Sur la composition de l'arôme de thé noir II

Bricout, J.; Viani, R.; Müggler‐Chavan, F.; Marion, J. P.; Rwymond, D.; Egli, R. H.

doi:10.1002/hlca.19670500610

Cited by 66 publications

(12 citation statements)

References 7 publications

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“…The natural occurrence of loliolide is mainly reported for plant material (Ghosal et al 1976). They have become especially known as fl avor compounds in tea and tobacco (Bricout et al 1967, Kodama et al 1982, Roberts & Rohde 1972. Loliolide is also reported to occur in the marine mollusk Dolabella ecaudata (Pettit et al 1980).…”

Section: Resultsmentioning

confidence: 99%

Chemical composition, acetylcholinesterase inhibitory and antifungal activities of Pera glabrata (Schott) Baill. (Euphorbiaceae)

Cardoso-Lopes¹,

Paula²,

Barbo³

et al. 2009

Rev. bras. Bot.

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− (Chemical composition, acetylcholinesterase inhibitory and antifungal activities of Pera glabrata (Schott) Baill. (Euphorbiaceae)). Pera glabrata (Schott) Baill. was selected for this study after showing a preliminary positive result in a screening of Atlantic Forest plant species in the search for acetylcholinesterase inhibitors and antifungal compounds. The bioassays were conducted with crude ethanol extract of the leaves using direct bioautography method for acetylcholinesterase and antifungal activities. This extract was partitioned with hexane, chloroform and ethyl acetate solvents. The active chloroform fraction was submitted to silica gel chromatography column affording 12 groups. Caffeine, an alkaloid, which showed detection limits of 0.1 and 1.0 μg for anticholinesterasic and antifungal activities, respectively, was isolated from group nine. After microplate analyses, only groups four, nine, 10, 11 and 12 showed acetylcholinesterase inhibitory activity of 40% or higher. The group 12 was purifi ed by preparative layer chromatography affording four sub-fractions. Two sub-fractions from this group were analyzed by gas chromatography-mass spectrometry and gas chromatography-fl ame ionization detector. The fi rst sub-fraction showed anticholinesterasic activity and contained two major compounds: 9-hydroxy-4-megastigmen-3-one (84%) and caffeine (6%). The second sub-fraction presented fi ve major compounds identifi ed as 9-hydroxy-4-megastigmen-3-one, isololiolide, (-) loliolide, palmitic acid and lupeol and did not show activity. Key words -9-hydroxy-4-megastigmen-3-one, biological activities, caffeine, EuphorbiaceaeResumo -(Composição química, atividades inibidora da acetilcolinesterase e antifúngica de Pera glabrata (Schott) Baill. (Euphorbiaceae)). Pera glabrata (Schott) Baill. foi selecionada para este estudo a partir de uma triagem de espécies vegetais da Mata Atlântica na busca de substâncias com atividades anticolinesterásica e antifúngica. A técnica da bioautografi a direta foi utilizada para a detecção das atividades anticolinesterásica e antifúngica. O extrato etanólico bruto obtido das folhas foi particionado com hexano, clorofórmio e acetato de etila. A fração clorofórmica ativa foi fracionada por cromatografi a em coluna de sílica gel fornecendo 12 grupos. Do grupo nove foi isolado o alcalóide cafeína com limites de detecção de 0,1 e 1,0 μg para as atividades anticolinesterásica e antifúngica, respectivamente. Após bioensaio em microplaca, somente os grupos quatro, nove, 10, 11 e 12 apresentaram inibição da acetilcolinesterase maior ou igual a 40%. O grupo 12 foi purifi cado por cromatografi a em camada delgada preparativa de sílica gel fornecendo quatro sub-frações. Duas sub-frações deste grupo foram analisadas por cromatografi a a gás-espectrometria de massas e cromatografi a a gás com detector de ionização de chama. A primeira sub-fração contém dois compostos majoritários: 9-hidroxi-4-megastigmen-3-ona (78%) e cafeína (6%), e apresentou atividade anticolinesterásica. A segunda

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Section: Resultsmentioning

confidence: 99%

Chemical composition, acetylcholinesterase inhibitory and antifungal activities of Pera glabrata (Schott) Baill. (Euphorbiaceae)

Cardoso-Lopes¹,

Paula²,

Barbo³

et al. 2009

Rev. bras. Bot.

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“…Both 494 and 495 were initially isolated as cat attractants from leaves from Actinidia polygama. 531 Therefore since then they also been recognized as avor components in many plant sources such as tobacco 535 and tea. 535 The total synthesis of (R)-dihydroactinidiolide ( 494) and (R)actinidiolide (495) with excellent enantiomeric excess (ee) and in high overall chemical yield by asymmetric catalytic (HDA) has been achieved.…”

Section: Hetero Diels-alder (Hda) Reactionmentioning

confidence: 99%

“…531 Therefore since then they also been recognized as avor components in many plant sources such as tobacco 535 and tea. 535 The total synthesis of (R)-dihydroactinidiolide ( 494) and (R)actinidiolide (495) with excellent enantiomeric excess (ee) and in high overall chemical yield by asymmetric catalytic (HDA) has been achieved. In addition and delightfully, a common intermediate generated in this approach for the total synthesis of 494 and 495 were found being useful for the synthesis of a series of related compounds (Scheme 72).…”

Section: Hetero Diels-alder (Hda) Reactionmentioning

confidence: 99%

Recent applications of the hetero Diels–Alder reaction in the total synthesis of natural products

et al. 2015

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“…5 Racemic˛-ionone has a strong sweet-floral odour, reminiscent of violet, and is industrially produced through cyclization of the product of condensation of citral 6,7 with acetone.˛-Ionone is present in nature as a secondary metabolite of carotenoids. It was identified as a flavour component of raspberries, 8 carrots, 9 black tea 10 and violet flowers (Viola odorata L. 11 ). In nature, -ionone occurs in its dextrorotatory form, which was assigned the absolute configuration (R) through correlation with mannol.…”

Section: Introductionmentioning

confidence: 99%

Scale‐up of analytical chromatography to the simulated moving bed separation of the enantiomers of the flavour norterpenoids α‐ionone and α‐damascone

Zenoni¹,

Quattrini²,

Mazzotti³

et al. 2002

Flavour & Fragrance J

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The scale-up of the HPLC separation of the enantiomers of the flavour norterpenoid ketones˛-ionone and˛-damascone from analytical to preparative scale was achieved using the chromatographic simulated moving bed (SMB) technique. Commercial HPLC columns, with heptakis-(2,3,6-per-O-methyl)-ˇ-cyclodextrin bound to silica gel as chiral stationary phase, were employed for the separation. High-purity enantiomers of both chiral compounds have been obtained with a rather satisfactory productivity.

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Sur la composition de l'arôme de thé noir II

Cited by 66 publications

References 7 publications

Chemical composition, acetylcholinesterase inhibitory and antifungal activities of Pera glabrata (Schott) Baill. (Euphorbiaceae)

Chemical composition, acetylcholinesterase inhibitory and antifungal activities of Pera glabrata (Schott) Baill. (Euphorbiaceae)

Recent applications of the hetero Diels–Alder reaction in the total synthesis of natural products

Scale‐up of analytical chromatography to the simulated moving bed separation of the enantiomers of the flavour norterpenoids α‐ionone and α‐damascone

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