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)

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",

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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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