Constituents of Isertia hypoleuca benth. (Rubiaceae)—I

Bohrmann, H.; Lau‐Cam, Cesar A.; Tashiro, John; Youngken, Heber W.

doi:10.1016/s0031-9422(00)85415-1

Cited by 14 publications

(2 citation statements)

References 13 publications

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“…Finally, we dealt with an N -acetyl derivative, C 21 H 26 N 2 O 2 ( 5 ), obtained in a very small amount (less than 1 mg), whose 1 H NMR spectrum in chloroform- d at room temperature (Table ) duplicates that of 4 , except for the appearance in 5 of a new signal at δ 5.42 (1 H, dd, J = 7.9 and 3.9 Hz) and HSQC (δ 70.1 d) assignable to a hydrogen geminal to the secondary hydroxyl group. The fragmentation patterns observed in the mass spectrum of 5 at m / z 159 and 130 suggested a quinuclidine derivative bearing a hydroxyl group at C-2 . These spectroscopic data indicated that 5 is N -acetylcinchonicinol or its C-2 epimer.…”

Section: Resultsmentioning

confidence: 85%

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Five New Alkaloids from the Leaves of Remijia peruviana

et al. 2004

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Three new indolylquinuclidine-type alkaloids, remijinine (1), epiremijinine (2), and 5-acetyl-apocinchonamine (3), and two new cinchonine-derived alkaloids, N-acetyl-deoxycinchonicinol (4) and N-acetyl-cinchonicinol (5), as well as the known alkaloids quinamine, conquinamine, cinchonine, and quinidine were isolated from the leaves of Remijia peruviana. The structures of the new alkaloids were elucidated on the basis of spectroscopic analysis, including homonuclear and heteronuclear correlation NMR experiments (COSY, ROESY, HMQC, and HMBC). The relative configuration at C-7 for remijinine (1) and, in consequence, for epiremijinine (2) was established by X-ray crystal structure analysis of the former.

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Section: Resultsmentioning

confidence: 85%

“…The fragmentation patterns observed in the mass spectrum of 5 at m/z 159 and 130 suggested a quinuclidine derivative bearing a hydroxyl group at C-2. 17 These spectroscopic data indicated that 5 is N-acetylcinchonicinol or its C-2 epimer.…”

Section: Resultsmentioning

confidence: 95%