Lentztrehalose A (Trehalase Resistant)

Code No. : 14678 CAS# : 1609356-99-1
Molecular Formula : C17H32O13
Molecular Weight : 444.430
Source : Lentzea sp. ML457-mF8
Supplied as : Powder
Purity : >80% (qNMR)
Long Term Storage : at -20 oC
Solubility : Soluble in MeOH, DMSO, H2O Insoluble in Hexane

Outline

• Shows antitumor activity in mice bearing S-180 sarcoma and Ehrlich carcinoma cells at 12.5-50 mg/kg/day without apparent toxicity to mammalian cells.
   
• Shows bone reinforcement and anti-obesity effect in a postmenopausal mouse model.
   
• Not digested by various microbes which metabolize trehalose.
  Resistant to porcine kidney trehalase.

Application Notes

Lentztrehalose A is a biologically stable analog of trehalose, isolated from the soilid-state culture of Lentzea sp. ML457-mF8. 1,2,3) While lentztrehalose A is resistant to porcine kidney trehalase and various microbes which degrades trehalose, 3) it shows tolehalose like bioactivities, such as bone reinforcement and anti-obesity effect in a postmenopausal mouse model. 1) Furthermore, lentztrehalose A has antitumor activity, which trehalose does not show, in mice bearing S-180 sarcoma and Ehrlich carcinoma cells at 12.5-50 mg/kg per day without apparent toxicity to mammalian cells. 1)

Effect of Chemicals	Name	Product Code	Link
Aflatoxin Production Inhibitor	Dioctatin A (HCl)	FNK-14700
Tumor Cell Migration Inhibitor	Migrastatin	FNK-10708
Anti-Tumor	Altemicidin	FNK-12151
	Bisucaberin	FNK-14659
	COMC	FNK-14701
	COTC	FNK-14675
	6-epi-COTC	FNK-14698
	Forphenicinol	FNK-09637
	Inostamycin A (Na Salt)	FNK-14652
	Lentztrehalose A	FNK-14678	Current Link
	Migrastatin	FNK-10708
	Oxanosine	FNK-00762
Immunomodifier	Forphenicinol	FNK-09637
Mannan Lectin	Benanomicin A	FNK-02966

Enzyme Inhibitors	Name	Product Code	Link
Alkaline Phosphatase Inhibitor	Forphenicine	FNK-09636
NADH:Ubiquinone Oxidoreductase Inhibitor	Piericidin A1	FNK-14688
β-Galactosidase Inhibitor	Pyridindolol	FNK-00372
Glyoxylase Ⅰ (GloⅠ) Inhibitor	COTC	FNK-14675
α-Glucosidase Inhibitor	6-O-Methylreticulol	FNK-14693
Glutathione S-Transferase (GST) Inhibitor	Benastatin A	FNK-00379
	Benastatin B	FNK-14653
	Benastatin C	FNK-00380
Glutathione S-Transferase (GST) π Class Inhibitor	Bequinostatin A	FNK-14681
	Bequinostatin C	FNK-14654
GRP78 Up-regulation suppressor	Piericidin A1	FNK-14688
GMP synthase Inhibitor	Oxanosine	FNK-00762
Human Dipeptidyl Aminopeptidase Ⅱ Inhibitor	Dioctatin A (HCl)	FNK-14700
Dipeptidyl Peptidase Ⅲ (DPP-Ⅲ) Inhibitor	Fluostatin B	FNK-14683
Protein Phosphatase 2A (PP2A) Inhibitor	Cytostatin (Na Salt)	FNK-10664
	Rubratoxin A	FNK-10663
Thymidylate Synthase Inhibitor	Vanoxonin	FNK-10744
Receptor Tyrosine Kinase Inhibitor	Erbstatin	FNK-14697
DNA Helicase Inhibitor	Heliquinomycin	FNK-10665
Dopamine β-Hydroxylase Inhibitor	Dopastin	FNK-00381
Trehalase Resistant Trehalose Analogue	Lentztrehalose A	FNK-14678	Current Link
	Lentztrehalose B	FNK-14679
	Lentztrehalose C	FNK-14680
Nucleoside Diphosphate Kinase (NDPK) Inhibitor	Cyclamidomycin	FNK-01541
Heparanase Inhibitor	Heparastatin<SF4>(HCl)	FNK-11829

Data Examples

Stable againt various bacteria and microorganisms


Lentztrehalose A, B, C or trehalose were added to the seven bacterial cultures, and the culture was incubated. Although trehalose was degraded and reduced, lentztrehaloses showed little degradation.

High stability against trehalase




Lentztrehalose A-C and trehalose were reacted with porcine kidney trehalase and the concentrations of released glucose were determined by a hexokinase assay. Lentztrehalose A-C showed no degradation and high stability against trehalose-degrading enzymes.

Concentration in mouse blood with oral administration



The blood kinetics of administered compounds are important for showing their activity in vivo. When mice were orally administered Lentztrehalose A-C, their blood levels increased significantly compared to trehalose.
 

Antitumor activity in tumor-bearing mice (Lentztrehalose A)

Tumor growth results in ICR mice bearing sarcoma 180 tumor cells administered orally(P.O.) or intravenous injection(I.V.) with 50 mg/kg of lentztrehalose A, trehalose or physiological saline(control) on the date indicated as above.
 

Life-prolonging effect in tumor-bearing mice (Lentztrehalose A)

Tumor growth results in ICR mice bearing S-180 sarcoma cells administered orally(P.O.) or intravenous injection(I.V.) at 50 mg/kg of Lentztrehalose A, Trehalose or physiological saline(control) on the date indicated as above.

References

1) Structure and biological properties of lentztrehalose: a novel trehalose analog. Wada S, et al. J Antibiot. 2014 67(4) 319-322. 2) Synthesis and determination of absolute configuration of lentztrehalose A. Zhang M, et al. Chem Pharm Bull. 2015 63(11) 961-966. 3) Stability and bioavailability of lentztrehaloses A, B, and C as replacements for trehalose. Wada S, et al. J Agric Food Chem. 2016 64(38) 7121-7126.