Abstract
A new trehalose analog, lentztrehalose [4-O-(2,3-dihydroxy-3-methylbutyl)trehalose], was isolated from an actinomycete Lentzea sp. Lentztrehalose is only weakly hydrolyzed by the trehalose-hydrolyzing enzyme, trehalase, so can be regarded as an enzyme-stable analog of trehalose. Although lentztrehalose does not show apparent toxicity to mammalian cells and microbes, it has antitumor activity in mice bearing S-180 sarcoma and Ehrlich carcinoma cells. In ovariectomized mice, lentztrehalose displayed a bone reinforcement effect in the femur that was superior to trehalose and induced non-morbid suppression of weight gain comparable with trehalose. These results indicate that enzyme-stable analogs of trehalose, such as lentztrehalose, may be more beneficial for human health and thus have potential as substitutes for trehalose as a sweetener.
Similar content being viewed by others
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
Accession codes
References
Elbein, A. D., Pan, Y. T., Pastuszak, I & Carroll, D. New insights on trehalose: a multifunctional molecule. Glycobiology 13, 17R–27R (2003).
Ohtake, S. & Wang, Y. J. Trehalose: current use and future applications. J. Pharm. Sci. 100, 2020–2053 (2011).
Nishizaki, Y. et al. Disaccharide-trehalose inhibits bone resorption in ovariectomized mice. Nutr. Res. 20, 653–664 (2000).
Ukawa, Y., Gu, Y., Ohtsuki, M., Suzuki, I. & Hisamatsu, M. Antitumor effect of trehalose on sarcoma 180 in ICR mice. J. Appl. Glycosci. 52, 367–368 (2005).
Arai, C. et al. Trehalose prevents adipocyte hypertrophy and mitigates insulin resistance. Nutr. Res. 30, 840–848 (2010).
Okuda, J., Miwa, I., Maeda, K. & Tokui, K. Rapid and sensitive, colorimetric determination of the anomers of D-glucose with D-glucose oxidase, peroxidase, and mutarotase. Carbohydr. Res. 58, 267–270 (1977).
Arai, C. et al. Trehalose suppresses lipopolysaccharide-induced osteoclastogenesis bone marrow in mice. Nutr. Res. 21, 993–999 (2001).
Kawaguchi, T. et al. Unusual amino acid derivatives from the mushroom Pleurocybella porrigens. Tetrahedron 66, 504–507 (2010).
Nakashima, T. et al. Trehangelins A, B and C, novel photo-oxidative hemolysis inhibitors produced by an endophytic actinomycete, Polymorphospora rubra K07-0510. J. Antibiot. 66, 311–317 (2013).
Shirling, E. B. & Gottlieb, D. Methods for characterization of Streptomyces species. Int. J. Syst. Bacteriol. 16, 313–340 (1966).
Staneck, J. L. & Roberts, G. D. Simplified approach to identification of aerobic actinomycetes by thin-layer chromatography. Appl. Microbiol. 28, 226–231 (1974).
Igarashi, M. et al. Waldiomycin, a novel WalK-histidine kinase inhibitor from Streptomyces sp. MK844-mF10. J. Antibiot. 66, 459–464 (2013).
Acknowledgements
We appreciate the help of Prof Sachi SriKantha, Gifu University, for his critical reading of this manuscript. We acknowledge the assistance of Dr M Igarashi, Dr R Sawa, Ms Y Kubota, Ms H Soutome, Mr K Inoue, Ms C Hayashi, Dr Y Takahashi and Dr K Yamazaki at the Institute of Microbial Chemistry for their support for this study and helpful discussion. This study was partially supported by the Japan Society for the Promotion of Science.
Author information
Authors and Affiliations
Corresponding author
Additional information
Supplementary Information accompanies the paper on The Journal of Antibiotics website
Supplementary information
Rights and permissions
About this article
Cite this article
Wada, Si., Ohba, Si., Someno, T. et al. Structure and biological properties of lentztrehalose: a novel trehalose analog. J Antibiot 67, 319–322 (2014). https://doi.org/10.1038/ja.2013.143
Received:
Revised:
Accepted:
Published:
Issue date:
DOI: https://doi.org/10.1038/ja.2013.143
Keywords
This article is cited by
-
Novel approaches for identification of anti-tumor drugs and new bioactive compounds
The Journal of Antibiotics (2018)
-
Biotechnical production of trehalose through the trehalose synthase pathway: current status and future prospects
Applied Microbiology and Biotechnology (2018)
-
Trehalose upregulates progranulin expression in human and mouse models of GRN haploinsufficiency: a novel therapeutic lead to treat frontotemporal dementia
Molecular Neurodegeneration (2016)
-
Novel autophagy inducers lentztrehaloses A, B and C
The Journal of Antibiotics (2015)