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Antioxidant and Anti-Inflammatory Flavonoids from the Flowers of Chuju, a Medical Cultivar of Chrysanthemum Morifolim Ramat

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Antioxidant and Anti-Inflammatory Flavonoids from the Flowers of Chuju, a Medical Cultivar of Chrysanthemum Morifolim Ramat J. Mex. Chem. Soc. 2017, 61(4), 282-289 Article © 2017, Sociedad Química de México ISSN 1870-249X Antioxidant and Anti-Inflammatory Flavonoids from the Flowers of Chuju, a Medical Cultivar of Chrysanthemum Morifolim Ramat Jun Hu,1 Wei Ma,2 Ning Li2,* and Kai-Jin Wang1,* 1 School of Life Sciences, Anhui University, 111 Jiulong Road, Hefei 230601, P. R. China 2 School of Pharmacy, Anhui Medical University, 81 Meishan Road, Hefei 230032, P. R. China *Corresponding authors E-mail address: [email protected] (N. Li), [email protected] (K. J. Wang) Received April 5th, 2017; Accepted June 23rd, 2017 Abstract Chuju, the flower of Chrysanthemum morifolim cv. Chuju, Resumen: La flor de Chrysanthemum morifolim cv. Chuju, conocida is a traditional medicine-food material used in China. Bioassay-guided popularmente como Chuju, se utiliza tradicionalmente como alimento chemical investigation on Chuju led the isolation of 16 flavonoids (1-16) y medicina en China. Un estudio químico biodirigido de un extracto de characterized as quercetin (1), isorhamnetin 3-O-b-D-glucoside (2), las flores condujo al aislamiento de 16 flavonoides, los cuales se carac- eriodictyol (3), pyracanthoside (4), apigenin (5), apigetrin (6), acace- terizaron como quercetina (1), isoramnetina 3-O-b-D-glucosido (2), tin (7), acacipetalin (8), luteolin (9), diosmetin (10), spinacetin (11), eriodictiol (3), piracantosido (4), apigenina (5), apigetrina (6), acaceti- axillarin (12), bonanzin (13), cirsiliol (14), chrysosplenol D (15) and na (7), acacipetalina (8), luteolina (9), diosmetina (10), espinacetina artemetin (16). Among them, compounds (11-16) were first reported (11), axilarina (12), bonanzina (13), cirsiliol (14), crisosplenol D (15) from the Chrsanthemum species. Chuju flavonoids displayed strong and artemetina (16). Los productos 11-16 se describen por primera vez antioxidant in DPPH (1, 1-diphenyl-2- picrylhydrazyl) radical scav- en la especie. Los flavonoides de Chuju demostraron una notable acti- enging assay, and high anti-inflammatory activity by inhibiting NO vidad antioxidante en el ensayo de captación del radical 2,2- dife- production in LPS-induced RAW 264.7 cells. These findings suggests nil-1-picrilhidrazilo (DPPH); asimismo presentaron un fuerte efecto that Chuju is an ideal source of natural flavonoids with significant an- antiinflamatorio in vitro, valorado a través de la inhibición de la pro- tioxidant and anti-inflammatory effects, and is worthy of further devel- ducción de NO en macrófagos RAW 264.7 estimulados con LPS. Estos opment as health-promoting food or supplement. resultados indican que Chuju es una fuente importante de flavonoides Keywords: Chrysanthemum morifolim cv. Chuju; Chuju flowers; fla- antiinflamatorios y antioxidantes con un potencial importante para su vonoids; antioxidant activity; anti-inflammatory activity. desarrollo como agente nutracéutico. Palabras clave: Chrysanthemum morifolim cv. Chuju; flores de Chu- ju; flavonoids; actividad antioxidante; actividad antiinflamatoria. Introduction Chrysanthemi Flos (CFs), termed as “Juhua” in Chinese, is the dried flower of Chrysanthemum morifolium Ramat (As- The oxidative stress emerges from the excessive generation of teraceae), which is a famous herbal medicine and food material reactive oxygen species (ROS). Persistent oxidative stress may in Southeast Asian countries such as China, South Korea, Ja- cause severe damages to proteins, lipids, DNA, and even result in pan and Singapore. C. morifolium was first originated in China, cell death [1]. These damages are often involved in the activation and has been cultivated for over 2000 years, forming a large of chronic inflammatory pathways leading to the progression of number of medicinal and horticultural cultivars during the long diseases including cancer, neurodegenerative disorders, athero- evolution. Hangju (C. morifolium cv. Hangju), Chuju (C. mori- sclerosis, cardiovascular diseases, diabetes, chronic kidney diseas- folium cv. Chuju), Gongju (C. morifolium cv. Gongju) and Boju es, and aging processes [2]. Antioxidants are considered beneficial (C. morifolium cv. Boju) are the four famous medicinal culti- for biological systems to scavenge ROS and protect cells from oxi- vars of C. morifolium recorded in Chinese Pharmacopeia. Chu- dative and inflammatory damages [3]. Synthetic antioxidants, such ju originated in Chuzhou, Anhui Province, China. Chuju was as propyl gallate (PG), butylated hydroxyanisole (BHA), tertiary once ranked first among the four famous medicinal cultivars of butyhydroquinone (TBHQ) and butylated hydroxytoluene (BHT), C. morifolium and chosen as the royal tribute in Qing Dynas- are widely used as food additives [4]. However, demands for nat- ty, and honored the national protected geographical indication urally occurring antioxidants have been increasing due to the con- (PGI) in 2002. Chuju was recorded the functions of scattering cerns about the safety of synthetic antioxidants [5]. As a class of cold, clearing away heat and toxins, and brightening eyes, and natural antioxidants, flavonoids have aroused much attention, and traditionally used for the treatment of head dizziness, pain and a lot of efforts have been made to search for antioxidant agents swelling of eyes, particular for diseases caused by upward-dis- from plants rich in flavonoids [6]. turbance of liver-yang [7]. Antioxidant and Anti-Inflammatory Flavonoids from the Flowers of Chuju, a Medical Cultivar of Chrysanthemum Morifolim Ramat 283 Previous studies demonstrated that CFs possessed anti-oxi- stronger antioxidant activities than that of the positive control dant, cardiovascular protection [8], anti-inflammation [9], hepa- ascorbic acid (SC50 = 28.40 μM). Five compounds (2, 5, 6, 10 to-protection [10], and anticancer [11] effects. Essential oil [12, and 11) exhibited moderate activity with the SC50 values ranged 13], terpenoids [9], flavonoids [14] and caffeoylquinic acids [15] from 51.62 to 130.42 μM. Compounds 7, 8, 13 and 16 appeared in CFs have been characterized. However, almost all the previous to have no activity because their SC50 values exceeded 500 μM. reports related to CFs were focused on Hangju, and no detailed Structure-activity relationships (SARs) analysis indicated investigation on Chuju has been carried out till now. that the B-ring hydroxylation pattern of flavonoids is the most Our preliminary experiments showed that Chuju were rich significant factor for DPPH antioxidant activity. The flavonoids in flavonoids. On the other hand, we found that the EtOH (1, 3, 4, 9, 12, 14 and 15) with an ortho 3’, 4’-dihydroxy mioety extract exhibited considerable antioxidant activity in 1, 1-di- in the B-ring possessed much higher antioxidant activity than phenyl-2-picrylhydrazyl radical (DPPH) assay and strongly in- compounds (2, 5, 6, 10 and 11) with only one free hydroxyl hibited the NO production in lipopolysaccharide (LPS)-induced group at C-3’ or C-4’ position in B-ring, due to the B-ring with murine macrophage RAW 264.7 cells. These results promoted 3’, 4’-dihydroxy could ensure the capacity for good radical us to perform a detailed bioassay guided chemical investigation stabilization by delocalization of the unpaired electron in the on Chuju, which led the isolation of 16 compounds from two aroxyl radical structure [27], this trend was further confirmed flavonoids-enriched fractions. Herin, the isolation, structural by the flavonoids (7, 8, 13 and 16) whose hydroxyl groups in determination, antioxidant and anti-inflammatory activities of B-ring have been substituted by methoxyl groups. Moreover, these flavonoids were described. comparison of the SC50 values of the glucosides (4 and 6) with their aglycones (3 and 5), indicated that the bigger group of O-glucosyl at C-7 had a negative effect on antioxidant activity Results and Discussion probaly for the steric hindrance; the same trend of effects were observed for compounds 1 and 2, the O-glucosyl at C-3 in com- Bioassay guided isolation and structural identification of pound 2 was partly responsible for the decrease of its antioxi- flavonoids 1-16 dant activity. The observation is consistent with those reported in previous literature [28, 29]. The 85% ethanol extract of the flowers of Chuju was parti- tioned by D101 macroporous resin CC to give four fractions Anti-inflammatory activity (A-D). In DPPH radical-scavenging assay, the antioxidant ac- tivity order of the four fractions was C > B > D > A; the same NO is one of the cellular inflammatory mediators of physiolog- order was shown in the experiment regarding the inhibitory ac- ical and pathological process [30, 31]. Stimulation of murine tivity on NO production in LPS-induced RAW 264.7 cells (Ta- macrophage RAW 264.7 cells by LPS induced inducible nitric ble 1). In total flavonoids content (TFC) experiment, fractions oxide synthase (iNOS) and overproduction of NO, which could C showed the highest level of TFC value, flowed by D, B and A be quantitative detected by colorimetric method. The results (Table 1). Thus, further purification was focused on the two fla- presented in Table 4 revealed that most of the flavonoids isolat- vonoids-enriched fractions (C and D). The isolated compounds ed from Chuju possessed considerable NO production inhibito- (Fig.1) included quercetin (1) [16], isorhamnetin 3-O-b-D-glu- ry activity. Comparing with the positive control ibuprofen (IC50 coside (2) [17], eriodictyol (3) [18], pyracanthoside (4) [19], = 30.57 μM), nine compounds (1, 5, 7, 9 - 11, 13, 14 and 16) apigenin (5) [20], apigetrin
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