The Absolute Stereostructure of Panaxytriol,a Biologically Active Diacetylenic Acetogenin, from Ginseng Radix Rubra.

Kobayashi, Mariko; Mahmud, Taifo; Umezome, Takashi; Kitagawa, Isao

doi:10.1248/cpb.43.1595

Cited by 12 publications

(6 citation statements)

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“…The chemical structure of panaxytriol was proposed by Kitagawa et al, following their initial isolation of the substance 44. 48 In 1995, Kobayashi et al proposed the absolute configuration of panaxytriol to be 3 R ,9 R ,10 R by the CD exciton chirality method and the modified Mosher ester method 49. Since this report, however, the issue of the relative and absolute configuration of panaxytriol has been a matter of controversy because of conflicting data 50.…”

Section: Diynes From Plantsmentioning

confidence: 99%

Synthesis of Naturally Occurring Polyynes

2006

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Over the past fifty years, hundreds of polyyne compounds have been isolated from nature. These often unstable molecules are found in sources as common as garden vegetables and as obscure as bacterial cultures. Naturally occurring polyynes feature a wide range of structural diversity and display an equally broad array of biological properties. Early synthetic efforts relied primarily on Cu-catalyzed, oxidative acetylenic homo- and heterocoupling reactions to assemble the polyyne framework. The past 25 years, however, have witnessed a renaissance in the field of polyyne natural product synthesis: transition-metal-catalyzed alkynylation reactions and asymmetric transformations have combined to substantially expand access to natural polyynes. This Review recounts these synthetic achievements and also highlights both the natural source(s) and biological relevance for many of these compounds.

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Section: Diynes From Plantsmentioning

confidence: 99%

Synthesis of Naturally Occurring Polyynes

2006

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“…Panaxytriol ( 272 ) is an active component of red Ginseng [232] and its chemical synthesis has been reported by several research groups. [233] Among them, Danishefsky and co-workers have shown that 272 promotes NGF-induced neurite outgrowth in PC-12 cells at a concentration of 60 μM.…”

Section: Neurotrophic Natural Productsmentioning

confidence: 99%

Neurotrophic Natural Products: Chemistry and Biology

2013

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Neurodegenerative diseases and spinal cord injury affect approximately 50 million people worldwide, bringing the total healthcare cost to over 600 billion dollars per year. Nervous system growth factors, that is, neurotrophins, are a potential solution to these disorders, since they could promote nerve regeneration. An average of 500 publications per year attests to the significance of neurotrophins in biomedical sciences and underlines their potential for therapeutic applications. Nonetheless, the poor pharmacokinetic profile of neurotrophins severely restricts their clinical use. On the other hand, small molecules that modulate neurotrophic activity offer a promising therapeutic approach against neurological disorders. Nature has provided an impressive array of natural products that have potent neurotrophic activities. This Review highlights the current synthetic strategies toward these compounds and summarizes their ability to induce neuronal growth and rehabilitation. It is anticipated that neurotrophic natural products could be used not only as starting points in drug design but also as tools to study the next frontier in biomedical sciences: the brain activity map project.

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“…Panaxytriol (272), ein wirksamer Bestandteil von Rotem Ginseng, [232] wurde von mehreren Arbeitsgruppen synthetisiert, [233] darunter Danishefsky et al, die nachwiesen, dass 272 in einer Konzentration von 60 mm das NGF-induzierte Neuritenwachstum in PC-12-Zellen begünstigt. [234] Talaumidin (273) ist ein Tetrahydrofuran-Neolignan, das aus der Wurzel von Aristolochia arcuata isoliert wurde.…”

Section: Neovibsanineunclassified

Neurotrophe Naturstoffe – ihre Chemie und Biologie

Lacoske

Theodorakis

2013

Angewandte Chemie

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Neurodegenerative Erkrankungen und Rückenmarksverletzungen betreffen weltweit etwa 50 Millionen Menschen und verursachen Gesundheitskosten von insgesamt mehr als 600 Milliarden Dollar pro Jahr. Nervenwachstumsfaktoren, d. h. Neurotrophine, sind potenzielle Therapeutika für diese Erkrankungen, denn sie können die Regeneration von Nerven fördern. Durchschnittlich 500 Publikationen jährlich belegen die Bedeutung der Neurotrophine in den biomedizinischen Wissenschaften und ihr Potenzial für therapeutische Anwendungen. Allerdings ist die klinische Verwendung von Neurotrophinen wegen ihres schlechten pharmakokinetischen Profils stark eingeschränkt. Niedermolekulare Verbindungen, die die neurotrophe Aktivität modulieren, bieten hingegen einen vielversprechenden Therapieansatz bei neurologischen Erkrankungen. Die Natur hat für eine beeindruckende Zahl von Naturstoffen mit starken neurotrophen Wirkungen gesorgt. Die aktuellen Strategien zur Synthese dieser Verbindungen sowie deren Fähigkeit, das Wachstum und die Erneuerung von Nervenzellen zu induzieren, bilden den Schwerpunkt dieses Aufsatzes. Es ist davon auszugehen, dass neurotrophe Naturstoffe nicht nur als Leitstrukturen in der Wirkstoffentwicklung genutzt werden können, sondern auch für das nächste große Projekt der Biomedizin: die Kartierung der Hirnaktivität (BAM, Brain Activity Map).

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The Absolute Stereostructure of Panaxytriol,a Biologically Active Diacetylenic Acetogenin, from Ginseng Radix Rubra.

Cited by 12 publications

References 0 publications

Synthesis of Naturally Occurring Polyynes

Synthesis of Naturally Occurring Polyynes

Neurotrophic Natural Products: Chemistry and Biology

Neurotrophe Naturstoffe – ihre Chemie und Biologie

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