TY - JOUR
T1 - Synthesis of acetyl and benzoyl esters of xanthorrhizol and its oxidation products and evaluation of their inhibitory activity against nitric oxide production
AU - Rahayu, Maya Damayanti
AU - Kusumaningrum, Susi
AU - Hayun, Hayun
N1 - Publisher Copyright:
© 2020 The Authors. Published by Innovare Academic Sciences Pvt Ltd.
PY - 2020/3
Y1 - 2020/3
N2 - Objective: Xanthorrhizol is known to have anti-inflammatory activity. However, new xanthorrhizol derivatives with improved anti-inflammatory activity and reduced toxicity are needed. Methods: In this study, the derivatives of xanthorrhizol were synthesized and spectroscopically characterized, and their inhibitory activities against nitric oxide [NO] production were evaluated in RAW 264.7 macrophage cells. Results: The first stage of synthesis produced compounds 2a and 2b in 58.49% and 63.26% yields, respectively. Compounds 2a and 2b were oxidized using potassium permanganate, giving compounds 3a and 3b in yields of 51.92% and 43.78%, respectively. Compounds 1, 2a, 3a, and 3b along with diclofenac sodium [the positive control] exhibited IC50 values for NO production of 31.82, 73.85, 354.05, 97.19, and 78.43 µM, respectively. In contrast, compound 2b did not show any inhibitory activity. Based on cytotoxicity assay, compounds 1, 2a, 2b, 3a, 3b, and diclofenac sodium had LD50 values of 30.97, 65.15, 31.15, 117.86, 53.40, and 51.67 µM, respectively. The NO inhibitory activities of compounds 2a, 3a, and 3b were lower than that of xanthorrhizol [compound 1]. However, cytotoxicity tests showed that compounds 2a, 3a, and 3b had reduced toxicities compared to xanthorrhizol. Conclusion: The modification of xanthorrhizol through esterification and oxidation produced derivative compounds with weaker anti-inflammatory activity but reduced cytotoxicity.
AB - Objective: Xanthorrhizol is known to have anti-inflammatory activity. However, new xanthorrhizol derivatives with improved anti-inflammatory activity and reduced toxicity are needed. Methods: In this study, the derivatives of xanthorrhizol were synthesized and spectroscopically characterized, and their inhibitory activities against nitric oxide [NO] production were evaluated in RAW 264.7 macrophage cells. Results: The first stage of synthesis produced compounds 2a and 2b in 58.49% and 63.26% yields, respectively. Compounds 2a and 2b were oxidized using potassium permanganate, giving compounds 3a and 3b in yields of 51.92% and 43.78%, respectively. Compounds 1, 2a, 3a, and 3b along with diclofenac sodium [the positive control] exhibited IC50 values for NO production of 31.82, 73.85, 354.05, 97.19, and 78.43 µM, respectively. In contrast, compound 2b did not show any inhibitory activity. Based on cytotoxicity assay, compounds 1, 2a, 2b, 3a, 3b, and diclofenac sodium had LD50 values of 30.97, 65.15, 31.15, 117.86, 53.40, and 51.67 µM, respectively. The NO inhibitory activities of compounds 2a, 3a, and 3b were lower than that of xanthorrhizol [compound 1]. However, cytotoxicity tests showed that compounds 2a, 3a, and 3b had reduced toxicities compared to xanthorrhizol. Conclusion: The modification of xanthorrhizol through esterification and oxidation produced derivative compounds with weaker anti-inflammatory activity but reduced cytotoxicity.
KW - Nitric oxide
KW - Oxidation
KW - Potassium permanganate
KW - Raw 264.7 cells
KW - Xanthorrhizol
UR - http://www.scopus.com/inward/record.url?scp=85084134565&partnerID=8YFLogxK
U2 - 10.22159/ijap.2020.v12s1.FF030
DO - 10.22159/ijap.2020.v12s1.FF030
M3 - Article
AN - SCOPUS:85084134565
SN - 0975-7058
VL - 12
SP - 135
EP - 138
JO - International Journal of Applied Pharmaceutics
JF - International Journal of Applied Pharmaceutics
IS - Special Issue 1
ER -