Saponin

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Structurally, they are glycosides with at least one glycosidic linkage between a sugar chain (glycone) and another non-sugar organic molecule (aglycone).{{Cn|date=September 2024}}

{{see also|Glycoside#Steroidal_glycosides_or_cardiac_glycosides}}

Steroid glycosides are saponins with 27-C atoms.{{Cite journal |last=Vincken |first=Jean-Paul |last2=Heng |first2=Lynn |last3=de Groot |first3=Aede |last4=Gruppen |first4=Harry |date=2007-02-01 |title=Saponins, classification and occurrence in the plant kingdom |url=https://linkinghub.elsevier.com/retrieve/pii/S0031942206006480 |journal=Phytochemistry |volume=68 |issue=3 |pages=275–297 |doi=10.1016/j.phytochem.2006.10.008 |issn=0031-9422|url-access=subscription }} They are modified triterpenoids where their aglycone is a steroid, 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, neurotrophic and antibacterial properties. These may also be used for partial synthesis of sex hormones or steroids.{{cite journal | vauthors = Rao AV, Gurfinkel DM | title = The bioactivity of saponins: triterpenoid and steroidal glycosides | journal = Drug Metabolism and Drug Interactions | volume = 17 | issue = 1–4 | pages = 211–235 | date = 2000 | pmid = 11201296 | doi = 10.1515/dmdi.2000.17.1-4.211 }}

Triterpene glycosides are natural glycosides present in various plants, herbs and sea cucumbers{{cite journal | vauthors = Kim SK, Himaya SW | title = Triterpene glycosides from sea cucumbers and their biological activities | journal = Advances in Food and Nutrition Research | volume = 65 | pages = 297–319 | date = January 2012 | pmid = 22361196 | doi = 10.1016/b978-0-12-416003-3.00020-2 | publisher = Academic Press | series = Marine Medicinal Foods | isbn = 978-0-12-416003-3 | veditors = Kim SK }} and possess 30-C atoms. These compounds consist of a triterpene aglycone attached to one or more sugar molecules. Triterpene glycosides exhibit a wide range of biological activities and pharmacological properties, making them valuable in traditional medicine and modern drug discovery.

The saponins are a subclass of terpenoids, the largest class of plant extracts. The amphipathic nature of saponins gives them activity as surfactants with potential ability to interact with cell membrane components, such as cholesterol and phospholipids, possibly making saponins useful for development of cosmetics and drugs.{{cite journal | vauthors = Lorent JH, Quetin-Leclercq J, Mingeot-Leclercq MP | title = The amphiphilic nature of saponins and their effects on artificial and biological membranes and potential consequences for red blood and cancer cells | journal = Organic & Biomolecular Chemistry | volume = 12 | issue = 44 | pages = 8803–8822 | date = November 2014 | pmid = 25295776 | doi = 10.1039/c4ob01652a | publisher = Royal Society of Chemistry | s2cid = 205925983 }} Saponins have also been used as adjuvants in development of vaccines,{{cite journal | vauthors = Sun HX, Xie Y, Ye YP | title = Advances in saponin-based adjuvants | journal = Vaccine | volume = 27 | issue = 12 | pages = 1787–1796 | date = March 2009 | pmid = 19208455 | doi = 10.1016/j.vaccine.2009.01.091 | doi-access = free }} such as Quil A, an extract from the bark of Quillaja saponaria.{{cite web | title=Quillaja | publisher=Drugs.com | date=2018 | url=https://www.drugs.com/npp/quillaja.html | access-date=26 December 2018 | archive-date=26 December 2018 | archive-url=https://web.archive.org/web/20181226233138/https://www.drugs.com/npp/quillaja.html | url-status=live }} This makes them of interest for possible use in subunit vaccines and vaccines directed against intracellular pathogens. In their use as adjuvants for manufacturing vaccines, toxicity associated with sterol complexation remains a concern.{{cite journal | vauthors = Skene CD, Sutton P | title = Saponin-adjuvanted particulate vaccines for clinical use | journal = Methods | volume = 40 | issue = 1 | pages = 53–59 | date = September 2006 | pmid = 16997713 | doi = 10.1016/j.ymeth.2006.05.019 }}

Quillaja is toxic when consumed in large amounts, involving possible liver damage, gastric pain, diarrhea, or other adverse effects. The NOAEL of saponins is around 300 mg/kg in rodents, so a dose of 3 mg/kg should be safe with a safety factor (see Therapeutic index) of 100.{{cite journal | vauthors = Younes M, Aquilina G, Castle L, Engel KH, Fowler P, Frutos Fernandez MJ, Fürst P, Gürtler R, Gundert-Remy U, Husøy T, Mennes W, Oskarsson A, Shah R, Waalkens-Berendsen I, Wölfle D, Boon P, Lambré C, Tobback P, Wright M, Rincon AM, Smeraldi C, Tard A, Moldeus P | title = Re-evaluation of Quillaia extract (E 999) as a food additive and safety of the proposed extension of use | journal = EFSA Journal | volume = 17 | issue = 3 | pages = e05622 | date = March 2019 | pmid = 32626248 | pmc = 7009130 | doi = 10.2903/j.efsa.2019.5622 }}

Saponins are used for their effects on ammonia emissions in animal feeding.{{cite web | vauthors = Zentner E |date=July 2011 |title=Effects of phytogenic feed additives containing quillaja saponaria on ammonia in fattening pigs |url=https://www.delacon.com/phytogenics/articles/Effects-of-phytogenic-feed-additives-containing-quillaja-saponaria-on-ammonia-in-fattening-pigs.pdf |access-date=27 November 2012 |archive-date=27 September 2013 |archive-url=https://web.archive.org/web/20130927195229/https://www.delacon.com/phytogenics/articles/Effects-of-phytogenic-feed-additives-containing-quillaja-saponaria-on-ammonia-in-fattening-pigs.pdf |url-status=live }} In the United States, researchers are exploring the use of saponins derived from plants to control invasive worm species, including the jumping worm.{{Cite news| vauthors = Roach M |date=2020-07-22|title=As Summer Takes Hold, So Do the Jumping Worms|language=en-US|work=The New York Times|url=https://www.nytimes.com/2020/07/22/realestate/invasive-jumping-worm-garden-summer.html|access-date=2020-07-30|issn=0362-4331|archive-date=27 July 2020|archive-url=https://web.archive.org/web/20200727052126/https://www.nytimes.com/2020/07/22/realestate/invasive-jumping-worm-garden-summer.html|url-status=live}}{{Cite web|date=2020-01-02|title=Invasive 'Jumping' Worms Are Now Tearing Through Midwestern Forests|url=https://www.audubon.org/news/invasive-jumping-worms-are-now-tearing-through-midwestern-forests|access-date=2020-07-30|website=Audubon|language=en|archive-date=9 August 2020|archive-url=https://web.archive.org/web/20200809054107/https://www.audubon.org/news/invasive-jumping-worms-are-now-tearing-through-midwestern-forests|url-status=live}}

The principal historical use of these plants was boiling down to make soap. Saponaria officinalis 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.

Saponins have historically been plant-derived, but they have also been isolated from marine organisms such as sea cucumber.{{cite journal | vauthors = Riguera R |date=August 1997 |title=Isolating bioactive compounds from marine organisms |journal=Journal of Marine Biotechnology |volume=5 |issue=4 |pages=187–193 |url=https://www.springerlink.com/content/m9cclbrm1y0e5ge5/}}{{dead link|date=February 2020|bot=medic}}{{cbignore|bot=medic}} They derive their name from the soapwort plant (genus Saponaria, family Caryophyllaceae), the root of which was used historically as a soap.{{cite book | vauthors = Birk Y, Peri I | veditors = Liener IE |chapter=Saponins |title=Toxic constituents of plant foodstuffs |publisher=Academic Press |location=New York City |year=1980 |pages=161 |edition=2nd |isbn=978-0124499607 }} In other representatives of this family, e.g. Agerostemma githago, Gypsophila spp., and Dianthus sp., saponins are also present in large quantities.{{cite journal | vauthors = Smakosz A, Matkowski A, Nawrot-Hadzik I | title = Phytochemistry and Biological Activities of Agrostemma Genus-A Review | journal = Plants | volume = 13 | issue = 12 | pages = 1673 | date = June 2024 | pmid = 38931105 | pmc = 11207627 | doi = 10.3390/plants13121673 | doi-access = free }} Saponins are also found in the botanical family Sapindaceae, including its defining genus Sapindus (soapberry or soapnut) and the horse chestnut, and in the closely related families Aceraceae (maples) and Hippocastanaceae. It is also found heavily in Gynostemma pentaphyllum (Cucurbitaceae) in a form called gypenosides, and ginseng or red ginseng (Panax, Araliaceae) in a form called ginsenosides. Saponins are also found in the unripe fruit of Manilkara zapota (also known as sapodillas), resulting in highly astringent properties. Nerium oleander (Apocynaceae), also known as White Oleander, is a source of the potent cardiac toxin oleandrin. Within these families, this class of chemical compounds is found in various parts of the plant: leaves, stems, roots, bulbs, blossom and fruit.{{Cite web |url=https://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=691 |title=Species Information |access-date=22 January 2015 |archive-date=18 February 2013 |archive-url=https://web.archive.org/web/20130218182149/https://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=691 |url-status=dead |work=Dr. Duke's Phytochemical and Ethnobotanical Databases}} Commercial formulations of plant-derived saponins, e.g., from the soap bark tree, Quillaja saponaria, and those from other sources are available via controlled manufacturing processes, which make them of use as chemical and biomedical reagents.{{cite web |url=http://www.sigmaaldrich.com/US/en/product/sigma/s4521

|title=Saponin from quillaja bark |publisher=Sigma-Aldrich |access-date=23 February 2022 |archive-date=17 March 2022 |archive-url=https://web.archive.org/web/20220317131211/https://www.sigmaaldrich.com/US/en/product/sigma/s4521

|url-status=live }} Soyasaponins are a group of structurally complex oleanane-type triterpenoid saponins that include soyasapogenol (aglycone) and oligosaccharide moieties biosynthesized on soybean tissues. Soyasaponins were previously associated to plant-microbe interactions{{cite journal | vauthors = Tsuno Y, Fujimatsu T, Endo K, Sugiyama A, Yazaki K | title = Soyasaponins: A New Class of Root Exudates in Soybean (Glycine max) | journal = Plant & Cell Physiology | volume = 59 | issue = 2 | pages = 366–375 | date = February 2018 | pmid = 29216402 | doi = 10.1093/pcp/pcx192 | doi-access = free }} from root exudates and abiotic stresses, as nutritional deficiency.{{cite journal | vauthors = Cotrim GD, Silva DM, Graça JP, Oliveira Junior A, Castro C, Zocolo GJ, Lannes LS, Hoffmann-Campo CB | title = Glycine max (L.) Merr. (Soybean) metabolome responses to potassium availability | journal = Phytochemistry | volume = 205 | pages = 113472 | date = January 2023 | pmid = 36270412 | doi = 10.1016/j.phytochem.2022.113472 | s2cid = 253027906 | bibcode = 2023PChem.205k3472C }}

In plants, saponins may serve as anti-feedants, and to protect the plant against microbes and fungi.{{Citation needed|date=March 2009}} Some plant saponins (e.g., from oat and spinach) may enhance nutrient absorption and aid in animal digestion. However, saponins are often bitter to taste, and so can reduce plant palatability (e.g., in livestock feeds), or even imbue them with life-threatening animal toxicity. Some saponins are toxic to cold-blooded organisms and insects 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.{{cite web | vauthors = Foerster H |date=22 May 2006 |title=MetaCyc Pathway: saponin biosynthesis I |url=https://BioCyc.org/META/NEW-IMAGE?type=PATHWAY&object=PWY-5203&detail-level=3 |url-status=live |archive-url=https://web.archive.org/web/20190915231530/https://biocyc.org/META/NEW-IMAGE?type=PATHWAY&object=PWY-5203&detail-level=3 |archive-date=15 September 2019 |access-date=23 February 2009}}

Most saponins, which readily dissolve in water, are poisonous to fish.{{citation |title=Fish-poison plants |journal=Bulletin of Miscellaneous Information (Royal Gardens, Kew) |volume=1930 |issue=4 |year=1930 |pages=129–153 |doi=10.2307/4107559|jstor = 4107559| vauthors = Howes FN }} Therefore, in ethnobotany, 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.{{citation | vauthors = Cannon JG, Burton RA, Wood SG, Owen NL |title=Naturally Occurring Fish Poisons from Plants |journal=J. Chem. Educ. |year=2004 |volume=81 |issue=10 |page=1457 |doi=10.1021/ed081p1457|bibcode=2004JChEd..81.1457C }}{{citation | vauthors = Bradley CE |title=Arrow and fish poison of the American southwest |volume=10 |issue=4 |pages=362–366 |work=Division of Biology, California Institute of Technology |doi=10.1007/BF02859766 |year=1956 |s2cid=35055877 }} {{Citation | vauthors = Webb LJ, Tracey JG, Haydock KP | author2-link=Geoff Tracey | author-link=Leonard Webb (academic) | title=An Australian phytochemical survey. III. Saponins in eastern Australian flowering plants | year=1959 | publication-date=1959 | pages=26 | publisher=CSIRO | doi=10.25919/5xj5-7648 | url=https://doi.org/10.25919/5xj5-7648}}

Although prohibited by law, fish-poison plants are still widely used by indigenous tribes in Guyana.{{cite journal | vauthors = Van Andel T |title=The diverse uses of fish-poison plants in Northwest Guyana |journal=Economic Botany |volume=54 |issue=4 |pages=500–512 |doi=10.1007/BF02866548 |year=2000 |bibcode=2000EcBot..54..500V |hdl=1874/23514 |s2cid=24945604 |hdl-access=free }}

On the Indian subcontinent, the Gondi people use poison-plant extracts in fishing.{{citation | vauthors = Murthy EN, Pattanaik C, Reddy CS, Raju VS |date=March 2010 |title=Piscicidal plants used by Gond tribe of Kawal wildlife sanctuary, Andhra Pradesh, India |journal=Indian Journal of Natural Products and Resources |volume=1 |issue=1 |pages=97–101 |url=https://nopr.niscair.res.in/handle/123456789/7696 |access-date=22 September 2010 |archive-date=21 July 2011 |archive-url=https://web.archive.org/web/20110721183513/https://nopr.niscair.res.in/handle/123456789/7696 |url-status=live }}

In 16th century, saponins-rich plant, Agrostemma githago, was used to treat ulcers, fistulas, and hemorrhages.{{cite journal | vauthors = Smakosz A, Matkowski A, Nawrot-Hadzik I | title = Phytochemistry and Biological Activities of Agrostemma Genus-A Review | journal = Plants | volume = 13 | issue = 12 | pages = 1673 | date = June 2024 | pmid = 38931105 | pmc = 11207627 | doi = 10.3390/plants13121673 | doi-access = free }}

Many of California's Native American tribes traditionally used soaproot (genus Chlorogalum), and/or the root of various yucca 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, and the Mattole.{{Cite book | vauthors = Campbell P |title=Survival skills of native California |publisher=Gibbs Smith |year=1999 |pages=433 |url=https://books.google.com/books?id=qSRLW5ziVFAC&q=soaproot+fish+poison&pg=PA433 |isbn=978-0-87905-921-7 |access-date=20 November 2020 |archive-date=28 February 2022 |archive-url=https://web.archive.org/web/20220228103955/https://books.google.com/books?id=qSRLW5ziVFAC&q=soaproot+fish+poison&pg=PA433 |url-status=live }}

File:Solanine.svg, a highly toxic alkaloid saponin found in the nightshade family. The lipophilic steroidal structure is the series of connected six- and five-atom rings at the right of the structure, while the hydrophilic chain of sugar units is to the left and below. Note the nitrogen atom in the steroid skeleton at right, indicating this compound is a glycoalkaloid.]]

The vast heterogeneity of structures underlying this class of compounds makes generalizations difficult; they're a subclass of terpenoids, oxygenated derivatives of terpene hydrocarbons. Terpenes in turn are formally made up of five-carbon isoprene 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 (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.

• Cardenolide
• Cardiac glycoside
• Phytochemical

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{{commons category|Saponins}}

{{Saponins}}

{{Glycosides}}

{{Terpenoids}}

{{Phytochemical}}

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Category:Saponaceous plants

Category:Wood extracts