CRINUM; AN ENDLESS SOURCE OF BIOACTIVE PRINCIPLES: A REVIEW. PART III; CRINUM ALKALOIDS: BELLADINE-, GALANTHAMINE-, LYCORENINE-, TAZETTINE-TYPE ALKALOIDS AND OTHER MINOR TYPES
HTML Full TextCRINUM; 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.
Keywords:Alkaloids,
Amaryllidaceae, Crinum, Galanthamine, |
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
No. | Alkaloid name | Molecular Formula | mp (˚C) / [α]D | Plant source | Plant parts | References | ||||
I- Belladine-type alkaloids: | ||||||||||
1 | Belladine. | C19H24NO3 | C. asiaticum L.C. latifolium Linn.
C. powellii Hort. |
--------
---- |
67
8 |
|||||
2 | Craugsodine. | C16H17NO3 | C. asiaticum L.C. augustum Rox. | FruitsFlower stems | 910 | |||||
3 | Isocraugsodine. | C16H17NO3 | 220˚ | C. asiaticum L.C. augustum Rox. | FruitsFruits | 99 | ||||
4 | Latisodine. | C17H21NO3 | 205–207˚ | C. latifolium Linn. | ---- | 11 | ||||
5 | Latisoline. | C24H31NO8 | – 48.5˚ (MeOH) | C. latifolium Linn. | ---- | 11 | ||||
6 | O-Methylnorbelladine. | C16H19NO3 | 161–164˚ | C. asiaticum L. C. augustum Rox.
C. kirkii Baker C. pratense |
--------
Bulbs ---- |
612
13 14 |
||||
7 | Ryllistine. | C19H25NO4 | 77–79˚ | C. asiaticum L. C. augustum Rox.
C. latifolium Linn. C. pratense |
--------
---- ---- |
66, 15
16 15 |
||||
II- Galanthamine-type alkaloids: | ||||||||||
8 | 3-O-Acetyl-sanguinine. | C17H19NO4 | 215 –218˚ /–13.5˚ (MeOH) | C. kirkii Baker | Bulbs | 13 | ||||
9 | Epinorgalanthamine. | C16H19NO3 | C. asiaticum var. japonicum | Aerial parts | 17 | |||||
10 | (–)-Galanthamine. | C17H21NO3 | 127–129˚ /–121.4˚ (EtOH) | C. amabile Donn.C. asiaticum L.
C. defixum Ker. C. laurentii Durand & Dewild C. macowanii Baker C. moorei Hook F.
C. powellii Hort. C. powellii Hort. var. krelagei |
BulbsBulbs
Bulbs ---- ---- Whole plant Bulbs Bulbs Bulbs |
1819
20 21 22 23 24 25 26 |
||||
11 | Galanthamine-N-demethyl [(–)-norgalanthamine]. | C16H19NO3 | 156–158˚ | C. asiaticum var. japonicum | Leaves | 27 | ||||
12 | Galanthamine-O, N- diacetyl. | C20H23NO5 | 204–205˚ | C. asiaticum var. japonicum C. augustum Rox. | -------- | 286 | ||||
13 | Lycoramine. | C17H22NO3 | C. powellii Hort. | Bulbs | 29 | |||||
14 | Narwedine. | C17H19NO3 | 188–189˚ +100˚(CHCl3) | C. amabile Donn. | Bulbs | 18 | ||||
15 | Sanguinine. | C15H17NO3 | C. kirkii Baker | Bulbs | 13 | |||||
III- Lycorenine-type alkaloids: | ||||||||||
16 | (+)-9-O-Demethyl-homolycorine. | C17H19NO4 | C. defixum Ker.C. moorei Hook F. | BulbsBulbs | 3024 | |||||
17 | Hippeastrine. | C17H17NO5 | 214–217˚ /+ 160˚ (CHCl3) | C. amabile Donn.C. asiaticum L.
C. defixum Ker. C. latifolium Linn. C. powellii Hort. |
BulbsBulbs
Bulbs Bulbs, Leaves Bulbs |
1819
20 30 29 |
||||
18 | Homolycorine. | C18H21NO4 | 173–175˚ | C. defixum Ker. | Bulbs | 30 | ||||
19 | 5-Hydroxy-homolycorine. | C18H21NO5 | C. defixum Ker. | Bulbs | 30 | |||||
20 | Neruscine (deoxylycorenine). | C18H23NO3 | C. powellii Hort. | Bulbs | 29 | |||||
IV- Tazettine-type alkaloids: | ||||||||||
21 | (+)-Criwelline (3-epitazettine). | C18H21NO5 | C. delagoense VerdoornC. erubescens Ait.
C. firmifolium var. hygrophilum C. macrantherum Engl. C. powellii Hort. C. powellii Hort. var. album |
Bulbs----
Whole plant Leaves ---- Bulbs |
3129
32 33 34 26 |
|||||
22 | 8-α-Ethoxy-precriwelline. | C20H25NO5 | +116.6˚ (CHCl3) | C. bulbispermum Milne. | Whole plant | 35 | ||||
23 | (+)-Macronine. | C18H19NO5 | C. erubescens Ait.C. macrantherum Engl. | BulbsLeaves | 3633 | |||||
24 | N-desmethyl-8-α-ethoxy-pretazettine. | C19H23NO5 | +160.63˚ (CHCl3) | C. bulbispermum Milne. | Whole plant | 35 | ||||
25 | N-desmethyl-8-β-ethoxy-pretazettine. | C19H23NO5 | +34˚ (CHCl3) | C. bulbispermum Milne. | Whole plant | 35 | ||||
26 | (+)-N-demethyl-macronine. | C17H17NO5 | C. erubescens Ait. | Bulbs | 36 | |||||
27 | (+)-N-demethylcarboethoxy-macronine. | C20H21NO7 | C. erubescens Ait. | Bulbs | 36 | |||||
28 | Ornamine. | C18H21NO3 | C. ornatum (L.f.ex Aiton) | Bulbs | 37 | |||||
29 | Ornazamine. | C18H22NO4 | C. ornatum (L.f.ex Aiton) | Bulbs | 37 | |||||
30 | Ornazidine. | C16H20NO3 | C. ornatum (L.f.ex Aiton) | Bulbs | 37 | |||||
31 | Precriwelline. | C18H21NO5 | C. powellii Hort. | Bulbs | 36 | |||||
32 | (+)-Tazettine. | C18H21NO5 | 202–208˚ /+160˚ (CHCl3) | C. amabile Donn.C. americanum L.
C. asiaticum L. C. laurentii Durand & Dewild C. moorei Hook F. C. powellii Hort. var. harlemense C. powellii Hort. var. krelagei |
BulbsLeaves
Bulbs ---- Bulb ---- Bulb |
6, 1838
19 25 24 39 29 |
||||
33 | Zeylamine. | C18H21NO5 | C. zeylanicum Linn. | Roots | 38 | |||||
V- Cherylline-type alkaloids: | ||||||||||
34 | Boit’s crinine. | C. moorei Hook F.C. powellii Hort. | -------- | 408, 34 | ||||||
35 | Cherylline. | C17H19NO3 | 212–213˚ / – 61.6˚ (EtOH) | C. bulbispermum Milne.C. latifolium Linn.
C. macowanii Baker
C. moorei Hook F.
C. powellii Hort. |
BulbsBulbs
Bulbs Whole plant Whole plant Bulblets Bulbs |
4141
42 43,44,45 23, 45 46 47 |
||||
36 | Latifine. | C17H19NO3 | C. latifolium Linn. | Leaves | 48 | |||||
VI- Narciclasine-type alkaloids: | ||||||||||
37 | Crinasiadine. | C14H9NO3 | 276–278˚ | C. asiaticum L. | ---- | 49 | ||||
38 | Crinasiatine. | C22H17NO4 | > 270˚ (dec.) | C. asiaticum L. | ---- | 49 | ||||
39 | Narcicrinine. | C14H17NO5 | C. oliganthum Urban | Leaves | 38 | |||||
VII- Other minor alkaloidal types: | ||||||||||
No. | Alkaloid name | Molecular Formula | Type | mp (˚C) / [α]D | Plant source | Plant parts | References | |||
40 | Augustamine. | C17H19NO4 | Augustamine | 173–175˚ | C. augustum Rox.C. bulbispermum Milne.
C. kirkii Baker C. latifolium Linn. |
Whole plantBulbs
Bulbs Leaves |
50, 51, 5253, 54
13 55 |
|||
41 | 4a, N-Dedihydro-noraugustamine. | C16H15NO4 | Augustamine | 127–130˚ /– 242.6˚(MeOH) | C. kirkii Baker | Bulbs | 13 | |||
42 | Noraugustamine. | C16H17NO4 | Augustamine | 149–151˚ /– 50˚ (MeOH) | C. kirkii Baker | Bulbs | 13 | |||
43 | Cripowelline A. | C25H31NO12 | Novel type | – 43.8˚ (MeOH) | C. powellii Hort. | Bulbs | 56 | |||
44 | Cripowelline B. | C25H33NO11 | Novel type | – 64.1˚ (MeOH) | C. powellii Hort. | Bulbs | 56 | |||
45 | 3-Hydroxy-8,9-methylene dioxy- phenanthridine. | C14H9NO3 | Phenanthridine | 215–218˚ | C. firmifolium var. hygrophilum | Whole plant | 32 | |||
46 | Trisphaeridine. | C14H9NO2 | Phenanthridine | 139–141˚ | C. americanum L.C. asiaticum L.
C. augustum Rox. C. bulbispermum Milne C. firmifolium var. hygrophilum C. kunthianum Roem. |
BulbsFruits
Leaves Bulbs Whole plant Leaves |
5758
53 53 32 59 |
|||
47 | Ismine. | C15H15NO3 | Ismine | 99–100˚ | C. firmifolium var. hygrophilumC. powellii Hort.
C. powellii Hort. var. album C. pratense |
Whole plantBulbs
Bulbs ---- |
3260
61 6 |
|||
48 | Latindine. | C41H31N3O10 | Clivimine | > 300˚ (dec.) | C. latifolium Linn. | ---- | 6, 15 | |||
49 | Mesembrenol. | C16H21NO3 | Sceletium | C. oliganthum Urban | ---- | 62 | ||||
50 | Perlolyrine. | C16H12N2O2 | β-carboline | 182–183˚ | C. augustum Rox. | Leaves | 53 | |||
51 | Asiaticumine A. | C. asiaticum var. sinicum | Bulbs | 63 | ||||||
52 | Asiaticumine B. | C. asiaticum var. sinicum | Bulbs | 63 | ||||||
53 | Cribetamine. | C. oliganthum Urban | Leaves | 38 | ||||||
54 | Macranthine. | C. macrantherum Engl. | Leaves | 33 | ||||||
55 | Macranthine-O-acetyl. | C. macrantherum Engl. | Leaves | 33 | ||||||
56 | Macranthine-O,O-diacetyl | C. macrantherum Engl. | Leaves | 33 | ||||||
57 | Yemensine. | C. yemense Defl. | ---- | 20 | ||||||
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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Ijpsr
John Refaat*, Mohamed S. Kamel , Mahmoud A. Ramadan and Ahmed A. Ali
Pharmacognosy Department, Faculty of Pharmacy, Minia University, 61519 Minia, Egypt
johnrefaat82@yahoo.com
13 June, 2012
14 August, 2012
27 September, 2012
http://dx.doi.org/10.13040/IJPSR.0975-8232.3(10).3630-38
01 October, 2012