Spectroscopic investigation of Ginkgo biloba terpene trilactones and their interaction with amyloid peptide Abeta(25-35).

Full Abstract

The beneficial effects of Ginkgo biloba extract in the "treatment" of dementia are attributed to its terpene trilactone (TTL) constituents. The interactions between TTLs and amyloid peptide are believed to be responsible in preventing the aggregation of peptide. These interactions have been investigated using infrared vibrational absorption (VA) and circular dichroism (VCD) spectra. Four TTLs, namely ginkgolide A (GA), ginkgolide B (GB), ginkgolide C (GC) and bilobalide (BB) and amyloid Abeta(25-35) peptide, as a model for the full length peptide, are used in this study. GA-monoether and GA-diether have also been synthesized and investigated to help understand the role of individual carbonyl groups in these interactions. The precipitation and solubility issues encountered with the mixture of ginkgolide+Abeta peptide for VA and VCD studies were overcome using binary ethanol-D(2)O solvent mixture. The experimental VA and VCD spectra of GA, GB, GC and BB, GA-monoether and GA-diether have been analyzed using the corresponding spectra predicted with density functional theory. The time-dependent experimental VA and VCD spectra of Abeta(25-35) peptide and the corresponding experimental spectra in the presence of TTLs indicated that the effect of the TTLs in modulating the aggregation of Abeta(25-35) peptide is relatively small. Such small effects might indicate the absence of a specific interaction between the TTLs and Abeta(25-35) peptide as a major force leading to the reduced aggregation of amyloid peptides. It is possible that the therapeutic effect of G. biloba extract does not originate from direct interactions between TTLs and the Abeta(25-35) peptide and is more complex.

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Author information

Author/s: He, Jiangtao (J); Petrovic, Ana G (AG); Dzyuba, Sergei V (SV); Berova, Nina (N); Nakanishi, Koji (K); Polavarapu, Prasad L (PL);

Affiliation: Department of Chemistry, Columbia University, New York, NY 10027, USA.

Grants: GM-MH068817 (Agency:United States NIGMS)

Journal and publication information

Publication Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy (Spectrochim Acta A Mol Biomol Spectrosc), published in England. (Language: eng)

Reference: 2008-Apr; vol 69 (issue 4) : pp 1213-22

Dates: Created 2008/03/14; Completed 2008/06/26;

PMID: 17693130, status: MEDLINE (last retrieval date: 11/6/2008)

Sourced from the National Library of Medicine. Abstract text and other information may be subject to copyright.

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MeSH headings (categories)

This article was linked to the MESH Headings shown below.

Amyloid beta-Protein - chemistry
Circular Dichroism
Cyclopentanes - chemistry
Furans - chemistry
Ginkgo biloba - chemistry
Ginkgolides - chemistry

Lactones - chemistry
Peptides
Spectrophotometry, Infrared
Terpenes - chemistry
Time Factors
Vibration

Associated Chemicals: Amyloid beta-Protein (0) ; Cyclopentanes (0) ; Furans (0) ; Ginkgolides (0) ; Lactones (0) ; Peptides (0) ; Terpenes (0) ; ginkgolide A (0) ; trilactone (0) ; ginkgolide C (15291-76-6) ; bilobalide (33570-04-6) ; ginkgolide B (99796-69-7)

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