Narirutin

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Narirutin
Narirutin.png
Names
IUPAC name
(2S)-4′,5-Dihydroxy-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)-14,25,43,44,45,73,74,75-Octahydroxy-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
Naringenin-7-O-rutinoside
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.034.655 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C27H32O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
    Key: HXTFHSYLYXVTHC-AJHDJQPGSA-N
  • InChI=1/C27H32O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
    Key: HXTFHSYLYXVTHC-AJHDJQPGBL
  • 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)OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)O)O)O)O)O)O)O)O
Properties
C27H32O14
Molar mass 580.539 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Narirutin is a flavanone-7-O-glycoside, consisting of the flavanone naringenin bonded with the disaccharide rutinose. [1]

It is found in orange juice. [1] [2]

Narirutin is found in citrus fruits such as Yuzu, grapefruit, mandarins, especially in their peels. There are reports that Narirutin is abundant in Jabara [3] (A fruit discovered and grown in the Kitayama village, Wakayama prefecture, Japan).

Narirutin is reported to be effective for allergies caused by immunoglobulin E antibodies. [3] Those allergies include hayfever and some cases of food allergy.

  1. When an allergen (pollen, dust) enters the body, the body produces immunoglobulin E antibodies, resulting in an antigen-antibody reaction.
  2. The antibodies are attached to mast cells, which release bioactive substances such as histamine and serotonin.
  3. Histamine causes expansion of blood vessels, resulting in allergic reactions such as low blood pressure, increased heart rate, skin itchiness, sneezing, runny nose, etc.

Narirutin is said to prevent the release of histamine by the mast cells, reducing the allergic symptoms. [3]

Ultraviolet 280 nm chromatogram after UHPLC separation of commercial orange juice. Narirutin is peak at 14.65 min. Orange juice UHPLC UV chromatogram.png
Ultraviolet 280 nm chromatogram after UHPLC separation of commercial orange juice. Narirutin is peak at 14.65 min.

References

  1. 1 2 Rouseff, Russell L.; Martin, Shirley F.; Youtsey, Charles O. (1987). "Quantitative survey of narirutin, naringin, hesperidin, and neohesperidin in citrus". Journal of Agricultural and Food Chemistry . 35 (6): 1027–1030. Bibcode:1987JAFC...35.1027R. doi:10.1021/jf00078a040. ISSN   0021-8561.
  2. ↑ Widmer W.W and Martin S.F. (1993). "Interferences with naringin and neohesperidin analysis by high performance liquid chromatography".
  3. 1 2 3 Tomida, Chisato; Otani, Yoshito; Sawada, Megumi (12 December 2020). "和歌山県北山村産柑橘類ジャバラの花粉症症状に対する効果 および客観的な花粉症治療効果指標の探索" (PDF).
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