1. Simultaneous SPE-LC Determination of Three Flavonoid Glycosides of Naringin, Neohesperidin and Hesperidin in Da-Cheng-Qi Decoction
Fengguo Xu, Ying Liu, Zunjian Zhang. Chromatographia 2007, 66, November (No. 9/10)
A number of HPLC methods have been developed for the determination of hesperetin, naringin and neohesperidin in Chinese medicinal materials, either aloneor in two combinations. Tong et al., Liang et al., Lei et al. and Wang et al. reported a HPLC-UV method to determine hesperidin in Frucyus Aurantii immaturus, Zhizhu Capsule and Pericarpium Citri Reticulatae, respec- tively. Yang et al. determined neohesperidin in Fructus Aurantii by RP-HPLC. Xia et al. reported an alternative method to determine hesperidin in Pericarpium Citri Reticulatae by semi-micro HPLC with electrochemical detection. In these studies only one compound was quantiﬁed. Afterwards, Yang et al. reported a modiﬁed HPLC method to simultaneous determine naringin and hesperidin in Fructus Aurantii. Besides, Kanaze et al. developed a simultaneous RP-HPLC method for the determination of diosmin, hesperidin and naringin in diﬀerent citrus fruit juices and pharmaceutical formulations. However, some of these methods are time-consuming, some are using gradient elution. And no rapid HPLC method combined with SPE has been developed for the simultaneous analysis of the three ﬂavonoid glycosides in compound traditional Chinese medicine remedies, a more complex system.
2. Antiallergic activity of unripe Citrus hassaku fruits extract and its ﬂavanone glycosides on chemical substance-induced dermatitis in mice
Kimihisa Itoh, Megumi Masuda, Shunsuke Naruto. J Nat Med (2009) 63:443–450
For the purpose of identiﬁcation of active constituents of unripe C. hassaku fruits, CH-ext was fractionated by solvent extraction to give a hexane-soluble fraction, an ethyl acetate-soluble fraction, a water-soluble fraction and a water–ethyl acetate-insoluble intermediate fraction. Among them, the ethyl acetate-soluble fraction and the water–ethyl acetate-insoluble intermediate fraction showed more potent histamine release inhibitory activities than the hexane-soluble fraction as described above in Fractionation of CH-ext, whereas the water-soluble fraction was inactive. On HPLC analysis, the ﬂavanone glycoside content (in milligrams per gram) of CH-ext was: naringin, 206.8; neohesperidin, 94.7; narirutin, 28.5; and hesperidin, 8.9.
That of the ethyl acetate-soluble fraction was: naringin, 345.9; neohesperidin, 189.4; narirutin, 56.3; and hesperidin, 41.6. That of the water–ethyl acetate-insoluble intermediate fraction was: naringin, 674.2; neohesperidin, 81.1; narirutin, not detected; and hesperidin, not detected. Thus the two fractions were ﬂavanone glycoside-rich fractions in which naringin and neohesperidin were major ﬂavanones, and narirutin as well as hesperidin were minor ﬂavanones. In the previous paper, we reported that four ﬂavanone glycosides of Citrus fruits, namely hesperidin, narirutin, naringin and neohesperidin, showed potent histamine release inhibitory activity. Percentage inhibition values at 1 mM of naringin, neohesperidin, narirutin, hesperidin and sodium cromoglycate (SCG, a reference compound) were 43.7, 26.7, 47.3, 49.8 and 36.5, respectively. On the basis of these ﬁnding, we reasonably assumed that the histamine release inhibitory effect of CH-ext is attributable to naringin and neohesperidin.
3. Determination of Metabolism of Neohesperidin by Human Intestinal Bacteria by UPLC-Q-TOF/MS
Wei Zhang • Shu Jiang • Dawei Qian. Chromatographia (2014) 77:439–445
Aurantii Fructus (Zhiqiao), the dried, immature fruit of Citrus aurantium L., is a well-known traditional Chinese medicine (TCM) with antioxidant, anti-tumor, antihypertension, anti-shock, etc. activities. Flavonoids are considered to be themajor bioactive constituents ofAurantii Fructus . The ﬂavanone glycoside neohesperidin which composed of the ﬂavanone hesperetin and the disaccharide neohesperidoside is a plentiful and inexpensive by-product of Aurantii Fructus. Neohesperidin has been investigated intensively and has been found to possess a wide range of pharmacological properties, such as anti-proliferative effect on human hepatoma cell lines, the suppression of infection-induced endotoxin shock in mice, anti-allergic, antioxidant, anti-estrogen, neuroprotective activity, and the inhibition of tumor promotion. It has free radical scavenging activity, as well as protective effects on potential gastric diseases . In addition, neohesperidin is important industrial precursors for converting to its corresponding dihydrochalcone, with sweet values relative to sucrose of 1,000 for neohesperidin dihydrochalcone. Therefore, neohesperidin are natural bioactive compounds with important health and industrial beneﬁts.