CRINUM; AN ENDLESS SOURCE OF BIOACTIVE PRINCIPLES: A REVIEW, PART II. CRINUM ALKALOIDS: CRININE-TYPE ALKALOIDS
HTML Full TextCRINUM; 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.
Keywords:Alkaloids,
Amaryllidaceae, Chemical constituents, Crinine, |
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
Alkaloid name | Molecular Formula | mp (˚C) / [α]D | Plant source | Plant parts | References | |
1 | 11-O-Acetyl-ambelline. | C20H23NO6 | 80–82˚ / –23.5˚ (CHCl3) | C. latifolium Linn. | ---- | 4 |
2 | 11-O-Acetyl-1,2-β-epoxy ambelline. | C20H23NO7 | 195–197˚ / –49.9˚ (MeOH) | C. latifolium Linn. | ---- | 4 |
3 | 1-O-Acetyl-bulbisine | C19H23NO6 | C. asiaticum var. sinicum | Leaves | 5 | |
4 | 2-O-Acetyl-bulbisine | C19H23NO6 | C. asiaticum var. sinicum | Leaves | 5 | |
5 | 2-O-Acetyl-crinamabine. | C18H22NO6 | C. asiaticum var. sinicum | Leaves | 5 | |
6 | 3-O-Acetyl-crinine (krepowine). | C18H19NO4 | 140–141˚ /+ 68.4˚ (EtOH)
+ 59.3˚(CHCl3) |
C. americanum L.C. bulbispermum Milne.
C. macowanii Baker C. moorei Hook F. C. powellii Hort. C. powellii Hort. var. krelagei |
BulbsBulbs
Bulbs Whole plant Bulbs ---- |
67, 8
9 10 11 12 |
7 | 3-O-acetyl-8-O-demethyl-maritidine. | C18H21NO4 | C. asiaticum var. sinicum | Leaves | 5 | |
8 | 3-O-Acetyl-hamayne. | C18H19NO5 | 110–112˚ / +49.3˚ (EtOH) | C. bulbispermum Milne.C. kirkii Baker
C. latifolium Linn. C. macowanii Baker C. moorei Hook F.
C. zeylanicum Linn. |
Whole plantBulbs
Bulbs Whole plant Whole plant Bulblets Bulbs |
1314
7 15 16 17 18 |
9 | 3-O-Acetyl-powelline | C19H21NO5 | 59–60˚ / +65.8˚ (CHCl3) | C. bulbispermum Milne. | Bulbs | 8 |
10 | Amabiline (Crinan-1,2-diol) | C16H19NO4 | 210˚ / –32˚ (EtOH) | C. amabile Donn.C. kirkii Baker
C. stuhlamanii Baker |
BulbsBulbs
Bulbs |
1920
21 |
11 | Ambelline. | C18H21NO5 | 260 –261˚ /–13.6˚ (MeOH)
+32˚ (CHCl3) |
C. amabile Donn.C. asiaticum L.
C. asiaticum var. japonicum C. augustum Rox.
C. powellii Hort. var.harlemense C. pretense C. stuhlamanii Baker C. yemense Defl. C. zeylanicum |
Bulbs----
---- ---- ---- ---- ---- Bulbs ---- Bulbs |
2223
23 23, 24 25, 26 27 12 21 28 29 |
12 | 3-[4'-(8'-aminoethyl)-phenoxy] bulbispermine. | C24H26N2O4 | +53.3˚ (CHCl3) | C. moorei Hook F. | Whole plant | 10 |
13 | 3,4-Anhydropowelline. | C17H17NO3 | + 22˚ (CHCl3) | C. bulbispermum Milne. | Bulbs | 8 |
14 | Augustine. | C17H19NO4 | 174 –176˚ /-44.8˚ (MeOH)
–46.25˚ (EtOH) |
C. amabile Donn.
C. americanum L. C. augustum Rox. |
BulbsBulbs
Leaves Whole plant |
1922
30 31, 32 |
15 | C17H21NO3 | 173–175˚ / –30˚ (MeOH) | C. augustum Rox. | Leaves | 8 | |
16 | Bowdensine. | C21H25NO7 | C. bulbispermum Milne. | Bulbs | 7 | |
17 | Bulbisine. | C17H21NO5 | 182–183˚ / +27.14(MeOH) | C. bulbispermum Milne. | Bulbs | 8 |
18 | Bulbispermine. | C16H17NO4 | C. bulbispermum Milne.
C. macowanii Baker C. yemense Defl. |
BulbsWhole plant
Whole plant Bulbs |
3313
34 35 |
|
19 | Buphanidrine. | C18H21NO4 | 90–92˚ / + 4.2˚ (EtOH) | C. erubescens Ait.C. kunthianum Roem.
C. latifolium Linn. C. macowanii Baker |
BulbsLeaves
Leaves Bulbs |
3637
38 9 |
20 | Buphanidrine-6-hydroxy. | C18H21NO5 | C. latifolium Linn.C. zeylanicum Linn. | Leaves---- | 3829 | |
21 | Buphanidrine-6-β-ethoxy. | C20H25NO5 | C. bulbispermum Milne.C. zeylanicum Linn. | Bulbs---- | 829 | |
22 | (–)-Buphanisine. | C17H19NO3 | 122–124˚ /– 20˚ (MeOH)
– 26˚ (EtOH) |
C. amabile Donn.
C. augustum Rox.
C. bulbispermum Milne. |
BulbsBulbs
Whole plants Bulbs Bulbs |
1922
31, 32 39 8 |
23 | (–)-Buphanisine-6-α-hydroxy. | C17H19NO4 | 126–128˚ / +40.04˚(EtOH) | C. augustum Rox.C. bulbispermum Milne. | Whole plantsBulbs | 31, 408, 41 |
24 | (–)-Buphanisine-6-β-hydroxy. | C17H19NO4 | 126–128˚ / +40.04˚(EtOH) | C. augustum Rox.C. bulbispermum Milne. | Whole plantsBulbs | 31, 408 |
25 | Buphanisine-6-α-ethoxy. | C19H23NO5 | C. augustum Rox.C. bulbispermum Milne. | LeavesBulbs | 88 | |
26 | Crinafolidine. | C19H23NO6 | C. latifolium Linn. | Fruits | 42 | |
27 | C18H21NO6 | C. latifolium Linn. | Fruits | 42 | ||
28 | Crinalbine. | C17H19NO5 | 130–132˚ / +24˚ (CHCl3) | C. bulbispermum Milne.C. powellii Hort. var. album | BulbsBulbs | 4344 |
29 | Crinamabine. | C16H20NO5 | 235–238˚ / +35˚ (MeOH) | C. amabile Donn. | Bulbs | 22 |
30 | Crinamabine-7-methoxy | C17H22NO6 | C. asiaticum var. sinicum | Leaves | 5 | |
31 | (–)-Crinamidine. | C16H18NO5 | 215–217˚ / –10˚ (CHCl3) | C. bulbispermum Milne.C. erubescens Ait.
C. kunthianum Roem. C. latifolium Linn. C. laurentii Durand & Dewild C. macowanii Baker
C. moorei Hook F.
C. powellii Hort. C. powellii Hort. var. krelagei |
BulbsBulbs
Leaves Leaves ---- Bulbs Whole plant Seeds, Bulbs Bulblets Whole plant ---- Bulbs |
736
37 38 45 9 15, 16 46, 47 17 16 45 44 |
32 | (+)-Crinamine. | C17H19NO4 | 199–201˚ /+157˚ (CHCl3)
+356.8˚(MeOH) |
C. ambile Donn.C. americanum L.
C. asiaticum L. C. asiaticum var. japonicum C. augustum Rox.
C. bulbispermum Milne.
C. defixum Ker. C. erubescens Ait. C. firmifolium var. hygrophilum C. glaucum Chevalier C. Jagus Dandy C. latifolium Linn. C. macowanii Baker
C. moorei Hook F. C. ornatum C. powellii Hort. C. powellii Hort. var. krelagei C. scabrum Herb. C. stuhlamanii Baker C. yemense Defl. C. zeylanicum Linn. |
BulbsLeaves
Bulbs Leaves Whole plant Bulbs Bulbs Whole plant Bulbs Bulbs Whole plant
Bulbs Bulbs Bulbs Bulbs Whole plant Bulblets Whole plant Bulbs Bulbs ---- Whole plant Bulbs Bulbs |
1930
23, 48 7, 49 31, 40 39 43 7, 16 50 36 51
52 53 52 7, 9 15, 16 17 16 54 55 8 50 21 18, 35 |
33 | (+)-Crinamine-6-α-hydroxy. | C17H19NO5 | 210˚ /+46˚ (CHCl3) | C. asiaticum L.C. bulbispermum Milne.
C. delagoense Verdoorn C. erubescens Ait. C. firmifolium C. firmifolium var. hygrophilum C. Jagus Dandy C. powellii Hort. C. scabrum Herb. C. zeylanicum Linn. |
----Whole plant
Bulbs Bulbs Bulbs Whole plant
Bulbs Bulbs Whole plant Bulbs |
2313, 16
9 36 56 51
53 27 50 18 |
34 | (+)-Crinamine-6-β-hydroxy. | C17H19NO5 | 210˚ /+46˚ (CHCl3) | C. asiaticum L.C. bulbispermum Milne.
C. delagoense Verdoorn C. erubescens Ait. C. firmifolium C. firmifolium var. hygrophilum C. Jagus Dandy C. powellii Hort. C. scabrum Herb. C. zeylanicum Linn. |
----Whole plant
Bulbs Bulbs Bulbs Whole plant
Bulbs Bulbs Whole plant Bulbs |
2313, 16
9 36 56 51
53 27 50 18 |
35 | (+)-Crinamine-6-β-methoxy. | C18H21NO5 | + 20.2° (MeOH) | C.augustum Rox.C. zeylanicum Linn. | BulbsBulbs | 3918 |
36 | Crinan-3α-ol. | C16H19NO3 | C. latifolium Linn. | Leaves | 38 | |
37 | C18H21NO5 | C. natans Linn.C. oliganthum Urban | BulbsBulbs | 5730 | ||
38 | (–)-Crinine. | C16H17NO3 | 209–210˚ /– 11˚ (CHCl3)
– 9˚ (EtOH) |
C. amabile Donn.C. americanum L.
C. asiaticum L. C. augustum Rox. C. bulbispermum Milne.
C. erubescens Ait. C. kirkii Baker C. lugardiae N.E.Br. C. latifolium Linn. C. macowanii Baker C. moorei Hook F.
C. powellii Hort. C. powellii Hort. var. album C. powellii Hort. var. harlemense C. powellii Hort. var. krelagei C. stuhlamanii Baker
|
BulbsBulbs
---- Leaves Bulbs Whole plants Bulbs Bulbs Bulbs, Roots Bulbs Whole plant Seeds Whole plant, Bulblets Bulbs Bulbs Bulbs Bulbs Bulbs ---- |
586
23 8 7, 43 16 36 20 59 7, 25 15, 16, 34 46 10, 16, 17 55 44 60
44 21 29 |
39 | (–)- Crinine-6-α-hydroxy. | C16H17NO4 | 268–270˚+13.58˚ (EtOH) | C. augustum Rox.C. bulbispermum Milne. | Whole plantBulbs | 408 |
40 | (–)- Crinine-6-β-hydroxy. | C16H17NO4 | 268–270˚+13.58˚ (EtOH) | C. augustum Rox.C. bulbispermum Milne. | Whole plantBulbs | 408 |
41 | Crinine-6-α-ethoxy. | C18H21NO4 | C. bulbispermum Milne. | Bulbs | 8 | |
42 | Crinisine. | C. asiaticum L.var. sinicum | Bulbs | 61 | ||
43 | ---- | 62 | ||||
44 | Deacetylbowdensine | C17H21NO5 | C. bulbispermum Milne.C. erubescens Ait. | BulbsBulbs | 736 | |
45 | 4a-Dehydroxy-crinamabine. | C16H19NO4 | 208–210˚ /+28˚ (MeOH) | C. amabile Donn.C. macowanii Baker | BulbsBulbs | 229 |
46 | Delagoenine. | C19H25NO5 | 120–122˚ /+34.2˚ (MeOH) | C. delagoense Verdoorn | Bulbs | 9 |
47 | C18H21NO5 | 132–134˚ / +28.2˚(MeOH) | C. delagoense Verdoorn | Bulbs | 9 | |
48 | 8-O-Demethyl-oxomaritidine | C16H17NO3 | Crinum asiaticum var. sinicum | Leaves | 5 | |
49 | C16H19NO3 | C. americanum L. | Roots | 30 | ||
50 | (+)-Dihydrohaemanthamine | C17H21NO4 | C. powellii Hort. | Bulbs | 60 | |
51 | Dihydro-oxo-demethoxy-haemanthamine. | C16H17NO3 | C. latifolium Linn. | Leaves | 38 | |
52 | C16H19NO3 | C. asiaticum var. sinicum | Leaves | 5 | ||
53 | C17H19NO3 | 123–125˚ / +129˚ (EtOH) | C. moorei Hook F. | Whole plantBulblets | 1617 | |
54 | 1-Epideacetyl-bowdensine | C17H21NO5 | 162–164˚ / +22˚ (CHCl3) | C. kunthianum Roem. C. macowanii Baker
C. moorei Hook F.
|
LeavesBulbs
Whole plant Whole plant Bulblets |
379
15, 16 10 17 |
55 | 1-Epijosephinine. | C18H20NO5 | Crinum asiaticum var. sinicum | Leaves | 5 | |
56 |
|
C16H17NO3 | 208–210˚ / + 102˚ (EtOH) | C. moorei Hook F. | Whole plant | 10 |
57 | 1,2-β-Epoxyambelline (cavinine). | C18H21NO6 | 244–245˚ /+22.4˚ (CHCl3)
–14.6˚ (MeOH) |
C. asiaticum L.C. augustum Rox.
C. latifolium Linn. C. pratense |
--------
---- ---- |
23, 2423, 24
24, 26 24 |
58 | Flexinine. | C16H17NO4 | 233–235˚ /–25.5˚ (CHCl3)
–12.7˚ (MeOH) |
C. amabile Donn.C. americanum L.
C. augustum Rox. C. erubescens Ait. C. kirkii Baker |
BulbsBulbs
Leaves Bulbs Bulbs |
226
8 36 20 |
59 | (+)-Haemanthamine(3-epicrinamine). | C17H19NO4 | 200–203˚ /+19.7˚ (MeOH) | C. americanum L.C. asiaticum L.
C. defixum Ker. C. glaucum Chevalier C. Jagus Dandy C. ornatum C. powellii Hort. var. album C. yemense Defl. |
Leaves----
Bulbs Bulbs Bulbs Bulbs Bulbs Whole plant |
3023
28 52 52 54 44 35 |
60 | Haemanthidine (pancratine). | C17H19NO5 | 189–190˚ / – 41˚ (CHCl3) | C. asiaticum L. | ---- | 23 |
61 | Haemultine. | C. powellii Hort. | Bulbs | 27 | ||
62 | Hamayne. | C16H17NO4 | 79–80˚ / +79˚ (EtOH) | C. americanum L.C. asiaticum L.
C. asiaticum var. japonicum C. bulbispermum Milne. C. delagoense Verdoorn C. firmifolium var. hygrophilum C. glaucum Chevalier C. Jagus Dandy C. kirkii Baker C. kunthianum Roem. C. latifolium Linn. C. lugardiae N.E.Br. C. macowanii Baker C.ornatum C. stuhlamanii Baker C. zeylanicum Linn. |
Roots----
---- Bulbs Bulbs Whole plant
Bulbs Bulbs Bulbs Leaves Bulbs Bulbs, Roots Whole plant Bulbs Bulbs Bulbs |
3049
49 33, 43 9 51
52 52, 53 14, 20 37 7 59 34 54 21 18 |
63 | 6-α-Hydroxy-crinamidine. | C17H19NO6 | 254–256˚ / +26˚ (MeOH) | C. latifolium Linn. | Leaves | 63 |
64 | (+)-11-Hydroxyvittatine. | C16H17NO4 | 225–227˚ / + 9˚ (MeOH) | C. bulbispermum Milne. | Bulbs | 64 |
65 | C17H19NO4 | 202˚ / +290˚ (CHCl3) | C. powellii Hort. var. krelagei | Bulbs | 44, 60 | |
66 | C16H19NO3 | 115–117˚ / –34˚ (CHCl3) | C. kirkii BakerC. macowanii Baker | BulbsBulbs | 209 | |
67 | Nerbowdine (hemanthine). | C17H21NO5 | C. erubescens Ait. | Bulbs | 36 | |
68 | C20H24N2O3 | C. oliganthum Urban | Whole plant | 30 | ||
69 | (–)-Oxocrinine. | C16H15NO3 | 185–186˚/ –24.6˚ (CHCl3) | C. americanum L. | Bulbs | 6 |
70 | (–)-Powellamine. | C16H17NO3 | 198–200˚ / – 49˚ (CHCl3) | C. powellii Hort. | Bulbs | 11, 55 |
71 | (+)-Powellamine (cripaline) | C16H17NO3 | C. powellii Hort. | Bulbs | 55, 60 | |
72 | C17H19NO4 | 200–201˚ | C. asiaticum L.C. asiaticum var. sinicum
C. bulbispermum Milne. C. erubescens Ait. C. kunthianum Roem. C. latifolium Linn. C. macowanii Baker
C. moorei Hook F.
C. powellii Hort. C. powellii Hort. var. album C. powellii Hort. var. harlemense C. powellii Hort. var. krelagei |
BulbsBulbs
Bulbs Bulbs Leaves Bulbs Bulbs Whole plant Seeds Bulbs Whole plant Bulbs Bulbs ----
Bulbs |
48, 6161
43 36 37 7 9 15, 16 46 47 10, 16 30, 55 44 55, 65
44 |
|
73 | Powelline-6-hydroxy. | C17H19NO5 | C. latifolium Linn. | Leaves | 38 | |
74 | Powelline-6-α-ethoxy | C19H23NO5 | C. bulbispermum Milne. | Bulbs | 8 | |
75 | (+)-siculine. | C18H19NO3 | C. asiaticum var. sinicum | Leaves | 5 | |
76 | Undulatine. | C18H21NO5 | 149–150˚ / –46˚ (CHCl3) | C. latifolium Linn.C. macowanii Baker
C. moorei Hook F.
C. powellii Hort. C. powellii Hort. var. krelagei C. yemense Defl. |
BulbsBulbs
Whole plant Bulblets Bulbs Bulbs ---- |
79
10 17 27 60 28 |
77 | Undulatine-6-hydroxy. | C18H21NO6 | 113–116˚ / +8.4˚ (MeOH) | C. latifolium Linn. | Leaves | 38 |
78 | (+)-Vittatine. | C16H17NO3 | 206–208˚ / +26˚ (MeOH) | C. bulbispermum Milne | Bulbs | 64 |
79 | Yemenine A. | C. yemense Defl. | Bulbs | 35 | ||
80 | Yemenine B. | C. yemense Defl. | Bulbs | 35 | ||
81 | Yemenine C. | C. yemense Defl. | Bulbs | 35 |
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.
Article Information
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3091-3100
873KB
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English
IJPSR
John Refaat *, Mohamed S. Kamel , Mahmoud A. Ramadan and Ahmed A. Ali
Pharmacognosy Department, Faculty of Pharmacy, Minia University 1, Minia-61519, Egypt
johnrefaat82@yahoo.com
06 May, 2012
02 July, 2012
17 August, 2012 CRINUM; AN ENDLESS SOURCE OF BIOACTIVE PRINCIPLES: A REVIEW, PART
http://dx.doi.org/10.13040/IJPSR.0975-8232.3(9).3091-00
01 September, 2012