Natürlich vorkommende Cumarin‐Derivate, VI. Über die Inhaltsstoffe von <i>Capnophyllum</i>‐Arten

Bohlmann, Ferdinand; Clausen, Ernst

doi:10.1002/cber.19701031125

Cited by 13 publications

(7 citation statements)

References 4 publications

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“…Structural determination of the coumarins (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13) The juice oil of Citrus hassaku contained a large amount (ca. 24%) of essential oil.…”

Section: Resultsmentioning

confidence: 99%

“…As a spasmogen, a BaCl 2 solution to a final concentration of 3 x 10 -4 M was used according to Yamada's procedure. 2) A test sample to final concentrations of 5 x 10-5 M, 2.5 X 10-5 M, and 1.25 x 10- 5 M was added to Magnus tube 3 min before adding the spasmogen, the data being shown in Table 1. Compounds 4,7, and 11 showed stronger activity than that of 1; however, the 6'-O-esterified marmins (8 and 11), the T-O-methylated marmin (9), and the 8' -oxoderivative (5) showed no activity under these conditions.…”

Section: Spasmolytic Activity Of the Isolated Compoundsmentioning

confidence: 99%

“…Previously, we have already reported three new coumarins from the juice oil. 3) This paper reports the isolation and structural determination of seven additional coumarins (4,5,6,8,9, 12, and 13) and the spasmolytic activity of ten coumarins (4-13) from the juice oil.…”

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confidence: 99%

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Coumarin Constituents of the Juice Oil fromCitrus hassakuand Their Spasmolytic Activity

Masuda

Muroya

Nakatani

1992

Bioscience, Biotechnology, and Biochemistry

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Ten 7-hydroxycoumarin derivatives (4-13), containing two newly identified compounds (8 and 9), were isolated from the juice oil of fruits of Citrus hassaku, along with aurapten (1), (+)-epoxyaurapten (2), and (+)-marmin (3), and their structures were absolutely determined by spectroscopic and chemical methods. The spasmolytic activity of the isolated compounds was measured by the Magnus method, using guinea pig ileums. Three compounds (4, 7, and 11) showed higher activity than that of aurapten (1). The other compounds showed no activity under these conditions. The structure and activity relationship is discussed.

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“…Structural determination of the coumarins (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13) The juice oil of Citrus hassaku contained a large amount (ca. 24%) of essential oil.…”

Section: Resultsmentioning

confidence: 99%

Section: Spasmolytic Activity Of the Isolated Compoundsmentioning

confidence: 99%

See 1 more Smart Citation

Coumarin Constituents of the Juice Oil fromCitrus hassakuand Their Spasmolytic Activity

Masuda

Muroya

Nakatani

1992

Bioscience, Biotechnology, and Biochemistry

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“…In experiments carried out on rats these terpenoid coumarins, especially 99, considerably decreased cholesterol and triglyceride blood levels [155]. Auraptenal (82), first isolated by Bohlmann from Capnophyllum peregrinum [212], was shown to possess spasmolytic [154] and antimicrobial activities [146]. Excavatin A (84) and excavatin B (92) were extracted from Clausena excavata Scheme 4.…”

Section: -Geranyloxycoumarinmentioning

confidence: 99%

Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Curini¹,

Cravotto²,

Epifano³

et al. 2006

CMC

271

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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“…The structures of known compounds 2-7 have been identified as isoscopoletin (2), 12) umbelliferone (3), 13) anisocoumarin H (4), 14) capnolactone (5), 15) aurapten (6) 16) and 7-[(E)-7 0 -hydroxy-3 0 ,7 0 -dimethylocta-2 0 ,5 0 -dienyloxy]-coumarin (7) (see Fig. 1).…”

mentioning

confidence: 99%