New aniline derivatives from the volva of Phallus rubrovolvatus and their anti-inflammatory activity

Jianhua Lv; Lan Yao; Shiyu Li; Jing Dong; Mingyu Ye; Dongyu Fan; Changtian Li; Fenghua Tian; Yu Li

doi:10.1016/j.bioorg.2021.105577

New aniline derivatives from the volva of Phallus rubrovolvatus and their anti-inflammatory activity

Bioorg Chem. 2022 Feb:119:105577. doi: 10.1016/j.bioorg.2021.105577. Epub 2021 Dec 23.

Authors

Jianhua Lv¹, Lan Yao¹, Shiyu Li¹, Jing Dong¹, Mingyu Ye¹, Dongyu Fan¹, Changtian Li², Fenghua Tian³, Yu Li⁴

Affiliations

¹ Engineering Research Center of Chinese Ministry of Education for Edible and Medicinal Fungi, Jilin Agricultural University, Changchun 130118, People's Republic of China.
² Engineering Research Center of Chinese Ministry of Education for Edible and Medicinal Fungi, Jilin Agricultural University, Changchun 130118, People's Republic of China. Electronic address: lct@jlau.edu.cn.
³ Department of Plant Pathology, College of Agriculture, Guizhou University, Guiyang 550025, People's Republic of China. Electronic address: fhtian@gzu.edu.cn.
⁴ Engineering Research Center of Chinese Ministry of Education for Edible and Medicinal Fungi, Jilin Agricultural University, Changchun 130118, People's Republic of China. Electronic address: liyu@jlau.edu.cn.

PMID: 34959178
DOI: 10.1016/j.bioorg.2021.105577

Abstract

Phallus rubrovolvatus is an important commercially cultivated mushroom species in China. However, the volva of P. rubrovolvatus usually discarded as a by-product due to the unpleasant flavor and difficulty in processing. In this study, we investigated the chemical constituents and bioactivities of the volva of P. rubrovolvatus. As a result, fifteen rare aniline derivatives, including twelve new compounds (1-11, 14) and three new natural products (12, 13, 15) were isolated from the volva. Their structures were determined using 1D and 2D NMR data and HR-ESI-MS data, while the relative and absolute configurations were confirmed by NOESY correlations and comparison between experimental and calculated ECD spectra. In addition, compounds 1-15 were tested for anti-inflammatory activity against lipopolysaccharide (LPS)-induced NO production in RAW264.7 macrophages. Compounds 4, 9 and 10 exhibited anti-inflammatory activity with IC₅₀ values ranging from 12.5 to 15.6 μM.

Keywords: Aniline derivatives; Anti-inflammatory activity; Chemical composition; Phallus rubrovolvatus.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aniline Compounds / chemistry
Aniline Compounds / isolation & purification
Aniline Compounds / pharmacology*
Animals
Anti-Inflammatory Agents, Non-Steroidal / chemistry
Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
Basidiomycota / chemistry*
Dose-Response Relationship, Drug
Lipopolysaccharides / antagonists & inhibitors
Lipopolysaccharides / pharmacology
Mice
Molecular Structure
Nitric Oxide / antagonists & inhibitors*
Nitric Oxide / biosynthesis
Plant Extracts / chemistry
Plant Extracts / isolation & purification
Plant Extracts / pharmacology*
RAW 264.7 Cells
Structure-Activity Relationship
Waste Products / analysis*

Substances

Aniline Compounds
Anti-Inflammatory Agents, Non-Steroidal
Lipopolysaccharides
Plant Extracts
Waste Products
Nitric Oxide

Supplementary concepts

Dictyophora rubrovolvata