Isolierung, Struktur und Synthese von 5.6.7.4′‐Tetrahydroxy‐3′‐methoxy‐flavon (Batatifolin), einem neuen Flavon aus Mikania batatifolia D.C.

Abstract

Aus Mikania batarijoha D. C . (Compositar) wurde das Flavon Batatifolin isoliert und ihm durch Synthese der Isomeren 5.6.7.4'-Tctrahydroxy-3'-methoxy-flavon (1) und 5.6.3'.4'-Tetrahydroxy-7-methoxy-flavon (5, Pedalitin) die Struktur I zugeordnct.Isolation, Structure, and Synthesis of 5,6,7,4'-Tetrahydroxy3'-methoxyflavone (Batatifoline), a new Flavone from Mikuniu bufutifoiu D.C.The flavone batatifoline has been isolated from Mikania bafnflfolin D. C. (Compositae). Its structure has been confirmed as 5,6,7,4'-tetrahydroxy-3'-mcthoxyflavonc (I) by synthesi.; of the isomers 1 and 5,6,3',4'-tetrahydroxy-7-methoxyflavone (5, Pedalitinc). lm Rahmen unserer phytochemischen Arbeiten uber Compositen der westlichen Hemisphire hatten wir Gelegenheit, die westindische Art Mikunia bututifolia D.C. (Tribus Eupatoriue), deren Vorkommen in den USA auf Sid-Florida und die Florida Keys beschrankt ist, zu untersuchen. Wir isolierten daraus neben Taraxasterol-acetat sowie einer Mischung von Mikanolid und Dihydromikanolid 1.2) ein neues Flavon, das wir Batatifolin nannten". Wir identifizierten es bereits als 5.6.7.4'-Tetrahydroxy-3'-methoxy-flavon (1) und synthetisierten es4).Batatifolin, C16HI2O7, enthilt eine Methoxylgruppe und liefert ein UV-Spektrum mit Maxima bei 256, 274 und 351 mp. Die I3ildung eines Tetraacetate5 sprach in Verbindung mit der enipirischen Formel fur ein Flavonoid mit 4 Hydroxylgruppen

Selective monoamine oxidase inhibitors. 4. 4-Aminophenethylamine derivatives with neuron-selective action

“…Similar methods have previously been used in the preparation of various 4-aminophenethylamine derivatives. [16][17][18] The route started from the corresponding aniline, which was , -dibenzylated with benzyl chloride in the presence of dimethylformamide and anhydrous potassium carbonate (11)(12)(13)(14) in Table II). The preparation of compound 11 from m-toluidine and benzyl chloride in aqueous solution has been previously described.19 The AT,JV-dibenzyl derivative of 3-ethylaniline was isolated as an oil and was used without further purification.…”

“…In the next step the jV,iV-dibenzylanilines were formylated by a standard Vilsmeier-Haack procedure to the corresponding benzaldehydes (15)(16)(17)(18)(19) II). The intermediate 4-(dibenzylamino)-d-methyl-d-nitrostyrenes were prepared by the condensation of the benzaldehydes with nitroethane in the presence of ammonium acetate.…”

“…The intermediate 4-(dibenzylamino)-d-methyl-d-nitrostyrenes were prepared by the condensation of the benzaldehydes with nitroethane in the presence of ammonium acetate. 16,17 All the ß-nitrostyrenes, except 4-(dibenzylamino)-2fluoro-d-methyl-d-nitrostyrene (20), were isolated as dark-red viscous oils, which were used directly in the next step involving lithium aluminum hydride reduction. The obtained 4-(dibenzylamino)-a-methylphenethylamines were not isolated but debenzylated in situ by catalytic hydrogenation in the presence of palladium.…”

“…The introduction of two methyl groups in the «-position of the phenethylamine side chain was achieved by a previously used route involving the reaction of the corresponding benzaldehyde with isopropylmagnesium bromide, thermal dehydration of the benzyl alcohol, and Ritter reaction of the obtained styrene. 16,17 The acetamide was hydrolyzed with hydrochloric acid and debenzylated by means of catalytic hydrogenation in the presence of palladium (8)(9)(10). The procedure is exemplified by the preparation of compound 10 in Scheme I. Pharmacology.…”

Micordilin, a complex elemanolide from Mikania cordifolia

“…The photolysis of 4-phenyltetrazolo[l,5-a][l,8]naphthyridines (11) in trifluoroacetic acid produces in high yield the corresponding 6//-indolo [2,[3][4][5][6][l,8]naphthyridines (2). Compounds 2, belonging to a hitherto unknown ring system, are interesting because of their structural resemblance to ellipticine and olivacine, two alkaloids which exhibit antitumor properties.…”