Sarracenin
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| Names | |
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| Preferred IUPAC name
Methyl (1S,3S,7R,8R,9R)-9-methyl-2,4,10-trioxatricyclo[5.3.1.03,8]undec-5-ene-6-carboxylate | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C11H14O5 | |
| Molar mass | 226.228 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sarracenin is an iridoid found in several plant species in the carnivorous family Sarraceniaceae[1]. It also occurs in other non-carnivorous plants such as Strychnos spinosa (Loganiaceae)[2] and Patrinia heterophylla (Caprifoliaceae)[3].
History
Sarracenin was first isolated from the roots of Sarracenia flava in 1976. Analysis of S. flava extracts was prompted by their use as a folk remedy by people of the Okefenokee swamp region[4].
Biosynthesis
Sarracenin is believed to be derived from loganin, with either morronoside or secologanin serving as intermediates in the biosynthetic process[4].
Uses
Sarracenin displays antimicrobial activity against several pathogens including Staphylococcus aureus, Streptococcus pyogenes, Shigella dysenteriae, Klebsiella pneumonia, Candida albicans, Candida tropicalis, Candida thrusei, and Candida stellatoidea[2]. It has also demonstrated cytotoxicity against three tumor cell lines: A375 (human melanoma cell), SGC-7901 (human gastric cancer cell), and HeLa[3].
Ecology
Sarracenin is the primary volatile present in the insect-attracting spoons of Heliamphora species. When Heliamphora plants were grown in a laboratory setting, sarracenin was rarely present in these spoons. Plants that did produce sarracenin generally attracted more insects than those without, suggesting a role in prey attraction or capture[5].
References
- ^ Hotti, Hannu; Gopalacharyulu, Peddinti; Seppänen-Laakso, Tuulikki; Rischer, Heiko (2017-02-21). "Metabolite profiling of the carnivorous pitcher plants Darlingtonia and Sarracenia". PLOS ONE. 12 (2): e0171078. doi:10.1371/journal.pone.0171078. ISSN 1932-6203. PMC 5319649. PMID 28222171.
{{cite journal}}: CS1 maint: PMC format (link) CS1 maint: unflagged free DOI (link) - ^ a b Tor-anyiin, T.; Igoli, J.; Anyam, J.; Anyam, J. N. (2015). "isolation and Antimicrobial Activity of Sarracenin From Root Bark of Strychnos Spinosa". undefined.
- ^ a b Sheng, Li; Yang, Yue; Zhang, Yi; Li, Ning (2019-05-23). "Chemical constituents of Patrinia heterophylla Bunge and selective cytotoxicity against six human tumor cells". Journal of Ethnopharmacology. 236: 129–135. doi:10.1016/j.jep.2019.03.005. ISSN 1872-7573. PMID 30853646.
- ^ a b Miles, D. Howard; Kokpol, Udom; Bhattacharyya, J.; Atwood, Jerry L.; Stone, Karen E.; Bryson, Thomas A.; Wilson, Charles (1976-03). "Structure of sarracenin. An unusual enol diacetal monoterpene from the insectivorous plant Sarracenia flava". Journal of the American Chemical Society. 98 (6): 1569–1573. doi:10.1021/ja00422a048. ISSN 0002-7863.
{{cite journal}}: Check date values in:|date=(help) - ^ Jaffé, Klaus; Blum, Murray S.; Fales, Henry M.; Mason, Robert T.; Cabrera, Aivlé (1995-03-01). "On insect attractants from pitcher plants of the genusHeliamphora (sarraceniaceae)". Journal of Chemical Ecology. 21 (3): 379–384. doi:10.1007/BF02036725. ISSN 1573-1561.