Novel antiproliferative falcarindiol furanocoumarin ethers from the root of Angelica japonica

Furumi, Kazuhiro; Fujioka, Toshihiro; Fujii, Hiroko; Okabe, Hikaru; Nakano, Yoritaka; Matsunaga, Hisashi; Mori, Masato; Mihashi, Kunihide

doi:10.1016/s0960-894x(97)10193-7

Cited by 34 publications

(24 citation statements)

References 3 publications

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“…These data were consistent with those published for the C 17 polyacetylene falcarindiol (Fig. 1a), which is a common component of apiaceous plant roots (Furumi et al, 1998). The 3(R), 8(S) stereochemistry of falcarindiol was confirmed by Mosher's ester methodology (Rieser et al, 1992;Su et al, 2002;Ward and Rhee, 1991) and the (S)-and (R)-MTPA esters were prepared and chemical shifts in the H 2 -1, H-2 and H-9/H-10 protons were measured for both derivatives (Fig.…”

Section: Resultssupporting

confidence: 92%

The anti-staphylococcal activity of Angelica dahurica (Bai Zhi)

et al. 2004

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Section: Resultssupporting

confidence: 92%

The anti-staphylococcal activity of Angelica dahurica (Bai Zhi)

et al. 2004

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“…All furanocoumarins showed but weak antiproliferative activity, although for some of them specificity emerged. Japoangelone was more active against B16F10 than MK-1 and HeLa; all japoangelols were almost equally active against the three tumor cell lines, though less so on MK-1 cells than on HeLa and B16F10 [95][96].…”

Section: D-glcomentioning

confidence: 88%

Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Curini¹,

Cravotto²,

Epifano³

et al. 2006

CMC

272

170

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Prenyloxycoumarins and prenyloxyfuranocoumarins (isopentenyloxy-, geranyloxy-, linear and cyclic sesquiterpenyloxy compounds and their biosynthetic derivatives) represent a family of secondary metabolites that have been considered for years just as intermediates of other coumarin-based compounds. Only in the last two decades these secondary metabolites have been recognized as interesting and valuable biologically active natural products. Up to now more than 160 compounds have been isolated from plants mainly belonging to the families of Rutaceae and Umbelliferae, comprising common edible vegetables and fruits like lemons, oranges and grapefruits. In view of the biological activity of some natural prenyloxycoumarins, very recently syntheses of structurally related analogs aimed to establish detailed structure-activity relationships have also been carried out. Many of the isolated prenyloxy- and prenyloxy-furanocoumarins and their semisynthetic derivatives were shown to exert in vitro and in vivo remarkable anti-tumoral, anti-inflammatory and anti-viral effects. The object of this review is to examine in detail the different types of prenyloxycoumarins and prenyloxyfuranocoumarins from the chemical, phytochemical and biological point of view.

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“…Acetoxy modifications found in the known Apiaceae acetate 25I and oplopandiol acetate (25H) from Oplopanax horridus increase selectivity towards Mycobacterium spp.. Falcarindiol ethers with furanocoumarins, named japoangelols A-D (25J-M), are novel structures with the potential for enhanced contact toxicity [300]; both polyacetylenes and furanocoumarins in Apiaceae species are known to cause dermatitis. Among these metabolites, falcarindiol had greater in vitro inhibitory activity against human gastric adenocarcinoma cells than any of the ethers 25J-M [301].…”

Section: New Natural Productsmentioning

confidence: 95%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

291

228

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Polyacetylenic natural products are a substantial class of often unstable compounds containing a unique carbon-carbon triple bond functionality, that are intriguing for their wide variety of biochemical and ecological functions, economic potential, and surprising mode of biosynthesis. Isotopic tracer experiments between 1960 and 1990 demonstrated that the majority of these compounds are derived from fatty acid and polyketide precursors. During the past decade, research into the metabolism of polyacetylenes has swiftly advanced, driven by the cloning of the first genes responsible for polyacetylene biosynthesis in plants, moss, fungi, and actinomycetes, and the initial characterization of the gene products.The current state of knowledge of the biochemistry and molecular genetics of polyacetylenic secondary metabolic pathways will be presented together with an up-to-date survey of new terrestrial and marine natural products, their known biological activities, and a discussion of their likely metabolic origins.

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Novel antiproliferative falcarindiol furanocoumarin ethers from the root of Angelica japonica

Cited by 34 publications

References 3 publications

The anti-staphylococcal activity of Angelica dahurica (Bai Zhi)

The anti-staphylococcal activity of Angelica dahurica (Bai Zhi)

Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Biosynthesis and function of polyacetylenes and allied natural products

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