Antioxidant Phenylpropanoid Glycosides from Ginkgo biloba Fruit and Identification of a New Phenylpropanoid Glycoside, Ginkgopanoside

Abstract

Ginkgo biloba (Ginkgoaceae), well-known as the oldest living plant species and often referred to as a “living fossil,” is a famous medicinal plant that has been used in multiple countries to improve numerous illnesses, including anxiety, dementia, peripheral artery disease, and eye problems. We conducted a phytochemical exploration of G. biloba fruit, commonly consumed as a functional food as part of an ongoing natural product chemical research for the discovery of bioactive phytochemicals with novel structures. The natural product chemical analysis of the methanol extract of G. biloba fruit using column chromatography and high-performance liquid chromatography separation under the guidance of a liquid chromatography–mass spectrometry (LC/MS)-based analysis identified six phenylpropanoid glycosides (1–6), including one new compound, ginkgopanoside (1). The structures of the isolated compounds were elucidated by nuclear magnetic resonance spectroscopic data and LC/MS analysis, and the absolute configuration of compound 1 was established by chemical reactions followed by the application of Snatzke’s method. The 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activities of the isolated compounds 1–6 and the aglycone 1a of 1 were evaluated, and we found that compounds 1–5 exhibited antioxidant activities with IC50 values in the range 32.75–48.20 μM, while the aglycone 1a exhibited greater radical scavenging activity (IC50 = 5.23 μM) comparable to that of ascorbic acid (IC50 = 2.54 μM), a positive control, implying that the present of glucose may decrease the DPPH scavenging activity. These findings provide experimental information that the active phenylpropanoid glycosides could represent natural antioxidants for use in pharmaceuticals and functional foods.

Global Natural Products Social (GNPS)-Based Molecular-Networking-Guided Isolation of Phenolic Compounds from Ginkgo biloba Fruits and the Identification of Estrogenic Phenolic Glycosides

“…Leaves of G. biloba have been used in traditional Chinese medicine for 5000 years [12]. Several secondary metabolites, including terpenoids, polyphenols, allyl phenols, organic acids, carbohydrates, fatty acids and lipids, inorganic salts, and amino acids, have been isolated from the G. biloba [40]. However, the main bioactive constituents are known as terpene trilactones and flavonoid glycosides, which are considered responsible for pharmacological activities, such as scavenging free radicals, lowering oxidative stress, reducing neural damage, reducing platelet aggregation, anti-inflammation, anti-tumor activities, and anti-aging effects [21,23,[53][54][55][56].…”

“…As a part of our ongoing natural product discovery program [34][35][36][37][38] and our continued efforts to identify new bioactive compounds from G. biloba [39,40], we undertook a comprehensive investigation of the bioactive compounds present in G. biloba fruits using MS/MS-based GNPS approaches. The GNPS-based molecular networking approach guided the isolation of extracts from G. biloba fruits, ultimately resulting in the identification of 11 compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11).…”

Plant-Derived Bioactive Compounds in the Management of Neurodegenerative Disorders: Challenges, Future Directions and Molecular Mechanisms Involved in Neuroprotection

“…Ginkgo biloba is a plant with medicinal properties that has been reported to improve dementia, eye problems, anxiety, and peripheral artery disease. LC/MS analysis of Ginkgo biloba identified many phenylpropanoid glycosides out of isolated compounds, and a few showed greater radical scavenging activity with anIC 50 value of 5.23 μM [ 49 ]. Aqueous extract of fruits from the Morus plant species was demonstrated to possess phenolics including cyanidin, kuromanin, and keracyanin, and the extract showed anti-AD properties by exhibiting antioxidant activity in vitro [ 50 ].…”

Isolation and Structural Elucidation of Unreported Prenylhydroquinone Glycoside from Sedum kamtschaticum Leaves and Its Effect on Hyperphosphorylated Tau Production in Aβ1–42-Treated SH-SY5Y Cells

“…Finally, to ascertain the absolute configuration of the sugar unit, enzymatic hydrolysis of compound 1 was conducted using glucosidase. The glucose unit's absolute configuration in compound 1 was determined to be in the D-configuration through LC-MS analysis following thiocarbamoyl-thiazolidine derivatization method (Figure S10) [23]. The 7.5 Hz coupling constant indicated the presence of the β-form of the anomeric proton in glucopyranose [24].…”