Guaijaverin
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Names
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IUPAC name
3-(α-L-Arabinopyranosyloxy)-3′,4′,5,7-tetrahydroxyflavone
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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
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Other names
Guajavarin Guaijaverin Guajaverin CHEMBL464507 Quercetin 3-arabinoside
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Identifiers
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ChEMBL
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ChemSpider
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EC Number
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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
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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
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Properties
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C20H18O11
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Molar mass
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434.353 g·mol−1
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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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 |
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Backbone | |
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Flavonols | Aglycones | |
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Conjugates | Glycosides of herbacetin | |
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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)
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Glycosides of myricetin | |
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Conjugates of quercetin | |
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O-Methylated flavonols | Aglycones | |
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Glycosides | of isorhamnetin |
- Narcissin (Isorhamnetin 3-O-rutinoside)
- Isorhamnetin 3-O-glucoside
- Tamarixetin 7-rutinoside
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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)
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Derivative flavonols | Aglycones |
- Noricaritin
- Dihydronoricaritin
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Glycosides | |
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Pyranoflavonols | |
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Furanoflavonols | |
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Semisynthetic | |
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