Synthesis and cardiomyocyte protection activity of crocetin diamide derivatives

Gao, Jin; Chen, Ming; Ren, Xuecong; Zhou, Xiaobo; Shang, Qianwen; Lü, Wenqi; Luo, Pei; Jiang, Zhi‐Hong

doi:10.1016/j.fitote.2017.06.014

Cited by 10 publications

(8 citation statements)

References 24 publications

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“…CC and TSC have similar pharmacological activities as CR (see below). Some bioactive synthetic analogues of CC have also been synthesized such as the diamide derivative of CC (Gao et al, 2017).…”

Section: Crocin and Related Compoundsmentioning

confidence: 99%

Crocins for Ischemic Stroke: A Review of Current Evidence

et al. 2022

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Crocins (CRs) and the related active constituents derived from Crocus sativus L. (Saffron) have demonstrated protective effects against cerebral ischemia and ischemic stroke, with various bioactivities including neuroprotection, anti-neuroinflammation, antioxidant, and cardiovascular protection. Among CRs, crocin (CR) has been shown to act on multiple mechanisms and signaling pathways involved in ischemic stroke, including mitochondrial apoptosis, nuclear factor kappa light chain enhancer of B cells pathway, S100 calcium-binding protein B, interleukin-6 and vascular endothelial growth factor-A. CR is generally safe and well-tolerated. Pharmacokinetic studies indicate that CR has poor bioavailability and needs to convert to crocetin (CC) in order to cross the blood-brain barrier. Clinical studies have shown the efficacy of saffron and CR in treating various conditions, including metabolic syndrome, depression, Alzheimer’s disease, and coronary artery disease. There is evidence supporting CR as a treatment for ischemic stroke, although further studies are needed to confirm their efficacy and safety in clinical settings.

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Section: Crocin and Related Compoundsmentioning

confidence: 99%

Crocins for Ischemic Stroke: A Review of Current Evidence

et al. 2022

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“…2,3 Lactone aminolysis is a common transformation that allows the direct conversion of lactones into the corresponding amides that are more stable and show better bioactivity than the corresponding acids or esters. 4,5 Hu et al prepared amide derivatives of 10-oxaginkgolide A via opening ring C with the amine. 6 Vogensen et al also observed the C ring opening during modification at the 7-position of ginkgolide C. 7 Besides, aminolysis of the lactone ring has the potential to significantly improve the solubility and bioactivity, which is an important way to discover drug candidates with better activity.…”

Section: Introductionmentioning

confidence: 99%

“…Lactone aminolysis is a common transformation that allows the direct conversion of lactones into the corresponding amides that are more stable and show better bioactivity than the corresponding acids or esters. , Hu et al prepared amide derivatives of 10-oxaginkgolide A via opening ring C with the amine . Vogensen et al.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

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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.

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“…The anti-TMV activity results revealed that crocin-1 and crocin-2 exhibited significantly higher activity levels than ribavirin. Crocin-1 and crocin-2 contain many polar groups and are easily soluble in water. − However, as a result of the poor fat solubility, there remains a deficiency of the structural modification and the analysis of the structure–activity relationship (SAR). Herein, a series of fat-soluble crocetin diesters have been successfully designed and synthesized.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Anti-Tobacco Mosaic Virus Activities of Crocetin Diesters

Zou

et al. 2021

J. Agric. Food Chem.

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The development of antiviral agents with an original structure and noticeable effect is always in great need. Natural products are important lead compounds in the development of new pesticides. Crocin-1 and crocin-2 were effectively isolated from Gardeniae fructus and found to have higher anti-tobacco mosaic virus (TMV) activity levels than ribavirin. A series of the crocetin diester derivatives were synthesized with separated crocetin-1 as material and evaluated for their anti-TMV activities. They could be dissolved in common organic solvents as dichloromethane, ethyl acetate, tetrahydrofuran, and methanol. Compounds 5, 9, 13, 14, and 15 displayed higher activities in vivo than ribavirin. Compound 14 with significantly higher antiviral activities than lead compounds (crocin-1 and crocin-2) emerged as a new antiviral candidate.

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Synthesis and cardiomyocyte protection activity of crocetin diamide derivatives

Cited by 10 publications

References 24 publications

Crocins for Ischemic Stroke: A Review of Current Evidence

Crocins for Ischemic Stroke: A Review of Current Evidence

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

Preparation and Anti-Tobacco Mosaic Virus Activities of Crocetin Diesters

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