Sarracenin
This article, Sarracenin, has recently been created via the Articles for creation process. Please check to see if the reviewer has accidentally left this template after accepting the draft and take appropriate action as necessary.
Reviewer tools: Inform author |
This article, Sarracenin, has recently been created via the Articles for creation process. Please check to see if the reviewer has accidentally left this template after accepting the draft and take appropriate action as necessary.
Reviewer tools: Inform author |
![]() | |
Names | |
---|---|
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)
|
|
ChemSpider | |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
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).
|
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.