cis- andtrans-Neocnidilide;1H- and13C-NMR Data of Some Phthalides

Fischer, F. C.; Gijbels, Marion J. M.

doi:10.1055/s-2006-962626

Cited by 27 publications

(27 citation statements)

References 14 publications

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“…In fact, all calculated values were found to be within 0-3 ppm from the experimental shifts of 3 and they are shown in Table 2. The I3c NMR data of several other naturally occurring (18) and synthetic phthalides (19) were also considered. On the bases of all the evidence, the structure of 3 was assigned to 4-carboxy-3-hydroxy-7-methoxy-6-methyl-1(3H)-isobenzofuranone and it was given the trivial name convolvulanic acid A.…”

mentioning

confidence: 99%

Phytotoxic metabolites of Phomopsisconvolvulus, a host-specific pathogen of field bindweed

Tsantrizos¹,

Ogilvie²,

Watson³

1992

Can. J. Chem.

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. Can. J. Chem. 70, 2276Chem. 70, (1992. Phornopsis corzvolvulus is a host-specific pathogen which causes leaf spots and anthracnose lesions in the important perennial weed Corzvolvulus arvensis (field bindweed). Investigation of the n~etabolites produced by the fungus led to the isolation of the known fungal metabolites ergosterol (1) and ergosterol peroxide (2), in addition to four novel phytotoxins: the phthalides convolvulanic acid A (3), convolvulanic acid B (4), convolvulol (5), and the a-pyrone convolvulopyrone (6). The latter compounds were assigned the structures of 4-carboxy-3-hydroxy-7-methoxy-6-methyll(3H)-isobenzofuranone (3), 4-carboxy-7-methoxy-6-methyl-1(3H)-isobenzofuranone (4), 4-(hydroxymethy1)-7-methoxy-6-methyl-l(3H)-isobenzofuranone (5), and 3-[4-methoxy-3-methyl-a-pyron-6-yl]-2-methyl-2-butenoic acid (6) [Traduit par la r6dactionl

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mentioning

confidence: 99%

Phytotoxic metabolites of Phomopsisconvolvulus, a host-specific pathogen of field bindweed

Tsantrizos¹,

Ogilvie²,

Watson³

1992

Can. J. Chem.

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“…Separation by silica gel column chromatography gave (AE)-1 and (AE)-3 in respective 50% and 13% yields, whose NMR spectral data were in accordance with those reported. 17) We next applied this method to the asymmetric synthesis of 1 and 3. The enzymatic resolution of (AE)-4 respectively gave known (S)-(À)-4 and (R)-(þ)-4 in 99.9% ee and 97.4% ee by using the modified method reported by Abad et al…”

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confidence: 99%

Asymmetric Synthesis and Sensory Evaluation of Sedanenolide

Oguro

Watanabe

2011

Bioscience, Biotechnology, and Biochemistry

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“…8) Whereas total amount of (E)-butylidenephthalide isolated from A. acutiloba was too small to assess biological activity, we isolated (E)-butylidenephthalide from commercially available butylidenephthalide (E/Z mixture) purchased from Lancaster Synthesis Ltd. (Lancashire, U.K.) using SiO 2 column chromatography. Their identity to the natural compounds was determined compared to the spectral data (NMR, GC, GC-MS) of isolated compounds from A. acutiloba and literature data.…”

Section: Methodsmentioning

confidence: 99%

“…Their identity to the natural compounds was determined compared to the spectral data (NMR, GC, GC-MS) of isolated compounds from A. acutiloba and literature data. 8) Both (E)-and (Z)-butylidenephthalide used for assay was Ͼ99% purity determined by GC and GC-MS analysis. Rotenone was purchased from Sigma-Aldrich Co. (St. Louis, MO, U.S.A.).…”

Section: Methodsmentioning

confidence: 99%

Comparison of Larvicidal, Adulticidal and Acaricidal Activity of Two Geometrical Butylidenephthalide Isomers

Tsukamoto

Nakatani

Yoshioka

et al. 2006

Biological & Pharmaceutical Bulletin

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Butylidenephthalide, the components of Angelica acutiloba var. sugiyamae HIKINO (Apiaceae) has the biological activities, such as centrally acting muscle relaxant 1) and antispasmodic effects 2) with characteristic odor. In our previous work,3) (Z)-butylidenephthalide was isolated as the potent insecticidal compound against adults and larvae of Drosophila melanogaster. Recently, Ahn et al. reported that butylidenephthalide was active constituent of Cnidium officinale against Dermatophagoides farinae and Tyrophagus putrescentiae, and more effective than acaricide, N,N-diethyl-mtoluamide (DEET). 4,5) Therefore, butylidenephthalide is the potential candidate for new natural pesticide. However, above report was unclear on stereochemistry of butylidenephthalide even though both (E)-and (Z)-butylidenephthalide were found from natural resources, and (E)-butylidenephthalide has not been tested against insects and mites.Geometrical stereoselectivity is often crucial on biological activities. Asahina et al. reported that synthetic fluoroquinolone derivatives were tested for antibacterial activity, and (Z)-isomers exhibited 2-to 32-fold more potent than corresponding (E)-isomers. 6) Against insects, the importance of geometry was discussed that binding affinity of juvenile hormone carrier protein from the hemolymph of Manduca sexta was decreased as (Z)-double bond are substituted for (E)-double bond in synthetic juvenile hormone analogues. 7)Therefore, evaluation of biological activity for geometrical isomers is required.Biological activity of (E)-butylidenephthalide against insects and mites has not been previously reported. In this paper, we investigated biological activities of (E)-butylidenephthalide against larvae and adults of D. melanogaster, adults of Ctenocephalides felis and two house dust mites, D. farinae and T. putrescentiae, and compared with (Z)-butylidenephthalide to investigate geometrical stereoselectivity. Rotenone (positive control for insecticidal activity) and DEET (positive control for acaricidal activity) were also tested. MATERIALS AND METHODSGC and GC-MS Analysis GC was performed on a Hewlett-Packard 5890A gas chromatograph equipped with a flame ionization detector (FID). The column was a fused silica capillary column (DB-5, 30 m length, 0.25 mm i.d.). Chromatographic conditions were as follows: oven temperature was programmed from 80 to 250°C at 4°C/min and held at 250°C for 15 min; injector and detector temperature were 270 and 280°C, respectively; carrier gas, helium at a flow rate of 40 cm/s. GC-MS was performed on a HewlettPackard 5972A mass selective detector interfaced with a Hewlett-Packard 5890A gas chromatograph fitted with a capillary column (HP-5MS, 30 m length, 0.25 i.d.). Chromatographic conditions were the same for the GC analysis.Chemicals (Z)-Butylidenephthalide was previously isolated from Angelica acutiloba.3) (E)-Butylidenephthalide was isolated from chloroform extract of A. acutiloba by SiO 2 (200 mesh) column chromatography (hexane : ethyl acetate ϭ93 : 7), repeatedly. The pu...

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cis- andtrans-Neocnidilide;¹H- and¹³C-NMR Data of Some Phthalides

Cited by 27 publications

References 14 publications

Phytotoxic metabolites of Phomopsisconvolvulus, a host-specific pathogen of field bindweed

Phytotoxic metabolites of Phomopsisconvolvulus, a host-specific pathogen of field bindweed

Asymmetric Synthesis and Sensory Evaluation of Sedanenolide

Comparison of Larvicidal, Adulticidal and Acaricidal Activity of Two Geometrical Butylidenephthalide Isomers

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