Prenylated flavanones from Monotes engleri: On-line structure elucidation by LC/UV/NMR

E. Garo, J. L. Wolfender, K. Hostettmann, W. Hiller, S. Antus, S. Mavi

Research output: Contribution to journalArticle

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Abstract

The CH2Cl2 extract of Monotes engleri Gilg. (Dipterocarpaceae) showed antifungal activity against the yeast Candida albicans in our bioautographic TLC assays. After a first fractionation of the crude extract, the bioactivity was located in one of the fractions. To perform an efficient targeted isolation of the active compounds, LC/UV/MS and LC/UV/NMR analyses of the crude extract and the active fraction were performed. LC/UV, LC/MS, and LC/NMR data (1D and 2D) allowed the identification of 1 as (2S)-2,3-dihydro- 5,7-dihydroxy-2-{3-hydroxy-4-[(3-methylbut-2-enyl)oxy]phenyl}-4H-t- benzopyran-4-one, a new prenylated flavanone, named monotesone A. Subsequent isolation of 1 has permitted the determination of its absolute configuration on the basis of CD measurements. Three other prenylated flavanones 2-4 were isolated from the same extract. Compound 3 was identified as 2-(3,5- dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-6,8-bis(3-methylbut-2-enyl)-4H-t- benzopyran-4-one, another new natural product, named monotesone B. The structures of 2 and 4 were established as selinone and lonchocarpol A, respectively. The antifungal activity against Candida albicans was determined for all compounds.

Original languageEnglish
Pages (from-to)754-763
Number of pages10
JournalHelvetica Chimica Acta
Volume81
Issue number4
Publication statusPublished - 1998

Fingerprint

Dipterocarpaceae
Flavanones
Candida
Complex Mixtures
Candida albicans
isolation
Nuclear magnetic resonance
nuclear magnetic resonance
yeast
Fractionation
Bioactivity
Biological Products
fractionation
Yeast
Assays
Yeasts
products
configurations
benzopyran-4-one

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Garo, E., Wolfender, J. L., Hostettmann, K., Hiller, W., Antus, S., & Mavi, S. (1998). Prenylated flavanones from Monotes engleri: On-line structure elucidation by LC/UV/NMR. Helvetica Chimica Acta, 81(4), 754-763.

Prenylated flavanones from Monotes engleri : On-line structure elucidation by LC/UV/NMR. / Garo, E.; Wolfender, J. L.; Hostettmann, K.; Hiller, W.; Antus, S.; Mavi, S.

In: Helvetica Chimica Acta, Vol. 81, No. 4, 1998, p. 754-763.

Research output: Contribution to journalArticle

Garo, E, Wolfender, JL, Hostettmann, K, Hiller, W, Antus, S & Mavi, S 1998, 'Prenylated flavanones from Monotes engleri: On-line structure elucidation by LC/UV/NMR', Helvetica Chimica Acta, vol. 81, no. 4, pp. 754-763.
Garo E, Wolfender JL, Hostettmann K, Hiller W, Antus S, Mavi S. Prenylated flavanones from Monotes engleri: On-line structure elucidation by LC/UV/NMR. Helvetica Chimica Acta. 1998;81(4):754-763.
Garo, E. ; Wolfender, J. L. ; Hostettmann, K. ; Hiller, W. ; Antus, S. ; Mavi, S. / Prenylated flavanones from Monotes engleri : On-line structure elucidation by LC/UV/NMR. In: Helvetica Chimica Acta. 1998 ; Vol. 81, No. 4. pp. 754-763.
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