Eriocitrin

Eriocitrin
Names
IUPAC name
(2S)-3′,4′,5-Trihydroxy-7-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]flavan-4-one
Systematic IUPAC name
(22S,42S,43R,44S,45S,46R,72R,73R,74R,75R,76S)-13,14,25,43,44,45,73,74,75-Nonahydroxy-76-methyl-22,23-dihydro-24H-3,6-dioxa-2(2,7)-[1]benzopyrana-4(2,6),7(2)-bis(oxana)-1(1)-benzenaheptaphan-24-one
Other names
Eriodictyol glycoside
Eriodictyol-7-O-rutinoside
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.033.321 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C27H32O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-6,9,16,18,20-30,32-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
    Key: OMQADRGFMLGFJF-MNPJBKLOSA-N
  • InChI=1/C27H32O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-6,9,16,18,20-30,32-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
    Key: OMQADRGFMLGFJF-MNPJBKLOBI
  • C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)Oc3cc(c4c(c3)O[C@@H](CC4=O)c5ccc(c(c5)O)O)O)O)O)O)O)O)O
Properties
C27H32O15
Molar mass 596.538 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Eriocitrin (eriodictyol glycoside) is a flavanone-7-O-glycoside between the flavanone eriodictyol and the disaccharide rutinose. It is commonly found in lemons and other citrus fruits.[1][2][3][4] It is colloquially called lemon flavonoid or a citrus flavonoid, one of the plant pigments that bring color to fruit and flowers. This antioxidant also predominates (38% in 1 study) in Peppermint infusions.

The compound has lipid-lowering properties in liver cells.[5] It is marketed as a dietary supplement, usually in conjunction with B and C vitamins and other substances, but there is no established medical use or FDA approved application of the compound.

  1. ^ Cao X, He Y, Kong Y, Mei X, Huo Y, He Y, Liu J (September 2019). "Elucidating the interaction mechanism of eriocitrin with β-casein by multi-spectroscopic and molecular simulation methods". Food Hydrocolloids. 94: 63–70. doi:10.1016/j.foodhyd.2019.03.006. ISSN 0268-005X. S2CID 107490400.
  2. ^ Miyake Y, Suzuki E, Ohya S, Fukumoto S, Hiramitsu M, Sakaida K, Osawa T, Furuichi Y (2006-11-13). "Lipid-Lowering Effect of Eriocitrin, the Main Flavonoid in Lemon Fruit, in Rats on a High-Fat and High-Cholesterol Diet". Journal of Food Science. 71 (9): S633–S637. doi:10.1111/j.1750-3841.2006.00192.x. ISSN 0022-1147.
  3. ^ Miyake Y, Yamamoto K, Morimitsu Y, Osawa T (1997-12-01). "Isolation of C -Glucosylflavone from Lemon Peel and Antioxidative Activity of Flavonoid Compounds in Lemon Fruit". Journal of Agricultural and Food Chemistry. 45 (12): 4619–4623. doi:10.1021/jf970498x. ISSN 0021-8561.
  4. ^ Miyake Y, Yamamoto K, Osawa T (1997). "Isolation of Eriocitrin (Eriodictyol 7-rutinoside) from Lemon Fruit (Citrus limon Burm. f.) and Its Antioxidative Activity". Food Science and Technology International, Tokyo. 3 (1): 84–89. doi:10.3136/fsti9596t9798.3.84. ISSN 1881-3976.
  5. ^ Hiramitsu M, Shimada Y, Kuroyanagi J, Inoue T, Katagiri T, Zang L, et al. (January 2014). "Eriocitrin ameliorates diet-induced hepatic steatosis with activation of mitochondrial biogenesis". Scientific Reports. 4: 3708. Bibcode:2014NatSR...4E3708H. doi:10.1038/srep03708. PMC 3892443. PMID 24424211.