Unknown

Dataset Information

0

Amide Derivatives of Ginkgolide B and Their Inhibitory Effects on PAF-Induced Platelet Aggregation.


ABSTRACT: Ginkgolides are the most important components of Ginkgo biloba extracts, whose lactone can be hydrolyzed in the aqueous environment. Although the hydrolyzed products have complex structures and their functions are not well-understood, opening the lactone ring is an important strategy in producing novel derivatives of ginkgolide. The preparation of a single pure aminolyzed ginkgolide for the study of its bioactivity and understanding of the process of aminolysis are challenging. To obtain stable aminolyzed products, four amide derivatives (2-5) of ginkgolide B (GB, 1) were prepared via the ring-opening reaction of its lactone with propylamine. These products were purified and fully identified by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) spectroscopy and were further evaluated for their ability to inhibit the PAF-induced platelet aggregation of rabbit platelets in vitro. Compound 2, which was obtained by selective aminolysis of the lactone ring C of GB, showed a much better inhibitory activity of platelet aggregation (IC50, 15 nM) than the parent compound GB (IC50, 442 nM). The other three products (3-5), which were obtained by the aminolysis of lactone rings C and F of GB, did not show platelet aggregation inhibitory activity. The results greatly extended our understanding of the chemistry of GB and provided important structural information for the exploration and development of new drugs based on ginkgolides in G. biloba.

SUBMITTER: Shang Q 

PROVIDER: S-EPMC8427636 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

altmetric image

Publications

Amide Derivatives of Ginkgolide B and Their Inhibitory Effects on PAF-Induced Platelet Aggregation.

Shang Qiang Q   Zhou Xiaobo X   Yang Ming-Rong MR   Lu Jing-Guang JG   Pan Yu Y   Zhu Guo-Yuan GY   Jiang Zhi-Hong ZH  

ACS omega 20210824 35


Ginkgolides are the most important components of <i>Ginkgo biloba</i> extracts, whose lactone can be hydrolyzed in the aqueous environment. Although the hydrolyzed products have complex structures and their functions are not well-understood, opening the lactone ring is an important strategy in producing novel derivatives of ginkgolide. The preparation of a single pure aminolyzed ginkgolide for the study of its bioactivity and understanding of the process of aminolysis are challenging. To obtain  ...[more]

Similar Datasets

| S-EPMC11865921 | biostudies-literature
| S-EPMC9268609 | biostudies-literature
| S-EPMC8267677 | biostudies-literature
| S-EPMC6259456 | biostudies-literature
| S-EPMC5065993 | biostudies-literature
| S-EPMC7144264 | biostudies-literature
| S-EPMC5516194 | biostudies-literature
| S-EPMC8648050 | biostudies-literature
| S-EPMC9127734 | biostudies-literature
| S-EPMC8230796 | biostudies-literature