A mogroside is a

triterpene Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the pre ...

glycoside In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ...

cucurbitane Cucurbitane is a tetracyclic chemical compound with formula . It is a polycyclic hydrocarbon, specifically triterpene. It is also an isomer of lanostane (specifically 19(10→9β)-abeolanostane), from which it differs by the formal shift of ...

derivatives found in certain plants, such as the fruit of the

gourd Gourds include the fruits of some flowering plant species in the family Cucurbitaceae, particularly '' Cucurbita'' and '' Lagenaria''. The term refers to a number of species and subspecies, many with hard shells, and some without. Many gourds ha ...

vine A vine is any plant with a growth habit of trailing or scandent (that is, climbing) stems, lianas, or runners. The word ''vine'' can also refer to such stems or runners themselves, for instance, when used in wicker work.Jackson; Benjamin; Da ...

Siraitia grosvenorii ''Siraitia grosvenorii'', also known as monkfruit, ''luo han guo'' (), or Swingle fruit, is a herbaceous perennial vine of the gourd family, Cucurbitaceae. It is native to southern China. The plant is cultivated for its fruit extract containing ...

'' (known as monkfruit or ''luohan guo'').Subhuti Dharmananda (January 2004)
"Luo han guo - Sweet fruit used as sugar substitute and medicinal herb"
Institute for Traditional Medicine, Portland, Oregon. Mogrosides are

extract An extract (essence) is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol, oil or water. Extracts may be sold as tinctures or absolutes or dried and powdered. The aromatic principles of ma ...

ed from ''S. grosvenorii'' and used in the manufacture of

sugar substitute A sugar substitute or artificial sweetener, is a food additive that provides a sweetness like that of sugar while containing significantly less food energy than sugar-based sweeteners, making it a zero-calorie () or low-calorie sweetener. Arti ...

Mogrosides

Mogrosides include: * 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 The total content of mogrosides in ''Siraitia grosvenorii'' fruit is 3.8% with Mogroside V having the highest content (0.8% to 1.3% w/w).

Biosynthesis

One analysis of 200 candidate

gene In biology, the word gene has two meanings. The Mendelian gene is a basic unit of heredity. The molecular gene is a sequence of nucleotides in DNA that is transcribed to produce a functional RNA. There are two types of molecular genes: protei ...

s of ''Siraitia grosvenorii'' revealed five

enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...

families involved in the synthesis of mogroside V:

squalene epoxidase Squalene monooxygenase (also called squalene epoxidase) is a eukaryotic enzyme that uses NADPH and diatomic oxygen to oxidize squalene to 2,3-oxidosqualene (squalene epoxide). Squalene epoxidase catalyzes the first oxygenation step in sterol bi ...

triterpenoid Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the pre ...

synthase In biochemistry, a synthase is an enzyme that catalyses a synthesis process. Note that, originally, biochemical nomenclature distinguished synthetases and synthases. Under the original definition, synthases do not use energy from nucleoside trip ...

epoxide hydrolase Epoxide hydrolases (EHs), also known as epoxide hydratases, are enzymes that metabolize compounds that contain an epoxide residue; they convert this residue to two hydroxyl residues through an epoxide hydrolysis reaction to form diol products. ...

cytochrome P450 Cytochromes P450 (P450s or CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that mostly, but not exclusively, function as monooxygenases. However, they are not omnipresent; for examp ...

s, and UDP-

glucosyltransferase Glucosyltransferases are a type of glycosyltransferase that enable the transfer of glucose. Examples include: * glycogen synthase * glycogen phosphorylase Glycogen phosphorylase is one of the phosphorylase enzymes (). Glycogen phosphorylase c ...

s. 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 In organic chemistry, a glycosyl group is a univalent free radical or substituent structure obtained by removing the hydroxyl () group from the hemiacetal () group found in the cyclic form of a monosaccharide and, by extension, of a lower ol ...

groups are added and catalyzed, leading to the sweet M4, M5, and M6 mogrosides.

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.

Uses

Some mogrosides are used in

traditional Chinese medicine Traditional Chinese medicine (TCM) is an alternative medicine, alternative medical practice drawn from traditional medicine in China. A large share of its claims are pseudoscientific, with the majority of treatments having no robust evidence ...

and some are extracted for manufacturing as

sweetener A sweetener is a substance added to food or drink to impart the flavor of sweetness, either because it contains a type of sugar, or because it contains a sweet-tasting sugar substitute. Various natural non-sugar sweeteners (NSS) and artificial s ...

s. Mogroside V

from ''S. grosvenorii'' fruit is 250 times sweeter than

sucrose Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula . For human consumption, sucrose is extracted and refined ...

, sold commercially in Norbu (sweetener).

References

External links

*{{Commonscatinline, Mogrosides Triterpene glycosides Sugar substitutes