On terpenes. CIV. The constitution of betulenols from oil from the buds of white birch (Betula alba L.)

Holub, M.; Herout, V.; Horák, Miroslav; Šorm, F.

doi:10.1135/cccc19593730

Cited by 27 publications

(5 citation statements)

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“…8 In contrast, Holub reported the occurrence of α-and β-betulenol, as well as α-betulenol acetate with different structures as the previous investigators, also isolated from Betula species. 9 Dhar et al reviewed the chemistry of the birch tree including the essential oil which appeared to support Holubs' previous work. 10 Hiltunen and co-workers reconfirmed by means of chemical reactions and gas chromatography / mass spectrometry (GC -MS), the occurrence of the main compounds as α-and β-betulenol and their relevant acetates in the bud oil of B. pubescens Ehrh., supporting Treibs' work.…”

Section: Introductionmentioning

confidence: 87%

“…[19][20][21][22] There have been many conflicts and disagreements concerning absolute configurations and structures of caryophyllene derivatives isolated from natural sources. [7][8][9]23 The buds of B. pendula, B. litwinowii and B. medwediewii collected from various parts of Turkey were hydrodistilled while B. browicziana and B. recurvata buds were subjected to simultaneous distillation-extraction method (SDE) using a Likens-Nickerson apparatus due to limited plant material. The bud oils were analysed by GC-MS.…”

Section: Resultsmentioning

confidence: 99%

“…[31][32][33][34] Recently, 14-hydroxy-β-caryophyllene (1) was reported to have antibacterial activity against Bacillus subtilis and Escherichia coli. 24 Our research into Betula species growing in Turkey has resulted in the isolation of new caryophyllene derivatives namely; 14-hydroxy-4,5-dihydro-β-caryophyllene (8), 4,5-dihydro-β-caryophyllene-14-al (9), and des-4-methyl-caryophyll-8(14)-en-5-one (10) from B. litwinowii. 15 14-Acetoxy-4,5-dihydro-β-caryophyllene (8a) was prepared from 14-hydroxy-4,5-dihydro-β-caryophyllene (8) (Figure 1).…”

Section: Scheme 4 Epoxidation Of 14-hydroxy-β-caryophyllene (1)mentioning

confidence: 99%

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Studies on Betula essential oils

Başer¹,

Demırcı²

2007

Arkivoc

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Essential oils were obtained from leaf, branch and buds of Betula species: B. pendula Roth, B. browicziana A.Güner, B. litwinowii Doluch., B. recurvata V. Vassil., and B. medwediewii Regel naturally growing in various parts of Turkey. Also buds of the common birch B. pendula essential oil from Germany and two species native to Finland namely, Betula pubescens ssp. czerepanovii (Orlova) Hämet-Ahti and Betula pubescens ssp. pubescens Erhr. were investigated. Betula essential oils were obtained by different distillation techniques such as hydrodistillation, microdistillation and Likens-Nickerson simultaneous distillation-extraction method (SDE). The resulting volatile compositions were elucidated by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) systems. Known and new sesquiterpenes were isolated from Betula essential oils using column chromatographic techniques. Structure determination of each isolated compound was carried out using 1D and 2D NMR spectroscopic techniques supported by MS, UV and GC FITR. Biological activities were determined both for essential oils and pure compounds isolated from the oils of Betula species. Antifungal, antibacterial and antioxidant activity results were carried out using various in vitro techniques.

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Section: Introductionmentioning

confidence: 87%

Section: Resultsmentioning

confidence: 99%

Section: Scheme 4 Epoxidation Of 14-hydroxy-β-caryophyllene (1)mentioning

confidence: 99%

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Studies on Betula essential oils

Başer¹,

Demırcı²

2007

Arkivoc

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“…Betulenols and their acetates were reported as the main components especially the oil obtained from the buds. [5][6][7][8][9][10] In the course of our studies on aromatic plants and in particular the essential oils of Betula species growing in Turkey, we have published some of our results. 14 when insufficient quantities of samples were available.…”

Section: Introductionmentioning

confidence: 99%

Essential oils from the buds of Betula spp. growing in Turkey

Demırcı

Başer²

2003

Flavour & Fragrance J

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The essential oils from buds of Betula browicziana A. Güner, B. litwinowii Doluch., B. medwediewii Regel, B. pendula Roth and B. recurvata V. Vassil. (Betulaceae) were either hydrodistilled using a Clevengertype apparatus or were subjected to Likens-Nickerson simultaneous distillation-extraction (SDE) when the plant material amounts were insufficient. The resulting bud essential oils were analysed by GC-MS. Main components were detected as 14-hydroxy-β-caryophyllene (1) and 14-hydroxy-4,5-dihydro-β-caryophyllene (2) in all the oil samples.

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“…Essential oils are produced by the leaves and especially the buds of birch species and the occurrence and composition of these oils have been reviewed [1]. The major components of these oils are the betulenols (14hydroxycaryophyllenes) [13][14][15], which comprise 20-37% of the bud oils. Weston & Smith due in part to the existence of anti-fungal products in the volatile oil from birch bark, although how long these volatile products survive in the bark and its derived objects is unknown.…”

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confidence: 99%

Sesquiterpenes from the Inner Bark of the Silver Birch and the Paper Birch

Weston

Smith

2012

Natural Product Communications

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The compositions of the mixtures of sesquiterpenoids, largely hydrocarbons that were found in the inner bark of the silver birch, Betula pendula Roth and the paper birch, Betula papyrifera Marshall, grown in New Zealand were analyzed by SPME-GCMS. The major components of the volatile oil from the inner bark of B. pendula were trans α-bergamotene (31%) and α-santalene (19%). This composition was quite different from that of the oil from the branches, buds and leaves of the same species from Turkey, but was very similar to that of the oil from the bark of B. pubescens from Russia. The major components of the oil from the inner bark of B. papyrifera were trans α-bergamotene (18%), ar-curcumene (12%), E-β-farnesene (12%), Z-β-farnesene (10%) and cis-α-bergamotene (8%).

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On terpenes. CIV. The constitution of betulenols from oil from the buds of white birch (Betula alba L.)

Cited by 27 publications

References 2 publications

Studies on Betula essential oils

Studies on Betula essential oils

Essential oils from the buds of Betula spp. growing in Turkey

Sesquiterpenes from the Inner Bark of the Silver Birch and the Paper Birch

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