57378-72-0 Usage
Description
4,5-Dicaffeoylquinic acid (4,5-DCQA) is a polyphenol originally isolated from G. fagetorum and G. pseudomollugo that has diverse biological activities, including anti-HIV replication, antioxidative, anti-inflammatory, and anti-melanogenic properties. It inhibits HIV-1 integrase 3'' end processing, 3’ end joining, and disintegration with IC50 values of 0.13, 0.24, and 0.3 μg/ml, respectively. It also inhibits HIV-1 replication in MT-2 T lymphoblastoid cells with an EC50 value of 2 μg/ml. 4,5-DCQA scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay (IC50 = 19.8 μM) and inhibits superoxide production in human neutrophils activated by N-formyl-Met-Leu-Phe (fMLF; ) and cytochalasin B (; IC50 = 1.49 μM). It decreases prostaglandin E2 (PGE2; ) production in LPS-stimulated U937 cells when used at concentrations of 5 and 10 μg/ml but increases it when used at 200 μg/ml and increases production of TNF-α at concentrations ranging from 5 to 200 μg/ml. It inhibits the synthesis of MCP3 in U937 cells. 4,5-DCQA (25 μM) inhibits melanogenesis by 84% and decreases the levels of proteins involved in melanin biosynthesis, including tyrosinase, TRP-1, DCT, and MITF in B16F1 murine melanocytes.
Check Digit Verification of cas no
The CAS Registry Mumber 57378-72-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,7,3,7 and 8 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 57378-72:
(7*5)+(6*7)+(5*3)+(4*7)+(3*8)+(2*7)+(1*2)=160
160 % 10 = 0
So 57378-72-0 is a valid CAS Registry Number.
InChI:InChI=1/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
57378-72-0Relevant articles and documents
Structure-activity relationship of caffeoylquinic acids on the accelerating activity on ATP production
Miyamae, Yusaku,Kurisu, Manami,Han, Junkyu,Isoda, Hiroko,Shigemori, Hideyuki
experimental part, p. 502 - 507 (2011/06/10)
Caffeoylquinic acid (CQA) is one of the phenylpropanoids which have various bioactivities such as antioxidant, antibacterial, anticancer, antihistamic, and other biological effects. We previously reported that 3,5-di-O-caffeoylquinic acid inhibited amyloid β1-42-induced cellular toxicity on human neuroblastoma SH-SY5Y cells and increased the mRNA expression level of glycolytic enzymes and the intracellular ATP level. To investigate structure-activity relationship on the accelerating activity on ATP production, we synthesized 1,4,5-tri-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid, 3,4,5-tri-O-caffeoylquinic acid, and other derivatives. Additionally, we evaluated intracellular ATP level in SH-SY5Y treated with each CQA derivative. As a result, 3,4,5-tri-O-caffeoylquinic acid showed the highest accelerating activity on ATP production among tested compounds. It was suggested that caffeoyl groups bound to quinic acid are important for activity and the more caffeoyl groups are bound to quinic acid, the higher accelerating activity on ATP production exhibits.