Chemistry of ginkgolides: structure–activity relationship as PAF antagonists

Hu, Lihong; Chen, Zhongliang; Cheng, Xiaofang; Xie, Yuyuan

doi:10.1351/pac199971061153

Cited by 28 publications

(27 citation statements)

References 8 publications

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“…This is in agreement with previous SAR studies of GB (2), [40][41][42] as well as a three-dimensional (3D)-quantitative SAR (QSAR) study on ginkgolides. 60 However, it is interesting to note that aromatic substitutions at 10-OH of GC (3) as in compounds 17, 19, and 21 improve the affinity to PAFR ca.…”

Section: Discussionsupporting

confidence: 92%

Ginkgolide Derivatives for Photolabeling Studies: Preparation and Pharmacological Evaluation

et al. 2002

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The terpene trilactones (TTLs), ginkgolides and bilobalide, are structurally unique constituents of Ginkgo biloba extracts, which exhibit various neuromodulatory properties. Although the TTLs are believed to be responsible for some of these effects, the specific interactions with targets in the central nervous system remain to be elucidated on a molecular level. Ginkgolides are known antagonists of the platelet-activating factor (PAF) receptor. Herein, we describe the first examination of the binding of native TTLs and their derivatives to the cloned PAF receptor, confirming that of the TTLs, ginkgolide B is the most potent PAF receptor antagonist. Ginkgolide derivatives carrying photoactivatable and fluorescent groups for the purpose of performing photolabeling have been prepared and evaluated using the cloned PAF receptor. These studies have shown that ginkgolide derivatives with aromatic photoactivatable substituents are potent PAF receptor antagonists with K i values of 0.09-0.79 µM and hence excellent ligands for clarifying the binding of ginkgolides to PAF receptor by photolabeling studies. Ginkgolide derivatives incorporating both fluorescent and photoactivatable groups still retained binding affinity to the PAF receptor and hence should be promising ligands for photolabeling and subsequent sequencing studies.

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Section: Discussionsupporting

confidence: 92%

Ginkgolide Derivatives for Photolabeling Studies: Preparation and Pharmacological Evaluation

et al. 2002

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“…A mixture of many active components including ginkgolides, bilobalide, ginkgolic acids, as well as KYNA and 6-HKA (Figure 3A) may account for its various pharmacological effects, such as the alleviation of VaD, early-stage AD, peripheral claudication and tinnitus of vascular origin [44][45][46][47] . Extraction of active principles from Ginkgo biloba Linn has been studied for a long time in China and high production levels and purity have been achieved [48][49][50][51] . Ginkgo biloba Linn leaf preparations were marketed in France and Germany 30 years ago for the treatment of cardiovascular disease, cerebrovascular diseases and dementia.…”

Section: Ginkgo Biloba Linnmentioning

confidence: 99%

Retrospect and prospect of active principles from Chinese herbs in the treatment of dementia

et al. 2010

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With an ageing population, dementia has become one of the world's primary health challenges. However, existing remedies offer limited benefits with certain side effects, which has prompted researchers to seek complementary and alternative therapies. China has long been known for abundant usage of various herbs. Some of these herbal decoctions are effective in stimulating blood circulation, supplementing vital energy and resisting aging, the lack of which are believed to underlie dementia. These herbs are regarded as new and promising sources of potential anti-dementia drugs. With the rapid evolution of life science and technology, numerous active components have been identified that are highly potent and multi-targeted with low toxicity, and therefore meet the requirements for dementia therapy. This review updates the research progress of Chinese herbs in the treatment of dementia, focusing on their effective principles.

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“…[172,173] Later, Hu et al prepared various degradation and elimination products of GA (1) and GB (2) as well as amide derivatives that lack rings C and D (Figure 3), but in all cases decreased PAFR antagonism was observed. [174,175] One goal of SAR studies is to put forward a pharmacophore model that can elucidate the activities of synthesized derivatives as well as predict the activity of novel derivatives.…”

Section: Sar Studies Of Ginkgolidesmentioning

confidence: 99%

Chemistry and Biology of Terpene Trilactones fromGinkgo Biloba

2004

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Ginkgo biloba, the ginkgo tree, is the oldest living tree, with a long history of use in traditional Chinese medicine. In recent years, the leaf extracts have been widely sold as phytomedicine in Europe and as a dietary supplement worldwide. Effects of Ginkgo biloba extracts have been postulated to include improvement of memory, increased blood circulation, as well as beneficial effects to sufferers of Alzheimer's disease. The most unique components of the extracts are the terpene trilactones, that is, ginkgolides and bilobalide. These structurally complex molecules have been attractive targets for total synthesis. Terpene trilactones are believed to be partly responsible for the neuromodulatory properties of Ginkgo biloba extracts, and several biological effects of the terpene trilactones have been discovered in recent years, making them attractive pharmacological tools that could provide insight into the effects of Ginkgo biloba extracts.

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Chemistry of ginkgolides: structure–activity relationship as PAF antagonists

Cited by 28 publications

References 8 publications

Ginkgolide Derivatives for Photolabeling Studies: Preparation and Pharmacological Evaluation

Ginkgolide Derivatives for Photolabeling Studies: Preparation and Pharmacological Evaluation

Retrospect and prospect of active principles from Chinese herbs in the treatment of dementia

Chemistry and Biology of Terpene Trilactones fromGinkgo Biloba

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