Catalpol
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IUPAC name
(1aS,1bS,2S,5aR,6S,6aS)-6-Hydroxy-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[2′,3′:4,5]cyclopenta[1,2-c]pyran-2-yl β-D-glucopyranoside
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Systematic IUPAC name
(2S,3R,4S,5S,6R)-2-{[(1aS,1bS,2S,5aR,6S,6aS)-6-Hydroxy-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[2′,3′:4,5]cyclopenta[1,2-c]pyran-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol | |
Identifiers | |
3D model (
JSmol ) |
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ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.017.568 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C15H22O10 | |
Molar mass | 362.331 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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Catalpol is an iridoid glucoside. This natural product falls in the class of iridoid glycosides, which are simply monoterpenes with a glucose molecule attached.
Natural occurrence
First isolated in 1962, catalpol was named for plants in the genus Catalpa in which it was discovered. Later in 1969, catalpol was found to be present in larger quantities in several plants in genus Rehmannia (Orobanchaceae).[1] It is also found in plants belonging to several families, including, but not limited to, Scrophulariaceae, Lamiaceae (including scullcap[2][3]), Plantaginaceae (Plantago sp[4]) and Bignoniaceae,[5] all of which being in the order Lamiales.
Because they feed on these plants, variable checkerspot butterflies (Euphydryas chalcedona) contain high amounts of catalpol,[6] which makes them unpalatable to predators and thus serves as a defense mechanism.[7]
Biosynthetic pathway
Though first isolated in the 1960s, there has been very little investigation of the
Footnotes
- ISBN 0-387-19309-X.
- ISBN 0853692890.)
{{cite book}}
: CS1 maint: multiple names: authors list (link - ^ Yaghmai and Benson, 1979 M.S. Yaghmai, G.G. Benson The wax hydrocarbons of Scutellaria lateriflora L Manchester, England (1979) 228–229 p
- ^ PMID 11117882.
- ^ .
- doi:10.1016/s0031-9422(00)89516-3.)
{{cite journal}}
: CS1 maint: multiple names: authors list (link - PMID 28563381.
- ^ Jansen, S. R. (1991). "Plant iridoids, their biosynthesis and distribution in angiosperms". Ecological Chemistry and Biochemistry of Plant Terpenoids. Clarence Press. pp. 133–158.