Triterpenes and Aromatic Meroterpenoids with Antioxidant Activity and Neuroprotective Effects from Ganoderma lucidum.

Cuifang Wang,Jiaying Ke,Chenlei Lian,Jieqing Liu,Xuemin Liu

doi:10.3390/molecules24234353

Cuifang Wang, Jiaying Ke + Show 3 more

Open Access

https://doi.org/10.3390/molecules24234353

Copy DOI

Abstract

Reactive oxygen/nitrogen species generated in the human body can cause oxidative damage associated with many degenerative diseases such as atherosclerosis, dementia, coronary heart diseases, aging, and cancer. There is a great interest in developing new antioxidants from Ganoderma fungus due to its low toxicity. As part of our ongoing search for antioxidative constituents from the fruiting bodies of Ganoderma lucidum, the chemical constituents were investigated and seven secondary metabolites, including one new lanostane triterpene (1), two known aromatic meroterpenoids (6–7), and four known triterpenes (2–5), were isolated by a series of chromatographic methods. The structures of the seven compounds were elucidated by spectroscopic techniques. The isolated compounds were tested in vitro for antioxidant potencies and neuroprotective activities against H2O2 and aged Aβ-induced cell death in SH-SY5Y cells. As a result, compounds 1, 6, and 7 exhibited potent antioxidant and neuroprotective activities. Additionally, all isolated compounds were tested for radical scavenging activities. Compounds 6 and 7 showed the comparable free radical scavenging activities with the standard drug in both ABTS (2, 2’-azobis (3-ethylbenzothiazole-6-sulfonaic acid)) and ORAC (oxygen radical absorbance capacity) experiments. The results from this study suggested that G. lucidum and its metabolites (especially the meroterpenoids) may be potential functional food ingredients for the antioxidation and prevention of neurogenerative diseases.

Highlights

Reactive oxygen species (ROS) can cause extensive damage to DNA, proteins, and lipids
Compound 1 was obtained as white powder (CH2 Cl2 ) with a molecular formula of C31 H48 O8 from the molecular ion peak [M+Na]+ at m/z 571.3241 in the high resolution electrospray ionization mass spectroscopy (HRESIMS)
Comparison of the 13 C nuclear magnetic resonance (NMR) data of 1 with those of methyl ganoderate G showed that the hydroxyl group (δ 72.48) in 1 replaced the carbonyl group (δ 216.8) in methyl ganoderate G at C-15, which was confirmed by the heteronuclear multiple bond correlation (HMBC) correlations of H-15 with C-16 and C-14; of Me-30 with C-15 (Figure S7 in Supplementary Material)

Summary

Introduction

Reactive oxygen species (ROS) can cause extensive damage to DNA, proteins, and lipids. This could be the fundamental cause of aging and many other important diseases such as cancer, cardiovascular diseases, and neurogeneration [1]. Deposition of different physicochemical forms of amyloid β peptide (Aβ) constitutes a major neuropathological hallmark of Alzheimer’s disease [2]. Owing to the increased demand for and importance of antioxidants in day-to-day life, the search for effective, nontoxic, natural compounds with antioxidant activity has increasingly become a matter of interest. Ganoderma lucidum is known as the “mushroom of immortality” and considered to be a panacea to cure all kinds of diseases in Chinese folklore. As demonstrated by the numerous publications, polysaccharides are important contributors to the antioxidant

Methods

Results

Conclusion