Flavonoids from the Flowers of Citrus ‘Hebesu’

Abstract

2(S)-3’,4'-dimethoxy-5,7-dihydroxyflavanone 7-O-neohesperidoside (1), hesperidin (2), astragalin (3), trifolin (4), nicotiflorin (5), narirutin (6), rutin (7), kaempferol 7-O-rutinoside (8), tangeretin (9) and nobiletin (10) were isolated from the MeOH extract of flowers of Citrus ‘Hebesu’. Structures of these compounds were elucidated on the basis of physical and spectral data. Absolute configuration and complete NMR spectral data for compound 1 are reported for the first time in this paper.

Keywords

Citrus ‘Hebesu’Homohesperetin Flowers Flavonoids

References

Guzmán-Gutiérrez

S.L.

, Navarrete

(2009) Pharmacological exploration of the sedative mechanism of hesperidin identified as the active principle of Citrus sinensis flowers. Planta Medica, 75, 295–301.

Hosseini

, Pkan

, Rakhshandeh

, Aghaie

, Sadeghnia

H.R.

, Rohbardar

M.G.

(2011) The effect of hydro-alcoholic extract of Citrus flower on pentylenetetrazole and maximal electroshock-induced seizures in Mice. World Applied Sciences Journal, 15, 1104–1109.

Adhikari-Devkota

, Elbashir

S.M.I.

, Watanabe

, Devkota

H.P.

(2018) Chemical constituents from the flowers of Satsuma mandarin and their free radical scavenging and α-glucosidase inhibitory activities. Natural Product Research, in press, DOI: 10.1080/14786419.2018.1425856.

Kim

M-J

, Yang

K-W

, Yang

E-J

, Kim

S.S.

, Park

K.J.

, An

H.J.

, Choi

Y.H.

, Lee

N.H.

, Hyun

C-G

. (2015) Citrus unshiu flower inhibits LPS-induced iNOS and COX-2 via MAPKs in RAW 264.7 macrophages cells. Oriental Journal of Chemistry, 31, 1915–1922.

Duan

, Guo

, Dou

L-L

, Yu

K-Y

, Liu

E-H

, Li

(2014) Comparison of chemical profiling and antioxidant activities of fruits, leaves, branches, and flowers of Citrus grandis ‘Tomentosa’. Journal of Agricultural and Food Chemistry, 62, 11122–11129.

Carvalho

M.G.

, Costa

P.M.

, Abreu

H.S.

(1999) Flavanones from Vernonia diffusa. Journal of the Brazilian Chemical Society, 10, 163–166.

Slade

, Ferreira

, Marais

J.P.

(2005) Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids. Phytochemistry, 66, 2177–2215.

Vedwati

, Kalidhar

S.B.

(2010) Chemical examination of juice of Citrus sinensis variety Jaffa. Journal of Indian Chemical Society, 87, 749–750.

Markham

K.R.

, Chari

V.M.

(1982) Carbon-13 NMR spectroscopy of flavonoids. In The Flavonoids Advances in Research. Horborne

J.B.

, Mabry

T.J.

, Mabry

(Ed). Chapman and Hall, New York, 19–134.

10.

Wei

, Xie

, Fisher

, Sutherland

I.A.

(2011) Separation of patuletin-3-O-glucoside, astragalin, quercetin, kaempferol and isorhamnetin from Flaveria bidentis (L.) Kuntze by elution-pump-out high-performance counter-current chromatography. Journal of Chromatography A, 1218, 6206–6211.

11.

Jung

M.J.

, Chung

H.Y.

, Choi

J.H.

, Choi

J.S.

(2003) Antioxidant principles from the needles of red pine, Pinus densiflora. Phytotherapy Research, 17, 1064–1068.

12.

Baek

, Lee

H.L.

, Kang

K.S.

, Kim

K.H.

(2017) Chemical constituents from the fruits of Citrus unshiu and their inhibitory effects on acetylcholinesterase. Macedonian Journal of Chemistry and Chemical Engineering, 36, 15–22.

13.

Kim

W.C.

, Lee

D.Y.

, Lee

C.H.

, Kim

C.W.

(2004) Optimization of narirutin extraction during washing step of the pectin production from citrus peels. Journal of Food Engineering, 63, 191–197.

14.

Duan

, Dou

L-L

, Yu

K-Y

, Guo

, Bai-Zhong

, Li

, Liu

E-H

. (2017) Polymethoxyflavones in peel of Citrus reticulata ‘Chachi’ and their biological activities. Food Chemistry, 234, 254–261.

15.

Scordino

, Sabatino

, Belligno

, Gagliano

(2011) Characterization of polyphenolic compounds in unripe Chinotto (Citrus myrtifolia) fruit by HPLC/PDA/ESI/MS-MS. Natural Product Communications, 6, 1857–1862.

16.

Russo

, Bonaccorsi

, Torre

, Cotroneo

, Dugo

, Mondello

(2013) Determination of bioactive compounds in the juice of Pummelo (Citrus grandis Osbeck). Natural Product Communications, 8, 171–174.

17.

Zou

, Wang

, Liu

, Luo

, Chen

, Su

(2013) Melitidin: A flavanone glycoside from Citrus grandis ‘Tomentosa’. Natural Product Communications, 8, 457–458.

18.

Matsumoto

, Nishikawa

, Furukawa

, Itano

, Tamura

, Hasei

, Watanabe

(2017) Antimutagenic effects of polymethoxy flavonoids of Citrus unshiu. Natural Product Communications, 12, 23–26.

Supplementary Material

Please find the following supplemental material available below.

For Open Access articles published under a Creative Commons License, all supplemental material carries the same license as the article it is associated with.

For non-Open Access articles published, all supplemental material carries a non-exclusive license, and permission requests for re-use of supplemental material or any part of supplemental material shall be sent directly to the copyright owner as specified in the copyright notice associated with the article.

0.00 MB

0.59 MB