Isolation and structure determination of three triterpenes from bark resin of juvenile European white birch

Hannu Taipale, Jouko Vepsäläinen, Reino Laatikainen, Paul Reichardt, Seppo Lapinjoki (Corresponding Author)

Research output: Contribution to journalArticleScientificpeer-review

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Abstract

3alpha-O-Malonyl-12beta-O-acetyl-25-hydroxy-(20S,24R)-epoxydammarane (papyriferic acid) and two previously unknown dammarane triterpenes were identified from diethylether extracts of bark resin from juvenile Betula pendula. H-1 and C-13 NMR spectroscopy showed that a compound appearing often in chromatographic analyses in amounts comparable with papyriferic acid is its 3beta-epimer. The third compound which is abundant in individuals with low levels of the other two compounds was shown to be 3beta-O-malonyl-12beta-O-acetyl-20(S)-hydroxydammar-24-ene (pendulic acid), i.e. an analogue of the 3beta-epimer of papyriferic acid with open and partially reduced C-17 side chain.
Original languageEnglish
Pages (from-to)755 - 758
Number of pages4
JournalPhytochemistry
Volume34
Issue number3
DOIs
Publication statusPublished - 1993
MoE publication typeA1 Journal article-refereed

Fingerprint

Betula
Triterpenes
Betula pendula
triterpenoids
resins
bark
Resins
acids
Nuclear magnetic resonance spectroscopy
Chromatography
Magnetic Resonance Spectroscopy
nuclear magnetic resonance spectroscopy
Acids
papyriferic acid
extracts

Cite this

Taipale, H., Vepsäläinen, J., Laatikainen, R., Reichardt, P., & Lapinjoki, S. (1993). Isolation and structure determination of three triterpenes from bark resin of juvenile European white birch. Phytochemistry, 34(3), 755 - 758. https://doi.org/10.1016/0031-9422(93)85354-T
Taipale, Hannu ; Vepsäläinen, Jouko ; Laatikainen, Reino ; Reichardt, Paul ; Lapinjoki, Seppo. / Isolation and structure determination of three triterpenes from bark resin of juvenile European white birch. In: Phytochemistry. 1993 ; Vol. 34, No. 3. pp. 755 - 758.
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abstract = "3alpha-O-Malonyl-12beta-O-acetyl-25-hydroxy-(20S,24R)-epoxydammarane (papyriferic acid) and two previously unknown dammarane triterpenes were identified from diethylether extracts of bark resin from juvenile Betula pendula. H-1 and C-13 NMR spectroscopy showed that a compound appearing often in chromatographic analyses in amounts comparable with papyriferic acid is its 3beta-epimer. The third compound which is abundant in individuals with low levels of the other two compounds was shown to be 3beta-O-malonyl-12beta-O-acetyl-20(S)-hydroxydammar-24-ene (pendulic acid), i.e. an analogue of the 3beta-epimer of papyriferic acid with open and partially reduced C-17 side chain.",
author = "Hannu Taipale and Jouko Veps{\"a}l{\"a}inen and Reino Laatikainen and Paul Reichardt and Seppo Lapinjoki",
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Taipale, H, Vepsäläinen, J, Laatikainen, R, Reichardt, P & Lapinjoki, S 1993, 'Isolation and structure determination of three triterpenes from bark resin of juvenile European white birch', Phytochemistry, vol. 34, no. 3, pp. 755 - 758. https://doi.org/10.1016/0031-9422(93)85354-T

Isolation and structure determination of three triterpenes from bark resin of juvenile European white birch. / Taipale, Hannu; Vepsäläinen, Jouko; Laatikainen, Reino; Reichardt, Paul; Lapinjoki, Seppo (Corresponding Author).

In: Phytochemistry, Vol. 34, No. 3, 1993, p. 755 - 758.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Isolation and structure determination of three triterpenes from bark resin of juvenile European white birch

AU - Taipale, Hannu

AU - Vepsäläinen, Jouko

AU - Laatikainen, Reino

AU - Reichardt, Paul

AU - Lapinjoki, Seppo

N1 - Project code: BIO9001

PY - 1993

Y1 - 1993

N2 - 3alpha-O-Malonyl-12beta-O-acetyl-25-hydroxy-(20S,24R)-epoxydammarane (papyriferic acid) and two previously unknown dammarane triterpenes were identified from diethylether extracts of bark resin from juvenile Betula pendula. H-1 and C-13 NMR spectroscopy showed that a compound appearing often in chromatographic analyses in amounts comparable with papyriferic acid is its 3beta-epimer. The third compound which is abundant in individuals with low levels of the other two compounds was shown to be 3beta-O-malonyl-12beta-O-acetyl-20(S)-hydroxydammar-24-ene (pendulic acid), i.e. an analogue of the 3beta-epimer of papyriferic acid with open and partially reduced C-17 side chain.

AB - 3alpha-O-Malonyl-12beta-O-acetyl-25-hydroxy-(20S,24R)-epoxydammarane (papyriferic acid) and two previously unknown dammarane triterpenes were identified from diethylether extracts of bark resin from juvenile Betula pendula. H-1 and C-13 NMR spectroscopy showed that a compound appearing often in chromatographic analyses in amounts comparable with papyriferic acid is its 3beta-epimer. The third compound which is abundant in individuals with low levels of the other two compounds was shown to be 3beta-O-malonyl-12beta-O-acetyl-20(S)-hydroxydammar-24-ene (pendulic acid), i.e. an analogue of the 3beta-epimer of papyriferic acid with open and partially reduced C-17 side chain.

U2 - 10.1016/0031-9422(93)85354-T

DO - 10.1016/0031-9422(93)85354-T

M3 - Article

VL - 34

SP - 755

EP - 758

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

IS - 3

ER -