Neuritogenesis of Herbal Geniposide-Related Compounds in PC12h Cells

Chiba, Kenzo; Yamazaki, Matsumi; Kikuchi, Masafumi; Machida, Koichi; Kikuchi, Masao

doi:10.1248/jhs.52.743

Cited by 5 publications

(2 citation statements)

References 14 publications

(14 reference statements)

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“…Furthermore, we have previously reported that several iridoid compounds, and their hydrolysates, have neuritogenic activity in PC12h cells [2][3][4], a subclone of a rat pheochromocytoma cell [5]. In particular, genipin, the aglycon of geniposide, potently induces neurite outgrowth.…”

Section: Introductionmentioning

confidence: 99%

New physiological function of secoiridoids: neuritogenic activity in PC12h cells

et al. 2010

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Previously, we have reported that geniposide isolated from an extract of Gardenia fructus has neuritogenic activity in PC12h cells, a subclone of rat pheochromocytoma cells. Furthermore, we have indicated that several geniposide-related iridoid compounds also had similar potent neuritogenic activity. In this study, we have examined the effects of various secoiridoid compounds [K-1, sweroside; K-2, swertiamarin; K-3, gentiopicroside; K-4, 6'-O-β-D: -glucopyranosylsweroside; K-5, 6'-O-β-D: -glucopyranosylgentiopicroside; K-6, 6'-O-β-D: -glucopyranosylswertiamarin; K-7, 5'-O-β-D: -glucopyranosylamarogentin; K-8, 5'-O-β-D: -glucopyranosylamaroswertin; H-1, n-butyl vogeloside; H-2, n-butyl epivogeloside; H-3, (7S)-secologanin butyl methyl acetal; H-4, (7R)-secologanin butyl methyl acetal; H-5, secologanin dimethyl acetal] isolated from various medicinal herbs. The secoiridoids H-1, H-2, H-3, H-4, and H-5 induced significant neurite outgrowth. Among these H-series compounds, H-2 was the most potent neuritogenic compound. Among the K-series compounds, K-1, K-2, K-3, and K-8 showed the most potent activity. These results suggest that secoiridoids have neuritogenic activity in PC12h cells and that these secoiridoid compounds are promising starting compounds for the development of neurotrophic factor-like and iridoid compounds.

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Section: Introductionmentioning

confidence: 99%

New physiological function of secoiridoids: neuritogenic activity in PC12h cells

et al. 2010

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“…1) Furthermore, we have previously reported that several iridoid compounds, and their hydrolysates, have neuritogenic activity in PC12h cells, [2][3][4] a subclone of a rat pheochromocytoma cell. 5) Genipin, the aglycon of geniposide (gardenia jasminoides), is a particularly potent inducer of neurite outgrowth.…”

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confidence: 99%

Neuritogenic Activities of 1-Alkyloxygenipins

Suzuki

Yamazaki

Chiba

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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We designed 1-alkyloxygenipins with the aim of improving the stability of genipins based on the structural and electronic properties of genipins, and prepared 1-alkyloxygenipins and examined their neuritogenic activities in PC12h cells. All genipin-derivatives exhibited electronic properties similar to those of genipin and induced significant neurite outgrowth. These compounds will be classified as nitric oxide synthase (NOS) activators (neuritogenic active compounds) since their lowest unoccupied molecular orbital (LUMO)-energies are similar to that of tetrahydrobiopterin (H4B). (1R)-isoPropyloxygenipin showed activity comparable to that of genipin, and unlike the parent compound genipin, it was found to be physiologically stable in rat liver homogenate.

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Synthesis of Stable Genipin Derivatives and Studies of Their Neuroprotective Activity in PC12 Cells

et al. 2012

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Modifications at C1, C7, C8, and C10 of genipin were conducted, and the neurotrophic effects of all derivatives were studied. Genipin derivatives 1-4 were obtained in mild to high yield. Compounds 1 and 4 are more stable than genipin if exposed to nucleophiles. All the derivatives display higher neurotrophic activities than genipin. Compound 4 is the most active, with the least optimal dose. Both genipin and 4 up-regulated the activity of nNOS in PC12 cells. The effect of 4 is inhibited not only by 7-NI, a specific inhibitor of nNOS, but also by L-NIO, a specific inhibitor of eNOS; in the case of genipin, its effect is only inhibited by 7-NI. All the results indicate that 4 is a promising lead compound for the development of new drugs in the treatment of neurodegenerative diseases with the ability to address multiple drug targets.

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Neuritogenesis of Herbal Geniposide-Related Compounds in PC12h Cells

Cited by 5 publications

References 14 publications

New physiological function of secoiridoids: neuritogenic activity in PC12h cells

New physiological function of secoiridoids: neuritogenic activity in PC12h cells

Neuritogenic Activities of 1-Alkyloxygenipins

Synthesis of Stable Genipin Derivatives and Studies of Their Neuroprotective Activity in PC12 Cells

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