Anti-Inflammatory Benzofuran Neolignans from the Fruits of Canarium album (Chinese Olive)

Abstract

Chinese olive is a well-known fruit in China. In this study, we explored anti-inflammatory phytochemicals of Chinese olive fruit, which led to the isolation of nine pairs of new enantiomers of benzofuran neolignans (1a/1b−9a/9b). Among them, the planar structures of compounds 1−3 were undescribed previously, and the absolute configurations of all compounds were reported first. Their stereostructures were elucidated on the basis of the interpretation of NMR, HRESIMS, and electronic circular dichroism (ECD) data, as well as ECD calculation. All compounds exhibited pronounced inhibitory effects on lipopolysaccharide-induced nitric oxide (NO) production in RAW 264.7 macrophages with IC 50 values ranging from 6.0 to 30.2 μM. Furthermore, compounds 6a and 6b exert anti-inflammatory effects by blocking the nuclear translocation of NF-κB, thereby reducing the expression of proinflammatory mediators COX-2, iNOS, IL-1β, and IL-6. This study could provide some guidance and evidence to the further development and utilization of the Chinese olive.

Identification of Scoparone from Chinese Olive Fruit as a Modulator of Macrophage Polarization

“…By processing several steps of the separation, we successfully identified scoparone (6,7-dimethoxycoumarin), which has been classified into the group of organic compounds known as coumarins and derivatives containing a 1-benzopyran moiety with a ketone group at the C-2 carbon atom (1-benzopyran-2-one), which belong to polycyclic aromatic compounds. Previous studies have reported approximately 15 pure compounds with anti-inflammatory effects from COE fruit extractions. − To our knowledge, this is the first study of the isolation of scoparone from COE fruit. After using a luciferase-based bioassay strategy, we calculated that the yield of scoparone from COE, COE-sup, COE-SD, and COE-SD11 was 0.48, 1.41, 28.67, and ∼100%, respectively.…”

The current status of old traditional medicine introduced from Persia to China

“…Chewing the fruit and swallowing the juice also helps to detoxify toxins from all kinds of fishes and turtles. Studies have proven that the chemicals of the fruits exert efficacy against some diseases, such as benzofuran neolignans for anti-inflammation ( Li et al, 2022b ), methyl brevifolincarboxylate ( Chen et al, 2020b ) and a polyphenolic compound isocorilagin ( Chen et al, 2020c ) both for influenza. The ethyl acetate fraction of Chinese olive was shown to regulate metabolic dysfunction in diabetes ( Yeh et al, 2017 ).…”

Pd-catalyzed decarboxylative 1,4-addition reactions of benzofuran-based azadienes with allyl phenyl carbonates

“…6 On the basis of previous works on the synthetic methodologies of both benzofuran-based azadienes and allyl phenyl carbonates, we devised and explored novel decarboxylative 1,4-addition reactions between benzofuran-based azadienes 1 and allyl phenyl carbonates 2 (Scheme 1-3). To our delight, we found that the newly designed decarboxylative 1,4-addition reactions proceeded efficiently and delivered structurally new and highly functionalized benzofuran skeletons with potential bioactivities 7 in acceptable chemical yields. Principally, the formation of the aromatic benzofuran ring in the products facilitates the observed 1,4-addition reactions in our work.…”