Undescribed C-Glycosylflavones from Corn Silk and Potential Anti-inflammatory Activity Evaluation of Isolates^{[ # ]}

Abstract

Phytochemical investigation of corn silk resulted in isolation and characterization of four flavone C-glycosides, chrysoeriol 6-C-β-oliopyranosyl-7-O-β-D-glucopyranoside (1), 3′-methoxycassiaoccidentalin A (2), chrysoeriol 6-C-β-boivinopyranosyl-7-O-β-D-glucopyranoside (3), and ax-4″-OH-3′-methoxymaysin (4), a triterpenoid, friedelin (5), two sterols, (22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol (6) and 6β-hydroxystigmasta-4,22-diene-3-one (7), and a mixture of β-sitosterol and stigmasterol. Compounds 1 and 2 were previously undescribed. Structure elucidation of the isolated compounds was attained using spectral data including 1D and 2D NMR and HRESIMS. Compounds1, 2, 5, and 6 inhibited iNOS activity in LPS-induced macrophages and decreased nitrite levels by 68.64 ± 4.46, 65.67 ± 6.47, 88.50 ± 0.50, and 94.00 ± 4.00%, respectively, at 50 µM. Compound 5 also showed inhibition of NF-κB (51.00 ± 1.50%). Compounds 1 and 2 induced NAG-1 activity in chondrocytes by 1.80 ± 0.05 and 2.00 ± 0.13 fold, respectively. The extract of corn silk, however, did not exhibit inhibition of iNOS or NF-κB but induced NAG-1 by 1.80 ± 0.51 fold.

Key words

Zea mays - Corn silk - Poaceae - C-Glycosylflavones - anti-inflammatory

^# Dedicated to Professor Dr. A. Douglas Kinghorn on the occasion of his 75th birthday.

Publication History

Received: 15 October 2021

Accepted after revision: 23 December 2021

Accepted Manuscript online:
24 December 2021

Article published online:
03 March 2022

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