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Assembly of Cell Mimicking Supported and Suspended Lipid Bilayer Models for the Study of Molecular Interactions

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Bilobalide and PC12 cells: A structure activity relationship study.

Toyonobu Usuki¹, Yukiko Yoshimoto¹, Makiko Sato¹

¹Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan.

Bioorganic & Medicinal Chemistry

|December 19, 2019

Summary

This summary is machine-generated.

Ginkgo biloba's bilobalide (BB) lactone groups are crucial for its neurite outgrowth effects. Modifications without these groups reduced activity, suggesting their importance in neuronal cell function and potential Alzheimer's disease treatments.

Keywords:

Bilobalide Derivatization PC12 SAR Terpene trilactone

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Area of Science:

Pharmacology
Neuroscience
Natural Products Chemistry

Background:

Ginkgo biloba extracts are explored for cognitive enhancement and Alzheimer's disease treatment.
Terpene trilactones (TTLs), including bilobalide (BB) and ginkgolides, are key active compounds.
Structure-activity relationship (SAR) studies on ginkgolides exist, but BB scaffold modifications are underexplored.

Purpose of the Study:

To investigate the impact of modifying bilobalide (BB) lactone moieties on its biological activities.
To assess the effects of BB derivatives on cell proliferation, neuroprotection against amyloid-beta (Aβ) peptides, and neurite outgrowth.

Main Methods:

Synthesis of bilobalide (BB) derivatives with modified lactone groups.
Evaluation of biological activities using assays for proliferating cell activity, neuroprotection against Aβ (1-40), and neurite outgrowth in PC12 cells.

Main Results:

BB derivatives retaining lactone groups demonstrated biological activity comparable to native BB.
Derivatives lacking lactone moieties exhibited diminished neurite outgrowth effects.
Cell proliferation and neuroprotection assays showed varied results, but neurite outgrowth was most sensitive to lactone modification.

Conclusions:

The lactone moieties of bilobalide (BB) are essential for its neurite outgrowth effects in PC12 neuronal cells.
These findings highlight the importance of specific structural features in BB for neurotrophic activity.
This study provides a foundation for future SAR studies on BB for potential therapeutic applications.