Lanostane Triterpenoids and Ergostane Steroids from Ganoderma luteomarginatum and Their Cytotoxicity

Abstract

Macrofungus Ganoderma luteomarginatum is one of the main species of Ganoderma fungi distributed in Hainan province of China, the fruiting bodies of which have been widely used in folk as a healthy food to prevent tumors. To explore the potential cytotoxic constituents from G. luteomarginatum, the phytochemical investigation on the ethyl acetate soluble fraction of 95% ethanolic extract from the fruiting bodies of this fungus led to the isolation of twenty-six lanostane triterpenoids (1–26), including three undescribed ones (1–3), together with eight ergostane steroids (27–34). The structures of three new lanostane triterpenoids were elucidated as lanosta-7,9(11)-dien-3β-acetyloxy-24,25-diol (1), lanosta-7,9(11)-dien-3-oxo-24,26-diol-25-methoxy (2), and lanosta-8,20(22)-dien-3,11,23-trioxo-7β,15β-diol-26-oic acid methyl ester (3) by the analysis of 1D, 2D NMR, and HRESIMS spectroscopic data. All isolates were assayed for their cytotoxic activities using three human cancer cell lines (K562, BEL-7402, and SGC-7901) and seven lanostane triterpenoids (1, 2, 7, 13, 18, 22, and 24), and one ergostane steroid (34) showed definite cytotoxicity with IC50 values that ranged from 6.64 to 47.63 μg/mL. Among these cytotoxic lanostane triterpenoids, compounds 2 and 13 showed general cytotoxicity against three human cancer cell lines, while compounds 1 and 18 exhibited significant selective cytotoxicity against K562 cells with IC50 values of 8.59 and 8.82 μg/mL, respectively. Furthermore, the preliminary structure–cytotoxicity relationships was proposed.

Polyaspers A and B, the First Ergosterol‐Polyether Adducts with Unprecedented 6/6/6/5/5/6/6/6/6 Nonacyclic Architecture from Aspergillus sp. TJ507

“…The structures of these compounds were established based on their NMR, HRESIMS, IR, ECD, and single‐crystal X‐ray diffraction data. Two known compounds were confirmed to be (3 β ,5 α ,6 α ,22 E )‐5,6‐epoxy‐3‐hydroxyergosta‐8,22‐dien‐7‐one ( 3 ), [ 32 ] and calvasterol B ( 4 ) [ 33 ] by comparing their NMR spectroscopic data as well as specific rotations with those reported in the literature.…”

Ganoderma adspersum (Ganodermataceae): Investigation of Its Secondary Metabolites and the Antioxidant, Antimicrobial, and Cytotoxic Potential of Its Extracts

“…Lanostane-type triterpenes have been examined for their cytotoxicity against different cancer cell lines, including lung, colon, pancreas, and breast cancers. These compounds, including the characteristic ganoderic acids, downregulated the proliferation and growth cycle of the tumor cells [ 53 ]. Even in silico studies have demonstrated their antiproliferative effects through the interaction with nuclear receptors such as the vitamin D receptor, diminishing the cell growth and activating cell differentiation [ 54 ].…”