Pancratium maritimum

O. elwesii Hook., Haemanthus puniceus L., Leucojum aestivum L. var. pulcheUum Salisb., L. vernum L., Pancratium maritimum L., Sprekelia formosissima Herb., Stembergia lutea (L.) Ker-Gawl., and Vallotta speciosa L Herb. 

The availability of the enantiomeric alkaloids vittatine (284) and crinine in labeled form through separate feeding experiments with labeled 343 in Pancratium maritimum L. and Nerine bowdenii, respectively, provided experiments which indicated the absolute configuration of narciclasine. Thus, the two alkaloids were obtained from [3, 5 -3H2]-O-methylnorbelladine. Experiments with multiply labeled 343 have previously shown that no 3H loss takes place during the biosynthesis,... 

Noteworthy results in the phytochemical studies, the N-oxides of several Amaryllidaceae alkaloids have been found for the first time in Amaryllidaceae plants, accompanied by the corresponding free bases (52) ungiminor-ine A-oxide (10) (from Pancratium maritimum), and O-methyllycorenine A-oxide (329) and homolycorine A-oxide (330) (from Lapiedra maritinezii). The stereochemistry of their nitrogen atoms was deduced based on 2D NOESY experiments. Furthermore, it has been established that these A-oxide derivatives are genuine natural products, and not artifacts, by the demonstration that the free bases are not converted into A-oxides when subjected to the same extraction procedure. It is noteworthy that the A-oxides have been isolated accompanied by the corresponding free bases. 

Pancratium littorale Jacq (pancratistatin), 402 Pancratium maritimum... 

Fig. (10). Narciclasine and its 4-O-P-D-glucopyranoside (45 and 46) extracted from bulbs and leaves of Pancratium maritimum L.

Although racemic crinine was well incorporated into narciclasine it was likely that only one enantiomer was involved in the biosynthesis, either crinine or vitta-tine (99). Accordingly, whereas narciclasine (92) and haemanthidine (106) were both labelled by [2,4- H2]vittatine in Pancratium maritimum, [2,4- H2]crinine was not incorporated into narciclasine in daffodils. The relative activities for positions 2 and 4 of narciclasine (92) after the vittatine feed were 2 1, confirming the finding that half the expected activity at C-4 is lost, presumably on hydroxy-lation. These results, when considered together with those from an X-ray study, allowed assignment of the stereostructure (92) to narciclasine (with revised relative stereochemistry). 

Several notable advances have been made in the analytical aspects of the alkaloids. Most alkaloids have proven amenable to separation and identification by gas phase (i), paper (2), and thin-layer (< ) chromatography. The potential of the latter method is particularly striking. Four alkaloids were isolated from Pancratium maritimum by 1960 using conventional chromatographic and crystallization methods. However,... 

This base (mp 248°—250° [a]jj +12° in MeOH) has been isolated from Pancratium maritimum (3) and Rhodophiala bifida (lid). It forms an 0,0-diacetyl derivative (mp 178°-180°). Upon mild treatment with mineral acid, it was converted to apohaemanthamine (CXIX). 

Several substances have been detected in the course of Amarylli-daceae alkaloid isolations which cannot be classified within any of the previous sections. Of these, belladine and 0-methylnorbelladine are basic substances of singular importance in the biosynthesis of the alkaloids of the family. Further discussion of these bases is reserved for Section X. Hordenine has been isolated from Pancratium maritimum (3) and Ungernia victoris (61). It appears to be a metabolite of tyrosine, an important amino acid percursor of the alkaloids of the family. Ismine, C15H15NO3 (mp 99.5°-100.5° [a]p +0° in CHCI3 picrate, mp 158°-159°), has been isolated from an unidentified Ismene spp., Crinum powellii, and Sprekelia formosissima in minute amounts (6). 

Maritidine C,7H2,N03 287.36 253-256 +25.1°(C2H50H) Pancratium maritimum, Hippeastrum ananuca. Narcissus tazetta 22331-07-3... 

Galanthamine para- ortho Narcissus pseudonarcissus Leucojum aestivum Galanthus niveali Galanthus elewesii Pancratium maritimum acetylcholinesterase inhibitor, treatment for Alzheimer s disease [4,8-10]... 

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