Protective Effect of Tetrahydroquinolines from the Edible Insect Allomyrina dichotoma on LPS-Induced Vascular Inflammatory Responses.

Inwha Park,Youngbum Yoo,Minkyun Na,Hyosoo Shin,Jae Sam Hwang,Jong-Sup Bae,Mi-Ae Kim,Wonhwa Lee,Hyelim Kim,Joonseok Oh

doi:10.3390/ijms21103406

Abstract

The larva of Allomyrina dichotoma (family Scarabaeidae) is an edible insect that is registered in the Korean Food Standards Codex as a food resource. The chemical study on the larvae of A. dichotoma resulted in the isolation of three new tetrahydroquinolines, allomyrinaines A–C (1–3), one new dopamine derivative, allomyrinamide A (4), and four known compounds (5–8). The structures were elucidated on the basis of 1D and 2D nuclear magnetic resonance (NMR) and MS spectroscopic data analysis. Allomyrinaines A–C (1–3) possessed three stereogenic centers at C-2, C-3, and C-4, whose relative configurations were determined by analyses of the coupling constants and the nuclear Overhauser enhancement spectroscopy (NOESY) data, as well as DP4+ calculation. The anti-inflammatory effects of compounds 1–4 were evaluated in human endothelial cells. Allomyrinaines A–C (1–3) could stabilize vascular barrier integrity on lipopolysaccharide (LPS)-induced vascular inflammation via inhibition of the nuclear factor-κB (NF-κB) pathway. The physiologically relevant concentration was confirmed by Q-TOF-MS-based quantitative analysis on allomyrinaines A–C in crude extract. This study suggests that allomyrinaines A–C (1–3) are bioactive constituents of A. dichotoma to treat vascular inflammatory disorder.

Highlights

The most commonly consumed insects are beetles (Coleoptera) [1]
(4) were were isolated isolated from from dichotoma larvae, and their structures were established by spectroscopic techniques, A. dichotoma larvae, and their structures were established by spectroscopic techniques, especially especially detailed magnetic resonance (NMR)(NMR)
We found that LPS induced the upregulation of the surface protein expressions of vascular cell adhesion molecule-1 (VCAM-1) and intercellular adhesion molecule-1 (ICAM-1) (Figure 3C,D) and that each compound inhibited this effect, suggesting that the inhibitory effects of each compound on the expression of Cell adhesion molecules (CAMs) are mediated via the attenuation of the LPS signaling pathway by each compound

Summary

Introduction

The most commonly consumed insects are beetles (Coleoptera) [1]. Allomyrina dichotomaL. (family Scarabaeidae, order Coleoptera), a rhinoceros beetle, is mainly distributed in Korea, Japan, China, and Taiwan. The most commonly consumed insects are beetles (Coleoptera) [1]. L. (family Scarabaeidae, order Coleoptera), a rhinoceros beetle, is mainly distributed in Korea, Japan, China, and Taiwan. The larva of A. dichotoma has been registered in the Korean Food. Standards Codex as a new food resource. Researches have focused on this insect resource for the development of functional food and medicinal material. Chemical investigations of A. dichotoma reported that it contains general nutrients such as fatty acids and nucleosides [2,3].

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