synthesis of dipeptide antibiotic in P. ananatis. Another unifying hypothesis is that the C-4(4')-hydroxylation of l-isoleucine in bacteria could result in the synthesis of signal molecules belonging to two classes: 2(5H)-furanones and analogs of N-acyl homoserine lactone.

4-Hydroxyisoleucine Dilution Calculator

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Preparing Stock Solutions of 4-Hydroxyisoleucine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.7949 mL 33.9743 mL 67.9486 mL 135.8973 mL 169.8716 mL
5 mM 1.359 mL 6.7949 mL 13.5897 mL 27.1795 mL 33.9743 mL
10 mM 0.6795 mL 3.3974 mL 6.7949 mL 13.5897 mL 16.9872 mL
50 mM 0.1359 mL 0.6795 mL 1.359 mL 2.7179 mL 3.3974 mL
100 mM 0.0679 mL 0.3397 mL 0.6795 mL 1.359 mL 1.6987 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 4-Hydroxyisoleucine

4-Hydroxyisoleucine attenuates the inflammation-mediated insulin resistance by the activation of AMPK and suppression of SOCS-3 coimmunoprecipitation with both the IR-beta subunit as well as IRS-1.[Pubmed:26887316]

Mol Cell Biochem. 2016 Mar;414(1-2):95-104.

It is known that 4-Hydroxyisoleucine (4-HIL) from seeds of Trigonella foenum-graecum has beneficial effects on low-grade inflammation; therefore, the insulin signaling as well as the anti-inflammatory effects of 4-HIL in TNF-alpha-induced insulin resistance in C2C12 myotubes was studied with an aim to dissect out the mechanism(s) of the inflammation-mediated insulin resistance. TNF-alpha suppressed insulin-stimulated glucose transport rate and increased Ser-307 phosphorylation of insulin receptor substrate-1 (IRS-1). However, the treatment of 4-Hydroxyisoleucine enhanced insulin-stimulated glucose transport rate via the activation of AMP-activated protein kinase (AMPK) in a dose-dependent manner. 4-HIL also increases the tyrosine phosphorylation of both IR-beta and IRS-1. Moreover, coimmunoprecipitation (Co-IP) of insulin receptor-beta (IR-beta) subunit with IRS-1 was found to be increased by 4-Hydroxyisoleucine. Concentration of SOCS-3 protein and coimmunoprecipitation of SOCS-3 protein with both the IR-beta subunit as well as IRS-1 was found to be decreased by 4-HIL. We conclude that the 4-Hydroxyisoleucine reverses the insulin resistance by the activation of AMPK and suppression of SOCS-3 coimmunoprecipitation with both the IR-beta subunit as well as IRS-1.

4-Hydroxyisoleucine ameliorates fatty acid-induced insulin resistance and inflammatory response in skeletal muscle cells.[Pubmed:25109277]

Mol Cell Endocrinol. 2014 Sep;395(1-2):51-60.

The 4-Hydroxyisoleucine (4-HIL), an unusual amino acid isolated from the seeds of Trigonella foenum-graecum was investigated for its metabolic effects to ameliorate free fatty acid-induced insulin resistance in skeletal muscle cells. An incubation of L6 myotubes with palmitate inhibited insulin stimulated-glucose uptake and -translocation of glucose transporter 4 (GLUT4) to the cell surface. Addition of 4-HIL strongly prevented this inhibition. We then examined the insulin signaling pathway, where 4-HIL effectively inhibited the ability of palmitate to reduce insulin-stimulated phosphorylation of insulin receptor substrate-1 (IRS-1), protein kinase B (PKB/AKT), AKT substrate of 160 kD (AS160) and glycogen synthase kinase 3beta (GSK-3beta) in L6 myotubes. Moreover, 4-HIL presented strong inhibition on palmitate-induced production of reactive oxygen species (ROS) and associated inflammation, as the activation of NF-kappaB, JNK1/2, ERK1/2 and p38 MAPK was greatly reduced. 4-HIL also inhibited inflammation-stimulated IRS-1 serine phosphorylation and restored insulin-stimulated IRS-1 tyrosine phosphorylation in the presence of palmitate, leading to enhanced insulin sensitivity. These findings suggested that 4-HIL could inhibit palmitate-induced, ROS-associated inflammation and restored insulin sensitivity through regulating IRS-1 function.

A novel l-isoleucine-4'-dioxygenase and l-isoleucine dihydroxylation cascade in Pantoea ananatis.[Pubmed:23554367]

Microbiologyopen. 2013 Jun;2(3):471-81.

A unique operon structure has been identified in the genomes of several plant- and insect-associated bacteria. The distinguishing feature of this operon is the presence of tandem hilA and hilB genes encoding dioxygenases belonging to the PF13640 and PF10014 (BsmA) Pfam families, respectively. The genes encoding HilA and HilB from Pantoea ananatis AJ13355 were cloned and expressed in Escherichia coli. The culturing of E. coli cells expressing hilA (E. coli-HilA) or both hilA and hilB (E. coli-HilAB) in the presence of l-isoleucine resulted in the conversion of l-isoleucine into two novel biogenic compounds: l-4'-isoleucine and l-4,4'-dihydroxyisoleucine, respectively. In parallel, two novel enzymatic activities were detected in the crude cell lysates of the E. coli-HilA and E. coli-HilAB strains: l-isoleucine, 2-oxoglutarate: oxygen oxidoreductase (4'-hydroxylating) (HilA) and l-4'-hydroxyisoleucine, 2-oxoglutarate: oxygen oxidoreductase (4-hydroxylating) (HilB), respectively. Two hypotheses regarding the physiological significance of C-4(4')-hydroxylation of l-isoleucine in bacteria are also discussed. According to first hypothesis, the l-isoleucine dihydroxylation cascade is involved in synthesis of dipeptide antibiotic in P. ananatis. Another unifying hypothesis is that the C-4(4')-hydroxylation of l-isoleucine in bacteria could result in the synthesis of signal molecules belonging to two classes: 2(5H)-furanones and analogs of N-acyl homoserine lactone.

In vitro anti-hyperglycemic activity of 4-hydroxyisoleucine derivatives.[Pubmed:25636873]

Phytomedicine. 2015 Jan 15;22(1):66-70.

The nonproteinogenic amino acid, 4-Hydroxyisoleucine (1) has been isolated in large quantities from the fenugreek (T. foenum-graecum) seeds. Few novel derivatives (3-11 and 13-18) were prepared from the naturally occurring 4-Hydroxyisoleucine (1) and screened for their in vitro glucose uptake stimulatory effect in L-6 skeletal muscle cells. The derivatives 6, 7, 8, 10 and 11 exhibited better glucose uptake stimulatory activity than parent compound, 4-Hydroxyisoleucine at 5 and 10microM concentrations and compounds 7 and 11 enhanced translocation of insulin sensitive glucose transporters-4 in skeletal muscle cells.

4-hydroxyisoleucine an unusual amino acid as antidyslipidemic and antihyperglycemic agent.[Pubmed:16246556]

Bioorg Med Chem Lett. 2006 Jan 15;16(2):293-6.

Trigonella foenum-graecum, commonly known as fenugreek, is an annual herbaceous plant. From the seeds of T. foenum-graecum an unusual amino acid, 4-Hydroxyisoleucine 5, has been isolated, which significantly decreased the plasma triglyceride levels by 33% (P<0.002), total cholesterol (TC) by 22% (P<0.02), and free fatty acids by 14%, accompanied by an increase in HDL-C/TC ratio by 39% in the dyslipidemic hamster model.

4-Hydroxyisoleucine improves insulin resistance by promoting mitochondrial biogenesis and act through AMPK and Akt dependent pathway.[Pubmed:25454462]

Fitoterapia. 2014 Dec;99:307-17.

4-Hydroxyisoleucine (4-HIL) is an unusual amino acid isolated from fenugreek seeds (Trigonella foenum graecum L). Various studies have shown that it acts as an antidiabetic agent yet its mechanism of action is not clear. We therefore investigated the effect 4-HIL on the high fructose diet fed streptozotocin induced diabetic rats and L6 myotubes. 4-HIL (50 mg/kg) has improved blood lipid profile, glucose tolerance and insulin sensitivity in a diabetic rat model. It has increased the glucose uptake in L6 myotubes in AMPK-dependent manner and upregulated the expression of genes (PGC-1alpha, PGC-1beta, CPT 1 and CPT 2), which have role in mitochondrial biogenesis and energy metabolism in the liver, skeletal muscles as well as in L6 myotubes. Interestingly, it also increased the AMPK and Akt expression along with their phosphorylated forms in the liver and muscle tissues of treated animals. Altogether we concluded that 4-HIL acts to improve insulin resistance by promoting mitochondrial biogenesis in high fructose diet fed STZ induced diabetic rats.

Description

4-Hydroxyisoleucine (4-​Hydroxy-​L-​isoleucine) is an amino acid which can be extracted and purified from fenugreek seeds. 4-Hydroxyisoleucine (4-​Hydroxy-​L-​isoleucine) displays an insulinotropic activity of great interest.

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