Sarracenin
Chemical compound
From Wikipedia, the free encyclopedia
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]
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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 | |
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3D model (JSmol) |
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| ChEMBL | |
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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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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]