First Chemical Investigation of Korean Wild Mushroom, <i>Amanita hemibapha</i> subsp. <i>javanica</i> and the Identification of Anti-<i>Helicobacter pylori</i> Compounds

• Main Authors: Seulah Lee (Author), Akida Alishir (Author), Tae Wan Kim (Author), Dong-Min Kang (Author), Rhim Ryoo (Author), Changhyun Pang (Author), Mi-Jeong Ahn (Author), Ki Hyun Kim (Author)
• Format: Book
• Published: MDPI AG, 2022-01-01T00:00:00Z.
• Subjects: article
• Online Access: Connect to this object online.
• Notes: 10.3390/ph15020152; 1424-8247
• Keywords: <i>Amanita hemibapha</i> subsp. <i>javanica</i>; Amanitaceae; fatty acid derivatives; steroids; LC/MS analysis; CEA; Medicine; R; Pharmacy and materia medica; RS1-441
• Source: Pharmaceuticals, Vol 15, Iss 2, p 152 (2022)

<i>Amanita hemibapha</i> subsp. <i>javanica</i> (Amanitaceae) is an edible Korean wild mushroom. <i>A. hemibapha</i> subsp. <i>javanica</i> is often confused with <i>A. subjunquillea</i>, known as the East Asian death cap, which is potentially fatal when ingested. This study aimed to conduct the first chemical investigation of <i>A. hemibapha</i> subsp. <i>javanica</i>, which resulted in the isolation of seven fatty acid derivatives (<b>1</b>-<b>7</b>) and three steroids (<b>8</b>-<b>10</b>) from the MeOH extract of its fruiting bodies, and their structures were determined by comparing their NMR spectroscopic data with those previously reported, along with the data from LC/MS. Compound <b>1</b> was reported previously without the identification of its absolute configuration; its structure, including the absolute configuration was confirmed for the first time, in this study, by using ¹H NMR and its fragmentation patterns in MS/MS data, and LC/MS analysis. A recently developed method using competing enantioselective acylation (CEA) coupled with LC/MS analysis was applied for determining the absolute configuration of compound <b>1</b>, which revealed the 11<i>S</i>-configuration. In the anti-<i>Helicobacter pylori</i> activity test, compound <b>3</b> showed antibacterial activity against <i>H. pylori</i> strain 51 with 38.0% inhibition, comparable to that of quercetin (34.4% inhibition) as a positive control. Specifically, compound <b>4</b> displayed the most potent antibacterial activity against <i>H. pylori</i> strain 51 with 80.5% inhibition at the final concentration of 100 μm with a MIC₅₀ value of 72 μm. These findings suggested that the active compound <b>4</b> is a natural antibiotic that may be used in the development of novel antibiotics against <i>H. pylori.</i> In addition, the first chemical investigation of <i>A. hemibapha</i> subsp. <i>javanica</i> revealed that this mushroom can serve as a promising natural source for the bioactive natural products.