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A new flavan-3,4-diol from Acacia auriculiformis by paper ionophoresis
- Source :
- The Biochemical journal. 98(2)
- Publication Year :
- 1966
-
Abstract
- 1. The heartwood of A. auriculiformis contains a typical mixture of analogues consisting of three isomeric flavan-3,4-diols, a dihydroflavonol, flavanone, flavonol and chalcone based on the 4′,7,8-trihydroxyl pattern. These were resolved by preparative paper chromatography and preparative paper ionophoresis. 2. Crystalline (−)-teracacidin [(2R,3R,4R)-4′,7,8-trihydroxy-2,3-cis-flavan-3,4-cis-diol] was obtained in high (10%) yield, and a new crystalline derivative of (−)-isoteracacidin [(−)-2,3-cis-3,4-trans isomer] was isolated. The crystalline methyl ether of a new (+)-2,3-trans-3,4-cis isomer was isolated. 3. The absolute configurations of (−)-isoteracacidin (2R,3R,4S) and of the (+)-2,3-trans-3,4-cis isomer (2R,3S,4S) were tentatively assigned on the basis of nuclear-magnetic-resonance spectroscopy, paper ionophoresis and paper-chromatographic comparison with the epimerization products of (−)-teracacidin. 4. Possible reasons for the absence of polymeric leuco-anthocyanidin tannins are discussed. 5. (±)-4′,7,8-Trihydroxydihydroflavonol and (±)-4′,7,8-trihydroxyflavanone were isolated for the first time. 6. The bark polyphenols consist mainly of polymeric leuco-delphinidins and leuco-cyanidins which redden exceptionally rapidly to light. The mechanism of this phenomenon is discussed.
- Subjects :
- Electrophoresis
Chalcone
Magnetic Resonance Spectroscopy
Chemical Phenomena
Chromatography, Paper
Applied Mathematics
General Mathematics
Diol
Acacia
Ether
Articles
In Vitro Techniques
Medicinal chemistry
chemistry.chemical_compound
Paper chromatography
Chemistry
chemistry
Flavan
Polyphenol
Organic chemistry
Epimer
Benzopyrans
Chromatography, Thin Layer
Flavanone
Subjects
Details
- ISSN :
- 02646021
- Volume :
- 98
- Issue :
- 2
- Database :
- OpenAIRE
- Journal :
- The Biochemical journal
- Accession number :
- edsair.doi.dedup.....3460d4e9f5d2f512fd45ef3bc2615f24