Gentisides A and B, two new neuritogenic compounds from the traditional Chinese medicine Gentiana rigescens Franch

Gao, Lijuan; Li, Jinyou; Qi, Jianhua

doi:10.1016/j.bmc.2010.02.004

Cited by 49 publications

(42 citation statements)

References 12 publications

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“…[5][6][7] Gentisides are a novel class of neuritogenic phenolic lipids, which we previously isolated from the traditional Chinese medicine Gentiana rigescens FRANCH 8,9) (Fig. 1).…”

Section: 2)mentioning

confidence: 99%

Synthesis and SAR Studies of Neuritogenic Gentiside Derivatives

Wang

Bian

Zhang

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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Tetradecyl 2,3-dihydroxybenzoate (ABG-001) has been designed and synthesised as a lead compound to treat Alzheimer's disease, based on structure-activity relationships of gentisides. In this paper, the alkyl chain and ester linkage group of ABG-001 were modified. Consequently, several series of novel gentiside derivatives were designed and synthesised, and their neuritogenic activity was evaluated in PC12 cells. Among all the tested compounds, S-dodecyl 2,3-dihydroxybenzothioate (15d, named as ABG-199) was the most potent; the compound induced significant neurite outgrowth at 0.1 µM, which was comparable to that of nerve growth factor at the optimal concentration of 40 ng/mL and ABG-001 at 1 µM. A brief study on the mechanism of action of ABG-199 revealed that extracellular signal-regulated kinase phosphorylation was involved in ABG-199-induced neurite outgrowth in PC12 cells. Key words neuritogenic activity; thioester; gentiside derivativeAlzheimer's disease (AD) is the most prevalent neurodegenerative disease in aged populations, and the number of cases is rapidly increasing. As one of the most important neurotrophic factors, the nerve growth factor (NGF) is essential for neuronal differentiation, growth, survival, function maintenance and prevention of ageing in central and peripheral systems.

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“…[5][6][7] Gentisides are a novel class of neuritogenic phenolic lipids, which we previously isolated from the traditional Chinese medicine Gentiana rigescens FRANCH 8,9) (Fig. 1).…”

Section: 2)mentioning

confidence: 99%

Synthesis and SAR Studies of Neuritogenic Gentiside Derivatives

Wang

Bian

Zhang

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…While gentiside C possessing the shortest alkyl chain length exhibiting the highest neuritogenic activity among all of the gentisides indicated that the length of the alkyl chain was important for the activity. 17,18 G. triflora polysaccharide enhanced thymus index and spleen swelling index, increased carbon clearance index, and significantly higher HC50, thus enhancing the specific and non-specific immune function of mice. 37 What's more "LongDan" was also used in the treatment of hypothyroid conditions.…”

Section: Antiproliferative Effecsmentioning

confidence: 99%

“…Their structure-activity relationships revealed that the length of alkyl chain was important for the activity, but the structural diversity at the end of the alkyl chain was not. 17,18 As the minor chemical constituents 4 Pharmacological Studies 4.1 Hepatoprotective Effect: "Long-Dan" is a famous hepatic used TCM herb for the treatment of hepatitis. The water extracts of G. scabra showed remarkable liver protective action by protecting the membranes of hepatocytes, inhibiting the immunoreaction occurred in liver, promoting the function of phagocytes, or enhancing the treatment for foreign body in damaged liver.…”

Section: Othersmentioning

confidence: 99%

Review on “Long-Dan”, one of the traditional Chinese medicinal herbs recorded in Chinese pharmacopoeia

Wang

et al. 2012

Nat. Prod. Bioprospect.

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"Long-Dan" is an important traditional Chinese medicinal (TCM) herb used widely for the treatment of inflammation, hepatitis, rheumatism, cholecystitis, and tuberculosis. In the Chinese Pharmacopoeia, the roots and rhizomes of four species from the genus Gentiana (Gentianaceae) are recorded as the original materials of "Long-Dan", called Gentianae Radix et Rhizoma. The species included G. manshurica, G. scabra, G. triflora and G. rigescens, which are distributed in different areas of China. Though iridoid and secoiridoid glucosides were reported as the main constituents in "Long-Dan", these four different species also resulted in different minor components, which may related to their pharmacological activities. Herein, we summarized the herbal textual study, distribution, chemical constituents, biological investigation and quality control of the recorded "Long-Dan" origins in Chinese Pharmacopoeia during the period 1960 to 2011.

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“…Among three hit compounds (vide infra), we chose the natural product analog 1 , ( Figure 1 ), a truncated form of gentiside B 2 , recently reported by Qi and co-workers as our initial lead structure. [28][29][30] Compound 1 is a simplifi ed analog of the natural product gentiside B, isolated from Gentiana rigescens, a plant used in traditional Chinese medicine. [ 28 ] This compound offers several benefi ts such as ease of access and excellent neurite outgrowth inducing capabilities in the PC12 cell assay.…”

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confidence: 99%