Recent Advances of Apigenin and Its Derivatives on Pharmacological Activities
XING Zhi-hua
School of Pharmacy, Harbin University of Commerce, Key Laboratory of Pharmacy Constructed by Central and Local, Key Laboratory for Drug Research on Prevention and Treatment of Geriatric Diseases of Heilongjiang Province, Harbin 150076, China
Abstract��Apigenin,as a natural drug, has a variety of pharmacological activities.The review articles of its anti-tumor, neuroprotection, protection of myocardial injury, reproductive endocrine regulation,antioxidant, hypoglycemic, anti-inflammatory, prevention and cure of cardiovascular diseases and other aspects have been reported. This paper summarized antiviral, antifungal, slimming, anti parasite, immune regulation, recover of spinal cord injury, osteogenic differentiation, osteoporosis, bone petrochemical, anti-inflammatory and anti gout of apigenin . At the same time, the synthetic route and pharmacological action of its derivative are also summarized, which provides a reference for its reasonable development and utilization.
��־��. �۲��ؼ���������ҩ�������о��½�չ[J]. �й�ҩѧ��־, 2018, 53(15): 1241-1247.
XING Zhi-hua. Recent Advances of Apigenin and Its Derivatives on Pharmacological Activities. Chinese Pharmaceutical Journal, 2018, 53(15): 1241-1247.
LIU H B,SUI H X, ZHI Y, et al. Acute toxicity,genetic toxicity and sub-chronic toxicity of apigenin[J].Chin J Food Hyg (�й�ʳƷ������־),2011,23(6):489-494.
[2]
HUANG J Y, YANG Y, LI Y R, et al. Research progress of apigenin[J]. Jiangsu Sci Technol Inf(���տƼ���Ϣ),2015,27(9):1193-1196.
[3]
LIN L W,XIN Q. Progress in the research of pharmacology of apigenin[J]. China Trop Med(�й��ȴ�ҽѧ),2012, 12(8):1023-1026.
[4]
WU C C,FANG C Y, CHENG Y J, et al. Inhibition of Epstein-Barr virus reactivation by the flavonoid apigenin[J].J Biomed Sci,2017,24(1):1-13.
[5]
HAKOBYAN A,ARABYAN E,AVETISYAN A, et al. Apigenin inhibits African swine fever virus infection in vitro[J].Arch Virol,2016,161(12):3445-3453.
[6]
HONG Y N, CHUN J,KIM Y S. Anti-adipogenic activity of Carduus crispus and its constituent apigenin in 3T3-L1 adipocytes by downregulating PPAR��and C/EBP��[J].Eur Food Res Technol,2016,242(9):1555-1563.
[7]
HIL H V D, SCHOTHORST E M V, STELT I V D, et al. Direct comparison of metabolic health effects of the avonoids quercetin,hesperetin,epicatechin,apigenin and anthocyanins in high-fat-diet-fed mice[J].Genes Nutr,2015,10(4):23.
[8]
MYOUNG H J, KIM G, NAM K W, et al. Apigenin isolated from the seeds of Perilla frutescens Britton var crispa (Benth.) inhibits food intake in C57BL/6J mice[J].Arch Pharm Res,2010,33(11):1741-1746.
[9]
YOON Y A, KIM H, LIRA Y. Relationships between the larval growth inhibition of caenorhabditis elegans by apigenin derivatives and their structures[J].Arch Pharm Res,2006,29(7):582-586.
[10]
YANO S, UMEDA D, YAMASHITA T, et al. Dietary flavones suppresses IgE and Th2 cytokines in OVA-immunized BALB/c mice[J].Eur J Nutr,2007,46(5):257-263.
[11]
GINWALA R,MCTISH E, RAMAN C, et al. Apigenin, a natural flavonoid,attenuates EAE severity through the modulation of dendritic cell and other immune cell functions[J].J Neuroimmun Pharmacol,2016,11(1):36-47.
[12]
CHOI K C, LEE B S, CHUNG W T, et al. Protective effects of apigenin and quercetin on aflatoxin B1-induced immunotoxicity in mice[J]. Food Sci Biotechnol, 2010,19(4):987-992.
[13]
ZHANG F, LI F, CHEN G.Neuroprotective effect of apigenin in rats after contusive spinal cord injury[J].Neurol Sci,2014,35(4):583-588.
[14]
ZHANG X, ZHOU C H,ZHA X, et al. Apigenin promotes osteogenic differentiation of human mesenchymal stem cells through JNK and p38 MAPK pathways[J].Mol Cell Biochem,2015,407(1-2):41-50.
[15]
GOTO T, HAGIWARA K, SHIRAI N, et al. Apigenin inhibits osteoblastogenesis and osteoclastogenesis and prevents bone loss in ovariectomized mice[J].Cytotechnology,2015,67(2):357-365.
[16]
LEE J H, ZHOU H Y, CHO S Y, et al. Anti-inflammatory mechanisms of apigenin: inhibition of cyclooxygenase-2 expression,adhesion of monocytes to human umbilical vein endothelial cells,and expression of cellular adhesion molecules[J].Arch Pharm Res,2007,30(10):1318-1327.
[17]
KILANI-JAZIRI S, MUSTAPHA N, MOKDAD-BZEOUICH I, et al. Flavones induce immunomodulatory and anti-inflammatory effects by activating cellular anti-oxidant activity:a structure-activity relationship study[J].Tumor Biol, 2016,37(5):6571-6579.
[18]
WANG J,LIAO Y Y, FAN J L, et al. Apigenin inhibits the expression of IL-6,IL-8,and ICAM-1 in DEHP-stimulated human umbilical vein endothelial cells and in vivo[J].Inflammation,2012,35(4):1466-1476.
[19]
KIM S J, LEE K T, CHOI H E, et al. Anti-inflammatory effects of flavonoids in Korean chrysanthemum species via suppression of inducible nitric oxide synthase and cyclooxygenase-2 in LPS-induced RAW 264.7 macrophages[J].Food Sci Biotechnol, 2015,24(3):975-985.
[20]
WANG J, LIU Y T, XIAO L, et al. Anti-inflammatory effects of apigenin in lipopolysaccharide induced inflammatory in acute lung injury by suppressing COX-2 and NF-kB pathway[J]. Inflammation,2014,37(6):2085-2090.
[21]
ZHANG S X, LIU X Y, SUN C M, et al. Apigenin attenuates experimental autoimmune myocarditis by modulating Th1/Th2 cytokine balance in mice[J].Inflammation,2016,39(2):678-686.
[22]
PATIL R H, BABU R L, NAVEEN K M, et al. Apigenin inhibits PMA-induced expression of pro-inflammatory cytokines and AP-1 factors in A549 cells[J].Mol Cell Biochem,2015,403(1-2):95-106.
[23]
PATIL R H, BABU R L, NAVEEN K M, et al. Anti-inflammatory effect of apigenin on LPS-induced pro-inflammatory mediators and AP-1 factors in human lung epithelial cells[J]. Inflammation,2016,39(1):138-147.
[24]
YAO F F,ZAHNG R,FU R J, et al. Effect and mechanism study of the same doses of quercetin and apigenin on hyperuricemic rats modern[J]. Prevent Med,2012,39(6):1365-1367.
[25]
LI C. The structure modification of apigenin and quercetin & 5-PBDMA block the potassium channel, hERG [D].Wuhan: Huazhong University of Science & Technology,2010.
[26]
LIU Y. Trimethylapigenin blocks cardiac potassium channels and increases late sodium current[D].Wuhan: Huazhong University of Science & Technology,2012.
[27]
XIANG H L,GENG Y J, WU Z J, et al. Synthesis and anti-hepatoma activities of apigenin etherified and brominated derivatives [J].J Hunan Normal Univ(Med Sci),2009,6(3):26-29.
[28]
CHEN L. Studies on the synthesis of bioactive apigenin and acacetin glycosides and flavonoids glycoconjugates[D].Changsha: Hunan University,2012.
[29]
GAO Q, LIAN G, LIN F. The first total synthesis of 7-O-��-D-glucopyranosyl-4'-O-��-L-rhamnopyranosyl apigenin via a hexanoyl ester-based protection strategy[J].Carbohydr Res, 2009, 344(4):511-515.
[30]
HAN T J. Design and synthesis of six kinds of flavone-7-phosphoramidate derivatives[D]. Dalian: Dalian University of Technoloby,2012.
[31]
DASKIEWICZ J B, DEPEINT F, VIORNERY L, et al. Effects of flavonoids on cell proliferation and caspase activation in a human colonic cell line HT29: an SAR study[J]. J Med Chem, 2005, 48(8):2790-2804.
[32]
YANG Y S,TAO L C,ZHANG Y P, et al. Structure aSm biological activity of the La(��) complex with apigenin[J]. Nat Prod Res Dev(��Ȼ�����о��뿪��),2014,26(9):1402-1406.
[33]
TANG X, ZHU X, LIU S, et al. Phytoestrogens induce differential estrogen receptor beta-mediated responses in transfected MG-63 cells[J]. Endocrine, 2008, 34(1-3):29-35.