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

doi:10.1016/0031-9422(93)85354-T

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 for this work

VTT Technical Research Centre of Finland

Research output: Contribution to journal › Article › Scientific › peer-review

14 Citations (Scopus)

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 language	English
Pages (from-to)	755-758
Journal	Phytochemistry
Volume	34
Issue number	3
DOIs	https://doi.org/10.1016/0031-9422(93)85354-T
Publication status	Published - 1993
MoE publication type	A1 Journal article-refereed

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@article{142d76815d5e426283be13a50877a995,

title = "Isolation and structure determination of three triterpenes from bark resin of juvenile European white birch",

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",

note = "Project code: BIO9001",

year = "1993",

doi = "10.1016/0031-9422(93)85354-T",

language = "English",

volume = "34",

pages = "755--758",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier",

number = "3",

}

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

SN - 0031-9422

VL - 34

SP - 755

EP - 758

JO - Phytochemistry

JF - Phytochemistry

IS - 3

ER -

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

Abstract

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