Sarracenin

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Sarracenin
Sarracenin.svg
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)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C11H14O5/c1-5-9-6-3-8(15-5)16-11(9)14-4-7(6)10(12)13-2/h4-6,8-9,11H,3H2,1-2H3
    Key: QGBCGMGBGAHJIT-UHFFFAOYSA-N
  • CC1C2C3CC(O1)OC2OC=C3C(=O)OC
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 pneumoniae , 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] Sarracenin is also present in the pitchers and lids of Darlingtonia californica and many Sarracenia species, likely serving the same purpose as in Heliamphora. [1]

References

  1. 1 2 Hotti H, Gopalacharyulu P, Seppänen-Laakso T, Rischer H (2017-02-21). "Metabolite profiling of the carnivorous pitcher plants Darlingtonia and Sarracenia". PLOS ONE. 12 (2) e0171078. Bibcode:2017PLoSO..1271078H. doi: 10.1371/journal.pone.0171078 . PMC   5319649 . PMID   28222171.
  2. 1 2 Tor-Anyiin TA, Igoli JO, Anyam JV, Anyam JN (2015). "Isolation and Antimicrobial Activity of Sarracenin From Root Bark of Strychnos Spinosa". Journal of Chemical Society of Nigeria. 40 (1). S2CID   55620516.
  3. 1 2 Sheng L, Yang Y, Zhang Y, Li N (May 2019). "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. PMID   30853646. S2CID   73727478.
  4. 1 2 Miles DH, Kokpol U, Bhattacharyya J, Atwood JL, Stone KE, Bryson TA, Wilson C (March 1976). "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.
  5. ↑ Jaffé K, Blum MS, Fales HM, Mason RT, Cabrera A (March 1995). "On insect attractants from pitcher plants of the genusHeliamphora (sarraceniaceae)". Journal of Chemical Ecology. 21 (3): 379–384. Bibcode:1995JCEco..21..379J. doi:10.1007/BF02036725. PMID   24234068. S2CID   12537352.
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