Alkaloids from the Tribe Bocconieae (Papaveraceae): A Chemical and Biological Review
Abstract
:1. Introduction
2. Chemical Constituents
Name | Type | Plant | Part | Ref. | |||||
---|---|---|---|---|---|---|---|---|---|
1 | 11-O-Methyldihydrochelerythrine | IA | B. arborea | — | [16] | ||||
2 | Angoline ((±)-6-methoxydihydro-chelerythrine) | IA | M. cordata | Stems | [17] | ||||
B. arborea | Leaves, stems | [2] | |||||||
M. microcarpa | Aerial parts, roots | [14,18,19] | |||||||
3 | 12-Methoxydihydrochelerythrine | IA | B. integrifolia | Leaves | [20] | ||||
4 | Dihydrochelerythrine | IA | B. integrifolia | Leaves | [20] | ||||
B. arborea | Aerial parts | [4] | |||||||
B. frutescens | Leaves | [3] | |||||||
M. microcarpa | Roots, leaves, whole plant | [14,21,22] | |||||||
M. cordata | Fruits | [23] | |||||||
B. pearcei | Fruits | [24] | |||||||
5 | 6, 12-Dimethoxydihydrocheleritrine | IA | B. arborea | — | [25] | ||||
6 | 8-Hydroxydihydrochelerythrine | IA | M. cordata. | Seeds | [26] | ||||
7 | 6-Butoxydihydrochelerythrine | IA | M. microcarpa | Roots | [14] | ||||
8 | Oxychelerythrine | IA | B. pearcei | Fruits | [24] | ||||
9 | Oxysanguinarine | IA | B. latisepala | Leaves, roots, seeds | [27] | ||||
B. arborea | — | [16] | |||||||
B. pearcei | Fruits | [24] | |||||||
M. cordata | — | [10] | |||||||
10 | Dihydrosanguinarine | IA | M. cordata | Fruits | [23] | ||||
B. integrifolia | Leaves | [20] | |||||||
B. arborea | Aerial parts | [4,16] | |||||||
M. microcarpa | Roots, leaves, whole plant | [14,21,22] | |||||||
B. Pearcei | Fruits | [24] | |||||||
11 | Dihydrochelirubine | IA | B. integrifolia | Leaves | [20] | ||||
B. pearcei | Fruits | [24] | |||||||
12 | 6-Methoxydihydrosanguinarine | IA | M. cordata | Fruits | [10] | ||||
M. microcarpa | Roots | [14] | |||||||
13 | 8-Methoxydihydrosanguinarine | IA | M. cordata | Seeds | [26] | ||||
14 | 6-Methoxydihydrochelirubine | IA | B. arborea | — | [25] | ||||
15 | 6-Ethoxysanguinarine | IA | M. cordata | — | [10] | ||||
M. microcarpa | Whole plant | [21] | |||||||
16 | Bocconoline | IA | B. cordata | — | [28] | ||||
M. cordata | — | [10] | |||||||
17 | (±)-6-Acetonyldihydrochelerythrine | IA | B. arborea | Barks, aerial parts | [2,15] | ||||
B. frutescens | Leaves | [3] | |||||||
M. cordata | Fruits | [10,23] | |||||||
18 | (±)-6-Acetonyldihydrosanguinarine | IA | B. arborea | Aerial parts | [2] | ||||
B. frutescens | Leaves | [3] | |||||||
M. cordata | Fruits | [10,23] | |||||||
M. microcarpa | Whole plant | [21] | |||||||
19 | Spallidamine(6-Carboxymethyldihydrosanguinarie) | IA | M. microcarpa | Roots | [14] | ||||
M. cordata | Whole plant | [12] | |||||||
20 | 6-Carboxymethyldihydrochelerythrine | IA | M. cordata | Whole plant | [12] | ||||
21 | Chelerythrine | IB | B. latisepala | Barks, stems, seeds | [27] | ||||
M. cordata | — | [29] | |||||||
B. frutescens | Roots, stalks and leaves | [30] | |||||||
M. microcarpa | — | [31] | |||||||
22 | Chelilutine | IB | M. cordata | Roots | [10] | ||||
M. microcarpa | — | [31] | |||||||
23 | 8-O-Demethylchelerythrine | IB | M. cordata | — | [29] | ||||
24 | 6-Ethoxychelerythrine | IB | M. cordata | — | [10] | ||||
25 | Norsanguinarine | IC | M. cordata | Fruits | [10] | ||||
26 | 12-Methoxynorchelerythrine | IC | B. pearcei | Fruits | [24] | ||||
27 | Pancorine | IC | M. microcarpa | Roots | [14] | ||||
28 | Norchelerythrine | IC | M. cordata | Whole plant | [12] | ||||
29 | Sanguinarine | IB | B. latisepala | Barks, stems | [27] | ||||
B. cordata | Leaves | [32] | |||||||
B. frutescens | Roots, stalks and leaves | [30] | |||||||
M. cordata. | Fruits | [29,33] | |||||||
M. microcarpa | Aerial parts | [18,19,34] | |||||||
30 | Bocconine (chelirubine) | IB | B. cordata | — | [35] | ||||
M. microcarpa | — | [31] | |||||||
31 | Macarpine | IB | M. cordata | Callus tissues | [10,36] | ||||
M. microcarpa | — | [31] | |||||||
32 | Maclekarpine A | IA | M. microcarpa | Roots | [14] | ||||
33 | Maclekarpine B | IA | M. microcarpa | Roots | [14] | ||||
34 | Maclekarpine C | IA | M. microcarpa | Roots | [14] | ||||
35 | 6 α-Isobutanonyldihydrochelerythrine | IA | M. cordata | Fruits | [23] | ||||
36 | 6 α-Isobutanonyldihydrosanguinarine | IA | M. cordata | Fruits | [23] | ||||
37 | Homochelidonine | ID | M. cordata | — | [10] | ||||
38 | Chelidonine | ID | B. frutescens | Roots | [37] | ||||
39 | Maclekarpine D | IA | M. microcarpa | Roots | [14] | ||||
40 | Maclekarpine E | IA | M. microcarpa | Roots | [14] | ||||
41 | 6-(1'-hydroxyethyl)-dihydrochelerythrine | IA | M. microcarpa | Roots | [14] | ||||
42 | R-6-((R)-1-Hydroxyethyl)-dihydrochelerythrie | IA | M. cordata | Whole plant | [12] | ||||
43 | Arnottianamide | IF | M. microcarpa | Roots | [14] | ||||
44 | Chelerythridimerine | IE | B. arborea | Barks | [38] | ||||
45 | Bis[6-(5, 6-dihydrochelerythrinyl)]ether | IE | M. microcarpa | Roots | [14] | ||||
46 | (±)-Sanguidimerine | IE | B. arborea | Aerial parts | [2] | ||||
M. cordata | Leaves | [10] | |||||||
47 | Chelidimerine | IE | B. arborea | Aerial parts | [2] | ||||
M. cordata | Leaves | [10] | |||||||
48 | (±)-Bocconarborine A | IE | B. arborea | Aerial parts | [2] | ||||
M. cordata | Leaves | [10] | |||||||
M. microcarpa | Whole plant | [21] | |||||||
49 | (±)-Bocconarborine B | IE | B. arborea | Aerial parts | [2] | ||||
M. cordata | Leaves | [10] | |||||||
50 | 1, 3-Bis(1l-hydrochelerythriny1)acetone | IE | B. arborea | — | [16] |
Name | Type | Plant | Part | Ref. | |
---|---|---|---|---|---|
51 | Berberine | II | B. frutescens M. cordata M. microcarpa | Roots, stalks, leaves — Roots | [30] [10] [31] |
52 | Berberrabine | II | M. microcarpa | Whole plant | [21] |
53 | Coptisine | II | B. frutescens M. microcarpa | Roots, stalks and leaves Roots | [30] [31] |
54 | Corysamine | II | B. frutescens | — | [37] |
55 | Columbamine | II | B. frutescens | Roots, stalks, leaves | [30] |
56 | Dehydrocorytenchine | II | M. cordata | Cultured cells | [39] |
57 | Dehydrocheilanthifoline | II | M. cordata | — | [40] |
58 | Tetrahydropalmatrubine | II | M. cordata | Cultured cells | [39] |
59 | Corytenchine | II | M. cordata | Cultured cells | [39] |
60 | (–)-Isocorypalmine | II | B. frutescens | Leaves, roots | [30,37,41] |
61 | (–)-Scoulerine | II | B. frutescens | Roots, leaves | [30,37] |
62 | (–)-cis-N-Methylcanadinium | II | B. frutescens | Roots | [37] |
63 | (–)-α-Canadine | II | B. frutescens | Roots, stalks, leaves | [30] |
64 | Dehydrocicanthifoline | II | M. cordata | — | [40] |
65 | β-Allocryptopine | III | M. microcarpa | Aerial parts, whole plant | [18,19,21] |
66 | α-Allocryptopine | III | B. cordata M. cordata B. latisepala M. microcarpa | Leaves Fruits Roots Whole plant | [32] [10] [27] [21] |
67 | Protopine | III | B. latisepala B.cordata B. frutescens M. cordata M. microcarpa | Leaves, roots Leaves Roots, stalks, leaves Cultured cells Aerial parts, whole plant | [27] [32] [30,41] [39] [19,21] |
68 | Cryptopine | III | M. cordata M. microcarpa | Fruits Aerial parts | [10] [18] |
69 | Protopine N-oxide | III | B. cordata | Whole plant | [10,42] |
70 | Papaverine | IV | M. cordata | Cultured cells | [39] |
71 | Laudanine | IV | M. cordata | Cultured cells | [43] |
72 | Codamine | IV | M. cordata | Cultured cells | [43] |
73 | Pseudocodamine | IV | M. cordata | Cultured cells | [43] |
74 | Rhoeadine | IV | B. frutescens | Leaves, stalks | [30,41] |
75 | N-p-Coumaroyltyramine | IV | M. microcarpa | Roots | [14] |
3. Biological Activities
3.1. Cytotoxicity against Tumor Cells
3.2. Insecticidal Activities
3.3. Antimicrobial Activity
3.4. Anti-Inflammatory Property
3.5. Effect on Cardiovascular System
3.6. Other Activities
4. Toxicity and Side Effects
5. Discussion and Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Yu, X.; Gao, X.; Zhu, Z.; Cao, Y.; Zhang, Q.; Tu, P.; Chai, X. Alkaloids from the Tribe Bocconieae (Papaveraceae): A Chemical and Biological Review. Molecules 2014, 19, 13042-13060. https://doi.org/10.3390/molecules190913042
Yu X, Gao X, Zhu Z, Cao Y, Zhang Q, Tu P, Chai X. Alkaloids from the Tribe Bocconieae (Papaveraceae): A Chemical and Biological Review. Molecules. 2014; 19(9):13042-13060. https://doi.org/10.3390/molecules190913042
Chicago/Turabian StyleYu, Xuelong, Xiaoli Gao, Zhixiang Zhu, Yuan Cao, Qian Zhang, Pengfei Tu, and Xingyun Chai. 2014. "Alkaloids from the Tribe Bocconieae (Papaveraceae): A Chemical and Biological Review" Molecules 19, no. 9: 13042-13060. https://doi.org/10.3390/molecules190913042