Anti-inflammatory sesquiterpene and triterpene acids from Mesona procumbens Hemsley

Hung-Tse Huang; I-Wen Lo; Geng-You Liao; Yu-Chi Lin; Yuh-Chiang Shen; Hui-Chi Huang; Tsung-Lin Li; Kung-Ta Lee; Yao-Haur Kuo; Chia-Ching Liaw

doi:10.3389/fchem.2022.1003356

Anti-inflammatory sesquiterpene and triterpene acids from Mesona procumbens Hemsley

Front Chem. 2022 Sep 15:10:1003356. doi: 10.3389/fchem.2022.1003356. eCollection 2022.

Authors

Hung-Tse Huang^{1

2}, I-Wen Lo³, Geng-You Liao⁴, Yu-Chi Lin¹, Yuh-Chiang Shen¹, Hui-Chi Huang⁵, Tsung-Lin Li³, Kung-Ta Lee², Yao-Haur Kuo^{1

6}, Chia-Ching Liaw^{1

7}

Affiliations

¹ National Research Institute of Chinese Medicine, Taipei, Taiwan.
² Department of Biochemical Science and Technology, National Taiwan University, Taipei, Taiwan.
³ Genomics Research Center, Academia Sinica, Taipei, Taiwan.
⁴ Institute of Physiology, School of Medicine, National Yang Ming Chiao Tung University, Taipei, Taiwan.
⁵ Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung, Taiwan.
⁶ Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University, Taichung, Taiwan.
⁷ Department of Biochemical Science and Technology, National Chiayi University, Chiayi, Taiwan.

Abstract

Mesona procumbens Hemsley is a plant conventionally processed to provide popular food materials and herbal medicines in Asia. In this study, six triterpene acids, including five new ones (mesonaic acids D-H, 1-5), and one proximadiol-type sesquiterpene (7) were isolated from the methanolic extract of the air-dried M. procumbens. Chemical structures of 1‒7 were established by spectroscopic methods, especially 2D NMR techniques (¹H-¹H COSY, HSQC, HMBC, and NOESY) and HRESIMS. Concerning their biological activities, compounds 1, 2, 6, and 7 were examined manifesting high inhibition toward the pro-inflammatory NO production with EC₅₀ values ranging from 12.88 to 21.21 µM, outrunning the positive control quercetin (24.12 µM). The mesoeudesmol B (7) identified from M. procumbens is the very first example, which exhibited high anti-inflammatory activity diminishing the level of the lipopolysaccharide-induced NO in RAW264.7 macrophage cells, thereby suppressing the secretion of pro-inflammatory cytokines TNF-α and IL-6 and the level of two critical downstream inflammatory mediators iNOS and COX-2.

Keywords: Mesona procumbens Hemsley; anti-inflammatory; mesoeudesmol; mesonaic acid; sesquiterpene; triterpene acid.