Triterpenoid Saponins
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Saponins (Latin ''sapon'', 'soap' + ''-in'', 'one of') are bitter-tasting, usually toxic plant-derived
secondary metabolite Secondary metabolites, also called ''specialised metabolites'', ''secondary products'', or ''natural products'', are organic compounds produced by any lifeform, e.g. bacteria, archaea, fungi, animals, or plants, which are not directly involved ...
s. They are
organic chemicals Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-cont ...
that become foamy when agitated in water and have high
molecular weight A molecule is a group of two or more atoms that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemi ...
. They are present in a wide range of plant species throughout the bark, leaves, stems, roots and flowers but particularly in
soapwort ''Saponaria'' is a genus of flowering plants in the family Caryophyllaceae, native to Asia and Europe, and are commonly known as soapworts. They are herbaceous perennials and annuals, some with woody bases. The flowers are abundant, five-petalle ...
(genus '' Saponaria''), a flowering plant, the
soapbark ''Quillaja saponaria'', the soap bark tree or soapbark, is an evergreen tree in the family Quillajaceae, native to warm temperate central Chile. In Chile it occurs from 32 to 40° South Latitude approximately and at up to 2000 m (6500&nb ...
tree (''
Quillaja saponaria ''Quillaja saponaria'', the soap bark tree or soapbark, is an evergreen tree in the family Quillajaceae, native to warm temperate central Chile. In Chile it occurs from 32nd parallel south, 32 to 40th parallel south, 40° South Latitude approxim ...
''), common corn-cockle (''
Agrostemma githago ''Agrostemma githago'', the common corn-cockle (also written "corncockle"), is a herbaceous annual flowering plant a member of Caryophyllaceae, also called the pink family or the carnation family of plants. The name of this genus is derived from ...
'' L.), baby's breath ( ''Gypsophila'' spp.) and
soybean The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean. Soy is a staple crop, the world's most grown legume, and an important animal feed. Soy is a key source o ...
s (''
Glycine max The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean. Soy is a staple crop, the world's most grown legume, and an important animal feed. Soy is a key source of f ...
'' L.). They are used in soaps, medicines (e.g. drug adjuvants), fire extinguishers, dietary supplements,
steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...
synthesis, and in carbonated beverages (for example, being responsible for maintaining the head on
root beer Root beer is a North American soft drink traditionally made using the root bark of the sassafras tree '' Sassafras albidum'' or the vine of '' Smilax ornata'' (known as sarsaparilla; also used to make a soft drink called sarsaparilla) as the ...
). Saponins are both water and fat soluble, which gives them their useful soap properties. Some examples of these chemicals are
glycyrrhizin Glycyrrhizin (glycyrrhizic acid or glycyrrhizinic acid) is the chief sweet-tasting constituent of ''Glycyrrhiza glabra'' (liquorice) root. Structurally, it is a saponin used as an emulsifier and gel-forming agent in foodstuffs and cosmetics. I ...
(
licorice Liquorice (Commonwealth English) or licorice (American English; see spelling differences; ) is the common name of ''Glycyrrhiza glabra'', a flowering plant of the bean family Fabaceae, from the root of which a sweet, aromatic flavouring is ...
flavoring) and
quillaia Quillaia is the milled inner Bark (botany), bark or small stems and branches of the soapbark (''Quillaja saponaria''). Other names include ''Murillo bark extract'', ''Panama bark extract'', ''Quillaia extract'', ''Quillay bark extract'', ''Soapba ...
(alt. quillaja), a bark extract used in beverages.


Classification based on chemical structure

Structurally, they are
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. ...
s with at least one glycosidic linkage between a
sugar chain A carbohydrate () is a biomolecule composed of carbon (C), hydrogen (H), and oxygen (O) atoms. The typical hydrogen-to-oxygen atomic ratio is 2:1, analogous to that of water, and is represented by the empirical formula (where ''m'' and ''n'' ma ...
( glycone) and another non-sugar organic molecule (
aglycone An aglycone (aglycon or genin) is the chemical compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid A steroid is an organic compoun ...
).


Steroid glycosides

Steroid glycosides are saponins with 27-C atoms. They are modified
triterpenoids 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 ...
where their
aglycone An aglycone (aglycon or genin) is the chemical compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid A steroid is an organic compoun ...
is a
steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...
, these compounds typically consist of a steroid aglycone attached to one or more sugar molecules, which can have various biological activities. These compounds are known for their significant
cytotoxic Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are toxic metals, toxic chemicals, microbe neurotoxins, radiation particles and even specific neurotransmitters when the system is out of balance. Also some types of dr ...
,
neurotrophic Neurotrophic factors (NTFs) are a family of biomolecules – nearly all of which are peptides or small proteins – that support the growth, survival, and differentiation of both developing and mature neurons. Most NTFs exert their trop ...
and
antibacterial An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention ...
properties. These may also be used for partial synthesis of sex hormones or
steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...
s.


Triterpene glycosides

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. ...
s are natural
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. ...
s present in various
plant Plants are the eukaryotes that form the Kingdom (biology), kingdom Plantae; they are predominantly Photosynthesis, photosynthetic. This means that they obtain their energy from sunlight, using chloroplasts derived from endosymbiosis with c ...
s,
herb Herbs are a widely distributed and widespread group of plants, excluding vegetables, with savory or aromatic properties that are used for flavoring and garnishing food, for medicinal purposes, or for fragrances. Culinary use typically distingu ...
s and
sea cucumber Sea cucumbers are echinoderms from the class (biology), class Holothuroidea ( ). They are benthic marine animals found on the sea floor worldwide, and the number of known holothuroid species worldwide is about 1,786, with the greatest number be ...
s and possess 30-C atoms. These compounds consist of 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 ...
aglycone An aglycone (aglycon or genin) is the chemical compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid A steroid is an organic compoun ...
attached to one or more sugar molecules.
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. ...
s exhibit a wide range of biological activities and pharmacological properties, making them valuable in traditional medicine and modern drug discovery.


Uses

The saponins are a subclass of terpenoids, the largest class of plant extracts. The
amphipathic In chemistry, an amphiphile (), or amphipath, is a chemical compound possessing both hydrophilic (''water-loving'', polar) and lipophilic (''fat-loving'', nonpolar) properties. Such a compound is called amphiphilic or amphipathic. Amphiphilic c ...
nature of saponins gives them activity as
surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...
s with potential ability to interact with
cell membrane The cell membrane (also known as the plasma membrane or cytoplasmic membrane, and historically referred to as the plasmalemma) is a biological membrane that separates and protects the interior of a cell from the outside environment (the extr ...
components, such as
cholesterol Cholesterol is the principal sterol of all higher animals, distributed in body Tissue (biology), tissues, especially the brain and spinal cord, and in Animal fat, animal fats and oils. Cholesterol is biosynthesis, biosynthesized by all anima ...
and
phospholipid Phospholipids are a class of lipids whose molecule has a hydrophilic "head" containing a phosphate group and two hydrophobic "tails" derived from fatty acids, joined by an alcohol residue (usually a glycerol molecule). Marine phospholipids typ ...
s, possibly making saponins useful for development of
cosmetics Cosmetics are substances that are intended for application to the body for cleansing, beautifying, promoting attractiveness, or altering appearance. They are mixtures of chemical compounds derived from either Natural product, natural source ...
and
drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...
s. Saponins have also been used as
adjuvants In pharmacology, an adjuvant is a drug or other substance, or a combination of substances, that is used to increase the efficacy or potency of certain drugs. Specifically, the term can refer to: * Adjuvant therapy in cancer management * Analge ...
in development of
vaccine A vaccine is a biological Dosage form, preparation that provides active acquired immunity to a particular infectious disease, infectious or cancer, malignant disease. The safety and effectiveness of vaccines has been widely studied and verifi ...
s, such as
Quil A Quillaia is the milled inner bark or small stems and branches of the soapbark (''Quillaja saponaria''). Other names include ''Murillo bark extract'', ''Panama bark extract'', ''Quillaia extract'', ''Quillay bark extract'', ''Soapbark extract'', a ...
, an
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 ...
from the bark of ''
Quillaja saponaria ''Quillaja saponaria'', the soap bark tree or soapbark, is an evergreen tree in the family Quillajaceae, native to warm temperate central Chile. In Chile it occurs from 32nd parallel south, 32 to 40th parallel south, 40° South Latitude approxim ...
''. This makes them of interest for possible use in
subunit vaccine A subunit vaccine is a vaccine that contains purified parts of the pathogen that are antigenic, or necessary to elicit a protective immune response. Subunit vaccine can be made from dissembled viral particles in cell culture or recombinant DNA expr ...
s and vaccines directed against intracellular pathogens. In their use as adjuvants for manufacturing vaccines, toxicity associated with
sterol A sterol is any organic compound with a Skeletal formula, skeleton closely related to Cholestanol, cholestan-3-ol. The simplest sterol is gonan-3-ol, which has a formula of , and is derived from that of gonane by replacement of a hydrogen atom on ...
complexation remains a concern. Quillaja is toxic when consumed in large amounts, involving possible
liver damage Liver disease, or hepatic disease, is any of many diseases of the liver. If long-lasting it is termed chronic liver disease. Although the diseases differ in detail, liver diseases often have features in common. Liver diseases File:Ground glas ...
, gastric pain,
diarrhea Diarrhea (American English), also spelled diarrhoea or diarrhœa (British English), is the condition of having at least three loose, liquid, or watery bowel movements in a day. It often lasts for a few days and can result in dehydration d ...
, or other
adverse effects An adverse effect is an undesired harmful effect resulting from a medication or other intervention, such as surgery. An adverse effect may be termed a "side effect", when judged to be secondary to a main or therapeutic effect. The term complic ...
. The
NOAEL The no-observed-adverse-effect level (NOAEL) denotes the level of exposure of an organism, found by experiment or observation, at which there is no biologically or statistically significant increase in the frequency or severity of any adverse effe ...
of saponins is around 300 mg/kg in rodents, so a dose of 3 mg/kg should be safe with a
safety factor In engineering, a factor of safety (FoS) or safety factor (SF) expresses how much stronger a system is than it needs to be for its specified maximum load. Safety factors are often calculated using detailed analysis because comprehensive testing i ...
(see
Therapeutic index The therapeutic index (TI; also referred to as therapeutic ratio) is a quantitative measurement of the relative safety of a drug with regard to risk of overdose. It is a comparison of the amount of a therapeutic agent that causes toxicity to the ...
) of 100. Saponins are used for their effects on
ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...
emissions in animal feeding. In the United States, researchers are exploring the use of saponins derived from plants to control invasive worm species, including the jumping worm.


Decoction

The principal historical use of these plants was boiling down to make soap. ''
Saponaria officinalis ''Saponaria officinalis'' is a common perennial plant from the family Caryophyllaceae. This plant has many common names, including common soapwort, bouncing-bet, crow soap, wild sweet William, and soapweed. There are about 20 species of soapwor ...
'' is most suited for this procedure, but other related species also work. The greatest concentration of saponin occurs during flowering, with the most saponin found in the woody stems and roots, but the leaves also contain some.


Biological sources

Saponins have historically been plant-derived, but they have also been isolated from marine organisms such as
sea cucumber Sea cucumbers are echinoderms from the class (biology), class Holothuroidea ( ). They are benthic marine animals found on the sea floor worldwide, and the number of known holothuroid species worldwide is about 1,786, with the greatest number be ...
. They derive their name from the soapwort plant (genus '' Saponaria'', family
Caryophyllaceae Caryophyllaceae, commonly called the pink family or carnation family, is a family (biology), family of flowering plants. It is included in the dicotyledon order Caryophyllales in the APG III system, alongside 33 other families, including Amaranth ...
), the root of which was used historically as a soap. In other representatives of this family, e.g. '' Agerostemma githago'', ''
Gypsophila ''Gypsophila'' () is a genus of flowering plants in the carnation family, Caryophyllaceae. They are native to Eurasia, Africa, Australia, and the Pacific Islands.Dianthus ''Dianthus'' ( ) is a genus of about 340 species of flowering plants in the family Caryophyllaceae, native mainly to Europe and Asia, with a few species in north Africa and in southern Africa, and one species (''D. repens'') in arctic North Am ...
'' sp., saponins are also present in large quantities. Saponins are also found in the botanical family
Sapindaceae The Sapindaceae are a family (biology), family of flowering plants in the order Sapindales known as the soapberry family. It contains 138 genera and 1,858 accepted species. Examples include Aesculus, horse chestnut, maples, ackee and lychee. The ...
, including its defining genus ''
Sapindus ''Sapindus'' is a genus of about thirteen species of shrubs and small trees in the lychee family, Sapindaceae and tribe Sapindeae. It is native to warm temperate to tropical regions of the world. The genus includes both deciduous and evergree ...
'' (soapberry or soapnut) and the
horse chestnut The genus ''Aesculus'' ( or ), with notable species including buckeye and horse chestnut, comprises 13–19 species of flowering plants in the family Sapindaceae. They are trees and shrubs native to the temperate Northern Hemisphere, with ...
, and in the closely related families
Aceraceae Aceraceae were recognized as a family of flowering plants also called the maple family. They contain two to four genera, depending upon the circumscription, of some 120 species of trees and shrubs. A common characteristic is that the leaves are ...
(maples) and
Hippocastanaceae Hippocastanoideae is a Family (biology), subfamily of flowering plants in the Sapindus, soapberry family Sapindaceae. The group was formerly treated as the separate families Aceraceae and Hippocastanaceae. molecular phylogeny, Molecular phylogene ...
. It is also found heavily in ''
Gynostemma pentaphyllum ''Gynostemma pentaphyllum'', also called jiaogulan (), is a dioecious, herbaceous climbing vine of the family Cucurbitaceae (cucumber or gourd family) widely distributed in South and East Asia as well as New Guinea. Jiaogulan is used to make ...
'' (
Cucurbitaceae The Cucurbitaceae (), also called cucurbits or the gourd family, are a plant family (biology), family consisting of about 965 species in 101 genera.
) in a form called gypenosides, and
ginseng Ginseng () is the root of plants in the genus ''Panax'', such as South China ginseng (''Panax notoginseng, P. notoginseng''), Korean ginseng (''Panax ginseng, P. ginseng''), and American ginseng (''American ginseng, P. quinquefol ...
or red ginseng (''
Panax The ''Panax'' (ginseng) genus belongs to the Araliaceae (ivy) Family (biology), family. ''Panax'' species are characterized by the presence of ginsenosides and gintonin. ''Panax'' is one of approximately 60 plant genera with a classical disjunct ...
'',
Araliaceae The Araliaceae are a family of flowering plants composed of about 43 genera and around 1500 species consisting of primarily woody plants and some herbaceous plants commonly called the ginseng family. The morphology of Araliaceae varies widely ...
) in a form called ginsenosides. Saponins are also found in the unripe fruit of ''
Manilkara zapota ''Manilkara zapota'', commonly known as sapodilla (), sapote, chicozapote, chicoo, chicle, naseberry, nispero, or soapapple, among other names, is an evergreen tree native to southern Mexico and Central America. An example natural occurrence is ...
'' (also known as sapodillas), resulting in highly astringent properties. ''
Nerium oleander ''Nerium oleander'' ( ), commonly known as oleander or rosebay, is a shrub or small tree cultivated worldwide in temperate and subtropical areas as an ornamental and landscaping plant. It is the Monotypic taxon, only species currently classifi ...
'' (
Apocynaceae Apocynaceae (, from '' Apocynum'', Greek for "dog-away") is a family of flowering plants that includes trees, shrubs, herbs, stem succulents, and vines, commonly known as the dogbane family, because some taxa were used as dog poison. Notable mem ...
), also known as White Oleander, is a source of the potent cardiac toxin
oleandrin Oleandrin is a cardiac glycoside found in the poisonous plant oleander (''Nerium oleander'' L.). As a main phytochemical of oleander, oleandrin is associated with the toxicity of oleander sap, and has similar properties to digoxin. Oleander has ...
. Within these families, this class of chemical compounds is found in various parts of the plant: leaves, stems, roots, bulbs, blossom and fruit. Commercial formulations of plant-derived saponins, e.g., from the soap bark tree, ''
Quillaja saponaria ''Quillaja saponaria'', the soap bark tree or soapbark, is an evergreen tree in the family Quillajaceae, native to warm temperate central Chile. In Chile it occurs from 32nd parallel south, 32 to 40th parallel south, 40° South Latitude approxim ...
'', and those from other sources are available via controlled manufacturing processes, which make them of use as chemical and biomedical reagents. Soyasaponins are a group of structurally complex oleanane-type triterpenoid saponins that include soyasapogenol (aglycone) and oligosaccharide moieties biosynthesized on
soybean The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean. Soy is a staple crop, the world's most grown legume, and an important animal feed. Soy is a key source o ...
tissues. Soyasaponins were previously associated to plant-microbe interactions from root exudates and abiotic stresses, as nutritional deficiency.


Role in plant ecology and impact on animal foraging

In plants, saponins may serve as anti-feedants, and to protect the plant against
microbes A microorganism, or microbe, is an organism of microscopic size, which may exist in its single-celled form or as a colony of cells. The possible existence of unseen microbial life was suspected from antiquity, with an early attestation in ...
and
fungi A fungus (: fungi , , , or ; or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and mold (fungus), molds, as well as the more familiar mushrooms. These organisms are classified as one ...
. Some plant saponins (e.g., from oat and spinach) may enhance
nutrient A nutrient is a substance used by an organism to survive, grow and reproduce. The requirement for dietary nutrient intake applies to animals, plants, fungi and protists. Nutrients can be incorporated into cells for metabolic purposes or excret ...
absorption and aid in animal
digestion Digestion is the breakdown of large insoluble food compounds into small water-soluble components so that they can be absorbed into the blood plasma. In certain organisms, these smaller substances are absorbed through the small intestine into th ...
. However, saponins are often bitter to taste, and so can reduce plant
palatability Palatability (or palatableness) is the hedonic reward (which is pleasure of taste in this case) provided by foods or drinks that are agreeable to the "palate", which often varies relative to the homeostatic satisfaction of nutritional and/or wa ...
(e.g., in livestock feeds), or even imbue them with life-threatening animal
toxicity Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacteria, bacterium, or plant, as well as the effect o ...
. Some saponins are toxic to cold-blooded organisms and
insect Insects (from Latin ') are Hexapoda, hexapod invertebrates of the class (biology), class Insecta. They are the largest group within the arthropod phylum. Insects have a chitinous exoskeleton, a three-part body (Insect morphology#Head, head, ...
s at particular concentrations. Further research is needed to define the roles of these natural products in their host organisms, which have been described as "poorly understood" to date.


Ethnobotany

Most saponins, which readily dissolve in water, are poisonous to
fish A fish (: fish or fishes) is an aquatic animal, aquatic, Anamniotes, anamniotic, gill-bearing vertebrate animal with swimming fish fin, fins and craniate, a hard skull, but lacking limb (anatomy), limbs with digit (anatomy), digits. Fish can ...
. Therefore, in
ethnobotany Ethnobotany is an interdisciplinary field at the interface of natural and social sciences that studies the relationships between humans and plants. It focuses on traditional knowledge of how plants are used, managed, and perceived in human socie ...
, they are known for their use by indigenous people in obtaining aquatic food sources. Since prehistoric times, cultures throughout the world have used fish-killing plants, typically containing saponins, for fishing. Although prohibited by law, fish-poison plants are still widely used by indigenous tribes in
Guyana Guyana, officially the Co-operative Republic of Guyana, is a country on the northern coast of South America, part of the historic British West Indies. entry "Guyana" Georgetown, Guyana, Georgetown is the capital of Guyana and is also the co ...
. On the Indian subcontinent, the
Gondi people The Gondi (Gōṇḍī) or Gond people, who refer to themselves as "Kōītōr" (Kōī, Kōītōr), are an ethnolinguistic group in India. Their native language, Gondi language, Gondi, belongs to the Dravidian languages, Dravidian family. They ...
use poison-plant extracts in fishing. In 16th century, saponins-rich plant, ''Agrostemma githago,'' was used to treat ulcers, fistulas, and hemorrhages. Many of California's
Native American Native Americans or Native American usually refers to Native Americans in the United States. Related terms and peoples include: Ethnic groups * Indigenous peoples of the Americas, the pre-Columbian peoples of North, South, and Central America ...
tribes traditionally used
soaproot The common names soap plant, soaproot and amole refer to the genus ''Chlorogalum''. They are native to western North America, with some species in Oregon but they are mostly found in California. Common names of the genus and several species deri ...
(genus ''Chlorogalum''), and/or the root of various
yucca ''Yucca'' ( , YUCK-uh) is both the scientific name and common name for a genus native to North America from Panama to southern Canada. It contains 50 accepted species. In addition to yucca, they are also known as Adam's needle or Spanish-bayon ...
species, which contain saponin, as a fish poison. They would pulverize the roots, mix with water to generate a foam, then put the suds into a stream. This would kill or incapacitate the fish, which could be gathered easily from the surface of the water. Among the tribes using this technique were the Lassik, the
Luiseño The Luiseño or Payómkawichum are an Indigenous people of California who, at the time of the first contacts with the Spanish in the 16th century, inhabited the coastal area of southern California, ranging from the present-day southern part of ...
, and the
Mattole The Mattole, including the Bear River Indians, are a group of Native Americans in California. Their traditional lands are along the Mattole and Bear Rivers near Cape Mendocino in Humboldt County, California. A notable difference between the Ma ...
.


Chemical structure

The vast heterogeneity of structures underlying this class of compounds makes generalizations difficult; they're a subclass of
terpenoid The terpenoids, also known as isoprenoids, are a class of naturally occurring organic compound, organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeabl ...
s, oxygenated derivatives of terpene hydrocarbons.
Terpene Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predomi ...
s in turn are formally made up of five-carbon
isoprene Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. It is produced by many plants and animals (including humans) and its polymers ar ...
units (The alternate steroid base is a terpene missing a few carbon atoms). Derivatives are formed by substituting other groups for some of the hydrogen atoms of the base structure. In the case of most saponins, one of these substituents is a sugar, so the compound is a glycoside of the base molecule. More specifically, the lipophilic base structure of a saponin can be a triterpene, a steroid (such as spirostanol or furostanol) or a
steroidal alkaloid Steroidal alkaloids have the basic steroidal skeleton with nitrogen-based functional groups attached to the skeleton. More specifically, they are distinguished by their tetracyclic cyclopentanoperhydrophenanthrene skeleton that marks their clos ...
(in which nitrogen atoms replace one or more carbon atoms). Alternatively, the base structure may be an acyclic carbon chain rather than the ring structure typical of steroids. One or two (rarely three) hydrophilic monosaccharide (simple sugar) units bind to the base structure via their hydroxyl (OH) groups. In some cases other substituents are present, such as carbon chains bearing hydroxyl or carboxyl groups. Such chain structures may be 1–11 carbon atoms long, but are usually 2–5 carbons long; the carbon chains themselves may be branched or unbranched. The most commonly encountered sugars are monosaccharides like glucose and galactose, though a wide variety of sugars occurs naturally. Other kinds of molecules such as organic acids may also attach to the base, by forming esters via their carboxyl (COOH) groups. Of particular note among these are sugar acids such as glucuronic acid and galacturonic acid, which are oxidized forms of glucose and galactose.


See also

*
Cardenolide A cardenolide is a type of steroid. Many plants contain derivatives, collectively known as cardenolides, including many in the form of cardenolide glycosides (cardenolides that contain structural groups derived from sugars). Cardenolide glycoside ...
*
Cardiac glycoside Cardiac glycosides are a class of organic compounds that increase the output force of the heart and decrease its rate of contractions by inhibiting the cellular sodium-potassium ATPase pump. Their beneficial medical uses include treatments for ...
*
Phytochemical Phytochemicals are naturally-occurring chemicals present in or extracted from plants. Some phytochemicals are nutrients for the plant, while others are metabolites produced to enhance plant survivability and reproduction. The fields of ext ...


References

{{Authority control Saponaceous plants Wood extracts