CRINUM; AN ENDLESS SOURCE OF BIOACTIVE PRINCIPLES: A REVIEW. PART III; CRINUM ALKALOIDS: BELLADINE-, GALANTHAMINE-, LYCORENINE-, TAZETTINE-TYPE ALKALOIDS AND OTHER MINOR TYPES

CRINUM; AN ENDLESS SOURCE OF BIOACTIVE PRINCIPLES: A REVIEW. PART III; CRINUM ALKALOIDS: BELLADINE-, GALANTHAMINE-, LYCORENINE-, TAZETTINE-TYPE ALKALOIDS AND OTHER MINOR TYPES 

John Refaat*¹, Mohamed S. Kamel ¹, Mahmoud A. Ramadan ² and Ahmed A. Ali ²

Pharmacognosy Department, Faculty of Pharmacy, Minia University ¹, 61519 Minia, Egypt

Pharmacognosy Department, Faculty of Pharmacy, Assiut University ², 71515 Assiut, Egypt

ABSTRACT

Crinums occupy an important position within plants of family Amaryllidaceae, and many of them have been broadly used in traditional and ethnomedicines throughout the world. Due to their richness in bioactive phytoconstituents, Crinums have been subjected to extensive chemical, cytological and pharmacological investigations that focused chiefly on their alkaloidal content. Continuing our appraisal about the results of phytochemical, biological and toxicological studies on Crinums and after considering lycorine- and crinine-alkaloids as the major classes in its two previous parts; the current part of our review work draws attention to members of the other less common alkaloidal classes as well as the new types that are not common in the family.

Tazettine

INTRODUCTION: The genus Crinum represents an important sector in family Amaryllidaceae with broad geographical distribution throughout the tropics, subtropics and warm temperate regions of the world ¹. Worldwide, Crinum comprises about 130 species distributed in Africa, America, southern Asia and Australia. The African lands enjoy most species and about twenty-two are endemic to Southern Africa ². Many species are common emetic, laxative, expectorant, diaphoretic, anti-asthmatic, analgesic, anti-inflammatory, anti-microbial and anti-tumor remedies in various folkloric medicines ³.

During the last decade, Crinums have extensively attracted the attention of phytochemists due to their pharmacologically active principles. Within the huge number and diverse classes of phytocompounds produced by these plants, members of this genus are best known biofactories for Amaryllidaceae alkaloids ⁴. It is worth mentioned that out of approximately 180 alkaloids have been isolated and identified from Crinums, about 120 bases belong to crinine- and lycorine-types. As a part of our ongoing comprehensive review work on various classes of Crinum alkaloidal and non-alkaloidal constituents as well as their biological activities, the present part of our work highlights bases of the less common alkaloidal classes e.g. belladine-, cherylline-, galanthamine-, lycorenine-, narciclasine- and tazettine-types as well as further uncommon minor types e.g. augustamine-, β-carboline-, phenanthridine-, sceletium-, ismine- and clivimine-type alkaloids together with their structural and stereochemical differences (Table 1 and Figure 2). Furthermore, their distribution in various species studied so far is also totally considered.

Biosynthesis of Amaryllidaceae alkaloids: Amaryllidaceae alkaloids are derived from the amino acids phenylalanine and tyrosine via norbelladine (Figure 1). The latter undergoes oxidative phenolic coupling to give rise to the different carbon skeletons of these alkaloids. Accordingly, norbelladine and its various O- and N- substituted derivatives are considered the key biosynthetic intermediates for Amaryllidaceae alkaloids. In their route of biosynthesis, the two six- membered rings are derived from the aromatic amino acids, while, the additional ring closures are produced by a mechanism of phenolate free radical coupling ⁵.

 FIGURE 1: PROBABLE PATHWAY TO NORBELLADINE

TABLE 1: A LIST OF ALKALOIDS ISOLATED FROM DIFFERENT CRINUM SPECIES

FIGURE 2: ALKALOIDS ISOLATED FROM DIFFERENT CRINUM SPECIES

 CONCLUSION: The genus Crinum can be considered a true representative of family Amaryllidaceae as it exhibits all the main chemical traits of this family. The extensive survey of literature showed that phytochemical analyses on Crinums have yielded a vast array of compounds, including about 180 alkaloids belonging to different types of Amaryllidaceae alkaloids. Crinine-, lycorine- and tazettine-types were found to be the most common among the isolated alkaloids, successively, while montanine-type has not yet been found in Crinum species.

In addition to these common classes of Amaryllidaceae alkaloids, Crinums yielded other types that are not common in the family e.g. augustamine-, β-carboline-, phenanthridine-, sceletium-, ismine- and clivimine-type alkaloids.  Accordingly, in light of the growing global demand for natural pharmaceuticals to face the every day challenging diseases by searching for prospective active substances from natural sources, Crinum plants emerge as an endless source of bioactive principles, especially Amaryllidaceae alkaloids. Additionally, both the unstudied species and new hybrids open the gate towards isolation of further new phytocompounds.

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    How to cite this article:

    Refaat J, Kamel MS, Ramadan MA and Ali AA: Crinum; An endless source of Bioactive Principles: A Review. Part III; Crinum Alkaloids: Belladine-, Galanthamine-, Lycorenine-, Tazettine-type Alkaloids and other minor types. Int J Pharm Sci Res. 3(10); 3630-3638.

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