A bicentennial of betulin

Hayek, E.; Jordis, Ulrich; Moche, Wolfgang; Sauter, F.

doi:10.1016/s0031-9422(00)97961-5

Cited by 121 publications

(90 citation statements)

References 138 publications

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“…When publishing our earlier studies about this material we came to the conclusion 3 that the substance in question is a betulin-containing pitch, i.e., the product of pyrolysis of wood or bark taken from a tree belonging to the family of birch-like trees (betulaceae), maybe even taken from the birch (betula) itself. These results were in analogy to some other ones obtained already earlier by us 4 and by other researchers 5 when studying (by a variety of methods) prehistoric organic materials found at many different sites in Central and Northern Europe. The present study should not only confirm our earlier results but aimed at additional and more specified information.…”

Section: Introductionsupporting

confidence: 91%

Studies in organic archaeometry I: Identification of the prehistoric adhesive used by the “Tyrolean Iceman” to fix his weapons

Sauter¹,

Jordis²,

Graf³

et al. 2000

Arkivoc

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The weapons of the glacier mummy of the chalcolithic "Man from the Hauslabjoch" (i.e. the "Tyrolean Iceman", nicknamed "Oetzi") contained traces of organic adhesives, obviously used to fix parts of his weapons (i.e., the flintstone arrowheads and the copper hatchet) to their respective shafts. In order to prove whether or not these adhesives might be birch bark pitches similar to some other organic materials found in Central and Northern Europe, model pitches were prepared from a large number of different trees and a sequence of analytical methods was developed to differentiate between the different species of trees. The crucial features of this analytical sequence consisted in the isolation of a characteristic terpene fraction by Kugelrohr distillation, followed by GC/MS analysis and by application of chemometrics to improve the interpretation of the GC/MS results. By this methodology it could be shown that Oetzi's weapons were glued by means of birch bark pitch. To prepare this, pyrolysis of the bark of the birch (betula pendula = betula verrucosa) obviously gave a tar, which on heating was converted into the thermoplastic pitch.

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Section: Introductionsupporting

confidence: 91%

Studies in organic archaeometry I: Identification of the prehistoric adhesive used by the “Tyrolean Iceman” to fix his weapons

Sauter¹,

Jordis²,

Graf³

et al. 2000

Arkivoc

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“…Although, non-hopanoid triterpenoid biomarkers are indicative for angiosperm input, they are not useful for a precise determination of the precursor plant family, with the exception of lupane derivatives which are generally more abundant in the Betulacea family (Hayek et al 1989;Regnery et al 2013). …”

Section: Sxcmentioning

confidence: 99%

Petrographic and biomarker analysis of xylite-rich coal from the Kolubara and Kostolac lignite basins (Pannonian Basin, Serbia)

Đoković¹,

Mitrović²,

Životić³

et al. 2018

Geologica Carpathica

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Abstract:The maceral and biomarker characteristics of 4 sublithotypes of xylite-rich coal (SXCs), pale yellow, dark yellow, brown and black, originating from the Kolubara and Kostolac lignite basins were determined. Based on these results, differences in sources and changes of organic matter (OM) resulting in formation of 4 SXCs were established. Conifers (particularly Cupressaceae, Taxodiaceae and Pinacea) had a significant impact on the precursor OM of all SXCs. The contribution of gymnosperm vs. angiosperm vegetation decreased in order pale yellow SXC > dark yellow SXC > brown SXC > black SXC. The distribution of non-hopanoid triterpenoids indicates that change of SXC colour from yellow to black is associated with reduced input of angiosperm plants from the Betulacea family. Differences in hopane distribution, bitumen content, proportion of short-chain n-alkanes and degree of aromatization of di-and triterpenoids of pale yellow SXC are controlled by microbial communities which took part in the diagenetic alteration of OM. The content of total huminites increased from black to pale yellow SXC, whereas contents of total liptinite and inertinite macerals showed the opposite trend. SXCs differ according to textinite/ulminite ratio, which sharply decreased from pale yellow to black SXC, reflecting increase in gelification of woody tissue. Regarding the composition of liptinite macerals, the SXCs mostly differ according to resinite/liptodetrinite and resinite/suberinite ratios, which are higher in yellow than in brown and black SXC. This result along with values of TOC/N ratio and Carbon Preference Index indicate that the contribution of well preserved woody material, including lignin tissue vs. the impact of epicuticular waxes decreased from yellow to black SXC.

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“…Tel que décrit dans les nombreuses revues de littérature publiées à ce sujet [Hayek et al, 1989; Baglin et al, 2003a; Patocka, 2003;Setzer et al, 2003;Ovesnâ et al, 2004;Bi et al, 2005; Sami et al, 2005; Mukherjee et al, 2006;Tolstikova et al, 2006a; Tolstikova et al, 2006b; Sporn et al, 2007], l'acide bétulinique (15) [Schmidt et al, 1997;Fulda et al, 1999;Fulda et al, 2000;Jung et al, 2007;. Noda et ses collaborateurs [1997] [Schmidt et al, 1997;Fulda et al, 1999; Wick et al, 1999;Fulda et al, 2000;Fulda et al, 2005; Galgon et al, 2005].…”

Section: Activités Biologiquesunclassified

“…Ce bidesmoside cyclique (122) jusqu'à ce jour [Bruneton, 1995]. Le bétulinol (16) connu aussi sous le nom de betulin, trochton et coryli-résinol est l'un des premiers produits naturels isolés (1788) d'une espèce végétale [Hayek et al, 1989]. Les écorces de différentes espèces de bouleau telles que Betula utilis [Chari et al, 1968], B. cordifoîia, B. populifolia, B. x caerulea [O'Connel et al, 1988], B. platyphylla [Fuchino et al, 1996;Zhang et al, 2003], B. davurica [Fuchino et al, 1998a], B. ovalifolia [Fuchino et al, 1998b], B.…”

Section: Synthèse Par Glycorandomisaûonunclassified

“…Tel que décrit dans les nombreuses revues de littérature publiées à ce sujet [Hayek et al, 1989;Baglin et al, 2003a;Patocka, 2003;Setzer et al, 2003;Ovesnâ et al, 2004;Bi et al, 2005;Sami et al, 2005;Mukherjee et al, 2006;Tolstikova et al, 2006a;Tolstikova et al, 2006b;Sporn et al, 2007], l'acide bétulinique (15) (15) sélective au mélanome humain . Dans cette étude, la capacité de l'acide bétulinique (15) .…”

Section: Activités Biologiquesunclassified

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Amélioration du comportement biopharmaceutique de triterpènes naturels anticancéreux par synthèse de saponines mono- et bidesmosidiques /

Gauthier¹

2008

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UIUQAC Mise en garde/AdviceAfin de rendre accessible au plus grand nombre le résultat des travaux de recherche menés par ses étudiants gradués et dans l'esprit des règles qui régissent le dépôt et la diffusion des mémoires et thèses produits dans cette Institution, l'Université du Québec à Chicoutimi (UQAC) est fière de rendre accessible une version complète et gratuite de cette oeuvre.Motivated by a desire to make the results of its graduate students' research accessible to all, and in accordance with the rules governing the acceptation and diffusion of dissertations and theses in this Institution, the Université du Québec à Chicoutimi (UQAC) is proud to make a complete version of this work available at no cost to the reader.L'auteur conserve néanmoins la propriété du droit d'auteur qui protège ce mémoire ou cette thèse. Ni le mémoire ou la thèse ni des extraits substantiels de ceux-ci ne peuvent être imprimés ou autrement reproduits sans son autorisation.The author retains ownership of the copyright of this dissertation or thesis. Neither the dissertation or thesis, nor substantial extracts from it, may be printed or otherwise reproduced without the author's permission. "L'imprévisible est dans la nature même de l'entreprise scientifique. Si ce qu 'on va trouver est vraiment nouveau, alors c'est par définition quelque chose d'inconnu à l'avance. "-François Jacob, médecin et biologiste français, prix Nobel de médecine (1965) Ill RESUME Cette thèse décrit les travaux réalisés concernant la synthèse et l'évaluation des activités anticancéreuse et hémolytique de saponines triterpéniques naturelles et nonnatureËes à génine de type lupane. D'une part, deux saponines naturelles à section a-L-rhamnopyranosyl-(l-»2)-a-L-arabinopyranose provenant de plantes de la médecine traditionnelle orientale, une librairie de huit saponines bidesmosidiques à génine bétulinol et acide bétulinique ainsi que plusieurs dérivés chacotriosidiques de type lupane et germanicane ont été préparés par l'utilisation judicieuse de différents groupements protecteurs et procédures de glycosylation. D'autre part, l'étude des relations structure-activité démontre que les sections osidiques hautement polaires à la position C-3 du squelette lupane ont, dans la plupart des cas, un impact négatif sur l'activité anticancéreuse tandis que l'activité est augmentée pour les triterpènes de type germanicane. En revanche, la présence d'une section L-rhamnose à cette position accroît la cytotoxicité des saponines de type lupane. Notablement, le bétulinol 3,28-O-bis-cc-L-rhamnopyranoside s'est révélé un puissant agent anticancéreux inhibant sélectivement la croissance des cellules provenant des cancers les plus prévalents chez l'homme (IC50 = 1,7-1,9 fimol # L"'). À l'inverse des saponines naturelles de type oléanane telles que Pa-hédérine et l'hédéracolchiside Ai, la majorité des saponines de type lupane, tout comme leurs homologues triterpéniques (bétulinol et acide bétulinique), n'induisent pas l'hémolyse des globules rouges (HD50 >100 jurnol'L" 1 ), et c...

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A bicentennial of betulin

Cited by 121 publications

References 138 publications

Studies in organic archaeometry I: Identification of the prehistoric adhesive used by the “Tyrolean Iceman” to fix his weapons

Studies in organic archaeometry I: Identification of the prehistoric adhesive used by the “Tyrolean Iceman” to fix his weapons

Petrographic and biomarker analysis of xylite-rich coal from the Kolubara and Kostolac lignite basins (Pannonian Basin, Serbia)

Amélioration du comportement biopharmaceutique de triterpènes naturels anticancéreux par synthèse de saponines mono- et bidesmosidiques /

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