Triterpenoid saponins
Encyclopedia
Triterpenoid saponins are triterpene
s which belong to the group of saponin
compounds. Triterpenes belong to a large group of compounds arranged in a four or five ring configuration of 30 carbons with several oxygens attached. Triterpenes are assembled from a C5 isoprene unit through the cytosolic mevalonate pathway to make a C30 compound and are steroidal in nature. Cholesterol is one example of a triterpene. Phytosterols and phytoecdysteroids are also triterpenes. The triterpenes are subdivided into some 20 groups, depending on their particular structures. Though all terpenoid compounds have bioactivity in mammals, it is the triterpenes that are most important to the adaptogen
ic effect found in plants such as Panax ginseng
or Eleutherococcus senticosus
. Most triterpenoid compounds in adaptogenic plants are found as saponin glycosides which refers to the attachment of various sugar molecules to the triterpene unit. These sugars can be easily cleaved off in the gut by bacteria, allowing the aglycone
(triterpene) to be absorbed. This allows them insert into cell membranes and modify the composition, influence membrane fluidity, and potentially affect signaling by many ligands and cofactors. Saponin glycosides reduce surface tension
of water with foaming and will break down lipids. Usually triterpene saponins are designated as such by the suffix ending –side, such as ginsenoside, or astragaloside, named for the plant genera they were first discovered in. Some, such as the ginsenosides and eleutherosides are designated Rx where the suffix x = a, a1, b2, is indicative of
the relative position of the saponin spots from top to bottom of a thin layer chromatogram.
Chemical compound: Common Name (Latin Name)
Triterpene
Triterpenes are terpenes consisting of six isoprene units and have the molecular formula C30H48.The pentacyclic triterpenes can be classified into lupane, oleanane or ursane groups.Animal- and plant-derived triterpenes exist, such as:*squalene...
s which belong to the group of saponin
Saponin
Saponins are a class of chemical compounds, one of many secondary metabolites found in natural sources, with saponins found in particular abundance in various plant species...
compounds. Triterpenes belong to a large group of compounds arranged in a four or five ring configuration of 30 carbons with several oxygens attached. Triterpenes are assembled from a C5 isoprene unit through the cytosolic mevalonate pathway to make a C30 compound and are steroidal in nature. Cholesterol is one example of a triterpene. Phytosterols and phytoecdysteroids are also triterpenes. The triterpenes are subdivided into some 20 groups, depending on their particular structures. Though all terpenoid compounds have bioactivity in mammals, it is the triterpenes that are most important to the adaptogen
Adaptogen
An adaptogen is a herbal product claimed to increase resistance to stress, trauma, anxiety and fatigue. The term is used mainly by herbalists who also refer to adaptogens as rejuvenating herbs, qi tonics, rasayanas, or restoratives...
ic effect found in plants such as Panax ginseng
Ginseng
Ginseng is any one of eleven species of slow-growing perennial plants with fleshy roots, belonging to the genus Panax of the family Araliaceae....
or Eleutherococcus senticosus
Eleutherococcus senticosus
Eleutherococcus senticosus is a species of small, woody shrub in the family Araliaceae native to Northeastern Asia. It is often colloquially referred to as Siberian Ginseng or eleuthero, and is sometimes shortened to E. senticosus in medical literature. E...
. Most triterpenoid compounds in adaptogenic plants are found as saponin glycosides which refers to the attachment of various sugar molecules to the triterpene unit. These sugars can be easily cleaved off in the gut by bacteria, allowing the aglycone
Aglycone
An aglycone is the non-sugar compound remaining after replacement of the glycosyl group from a glycoside by a hydrogen atom. The spelling aglycon is sometimes encountered .Classes of phytochemicals found in the aglycone and glycosides forms :...
(triterpene) to be absorbed. This allows them insert into cell membranes and modify the composition, influence membrane fluidity, and potentially affect signaling by many ligands and cofactors. Saponin glycosides reduce surface tension
Surface tension
Surface tension is a property of the surface of a liquid that allows it to resist an external force. It is revealed, for example, in floating of some objects on the surface of water, even though they are denser than water, and in the ability of some insects to run on the water surface...
of water with foaming and will break down lipids. Usually triterpene saponins are designated as such by the suffix ending –side, such as ginsenoside, or astragaloside, named for the plant genera they were first discovered in. Some, such as the ginsenosides and eleutherosides are designated Rx where the suffix x = a, a1, b2, is indicative of
the relative position of the saponin spots from top to bottom of a thin layer chromatogram.
Common medicinally active triterpenoid saponins from adaptogenic plants
Triterpenoids in PlantsChemical compound: Common Name (Latin Name)
- 20-hydroxyecdysone20-hydroxyecdysone20-Hydroxyecdysone is a naturally occurring ecdysteroid hormone which controls the ecdysis and metamorphosis of arthropods. It is therefore one of the most common moulting hormones in insects, crabs, etc...
: maral root (Rhaponticum carthamoides) - araloside: spikenard (Aralia mandshurica)
- astragaloside: huang qi (Astragalus membranaceus)
- bacoside: brahmi (Bacopa monniera)
- cucurbitacinCucurbitacinCucurbitacin is any of a class of biochemical compounds that some plants — notably members of the family Cucurbitaceae, that includes the common pumpkins and gourds — developed in order to defend themselves from herbivores...
: bryonia (Bryonia alba) - eleutheroside: Siberian ginseng (Eleutherococcus senticosusEleutherococcus senticosusEleutherococcus senticosus is a species of small, woody shrub in the family Araliaceae native to Northeastern Asia. It is often colloquially referred to as Siberian Ginseng or eleuthero, and is sometimes shortened to E. senticosus in medical literature. E...
) - ginsenosideGinsenosideGinsenosides are a class of steroid glycosides, and triterpene saponins, found exclusively in the plant genus Panax .Ginsenosides have been the target of research, as they are viewed as the active compounds behind the claims of ginseng's efficacy...
: ginseng (Panax ginseng) - gymnemic acidGymnemic acidGymnemic acids are glycosides isolated from the leaves of Gymnema sylvestre . Gymnemic acids like ziziphin and hodulcine are anti-sweet compounds, or sweetness inhibitors. After chewing the leaves, solutions sweetened with sucrose taste like water.More than 20 homologues of gymnemic acid are found...
: gurmar (Gymnema sylvestreGymnema sylvestreGymnema sylvestre is a herb native to the tropical forests of southern and central India where it has been used as a natural treatment for diabetes for nearly two millennia.-Description:...
) - gypenoside: jiaogulan (Gynostemma pentaphyllum)
- tanshenoside: bellflower (Codonopsis pilosulaCodonopsis pilosulaCodonopsis pilosula , also known as dang shen or poor man's ginseng, is a perennial species of flowering plant native to Northeast Asia and Korea and usually found growing around streambanks and forest openings under the shade of trees....
) - tinosporoside: guruchi (Tinospora cordifoliaTinospora cordifoliaTinospora cordifolia, which is known by the common name Guduchi, is an herbaceous vine of the family Menispermaceae indigenous to the tropical areas of India, Myanmar and Sri Lanka....
) - withanolideWithanolideWithanolides are a group of at least 300 naturally occurring chemical compounds. They occur as secondary metabolites primarily in genera of the Nightshade family, for example in the tomatillo. Structurally, withanolides consist of a steroid backbone bound to a lactone or one of its derivatives;...
: ashwagandha (Withania somnifera)