Three new 3-formyl-2-arylbenzofurans from Itea yunnanensis and their anti-hepatocellular carcinoma effects

Abstract

Five 3-formyl-2-arylbenzofuran derivatives, including three new compounds (1-3) and two known analogues (4-5), were identified from the 95% EtOH extract of Itea yunnanensis. Extensive spectroscopic analyses were performed for the structure elucidation of all new benzofurans, and single-crystal X-ray diffraction analyses were further employed for the structure verification of iteafuranals C (1) and D (2). In MTT assay, iteafuranal E (3) and iteafuranal A (4) displayed significant growth inhibition effect on SK-Hep-1 cells with IC 50 values of 5.365 μM and 6.013 μM, respectively.The colony formation assay of 3 and 4 further confirmed their remarkable inhibitory effect on cell growth. Preliminary mechanism study demonstrated that 3 remarkably down-regulated the phosphorylation level of ERK, which suggested 3 could inhibit cell growth and induce apoptosis of SK-Hep-1 cells by blocking RAS/RAF/MEK/ERK signaling pathway. This study highlighted the potential of 3-fomyl-2-benzofuran derivatives as novel lead compounds to treat Hepatocellular carcinoma.

Two New Compounds Isolated from the Itea omeiensis and Their Anti‐oxidant Activities

“…[3] Among them, several Itea species were used as folk medicines to cure diseases such as cough, snakebite and traumatic injury, [4] indicating their potential application in the field of new drug discovery. In our previous chemical investigations on Itea plants, flavonoids and 2-arylbenzo[b]furans were identified as their anti-oxidant and anti-hepatocellular carcinoma components, [5][6][7][8] which further validated the research value of Itea plants in drug discovery. Itea omeiensis C. K. Shneider is mainly distributed in western China, [3] and widely used as a folk medicine to serve as tonic, and to cure cough as well as throast-swelling.…”

Qualitative and quantitative method for quality control of Itea ilicifolia based on antioxidant Q‐markers

“…However, the samples displayed high similarities in fingerprint analyses, suggesting the necessity of quantification of Q‐markers in quality control. In addition, iteafuranal A, which belongs to the 2‐arylbenzofurans widely present in Itea genus plants (Bohm et al, 1999; Luo et al, 2014), exhibited a significant inhibitory effect on the proliferation of SK‐Hep‐1 cells with an IC 50 value of 6.01 μ m in our previous study (Lang et al, 2022), indicating that iteafuranal A may be conceived of as an important indicator with strong specificity when evaluating its anti‐hepatoma quality.…”

“…Based on comparison of retention times and characteristic UV spectral patterns with those of reference substances (Figures S1 and S2), 10 common peaks were identified as isoorientin (second peak), orientin (third peak), vitexin (fifth peak), isovitexin (sixth peak), iteafuranal E (ninth peak), iteafuranal D (thirteenth peak), iteafuranal F (fourteenth peak), iteafuranal C (fifteenth peak), iteafuranal A (sixteenth peak) and ( E )‐2‐(4‐hydroxyphenyl)‐5‐(prop‐1‐en‐1‐yl) benzofuran‐3‐ carbaldehyde (seventeenth peak) (Lang et al, 2022).…”

“…T A B L E 2 Similarity evaluation between 14 batches of I. ilicifolia samples. (E)-2-(4-hydroxyphenyl)-5-(prop-1-en-1-yl) benzofuran-3-carbaldehyde (seventeenth peak) (Lang et al, 2022).…”

Anticancer therapeutic potential of benzofuran scaffolds

“…Thus, the 3-formylbenzofuran derivatives 3b and 3c had the potential to be lead structures as anti-hepatocellular carcinoma agents. 31 …”