Dimeric pyrroline alkaloids from Lilium candium L.

Abstract

Dimeric compounds 5,5’-oxydi(3-methyl-3-pyrrolin-2-one) and 5-hydroxy-3-methyl-1-(3’-methyl-2’-oxo-3’-pyrrolin-2-one were isolated from bulbs of Lilium candidum L., family Liliaceae. Structure of these compounds has been confirmed by spectral measurements. The ether link between two substituted pyrroline rings represents a new type of dimeric alkaloids.

Fulvanines J−K, two rare lactam pyrrole alkaloids from Hemerocallis fulva

“…The IR absorption bands at 3422, 1709 and 1655 cm À 1 indicated the presence of NÀ H functional or hydroxyl group, carbonyl group and olefinic group, respectively. The 1 H and 13 C NMR spectra (Table 1 ). [10] Apart from the p-coumaroyl section and glycerol section, the 1 H and 13 C NMR spectra (Table 1) of 1 also showed the presence of a jatropham section with the characteristic signals of a olefinic group (δ(H) 6.72-6.68 (m, 1H); δ(C) 140.8 (C-4), 138.…”

“…The 1 H and 13 C NMR spectra (Table 1 ). [10] Apart from the p-coumaroyl section and glycerol section, the 1 H and 13 C NMR spectra (Table 1) of 1 also showed the presence of a jatropham section with the characteristic signals of a olefinic group (δ(H) 6.72-6.68 (m, 1H); δ(C) 140.8 (C-4), 138. 5 (C-3)), one carbonyl group(δ(C) 175.5 (C-2)), a methine group (δ(C) 85.8 (C-5); δ(H) 5.50-5.45 (m, 1H)), and a methyl group (δ(H) 1.87 (t, J = 2.4 Hz, 3H); δ(C) 10.5 (CH 3 )).…”

“…The absolute configuration of compound 1 at C-5 was identified as S by comparison of the CD spectrum of 1 with that of (R)-dihydromaleimide, showing positive Cotton effects at 198 nm ([θ] = + 10) in the π-π* region. [12] Therefore, compound The six known pyrrole alkaloids, 5,5'-oxydi(3-methyl-3-pyrrolin-2-one) (3), [13] (À )-5-hydroxy-3-methyl-3-pyrrolin-2-one (jatropham) (4), [14] (�)-5-O-methyljatropham (5), [14] perlolyrine (6), [15] butyl-2-formyl-5-(hydroxymethyl)-1H-pyrrole-1-butanoate (7), [16] and hemerocallisamine II (8), [17] were isolated from the flower of H. fulva for the first time. The results of this paper enriched the chemical data of the pyrrole alkaloids, especially the lactam with jatropham structrual features, which should be the characteristic chemical constituents of genus H. The jatropham was reported firstly from Jatropha macrorrhiza (Euphorbiaceae), whereafter it and its derivatives have been isolated from Lilium hansonii, L. Candidum, and L. martagon (family Liliaceae) [11,14] and proved to be the characteristic constituents of L. genus.…”

“…CD Spectra were recorded on a JASCO J-715 spectropolarimeter [λ ([θ]) in nm]. 1 H-NMR (600 MHz), 13 C NMR (150 MHz) and 2D NMR (HSQC, HMBC and ROESY) spectra were recorded at room temperature on DRX-600 spectrometer and DRX-400 spectrometer (Bruker, Germany) in CH 3 OH. Analytical TLC and PTLC were carried out on precoated silica gel GF254 plates (Yantai Institute of Chemical Technology, Yantai, China).…”

Azetidine, pyrrole, pyrrolidine, piperidine, and pyridine alkaloids

“…The red alga Gracilariopsis [emanelformis, of the Pacific Northwest, contains two new pyrroles, (3) and (4), identified by spectroscopic methods (mainly high-field NMR and MS).3 Glycerinopyrine, a metabolite from Streptomyces violaceus, is to be formulated as (9, chiefly on spectral evidence.l Quararibea funebris flowers, long used by Mexican Indians as a chocolate flavouring, contain funebradiol, a new pyrrole lactone (6), formulated by spectral study." The Caribbean sea sponge Agelas clathrodes contains (2) penaresidine B clathrodine, a pyrrole imidazole alkaloid formulated as (7) from spectral data.6 Three pyrrololactam alkaloids have been isolated from the S. China Sea sponge Phacellia,jusca; they are formulated as (8), (9), and (10) on spectral evidence. The structure of (8) was confirmed by X-ray diffraction analysis;' it is identical with the previously known aldisine.…”