Two 6,7-dioxygenated coumarins from Pterocaulon virgatum

Debenedetti, Sílvia; Nadinic, Elena L.; Coussio, J.; Kimpe, Norbert De; Boeykens, Marc

doi:10.1016/s0031-9422(98)00020-x

Cited by 23 publications

(18 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The substitution pattern for the B-ring was shown to be 3′,4′-dimethoxy by its 1 H-NMR and EI-MS spectra. The 1 H-NMR spectra of compound 3 (Table 1) were similar to those of 2, except for the presence of a 2-hydroxy-3-methylbut-3-enyloxy group 19) )] instead of a 3-methylbut-2-enyloxy group signal in 2. The EI-MS spectrum showed a peak at m/z 357 that was assigned to the fragment ion produced by the loss of the 2-hydroxy-3-methylbut-3-enyl radical from the molecular ion, supporting the presence of the 2-hydroxy-3-methylbut-3-enyloxy group.…”

Section: Chartmentioning

confidence: 80%

Isolation of Six New Flavonoids from <i>Melicope triphylla</i>

Higa

Imamura

Shimoji

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Six new flavonoids-5-hydroxy-3,8-dimethoxy-3′,4′:6,7-bismethylenedioxyflavone (1), 3,3′,4′,5-tetramethoxy-7-(3-methylbut-2-enyloxy)flavone (2), 7-(2-hydroxy-3-methylbut-3-enyloxy)-3,3′,4′,5-tetramethoxyflavone (3), 7-(2-hydroxy-3-methylbut-3-enyloxy)-3,5-dimethoxy-3′,4′-methylenedioxyflavone (4), 7-(2-hydroxy-3-methyl but-3-enyloxy)-3,3′,4′,5,8-pentamethoxyflavone (5), and 7-(2-hydroxy-3-methylbut-3-enyloxy)-3,5,8-tri methoxy-3′,4′-methylenedioxyflavone (6)-were isolated from the leaves of Melicope triphylla. In addition, six already known flavonoids were also detected: 5-hydroxy-3,6,7-trimethoxy-3′,4′-methylenedioxyflavone (7), 5,7-dihydroxy-3,3′,4′,8-tetramethoxyflavone (8), 4′,5-dihydroxy-3,3′,7,8-tetramethoxyflavone (9), 3,5,6,7,8-penta methoxy-3′,4′-methylenedioxyflavone (10), 3,5,6,7-tetramethoxy-3′,4′-methylenedioxyflavone (11), and 3,3′,4′,5,6,7,8-heptamethoxyflavone (12). The structures of the new compounds were established by spectroscopic methods. Compound 2 displayed ichthyotoxic activity against Japanese killifish (medaka in Japanese) (Oryzias latipes var.) at 10 ppm.

show abstract

Section: Chartmentioning

confidence: 80%

Isolation of Six New Flavonoids from <i>Melicope triphylla</i>

Higa

Imamura

Shimoji

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

“…Algumas cumarinas isoladas de espécies de Pterocaulon podem ser citadas: 6,7-dimetoxicumarina de P. sphacelatum, oito cumarinas do extrato etéreo das partes aéreas de P. balansae e P. lanatum (MA-GALHÃES et al, 1981) e uma cumarina 5,6,7,8-tetraoxigenada, denominada purpurenol de P. purpurascens (Debenedetti et al, 1991). Debenedetti et al (1997) realizaram uma revisão estrutural das cumarinas denominadas sabandinol e sabandinona e a descrição de mais duas novas cumarinas denominadas de virgatenol e virgatol (Debenedetti et al, 1998). Também foram isoladas de P. virgatum as seguintes substâncias: taraxasterol, esqualeno, taxifolina 7-O-prenilada, entre outros compostos (Bohlmann et al, 1981).…”

Section: Introductionunclassified

Estudo fitoquímico da espécie Pterocaulon interruptum DC. (Asteraceae)

Heemann¹,

Miguel²,

Miguel³

et al. 2006

Rev. Bras. Cienc. Farm.

View full text Add to dashboard Cite

“…199.5°C; 1 H-NMR δ (CDCl 3 ): 6.07 (2H, s), 6.28 (1H, d, J=9. The structure of compounds (2-6) were elucidated and confirmed by 1 H and 13 C-NMR, MS, and by subsequent comparisons with reference data from the available literature (Duddeck and Kaiser 1982;Tsukamoto et al 1984;Afek et al 1986;Debenedetti et al 1998;Maes et al 2005).…”

Section: Synthesis Procedures and Spectral Data Of Coumarinmentioning

confidence: 92%

Antitermite Activities of Coumarin Derivatives and Scopoletin from Protium javanicum Burm. f.

et al. 2010

View full text Add to dashboard Cite

The antitermite (termiticidal and antifeedant) activity of Protium javanicum Burm. f. extract was investigated. The ethyl acetate fraction was active. Scopoletin (1), quercetin, and stigmasterol were isolated by bioassay-guided fractionation. Scopoletin had the highest activity among the three compounds. In order to investigate the structure-activity relationship (SAR) of the methoxy and hydroxy groups at the C-6 and C-7 positions of the coumarin skeleton, we synthesized several coumarin derivatives whose chemical structures are similar to scopoletin. Scopoletin exhibited the strongest termiticidal activity among the 10 compounds tested, followed by 6-methoxycoumarin (3), 6-hydroxycoumarin (7), and umbelliferone (8). All compounds except coumarin (9) showed antifeedant activity.

show abstract

Two 6,7-dioxygenated coumarins from Pterocaulon virgatum

Cited by 23 publications

References 9 publications

Isolation of Six New Flavonoids from <i>Melicope triphylla</i>

Isolation of Six New Flavonoids from <i>Melicope triphylla</i>

Estudo fitoquímico da espécie Pterocaulon interruptum DC. (Asteraceae)

Antitermite Activities of Coumarin Derivatives and Scopoletin from Protium javanicum Burm. f.

Contact Info

Product

Resources

About