CRINUM; AN ENDLESS SOURCE OF BIOACTIVE PRINCIPLES: A REVIEW, PART II. CRINUM ALKALOIDS: CRININE-TYPE ALKALOIDS

CRINUM; AN ENDLESS SOURCE OF BIOACTIVE PRINCIPLES: A REVIEW, PART II. CRINUM ALKALOIDS: CRININE-TYPE ALKALOIDS 

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

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

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

ABSTRACT

Crinum is a genus of about 130 species belonging to family Amaryllidaceae with wide geographical distribution throughout the tropics, subtropics and warm temperate regions of the world. These plants are not only showy ornamentals but they possess significant folkloric and commercial reputation as well. Long ago, Crinums have been subjected to extensive chemical, cytological and pharmacological investigations. Phytochemical investigations have resulted in isolation of several diverse classes of phytocompounds and have been focused predominantly on alkaloids. The present part of our review work about the phytochemical, biological and toxicological studies on Crinums summarizes crinine-type alkaloids isolated up to now as well as their structural and stereochemical differences, in addition to their distribution in different Crinum species.

Crinum

INTRODUCTION: Crinum is a perennial bulbous herb belonging to tribe Amaryllideae of family Amaryllidaceae and contains about 130 species distributed in Africa, America, southern Asia and Australia. African lands enjoy most species and about twenty-two are endemic to Southern Africa ¹. Amaryllidaceae species are considered an exclusive source of Amaryllidaceae alkaloids that possess wide range of interesting biological activities.

Besides their popularity as ornamental plants with beautiful and elegant flowers, they possess different interesting medicinal effects such as analgesic, immunostimulating, antineoplastic, antiviral and antimicrobial effects. Since about 1950s, Crinums have been subjected to extensive chemical and biological investigations due to their richness in pharmacologically active principles, especially alkaloids ².

Therefore, 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 reviews crinine-type alkaloids isolated from Crinums in addition to their structural and stereochemical differences as the most common type among Crinum alkaloids. Additionally, their distribution in various species studied so far is also completely considered (out of around 130 species, only about thirty-five have been phytochemically investigated) ³.

Crinine-type alkaloids: Phytochemical investigations of different plant parts of many Crinum species have yielded a large number of alkaloids belonging to the 5, 10b-ethanophenanthridine nucleus (crinine-type) (Table 1 and Figure 2). The isolated alkaloids of this type exhibited a wide and variable substitution patterns and according to their stereochemistry, they can be generally divided into two skeletons; (–)-Crinane and (+)-Crinane skeletons (Figure 1).

  (–)-CRINANE SKELETON                                                     (+)-CRINANE SKELETON

FIGURE 1: BASIC SKELETONS OF CRININE-TYPE ALKALOIDS WITH COMMON SUBSTITUTION POSITIONS

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

FIGURE 2: CRININE-TYPE ALKALOIDS ISOLATED FROM DIFFERENT CRINUM SPECIES

CONCLUSION: This current part of our review work highlights crinine-type alkaloids isolated to date from the genus Crinum in addition to their structural differences and distribution in different species. As an endless source of bioactive principles, the extensive survey of literature presents crinine-type alkaloids as the major class within the isolated Crinum chemical constituents and about 81 bases belonging to this alkaloidal type were isolated and identified. Moreover, the unstudied species are still calling for phytochemical investigations that will add new members of these important bases.

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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 II. Crinum alkaloids: Crinine-Type Alkaloids. Int J Pharm Sci Res. 3(9); 3091-3100.

     

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