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Molecules 2014, 19(4), 4466-4478; doi:10.3390/molecules19044466
Article

Quantitative Analysis of the Flavonoid Glycosides and Terpene Trilactones in the Extract of Ginkgo biloba and Evaluation of Their Inhibitory Activity towards Fibril Formation of β-Amyloid Peptide

1, 1,2, 1,2, 1, 1,2, 1, 1,*  and 1,2,*
1 School of Chinese Medicine, Hong Kong Baptist University, Kowloon Tong, Kowloon, Hong Kong, China 2 State Key Lab of Quality Research in Chinese Medicine, Macau Institute for Applied Research in Medicine and Health, Macau University of Science and Technology, Macau, China
* Authors to whom correspondence should be addressed.
Received: 13 March 2014 / Revised: 1 April 2014 / Accepted: 3 April 2014 / Published: 10 April 2014
(This article belongs to the Section Metabolites)
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Abstract

The standard extract of Ginkgo biloba leaves (EGb761) is used clinically in Europe for the symptomatic treatment of impaired cerebral function in primary degenerative dementia syndromes, and the results of numerous in vivo and in vitro studies have supported such clinical use. The abnormal production and aggregation of amyloid β peptide (Aβ) and the deposition of fibrils in the brain are regarded as key steps in the onset of Alzheimer’s Disease (AD), and the inhibition of Aβ aggregation and destabilization of the preformed fibrils represent viable approaches for the prevention and treatment of AD. Flavonoid glycosides and terpene trilactones (TTLs) are the two main components of EGb761 which represent 24 and 6% of the overall content, respectively. In our research, seven abundant flavonoid glycosides 17 were isolated from the extract of Ginkgo biloba leaves and characterized by spectroscopic analysis. Furthermore, an ultra-high performance liquid chromatography method was established for the simultaneous quantification of these seven flavonoids. The inhibitory activities of these flavonoids, as well as four TTLs, i.e., ginkgolides A, B, and C and bilobalide (compounds 811), were evaluated towards Aβ42 fibril formation using a thioflavin T fluorescence assay. It was found that three flavonoids 1, 3 and 4 exhibited moderate inhibitory activities, whereas the other four flavonoids 2, 5, 6 and 7, as well as the four terpene trilactones, showed poor activity. This is the first report of the inhibition of Aβ fibril formation of two characteristic acylated flavonoid glycosides 6, 7 in Ginkgo leaves, on the basis of which the structure-activity relationship of these flavonoids 17 was discussed.
Keywords: Ginkgo biloba; inhibitory activity; β-amyloid fibril formation; quantitative analysis; flavonoid glycoside; terpene trilactone Ginkgo biloba; inhibitory activity; β-amyloid fibril formation; quantitative analysis; flavonoid glycoside; terpene trilactone
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Xie, H.; Wang, J.-R.; Yau, L.-F.; Liu, Y.; Liu, L.; Han, Q.-B.; Zhao, Z.; Jiang, Z.-H. Quantitative Analysis of the Flavonoid Glycosides and Terpene Trilactones in the Extract of Ginkgo biloba and Evaluation of Their Inhibitory Activity towards Fibril Formation of β-Amyloid Peptide. Molecules 2014, 19, 4466-4478.

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