7- Methoxy-8- dictamnine

Furoquinoline Alkaloids.—Delbine and montrifoline, the new alkaloids of Monnieria trifolia, were shown by spectroscopic studies to be 4-methoxy-furoquinolines. Delbine is a hydroxy-methoxy-dictamnine, and, as it gives kokusaginine (1 R1 = R2 = OMe, R3 = H) on reaction with diazomethane, the substituents are in positions 6 and 7 since it is not identical with helipavifoline (1 R1 = OMe, R2 = OH, R3 = H) (cf Vol. 7, p. 83), delbine apparently is 6-hydroxy-7-methoxydictamnine (14). Montrifoline was assigned structure (15) on... 

Hydroxydictamnine, described as 7-O-demethylevolitrine, was isolated first from Evodia elleryana F. Muell (139) it was later obtained from Melicope confusa (Mesr.) Liu and named confusameline (132). The structure was established by conversion with diazomethane into 7-methoxy-dictamnine (evolitrine). 

Cell suspension cultures of R. graveolens grown in the presence of 4-hydroxy-2-quinolone show increased amounts of quinoline and furoquinoline alkaloid production. For example, the concentration of dictamnine increased as long as 4-hydroxy-2-quinolone was present in the culture medium as soon as the quinolone was depleted, rapid transformation of dictamnine into 8-methoxy-dictamnine was observed. ... 

Those benzo[6]furan- or dihydrobenzo[6]furan-containing compounds whose biological activities were not mentioned are skimmianine and dictamnine from Teclea trichocarpa Enge. (Rutaceae) <02JNP956>, millettocalyxin C and pongol methyl ether from stem barks of Millettia erythrocalyx <02JNP589>, latifolol from the stem of Gnetum latifolium Blume <02P(61)959>, 6-methoxy-[2 ,3 7,8]-furanoflavanone and 2,5-dimethoxy-4-hydroxy-[2 ,3 7,8]-... 

Dictamnine (XII) and its methoxy and methylenedioxy derivatives are widespread among the members of the Rutaceae, the most commonly occurring being skimmianine (XIII), which has now been reported in a total of 49 plant sources. Numerous new isolations of other known members of the group have been recorded Table I summarizes all reported occurrences to date. 

The antiplasmodial activity of five akaloids (y - fagarine, N-benzoyltryamine, skimmianine, dictamnine and 4-methoxy-l methyl-2(lH)-quinoline), extracted by decoction from Zanthoxylum tsihanimposa stem bark were tested upon P. falciparum. The quinoline alkaloid y-fagarine was the most potent of five alkaloids, being found to be 3. 4 times more active than dictamnine and 1.4 times more active than skimmianine. The presence of the methoxy group in positions C4 and C8 appears to be important for bioactivity (20). 

Methoxy-8-(3 niethylbut-2-enyloxyl)-dictamnine (82) is obtained from Zathoxylum arborescens (J.A. Grina,... 

Introduction of the prenyl residue on to the quinoline skeleton can apparently occur with either a hydroxy- or a methoxy-group at C-4, for (167) and (168) are equally efficient precursors for dictamnine (172) and (174). Methylation of the oxygen function at C-2 as well, however, blocks further reaction, as seen in the isolation of inactive alkaloid after feeding [2,4- C2]-2,4-dimethoxyquinoline. The prenylquinolines (169) and (170) are also equally efficient precursors for dictamnine (172) and (174), and are thus presumably successive intermediates in furoquinoline biosynthesisit is known that the methyl group of (170) is retained in the genesis of skimmianine (173). ... 

C. temata (230). 4-Methoxy[3-14C]-2-quinolone is incorporated efficiently into dictamnine in S. japonica (224), but may be an unnatural precursor because the quinolone labeled on the 4-methoxy group is not incorporated into skimmianine in C. ternata and apparently undergoes demethylation to... 

The prenylquinoline derivatives (142), (143), and (147) and 4-hydroxy- and 4-methoxy-2-quinolone are good precursors for dictamnine. Incorporation of... 

Insecticide, antifeedant, nematicide activities l-Hydroxy-3-methoxy-Al-methyIacridone, rc/-(3/f,4/f)-(-)-3-Methoxy-4,5-dihydroxy-4-(4-methoxyphenyI)-3,4-dihydroquinoIin-2-one, re/-(3/f,4/f)-(-)-3-Methoxy-4-hydroxy-4-(4-methoxyphenyI)-3,4-dihydroqumolin-2-one, arborinine, atanine, dictamnine, evolitrine, leiokinine A and B, Al-methyIquinoIiniimi-2-carboxyIate, penigequinolOTie A and B, (-)-peniprequinoIone, quinolactacide, vasicine, vasicinol, vasicinone, xanthoxoline [22, 25, 29, 33-36, 39,41],... 

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