Geschmack ist vorhersagbar: Mit FlavorMiner. FlavorMiner heißt das Tool, das IPB-Chemiker und Partner aus Kolumbien jüngst entwickelt haben. Das Programm kann, basierend auf maschinellem Lernen (KI), anhand der…
Seit Februar 2021 bietet Wolfgang Brandt, ehemaliger Leiter der Arbeitsgruppe Computerchemie am IPB, sein Citizen Science-Projekt zur Pilzbestimmung an. Dafür hat er in regelmäßigen Abständen öffentliche Vorträge zur Vielfalt…
Kolbe, A.; Porzel, A.; Schmidt, J.; Adam, G.;A new synthesis of [26,28-2H6]brassinolide and [26,28-2H6]castasterone via an unusual methyl migrationJ. Label. Compd. Rad.46231-242(2003)DOI: 10.1002/jlcr.662
Deuterium‐labelled brassinosteroids, namely [26,28‐2H6]castasterone, 8 , and [26,28‐2H6]brassinolide, 9 , were synthesized starting from 6,6‐ ethylenedioxy‐20‐formyl‐2α,3α‐isopropylidenedioxy‐5α‐pregnane, 1 , and 3‐[2H3]methyl‐but‐1‐yne‐[4,4,4‐2H3], 11 . Upon alkylating cleavage of the epoxide 6 with trimethylaluminium‐n‐butyllithium an unusual migration of a neighbouring [2H3]methyl group takes place to afford deuteriation at positions 26 and 28.
Publikation
Voigt, B.; Porzel, A.; Adam, G.; Golsch, D.; Adam, W.; Wagner, C.; Merzweiler, K.;Synthesis of 2,24-Diepicastasterone and 3,24-Diepicastasterone as Potential Brassinosteroid Metabolites of the Cockroach Periplaneta americanaCollect. Czech. Chem. Commun.6791-102(2002)DOI: 10.1135/cccc20020091
Investigations of the metabolic conversion of the phytohormone 24-epicastasterone (1) in the cockroach Periplaneta americana (L.) required the synthesis of 2,24-diepicastasterone (4), 3,24-diepicastasterone (7b) and 2-dehydro-3,24-diepicastasterone (9) as reference standards. 2,24-Diepicastasterone (4) was synthesized from 2α,3α-epoxy derivative 2 as well as from the 2β,3β-epoxy-22,23-diol 3 by acid-catalyzed water addition to the epoxy function leading to the desired 2β,3α-trans functionality. 3,24-Diepicastasterone (7b) was prepared by NaBH4-reduction of the 3-oxo derivative 6. Upon deprotection conditions from the ketol acetonides 6 and 8 in both cases 2-dehydro-3,24-diepicastasterone (9) was obtained. The structure of 2,24-diepicastasterone (4) was confirmed by X-ray analysis.
Publikation
Lien, T. P.; Kamperdick, C.; Schmidt, J.; Adam, G.; Sung, T. V.;Apotirucallane triterpenoids from Luvunga sarmentosa (Rutaceae)Phytochemistry60747-754(2002)DOI: 10.1016/S0031-9422(02)00156-5
The leaves of Luvunga sarmentosa (Bl.) Kurz. yielded eight apotirucallane triterpenoids named luvungins A–G, and 1α-acetoxyluvungin A. Characteristic of the structure are the seven-membered lactone-ring A, the α-hydroxyl or α-acetoxyl group at C-7 and an oxygen bridge in the side chain giving five-, six- or seven-membered rings, respectively. Because of a hemiacetal function at C-21, luvungin C occurred as a mixture of 21-epimers. The structures have been elucidated on the basis of MS and NMR spectral data. In addition, two known coumarins ostruthin (6-geranyl-7-hydroxycoumarin) and 8-geranyl-7-hydroxycoumarin as well as five known triterpenes friedelin, flindissone, melianone, niloticin and limonin were isolated.The leaves of Luvunga sarmentosa (Bl.) Kurz. yielded eight apotirucallane triterpenoids named luvungins A–G and 1α-acetoxyluvungin A. Characteristic for the luvungins were the seven-membered lactone-ring A, the α-hydroxyl or α-acetoxyl group at C-7 and an oxygen bridge in the side chain giving five-, six- or seven-membered rings.
Publikation
Anh, N. T. H.; Sung, T. V.; Wessjohann, L.; Adam, G.;The iridois and iridoid glycosid from the Rehmanuia glutinosa RhizomeVietnam J. Chem.4017-22(2002)