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.
Highlights
Ginkgo biloba, the single surviving species in the Ginkgo family (Ginkgoaceae), is native to southeastern China and is distributed throughout Korea and Japan
The exhaustive phytochemical examination of the n-butanol-soluble fraction by repeated column chromatography and preparative and semi-preparative high-performance liquid chromatography (HPLC; Figure 1) under the monitoring of liquid chromatography–mass spectrometry (LC/MS) analysis led to the isolation of six phenylpropanoid glycosides (1–6; Figure 2)
The detection of each purified compound was analyzed by an LC-MS, Agilent 1200 Series analytical system equipped with a photodiode array (PDA) detector combined with a 6130 Series ESI mass spectrometer
Summary
The single surviving species in the Ginkgo family (Ginkgoaceae), is native to southeastern China and is distributed throughout Korea and Japan. Considering the pharmacological properties of G. biloba extracts, G. biloba has been thoroughly examined for its bioactive phytochemicals by many research groups [5,6,7,8,9], where terpene trilactones and flavonoids have been identified as the major bioactive components in G. biloba. One of the representative ginkgolides, ginkgolide B, was effective in reducing the frequency of migraine attacks [7] and preventing cardiovascular disease through antioxidant activity and inhibition of platelet aggregation [8]. As another major bioactive component of G. biloba, flavonoids, such as myricetin and quercetin, have been shown to reduce oxidative metabolism in brain neurons [9]. Diverse bioactive compounds from G. biloba have been attractive for natural product chemists to discover novel bioactive natural products
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
