Chemie der Ginkgolide, II. Isolierung und Strukturaufklärung eines neuen Ginkgolids

Weinges, Klaus; Hepp, M.; Jaggy, H.

doi:10.1002/jlac.198719870368

Cited by 62 publications

(29 citation statements)

References 6 publications

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“…In the case of Ginkgo biloba , a plethora of spectroscopic information has been published over the last 40 years. 41 In fact, 1 H NMR data of the TTLs in DMSO- d 6 have been described in several reports, 42–44 including one of the seminal works on the structure of the ginkgolides by Nakanishi. 45 A similar scenario exists for the flavonoids, since all four compounds have been found in numerous plants.…”

Section: Resultsmentioning

confidence: 99%

The Tandem of Full Spin Analysis and qHNMR for the Quality Control of Botanicals Exemplified with Ginkgo biloba

et al. 2012

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Botanical dietary supplements and herbal remedies are widely used for health promotion and disease prevention. Due to the high chemical complexity of these natural products, it is essential to develop new analytical strategies to guarantee their quality and consistency. In particular, the precise characterization of multiple botanical markers remains a challenge. This study demonstrates how a combination of computer-aided spectral analysis and 1D quantitative 1H NMR spectroscopy (qHNMR) generates the analytical foundation for innovative means of simultaneously identifying and quantifying botanical markers in complex mixtures. First, comprehensive 1H NMR profiles (fingerprints) of selected botanical markers were generated via 1H iterative Full Spin Analysis (HiFSA) with PERCH. Next, the 1H fingerprints were used to assign specific 1H resonances in the NMR spectra of reference materials, enriched fractions and crude extracts of Ginkgo biloba leaves. These 1H fingerprints were then used to verify the assignments by 2D NMR. Subsequently, a complete purity and composition assessment by means of 1D qHNMR was conducted. As its major strengths, this tandem approach enables the simultaneous quantification of multiple constituents without the need for identical reference materials, the semi-quantitative determination of particular sub-classes of components, and the detection of impurities and adulterants.

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Section: Resultsmentioning

confidence: 99%

The Tandem of Full Spin Analysis and qHNMR for the Quality Control of Botanicals Exemplified with Ginkgo biloba

et al. 2012

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“…It is noteworthy that 7-OH present in GC (3) does not react under any of the above-mentioned reaction conditions. Generally, the position of the substituent was determined from the 1 H NMR coupling of appropriate protons in dimethyl sulfoxide (DMSO)-d 6 , as well as by correlation spectroscopy (COSY) spectra. The relative chemical shift of 12-H in DMSO-d 6 can also be used in differentiating 1-and 10-OH substitutions.…”

Section: Synthesismentioning

confidence: 99%

“…Generally, the position of the substituent was determined from the 1 H NMR coupling of appropriate protons in dimethyl sulfoxide (DMSO)-d 6 , as well as by correlation spectroscopy (COSY) spectra. The relative chemical shift of 12-H in DMSO-d 6 can also be used in differentiating 1-and 10-OH substitutions. 42 The coupling of GB (2) with 4-benzoylbenzoic acid using 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl (EDC) and 4-(dimethylamino)pyridine (DMAP) occurred exclusively at 10-OH to give 10-benzophenonecarbonyl GB (22) in good yield (Scheme 3).…”

Section: Synthesismentioning

confidence: 99%

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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“…The first ones were regarded as diterpenes and the bilobalide as sesquiterpene (C15 closed terpene). Structures of ginkgolides A, B, and C were determined by two Japanese groups in the sixties of past century [4][5][6] whereas the structures of the bilobalide [7] and ginkgolide J [8] were discovered few years later. They are highly oxidable compounds, especially in the presence of air's oxygen.…”

Section: Introductionmentioning

confidence: 99%

Development and Validation of a Gas Chromatographic Method for Identification and Quantification of Terpene Trilactones in Ginkgo biloba L. Extract and Pharmaceutical Preparations~!2009-10-28~!2010-01-15~!2010-06-09~!

Sayadi¹,

Missaoui²,

Jamoussi³

et al. 2010

TOCBMJ

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A gas chromatographic method was developed and validated for the determination of bilobalide and ginkgolides A, B, C and J in Ginkgo biloba L. The Ginkgo terpene trilactones have been dissolved in 57% of pure ethanol in purified water and separated by extraction with a mixture of toluene/ethyl acetate. After evaporation of the solvent with nitrogen and derivatization, these chemical markers have been quantified using GC-FID. The intra-day RSD was ranged from 1.13% for bilobalide to 2.34% in case of ginkgolides. The inter-day RSD was ranged from 2.54% and 3.68% for, bilobalide and ginkgolides respectively. Mean recoveries were 99.78% ± 0.82% and 99.48% ± 0.86% for ginkgolides and bilobalide, respectively. Based on chromatograms, the response of the terpene trilactones was linearly dependent on the terpene concentration, i.e. linear calibration curve was found in the range of the method and was applied to analyze standard extract (containing 5-7% total terpenoids and 22-25% total flavonoids) as working standard and for the analysis of six Ginkgo pharmaceutical products offered on the market.

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Chemie der Ginkgolide, II. Isolierung und Strukturaufklärung eines neuen Ginkgolids

Abstract: Aus Bliittern des Ginkgo-Baumes wird ein neues Ginkgolid (S) isoliert, das wir als Ginkgolid J bezeichnen. Die Strukturaufklk rung gelang sowohl mit spektroskopischen Methoden als auch durch chemische Korrelation mit Ginltgolid C.

Cited by 62 publications

References 6 publications

The Tandem of Full Spin Analysis and qHNMR for the Quality Control of Botanicals Exemplified with Ginkgo biloba

The Tandem of Full Spin Analysis and qHNMR for the Quality Control of Botanicals Exemplified with Ginkgo biloba

Ginkgolide Derivatives for Photolabeling Studies: Preparation and Pharmacological Evaluation

Development and Validation of a Gas Chromatographic Method for Identification and Quantification of Terpene Trilactones in Ginkgo biloba L. Extract and Pharmaceutical Preparations~!2009-10-28~!2010-01-15~!2010-06-09~!

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