Mogroside

A mogroside is a glycoside of cucurbitane derivatives found in certain plants, such as the fruit of the gourd vine Siraitia grosvenorii (known as monkfruit or luohan guo).[1][2] Mogrosides are extracted from S. grosvenorii and used in the manufacture of sugar substitutes.[1][2]

Structural formula of mogroside 2 E

Mogrosides
Structural formula of mogroside V
Structural formula of mogroside VI

Mogrosides include:[1][2]

  • Mogrol
  • Mogroside II A1
  • Mogroside II B
  • 7-Oxomogroside II E
  • 11-Oxomogroside A1
  • Mogroside III A2
  • 11-Deoxymogroside III
  • 11-Oxomogroside IV A
  • Mogroside V
  • 7-Oxomogroside V
  • 11-Oxo-mogroside V
  • Mogroside VI
  • Siamenoside I

Mogroside V is the main component of Siraitia grosvenorii fruit, constituting 0.5% to 1.4% of the dried fruit.[3]

Biosynthesis

One analysis of 200 candidate genes of Siraitia grosvenorii revealed five enzyme families involved in the synthesis of mogroside V: squalene epoxidases, triterpenoid synthases, epoxide hydrolases, cytochrome P450s, and UDP-glucosyltransferases.[1] The metabolic pathway for mogroside biosynthesis involves an initial stage of fruit development when squalene is metabolized to di-glucosylated, tetra-hydroxycucurbitadienols, then during fruit maturation, branched glucosyl groups are added and catalyzed, leading to the sweet M4, M5, and M6 mogrosides.[1]

Stability

Mogroside V appears to be heat stable in the range of 100 to 150 degrees Celsius for 4 hours and up to 8 hours in boiling water. It is stable at a pH of between 3 and 12 when stored from 2 to 8 degrees Celsius.[4]

Uses

Some mogrosides are used in traditional Chinese medicine[2] and some are extracted for manufacturing as sweeteners.[1] Mogroside V extract from S. grosvenorii fruit is 250 times sweeter than sucrose,[1] sold commercially in Norbu (sweetener).

References
  1. Itkin, M.; Davidovich-Rikanati, R.; Cohen, S.; Portnoy, V.; Doron-Faigenboim, A.; Oren, E.; Freilich, S.; Tzuri, G.; Baranes, N.; Shen, S.; Petreikov, M.; Sertchook, R.; Ben-Dor, S.; Gottlieb, H.; Hernandez, A.; Nelson, D. R.; Paris, H. S.; Tadmor, Y.; Burger, Y.; Lewinsohn, E.; Katzir, N.; Schaffer, A. (2016). "The biosynthetic pathway of the nonsugar, high-intensity sweetener mogroside V from Siraitia grosvenorii". Proceedings of the National Academy of Sciences of the United States of America. 113 (47): E7619–E7628. doi:10.1073/pnas.1604828113. PMC 5127336. PMID 27821754.
  2. Subhuti Dharmananda (January 2004), "Luo han guo - Sweet fruit used as sugar substitute and medicinal herb". Institute for Traditional Medicine, Portland, Oregon.
  3. Li C, Lin L, Sui F, Jiang T (2014). "Chemistry and pharmacology of Siraitia grosvenorii: a review". Chinese Journal of Natural Medicines. 12 (2): 89–102. doi:10.1016/S1875-5364(14)60015-7. PMID 24636058.
  4. Younes, Maged; Aquilina, Gabriele; Engel, Karl‐Heinz; Fowler, Paul; Frutos Fernandez, Maria Jose; Fürst, Peter; Gürtler, Rainer; Gundert‐Remy, Ursula; Husøy, Trine; Mennes, Wim; Moldeus, Peter; Oskarsson, Agneta; Shah, Romina; Waalkens‐Berendsen, Ine; Wölfle, Detlef; Degen, Gisela; Herman, Lieve; Gott, David; Leblanc, Jean-Charles; Giarola, Alessandra; Rincon, Ana Maria; Tard, Alexandra; Castle, Laurence (11 December 2019). "Safety of use of Monk fruit extract as a food additive in different food categories". EFSA Journal. 17 (12). doi:10.2903/j.efsa.2019.5921. PMC 7008860. PMID 32626208.
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