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'[[File:Solanine chemical structure.png|thumb|Chemical structure of the saponin [[solanine]]]] '''Saponins''' a class of chemical compounds found in particular abundance in various plant species. More specifically, they are [[amphipathic]] [[glycoside]]s grouped phenomenologically by the soap-like foam they produce when shaken in [[aqueous]] solutions, and structurally by having one or more [[hydrophilic]] glycoside moieties combined with a [[lipophilic]] [[triterpene]] or [[steroid]] derivative.<ref name=hosettman>{{cite book |first=K. |last=Hostettmann |author2=A. Marston |title=Saponins |publisher=[[Cambridge University Press]] |location=[[Cambridge]] |year=1995 |page=3ff |isbn=978-0-521-32970-5 |oclc=29670810}}</ref><ref name=cornell>{{cite web |url=http://www.ansci.cornell.edu/plants/toxicagents/saponin.html |title=Saponins |date=14 August 2008 |publisher=[[Cornell University]] |accessdate=23 February 2009}}</ref> ==Structural variety and biosynthesis== The [[aglycone]] (glycoside-free) portions of the saponins are termed [[sapogenin]]s. The number of saccharide chains attached to the sapogenin/aglycone core can vary{{spaced ndash}}giving rise to another dimension of nomenclature (monodesmosidic, bidesmosidic, etc.<ref name=hosettman/>){{spaced ndash}}as can the length of each chain. A somewhat dated compilation has the range of saccharide chain lengths being 1–11, with the numbers 2–5 being the most frequent, and with both linear and branched chain saccharides being represented.<ref name=hosettman/> Dietary monosaccharides such as [[Glucose|<small>D</small>-glucose]] and [[galactose|<small>D</small>-galactose]] are among the most common components of the attached chains.<ref name=hosettman/> The lipophilic aglycone can be any one of a wide variety of [[polycyclic compound|polycyclic]] [[Organic chemistry#Molecular structure of an organic compound|organic structure]]s originating from the serial addition of 10-carbon (C10) [[terpene]] units to compose a C30 triterpene skeleton,<ref name=dixon>{{cite web |url=http://www.noble.org/Plantbio/Dixon/Personnel/project_summaries/Saponin.html |title=Project Summary: Functional Genomics of Triterpene Saponin Biosynthesis in Medicago Truncatula |accessdate=23 February 2009}}</ref><ref name=metacyc2008a>{{cite web |url=http://BioCyc.org/META/NEW-IMAGE?type=PATHWAY&object=PWY-5203&detail-level=3 |title=MetaCyc Pathway: saponin biosynthesis I |first=Hartmut |last=Foerster |date=22 May 2006 |accessdate=23 February 2009}}</ref> often with subsequent alteration to produce a C27 steroidal skeleton.<ref name=hosettman/> The subset of saponins that are steroidal have been termed saraponins.<ref name=cornell/> Aglycone derivatives can also incorporate nitrogen, so some saponins also present chemical and pharmacologic characteristics of [[alkaloid]] natural products. The figure at right above presents the structure of the alkaloid [[phytotoxin]] [[solanine]], a monodesmosidic, branched-saccharide steroidal saponin. (The lipophilic steroidal structure is the series of connected six- and five-membered rings at the right of the structure, while the three oxygen-rich sugar rings are at left and below. Note the nitrogen atom inserted into the steroid skeleton at right.) ==Sources== Saponins have historically been understood to be plant-derived, but they have also been isolated from marine organisms such as sea cucumber.<ref name=hosettman/><ref name=riguera>{{cite journal |first=Ricardo |last=Riguera |date=August 1997 |title=Isolating bioactive compounds from marine organisms |journal=Journal of Marine Biotechnology |volume=5 |issue=4 |pages=187–193 |url=http://www.springerlink.com/content/m9cclbrm1y0e5ge5/}}{{dead link|date=February 2020|bot=medic}}{{cbignore|bot=medic}}</ref> Saponins are indeed found in many plants,<ref name=hosettman/><ref name=birk>{{cite book |first=Irvin E |last=Liener |title=Toxic constituents of plant foodstuffs |publisher=[[Academic Press]] |location=[[New York City]] |year=1980 |page=161 |isbn=978-0-12-449960-7 |oclc=5447168}}{{Verify source|date=March 2009}}</ref> and derive their name from the soapwort plant (genus ''[[Saponaria]]'', family [[Caryophyllaceae]]), the root of which was used historically as a soap.<ref name=cornell/> Saponins are also found in the botanical family [[Sapindaceae]], including its defining genus ''[[Sapindus]]'' (soapberry or soapnut) and the [[Aesculus_hippocastanum|horse chestnut]], and in the closely related families [[Aceraceae]] (maples) and [[Hippocastanaceae]]). It is also found heavily in ''[[Gynostemma pentaphyllum]]'' (''[[Gynostemma]]'', [[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. Within these families, this class of chemical compounds is found in various parts of the plant: leaves, stems, roots, bulbs, blossom and fruit.<ref>http://sun.ars-grin.gov:8080/npgspub/xsql/duke/plantdisp.xsql?taxon=691</ref> Commercial formulations of plant-derived saponins, e.g., from the soap bark (or soapbark) tree, ''[[Quillaja saponaria]]'', and those from other sources are available via controlled manufacturing processes, which make them of use as chemical and biomedical reagents.<ref name=signma-aldrich>{{cite web |url=http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=S4521%7CSIGMA&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&F=SPEC |title=Saponin from quillaja bark |publisher=[[Sigma-Aldrich]] |accessdate=23 February 2009}}</ref> In China, the rhizomes (tubers) of ''[[Dioscorea zingiberensis]]'' C.H. Wright also produces steroidal saponins (TSS) as part of a treatment for [[cardiovascular disease]].<ref>{{cite journal |last1=Li |first1=H. |last2=Huang |first2=W. |last3=Wen |first3=Y. |last4=Gong |first4=G. |last5=Zhao |first5=Q. |last6=Yu |first6=G. |title=Anti-thrombotic activity and chemical characterization of steroidal saponins from Dioscorea zingiberensis C.H. Wright. |journal=Fitoterapia |date=December 2010 |volume=81 |issue=8 |pages=1147–56 |doi=10.1016/j.fitote.2010.07.016 |pmid=20659537 }}</ref> == Test == ; Froth Test: Uses plant Gogo (bark) ''Entada phaseoloides'' as control. The positive result shows a honeycomb froth that is higher than 2&nbsp;cm that persists for 10 minutes or longer. Blood Agar Media (BAM): Is an agar cup semi-quantitative method that shows positive result of hemolytic halos.<ref>Antibacterial activity of leave extracts of Nymphaea lotus (Nymphaeaceae) on [[Methicillin-resistant Staphylococcus aureus]] (MRSA) and Vancomycin resistant Staphylococcus aureus (VRSA) isolated from clinical samples. Akinjogunla OJ, Yah CS, Eghafona NO and Ogbemudia FO, Annals of Biological Research, 2010, 1 (2), pages 174–184</ref> == Role in plant ecology and impact on animal foraging == In plants, saponins may serve as anti-feedants,<ref name=cornell/><ref name=metacyc2008a/> 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.<ref name=metacyc2008a/> Some saponins are toxic to cold-blooded organisms and insects at particular concentrations.<ref name=metacyc2008a/> 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.<ref name=metacyc2008a/> ==Ethnobotany== Most saponins, which readily dissolve in water, are poisonous to fish.<ref>{{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|last1 = Howes|first1 = F. N.}}</ref> Therefore, in [[ethnobotany]], they are primarily known for their use by indigenous people in obtaining aquatic food sources. Since prehistoric times, cultures throughout the world have used fish-killing plants, mostly those containing saponins, for fishing.<ref>{{citation |authors=Jonathan G. Cannon, Robert A. Burton, Steven G. Wood, and Noel L. Owen |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 }}</ref><ref>{{citation |author=C. E. Bradley |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 }}</ref> Although prohibited by law, fish-poison plants are still widely used by indigenous tribes in [[Guyana]].<ref>{{citation |author=Tinde Van Andel |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 }}</ref> On the Indian subcontinent, the [[Gondi people]] are known for their use of poison-plant extracts in fishing.<ref>{{citation |author=Murthy E N, Pattanaik, Chiranjibi, Reddy, C Sudhakar, Raju, V S |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=http://nopr.niscair.res.in/handle/123456789/7696}}</ref> Many of California's [[Native Americans in the United States|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, mixing in water to create a foam, and then add the suds to 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 [[Eel River Athapaskan peoples|Lassik]], the [[Luiseño people|Luiseño]], and the [[Mattole]].<ref>{{Cite book |last=Campbell |first=Paul |title=Survival skills of native California |publisher=Gibbs Smith |edition= |year=1999 |pages=433 |url=https://books.google.com/books?id=qSRLW5ziVFAC&pg=PA433&lpg=PA433&dq=soaproot+fish+poison#v=onepage&q=soaproot%20fish%20poison&f=false |isbn=978-0-87905-921-7}}</ref> <ref><ref><ref></ref></ref></ref>==Research and uses== The [[amphipathic]] nature of saponins gives them activity as [[surfactant]]s with potential ability to interact with [[cell membrane]] components, such as [[cholesterol]] and [[phospholipid]]s, possibly making saponins useful for development of [[cosmetics]] and [[drug]]s.<ref name="lorent">{{cite journal | last=Lorent | first=Joseph H. | last2=Quetin-Leclercq | first2=Joëlle | last3=Mingeot-Leclercq | first3=Marie-Paule | 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 and Biomolecular Chemistry | publisher=Royal Society of Chemistry | volume=12 | issue=44 | date=2014-11-28 | issn=1477-0520 | pmid=25295776 | doi=10.1039/c4ob01652a | pages=8803–8822| url=https://semanticscholar.org/paper/e9fe89606e655ae732b91e133fcb29ef62a96d42 }}</ref> Saponins have also been used as [[adjuvant]]s in development of [[vaccine]]s,<ref name="sun">{{cite journal | last=Sun | first=Hong-Xiang | last2=Xie | first2=Yong | last3=Ye | first3=Yi-Ping | title=Advances in saponin-based adjuvants | journal=Vaccine | volume=27 | issue=12 | year=2009 | issn=0264-410X | pmid=19208455 | doi=10.1016/j.vaccine.2009.01.091 | pages=1787–1796}}</ref> such as [[Quil A]], an [[extract]] from the bark of ''[[Quillaja saponaria]]'' Molina (commonly called "quillaja").<ref name=lorent/><ref name="drugs">{{cite web | title=Quillaja | publisher=Drugs.com | date=2018 | url=https://www.drugs.com/npp/quillaja.html | accessdate=26 December 2018}}</ref> This makes them of interest for possible use in [[subunit vaccine]]s and vaccines directed against intracellular pathogens.<ref name=sun/> In their use as [[adjuvant]]s in the production of vaccines, toxicity associated with [[sterol]] complexation remains a concern.<ref name=skene>{{cite journal |first=Caroline D. |last=Skene |author2=Philip Sutton |title=Saponin-adjuvanted particulate vaccines for clinical use |journal=Methods |volume=40 |issue=1 |pages=53–9 |date=1 September 2006 |pmid=16997713 |doi=10.1016/j.ymeth.2006.05.019}}</ref> While saponins are promoted commercially as dietary supplements and [[food ingredient]]s,<ref>{{cite web|url=http://www.webmd.com/vitamins-supplements/ingredientmono-39-tribulus.aspx?activeingredientid=39&activeingredientname=tribulus|title=Tribulus|publisher=WebMD|accessdate=July 31, 2015}}</ref> and are used in [[traditional medicine]] preparations from [[licorice]],<ref name=asl>{{cite journal |first=Marjan Nassiri |last=Asl |author2=Hossein Hosseinzadeh |title=Review of pharmacological effects of ''Glycyrrhiza'' sp. and its bioactive compounds |journal=[[Phytotherapy Research]] |volume=22 |issue=6 |pages=709–24 |date=1 June 2008 |pmid=18446848 |doi=10.1002/ptr.2362}}</ref><ref name=xu>{{Cite book |author1=Xu R |author2=Zhao W |author3=Xu J |author4=Shao B |author5=Qin G |title=Studies on bioactive saponins from Chinese medicinal plants |volume=404 |pages=371–82 |year=1996 |pmid=8957308 |doi=10.1007/978-1-4899-1367-8_30 |series=Advances in Experimental Medicine and Biology |isbn=978-1-4899-1369-2}}</ref> there is no [[evidence-based medicine|high-quality clinical evidence]] that they have any beneficial effect on human health.<ref name=drugs/> Quillaja is toxic when consumed in large amounts, involving possible [[hepatotoxicity|liver damage]], gastric pain, [[diarrhea]], or other [[adverse event|adverse effects]].<ref name=drugs/> Saponins are used for their effects on [[ammonia]] emissions in animal feeding.<ref name=zentner>{{cite web |first=Eduard |last=Zentner |date=July 2011 |title=Effects of phytogenic feed additives containing quillaja saponaria on ammonia in fattening pigs |url=http://www.delacon.com/phytogenics/articles/Effects-of-phytogenic-feed-additives-containing-quillaja-saponaria-on-ammonia-in-fattening-pigs.pdf |accessdate=27 November 2012}}</ref> The plant Çöven, Gypsophila simonii is widely distributed throughout Çankırı, where it is a native species, and Turkey. In this study, chemical and physical properties of unripe saponins obtained by extraction from the roots of Gypsophila simonii, an endemic plant, were isolated and investigated. Purified aglycones recovered from acid hydrolysis of the saponins were separated by reversed chromatography on a thin layer of silica gel. Phytochemical tests showed the presence of terpenoids in the crude extracts. <ref>Yücekutlu A.N., Bildacı,I., (2008). Determination of Plant Saponins and Some of Gypsophila Species: A review of the literature, Hacettepe J. Biol. & Chem., Volume 36, Issue 2, 129-135.</ref> == See also == * [[Phytochemical]] * [[Triterpenoid saponins]] ==References== {{Reflist|2}} 25. Yücekutlu A.N., Bildacı,I., (2008). Determination of Plant Saponins and Some of Gypsophila Species: A review of the literature, Hacettepe J. Biol. & Chem., Volume 36, Issue 2, 129-135. ==External links== {{commons category|Saponins}} * [http://cancerweb.ncl.ac.uk/cgi-bin/omd?saponin Medical Dictionary on Saponin] * [https://www.sciencedaily.com/releases/2003/09/030909070840.htm Saponins in Wine], by ScienceDaily, accessed Sep 9,2003 * [http://micro.magnet.fsu.edu/phytochemicals/pages/saponin.html Molecular Expressions Phytochemical Gallery – Saponin] * [http://lpi.oregonstate.edu/sp-su98/saponins.html Saponins: Suprising &#91;sic&#93; benefits of desert plants] * [https://web.archive.org/web/20050206095031/http://www.dkc.cl/03%20USES.htm Other uses of Quillaja Saponins and derived products], some works of different authors. * [https://www.newscientist.com/article/mg14519651.400-how-to-survive-the-worlds-worst-diet.html How to survive the world's worst diet] * [http://www.inchem.org/documents/jecfa/jecmono/v48je03.htm Quillia Extracts] JECFA Food Additives Series 48 {{Saponins}} {{Glycosides}} {{Terpenoids}} {{Phytochemical}} {{Use dmy dates|date=July 2011}} [[Category:Saponins|Saponins]] [[Category:Saponaceous plants]]'