Veronicastroside

Veronicastroside (identical to Lonicerin[1]) is a flavone, a type of flavonoid. It is the 7-O-neohesperidoside of luteolin. It can be found in Veronicastrum sibiricum var. japonicum[2] and in Teucrium gnaphalodes.[3]

Veronicastroside
Chemical structure of veronicastroside
Names
IUPAC name
3′,4′,5-Trihydroxy-7-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyloxy]flavone
Systematic IUPAC name
7-{[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5-hydroxy-4H-1-benzopyran-4-one
Other names
Luteolin 7-O-neohesperidoside
Scolymoside
Lonicerin
Luteolin-7-rutinoside
Luteoline-7-rhamnoglucoside
Identifiers
3D model (JSmol)
ChemSpider
KEGG
UNII
  • InChI=1S/C27H30O15/c1-9-20(33)22(35)24(37)26(38-9)42-25-23(36)21(34)18(8-28)41-27(25)39-11-5-14(31)19-15(32)7-16(40-17(19)6-11)10-2-3-12(29)13(30)4-10/h2-7,9,18,20-31,33-37H,8H2,1H3/t9-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
    Key: SHPPXMGVUDNKLV-KMFFXDMSSA-N
  • InChI=1/C27H30O15/c1-9-20(33)22(35)24(37)26(38-9)42-25-23(36)21(34)18(8-28)41-27(25)39-11-5-14(31)19-15(32)7-16(40-17(19)6-11)10-2-3-12(29)13(30)4-10/h2-7,9,18,20-31,33-37H,8H2,1H3/t9-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
    Key: SHPPXMGVUDNKLV-KMFFXDMSBP
  • C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2Oc3cc(c4c(=O)cc(oc4c3)c5ccc(c(c5)O)O)O)CO)O)O)O)O)O
Properties
C27H30O15
Molar mass 594.52 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Inagaki, Isao; Sakushima, Akiyo; Hisada, Sueo; Nishibe, Sansei; Morita, Naokata (1974). Lonicerinとveronicastrosideの比較 [Comparison of lonicerin and veronicastroside]. Yakugaku Zasshi (in Japanese). 94 (4): 524–525. doi:10.1248/yakushi1947.94.4_524. PMID 4473018.
  2. Inouye, Hiroyuki; Aoki, Yasuhiko; Wagner, Hildebert; Hörhammer, Ludwig; Aurnhammer, Gerold; Budweg, Wolfgang (1969). "Die Flavonglykoside von Veronicastrum sibiricum Pennell var. japonicum Hara und Synthese des Luteolin-7-neohesperidosids (Veronicastrosid)". Chemische Berichte (in German). 102 (9): 3009–3013. doi:10.1002/cber.19691020917. PMID 5806152.
  3. Barberán, F. A. T.; Gil, M. I.; Tomás, F.; Ferreres, F.; Arques, A. (1985). "Flavonoid aglycones and glycosides from Teucrium gnaphalodes". Journal of Natural Products. 48 (5): 859–860. doi:10.1021/np50041a040.
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