(±)-heterocarpine, a hydroxymethylated isoquinoline alkaloid from ceratocapnos heterocarpa

Suau, Rafael; Posadas, Natalia; Silva, M.Victoria; Valpuesta, Marı́a

doi:10.1016/s0031-9422(98)00198-8

Cited by 10 publications

(4 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The new 2-benzylisoquinoline alkaloid heterocarpine 35 has been isolated from Ceratocapnos heterocarpa and its structure has been confirmed by its synthesis from the iminium salt 36, through the tetrahydroisoquinolines 37a, 37b and 37c. 40 It was reported in the previous review that dehassiline, assigned the structure 39, is not identical with the base of this structure prepared by synthesis; a further study has shown that it is not identical with the isomeric base 38, prepared by the stereoselective reduction of the related 3,4-dihydroisoquinolinium salt. 41 The bis-quaternary salt 40, which is an analogue of atracurium has been prepared from tetrahydropapaverine.…”

Section: Naphthylisoquinolinesmentioning

confidence: 91%

β-Phenylethylamines and the isoquinoline alkaloids (July 1998 to June 1999)

Bentley

2000

Nat. Prod. Rep.

View full text Add to dashboard Cite

Section: Naphthylisoquinolinesmentioning

confidence: 91%

β-Phenylethylamines and the isoquinoline alkaloids (July 1998 to June 1999)

Bentley

2000

Nat. Prod. Rep.

View full text Add to dashboard Cite

“…( S )‐(−)‐MLC and racemic (±)‐MLC were obtained from the Department of Organic Chemistry, in University of Málaga, Suau et al .…”

Section: Methodsmentioning

confidence: 99%

“…( S )‐(−)‐MLC was isolated from the plant ( C. heterocarpa ) by extraction with methanol and subsequently separated by liquid chromatography column and preparative thin‐layer chromatography . The racemic was synthesized (joined with (±)‐epimalacitanine) of which was separated by preparative thin‐layer chromatography reacting glycolaldehyde norcrasilofoline with 2.5 M hydrochloric acid medium.…”

Section: Methodsmentioning

confidence: 99%

HPLC enantioseparation of alkaloid malacitanine using fluorimetric/polarimetric detection

Sánchez

Dı́az²,

Aguilar³

et al. 2012

J of Separation Science

View full text Add to dashboard Cite

This work reports two methods developed for the separation and determination of the enantiomers of the new alkaloid malacitanine (MLC) and the determination of the enantiomeric purity in mixtures. First, the isomers were separated using a Chirex 3020 (250 mm × 4.6 mm, 5 μm) chiral column with a mobile phase of cyclohexane-1,2-dichloroethane-ethanol-trifluoroacetic acid (64:30:6:0.6, v/v/v/v) at a flow rate of 1 mL/min and fluorimetric detection. Obtained retention times were 12.4 and 15.9 min (+ and -) with a resolution Rs of 1.13. Relative standard deviations (RSDs) were 2.5 and 2.4% at the 0.5-μg level (four determinations). Second, a nonenantioselective procedure for the determination of enantiomeric purity of MLC using a Lichrospher ® Si-60 (250 mm × 5 mm, 5 μm) normal phase with a mobile phase of 100% ethanol at a flow rate of 0.9 mL/min coupled to two detectors in series, fluorimetric and polarimetric. RSD of 3.3% was obtained. Calculated enantiomeric purity by chiral chromatography gave 48.6% (-)-MLC in the near racemic product. Using polarimetric signal of the nonseparated enantiomers and comparing the slopes of the calibration curves (enantiomers) from the racemic product gave 47.8% (-)-MLC content. A study of accuracy of (-)-MLC gave recoveries from 98.3 to 100.7%.

show abstract

“…Despite the abundance of 1-substituted tetrahydroisoquinolines, the presence of an hydroxymethyl group as a substituent at position C-1 of the isoquinoline nucleus is uncommon among the simple naturally occurring tetrahydroisoquinolines. 2 Typical examples of the rare occurrence of this feature among the natural products isolated from higher plants include calycotomine (1), 3 hedycarine (2), 4 heterocarpine (3), 5 from Ceratocapnos heterocarpa, and deglucopterocereine (4), 6 its N-oxide (5), and its (-)-5b-O-glucopyranoside (glucopterocereine) 7 from Pterocereus gaumeri. Structurally related to these tetrahydroisoquinolines is the b-adrenergic receptor antagonist MY336-a (6), 8a,b of fungal origin, which was isolated from the fermentation broth of Streptomyces gabonae KY2234 and which displays a second hydroxymethyl group at C-3 ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%