TY - JOUR
T1 - Synthesis and radical-scavenging activity of C-methylated fisetin analogues
AU - Imai, Kohei
AU - Nakanishi, Ikuo
AU - Ohkubo, Kei
AU - Ohno, Akiko
AU - Mizuno, Mirei
AU - Fukuzumi, Shunichi
AU - Matsumoto, Ken ichiro
AU - Fukuhara, Kiyoshi
N1 - Funding Information:
This work was partially supported by Grant-in-Aid ( 15K18901 to K.I., 26460056 to I.N. and 18K06588 to K.F.) from the Ministry of Education, Culture, Sports, Science and Technology , Japan.
Publisher Copyright:
© 2019
PY - 2019/4/15
Y1 - 2019/4/15
N2 - The radical-scavenging reaction of fisetin, a natural antioxidant found in strawberries, is known to proceed via hydrogen transfer to produce a fisetin radical intermediate. Thus, introduction of an electron-donating group into the fisetin molecule is expected to stabilize the radical, leading to enhanced radical-scavenging activity. In this study, fisetin derivatives in which methyl substituents were introduced at the ortho positions relative to the catechol hydroxyl groups were synthesized and their radical scavenging activities were evaluated and compared with that of the parent fisetin molecule. Among the methyl derivatives, 5′-methyl fisetin, in which the inherent planar structure of fisetin was retained, exhibited the strongest radical scavenging activity. Introduction of methyl substituents may be effective for the enhancement of various biological activities of antioxidants, particularly radical-scavenging activity.
AB - The radical-scavenging reaction of fisetin, a natural antioxidant found in strawberries, is known to proceed via hydrogen transfer to produce a fisetin radical intermediate. Thus, introduction of an electron-donating group into the fisetin molecule is expected to stabilize the radical, leading to enhanced radical-scavenging activity. In this study, fisetin derivatives in which methyl substituents were introduced at the ortho positions relative to the catechol hydroxyl groups were synthesized and their radical scavenging activities were evaluated and compared with that of the parent fisetin molecule. Among the methyl derivatives, 5′-methyl fisetin, in which the inherent planar structure of fisetin was retained, exhibited the strongest radical scavenging activity. Introduction of methyl substituents may be effective for the enhancement of various biological activities of antioxidants, particularly radical-scavenging activity.
KW - Antioxidant
KW - Antioxidant activity
KW - Fisetin
KW - Methyl group
KW - Radical-scavenging activity
UR - http://www.scopus.com/inward/record.url?scp=85062224720&partnerID=8YFLogxK
U2 - 10.1016/j.bmc.2019.02.033
DO - 10.1016/j.bmc.2019.02.033
M3 - Article
C2 - 30846403
AN - SCOPUS:85062224720
SN - 0968-0896
VL - 27
SP - 1720
EP - 1727
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 8
ER -