Pituranthoside from Pituranthos triradiatus

Halim, Ahmed F.; Saad, H.-E. A.; Lahloub, M. F.; Ahmed, Atallah F.

doi:10.1016/0031-9422(95)00236-z

Cited by 18 publications

(22 citation statements)

References 7 publications

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“…[60] 7-(7-hydroxy-3,7-dimethylocta-2,5-dienyloxy)-coumarin (79) HO Clausena excavata, [137] Esenbeckia grandiflora, [138] Phebalium spp., [60] Phellodendron chinense, [147] Zanthoxylum schinifolium [141] Epoxyauraptene (80) O Aegle marmelos, [148] Aster yunnanensis, [149] Citrus spp., [150][151][152] Zanthoxylum schinifolium [140] 7-(3,7-dimethyl-6-oxooct-2-enyloxy)-coumarin (81) O Baccharis darwinii, 153] Citrus hassaku [154] Auraptenal (82) O Capnophyllum peregrinum, [155] Citrus hassaku [154] 7-(5,6-dihydroxy-3,7-dimethylocta-2,7-dienyloxy)-coumarin (83) OH OH Zanthoxylum schinifolium [141] Excavatin A (84) HO OH Clausena excavata [137] Marmin (85) OH HO Aegle marmelos, [156] Aster praealtus. [157] Aurantii fructus immaturus, [158] Citrus grandis, [159] Citrus hassaku, [154] Eremocitrus glauca, [160] Ferula malacophyla , [161] Geijera parviflora, [162] Pituranthos triradiatus, [163] Xue-Fu-Zhu-YuTang [164] Marmin 7-(methylether) (86)…”

Section: R Main Sourcesmentioning

confidence: 99%

Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Curini¹,

Cravotto²,

Epifano³

et al. 2006

CMC

274

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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Section: R Main Sourcesmentioning

confidence: 99%

Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Curini¹,

Cravotto²,

Epifano³

et al. 2006

CMC

274

170

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“…2,3 The essential oil of P. scoparius has been described as antispasmodic. 4 Phytochemical studies have been carried out on P. triradiatus [5][6][7] and P. tortuosus 8,9 especially to determine the composition with regard to coumarin, polyacetylenic compounds, flavonoïds and sterols. Few essential oils of the genus have been analysed; only these of P. tortuosus 8 and P. scoparius 10 have been studied.…”

Section: Introductionmentioning

confidence: 99%

Composition of seeds and stems essential oils of Pituranthos scoparius (Coss. & Dur.) Schinz

Vérité¹,

Nacer

Kabouche³

et al. 2004

Flavour & Fragrance J

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The composition of the essential oils of stems and seeds of Pituranthos scoparius was determined by GC-MS. Almost 50 compounds were identified. In the seed oil, the main compounds were α α α α α-pinene (8.2%), β β β β β-pinene (4.6%), p-cymene (7.5%), limonene (11.2%), thymol (5.9%), myristicin (11.1%) and dill apiole (12.2%); in the stem oil, the main compounds were α α α α α-pinene (6.8%), α α α α α-phellandrene (7.1%), limonene (9.8%), methyl eugenol (5.6%) germacrene D (12.7%), myristicin (7.2%), spathulenol (4.5%) and β β β β β-eudesmol (4.1%).

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“…The HMBC correlations between H-1'/C-7, H-4'/C-2', H-7'/C-2', and H-7'/C-4' showed the presence of 3-methylhex-2'-enoxy group located at C-7 of the coumarin moiety. The geometry about 2', 3'-trisubstituted double bound was determined, like pituranthoside, as trans rather than cis based on the fine splitting pattern of the 2'-vinyl proton (t, J= 6.6 Hz) [9,10].Furthermore, the HMBC correlation between H-1''/C-6' and the similarity of NMR data of the sugar moiety of 2 with that of 1 suggested that C-6' was glycosylated with β-D-glucopyranose. Finally, the structure of 2 was determined as 7-(((E)-3'-methyl-6'-((2'', 3'', 4''-trihydroxy-6''-(hydroxymethyl) tetrahy dro-2H-pyran-1''-yl) oxy) hex-2'-en-1'-yl) oxy)-2H-chromen-2-one, and we named this compound PhellodenolJ.…”

Section: Resultsmentioning

confidence: 99%