Divergent Synthesis of Mogrosides

Area of Science:

• Organic Chemistry
• Natural Product Synthesis
• Glycoscience

Background:

• Mogrosides are key sweet compounds from Monk fruit (Siraitia grosvenorii).
• Efficient synthesis of diverse mogrosides is crucial for biological evaluation.
• Previous synthetic routes lacked generality and accessibility.

Purpose of the Study:

• To develop a general and efficient synthesis of mogrosides and their analogues.
• To improve accessibility of mogroside family members for research.
• To explore structure-activity relationships through novel analogues.

Main Methods:

• Synthesis initiated from the readily available aglycone, mogrol.
• Key steps involved selective protection/deprotection strategies for hydroxyl groups (24-OH, 25-OH, 3-OH, 11-OH).
• Glycosylation employed N-phenyltrifluoroacetimidate donors for installing branched carbohydrate residues.

Main Results:

• Successfully synthesized naturally occurring mogrosides IIE, III, IIIE, and siamenoside I.
• Generated three novel non-natural α-L-rhamnose-containing analogues of siamenoside I.
• Demonstrated a diversity-oriented approach for broad mogroside family access.

Conclusions:

• The developed synthetic strategy offers a versatile platform for mogroside synthesis.
• This work significantly enhances the availability of mogrosides and analogues for biological investigation.
• Facilitates future studies on the bioactivity and therapeutic potential of Monk fruit constituents.