Guaijaverin
Names
IUPAC name
3-(α-L -Arabinopyranosyloxy)-3′,4′,5,7-tetrahydroxyflavone
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S ,3R ,4S ,5S )-3,4,5-trihydroxyoxan-2-yl]oxy}-4H -1-benzopyran-4-one
Other names
Guajavarin Guaijaverin Guajaverin CHEMBL464507 Quercetin 3-arabinoside
Identifiers
ChEMBL
ChemSpider
EC Number
InChI=1S/C20H18O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15,17,20-26,28H,6H2/t12-,15-,17+,20-/m0/s1
Key: PZZRDJXEMZMZFD-IEGSVRCHSA-N
C1[C@@H]([C@@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
Properties
C 20 H 18 O 11
Molar mass
434.353 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Guaijaverin is the 3-O -arabinoside of quercetin . It is found in the leaves of Psidium guajava , the common guava.[ 1] [ 2] [ 3]
References
^ Prabu, G.R.; Gnanamani, A.; Sadulla, S. (2006). "Guaijaverin – a plant flavonoid as potential antiplaque agent against Streptococcus mutans". Journal of Applied Microbiology . 101 (2): 487– 495. doi :10.1111/j.1365-2672.2006.02912.x . PMID 16882158 . S2CID 11574034 .
^ Seshadri, T.R.; Vasishta, Krishna (1965). "Polyphenols of the leaves of psidium guava—quercetin, guaijaverin, leucocyanidin and amritoside". Phytochemistry . 4 (6): 989– 992. Bibcode :1965PChem...4..989S . doi :10.1016/S0031-9422(00)86281-0 .
^ El Khadem, H.; Mohammed, Y. S. (1958). "675. Constituents of the leaves of Psidium guaijava, L. Part II. Quercetin, avicularin, and guaijaverin". Journal of the Chemical Society (Resumed) : 3320. doi :10.1039/JR9580003320 .
Flavonols and their conjugates
Backbone
Flavonols
Aglycones Conjugates
Glycosides of herbacetin Glycosides of kaempferol
Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)
Glycosides of myricetin Conjugates of quercetin
O -Methylated flavonols
Aglycones Glycosides
of isorhamnetin
Narcissin (Isorhamnetin 3-O-rutinoside)
Isorhamnetin 3-O-glucoside
Tamarixetin 7-rutinoside
other
Azalein (Azaleatin 3-O-α-L-rhamnoside)
Centaurein (Centaureidin 7-O-glucoside)
Eupalin (Eupalitin 3-0-rhamnoside)
Eupatolin (Eupatolitin 3-O-rhamnoside)
Jacein (Jaceidin 7-O-glucoside)
Patulitrin (Patuletin 7-O-glucoside
Xanthorhamnin (Rhamnetin glycoside)
Derivative flavonols
Aglycones
Noricaritin
Dihydronoricaritin
Glycosides
Pyranoflavonols
Furanoflavonols
Semisynthetic