1-Deoxynojirimycin (DNJ or 1-DNJ), also called duvoglustat or moranolin, is an

alpha-glucosidase inhibitor Alpha-glucosidase inhibitors (AGIs) are oral anti-diabetic drugs used for diabetes mellitus type 2 that work by preventing the digestion of carbohydrates (such as starch and sucrose, table sugar). Naturally occurring AGIs are found in raw plants/he ...

, most commonly found in

mulberry ''Morus'', a genus of flowering plants in the family Moraceae, consists of 19 species of deciduous trees commonly known as mulberries, growing wild and under cultivation in many temperate world regions. Generally, the genus has 64 subordinat ...

leaves. Although it can be obtained in small quantities by brewing an

herbal tea Herbal teas, technically known as herbal infusions, and less commonly called tisanes (UK and US , US also ), are beverages made from the infusion or decoction of herbs, spices, or other plant material in hot water. Often herb tea, or the plai ...

from mulberry leaves, interest in commercial production has led to research on developing mulberry tea higher in DNJ, and on alternate routes of production, such as via ''

Bacillus ''Bacillus'', from Latin "bacillus", meaning "little staff, wand", is a genus of Gram-positive, rod-shaped bacteria, a member of the phylum ''Bacillota'', with 266 named species. The term is also used to describe the shape (rod) of other so-sh ...

'' species.

Biosynthesis

1-Deoxynojirimycin is a polyhydroxylated piperidine alkaloid produced from D-Glucose in various plants, such as ''Commelina communis'', and in the ''Streptomyces'' and ''Bacillus'' bacteria. High quantities of this

iminosugar An iminosugar, also known as an iminosaccharide, is any analog of a sugar where a nitrogen atom has replaced the oxygen atom in the ring of the structure. Iminosugars are common components of plants and may be responsible for some of their medic ...

are produced in ''Bacillus subtilis'', a process initiated by a TYB gene cluster composed of gabT1 (aminotransferase), yktc1 (phosphatase), and gutB1 (oxidoreductase). In ''Bacillus subtilis,'' D-glucose first undergoes glycolysis, opening the 6-member ring and producing fructose-6-phosphate. GabT1 catalyzes transamination at the C2 position, followed by a dephosphorylation by the Yktc1 enzyme, resulting in 2-amino-2-deoxy-D-mannitol (ADM), an essential precursor. Regio-selective oxidation by GutB1 occurs at the exposed C6 hydroxyl of ADM, pushing a C2-N-C6 cyclization of the resulting 6-oxo intermediate, creating manojirimycin (MJ). Epimerization of MJ at the C2 position yields the nojirimycin isomer. Nojirimycin is then dehydrated (loss of -OH at C1 position), along with reduction of the imine moiety. This results in the product 1-DNJ. Biosynthesis of 1-deoxynojirimycin in Bacillus Subtilis

Biosynthesis of 1-deoxynojirimycin in Bacillus Subtilis

Pathway variations

In the ''Streptomyces subrutilus'' species, a secondary pathway branching from the manojirimycin precursor results in 1-deoxymanojirimycin via dehydration and reduction of the isomer. However, ''Bacillus subtilis'' does not produce 1-deoxymanojirimycin despite the presence of the manojirimycin precursor. Iminosugar biosynthesis in ''Commelina communis'' involves C1-C5 cyclisation of the original D-glucose precursor without the subsequent inversion.

References

{{DEFAULTSORT:Deoxynojirimycin, 1- Iminosugars

Biosynthesis

Pathway variations

See also

References