Table 4.
Phytochemicals present in different parts (seeds, roots, stems, fruits, flowers, leaves, testa, and whole plant) of Peganum harmala L. and overall profile of Peganum multisectum (Maxim.) Bobrov and Peganum nigellastrum Bunge.
| Plant parts | Phytoconstituents | References |
|---|---|---|
| Peganum harmala L. | ||
|
| ||
| Seeds | Hexadecanoic acid; methyl linoleate; methyl oleate; 9-octadecenoic acid; ethyl linoleate; ethyl oleate; harmaline; harmine; delta-tocopherol | [42] |
| Harmine | [43] | |
| Harmaline; harmine; asparagine; sucrose; choline; phosphorylcholine | [44] | |
| Harmine; vasicinone; pegamine; H3-hydroxylated; pegamine dimer; ruine; deoxyvasicinone; tetrahydroharmin; peganine; harmaline; harmalol; pegaline; dexoypeganine | [45] | |
| 2-Oxoindole alkaloids; (±)-peganumalines A-E; peganumaline | [46] | |
| p-Coumaric acid; rutin; catechin; hesperetin; chloregenic acid | [47] | |
| Peganine A; peganine B; peganumal A; peganumal B; pegaharmine F; pegaharmine G; pegaharmine H; pegaharmine I; pegaharmine J; pegaharmine K | [48] | |
| Peganine B; peganumal A; peganumal B; pegaharmine F; pegaharmine G; pegaharmine H; pegaharmine I | [49] | |
| 3α-Acetoxy-27-hydroxyolean-12-en-28-oic acid methyl ester; syringin; [5]-caffeyl alcohol 4-O-β-D-glucopyranoside; coniferin; syringinoside; N-acetyl-9-syringinoside | [50] | |
| Pegaharmine A; pegaharmine B; pegaharmine C; pegaharmine D; pegaharmine E | [51] | |
| Peganone I (3,6-dihydroxy-8-methoxy-2-methylanthraquinone); peganone II (8-hydroxy-7-methoxy-2-methylanthraquinone) | [52] | |
| Harmine; harmaline; harmol; harmalol; harmane; norharmane | [53] | |
| Indole; quinoline,2,3,4-trimethyl-; tetrahydroharman; oleanitrile; tetrahydroharmine; harmaline; harmine; 9-octadecenamide, (z)-; 6-methoxytetrahydro-1-norharmanone; 4-amino-2-ethyl-3 methylquinoline | [54] | |
| 2-Carboxyl-3,4-dihydroquinazoline; 3-hydroxylated harmine; 1-hydroxy-7-methoxy-β-carboline; acetylnorharmine; harmic acid methyl ester; 2-aldehyde-tetrahydroharmine; harmalanine; harmine N-oxide; 2-carboxyl-3,4-dihydroquinazoline; 6-methoxyindoline; 1-O-β-D-xylopyranose sinapyl alcohol | [55] | |
| [5]-Vasicinone-Glu; [5]-vasicinone-Glu | [56] | |
| 3-Hydroxy-3-(N-acetyl-2-aminoethyl)-6-methoxyindol-2-one; 11-methyoxyl-rutaecarpine | [57] | |
| Harmic acid; 4,5-dihydroblumenol | [58] | |
| Oleic acid; linoleic acid ((Z,Z)-9,12-octadecatrienoic acid); linolenic acid; palmitic acid (hexadecanoic acid); arachidic acid | [59] | |
| Peganumine A | [60] | |
| Peganumine A; peganumine B | [61] | |
| Harmalidine | [62] | |
| Harmalacidine | [63] | |
| Diglycoside vasicine; vasicine; vasicinone; harmalol; ruine; harmol; 8-hydroxy-harmine; tetrahydroharmine; harmaline; harmine | [64] | |
| Norharmane | [65] | |
| Harmane; harmol; harmine | [66] | |
| Tetrahydroharmine | [67] | |
| Harmine; harmaline; vasicine; vasicinone | [68] | |
| Quercetin-3-O-gentiobioside; quercetin-3-O-rutinoside; kaempferol-3-methyoxyl-5-O-rutinoside; kaempferol-3,5-dimethyxyl-7-O-glucoside; stearic acid; kaempferol-3-methyoxyl-7-O-glucoside; isorhamnetin-7-O-glucoside; isorhamnetin-3-O-rutinoside; anthraquinone glucoside; 9,14-dihydroxyoctadecanoic acid | [69] | |
| Dodecane; tetradecane; methyl dodecanoate; hexadecane; 2-octanol benzoate; heptadecane; methyl tetradecanoate; 2,6,10,14-tetramethyl pentadecane; octadecane; 2,6,10,14-tetramethyl hexadecane; nonadecane; methyl hexadecanoate; dibutyl phthalate; eicosane; methyl oleate; henicosane; docosane; harmine; tricosane | [70] | |
| Acacetin 7-0-rhamnoside; acacetin 7-0-[6″-0-glucosyl-2″-O-(3‴-acetylrhamnosyl)] glucoside; acacetin 7-O-(2‴-O-rhamnosyl-2″-O-glucosyl)glucoside; 2‴-0-rhamnosyl-2″-0-gluco-sylcytisoside | [71] | |
| Ruine; dihydroharmane; dihydroruine; tetrahydroharmol; harmalicine | [72] | |
|
| ||
| Roots | Threonine; acetic acid; lysine; proline; phosphorylcholine; sucrose; β-glucose; formic acid; asparagine; 4-hydroxyisoleucine | [44] |
| Harmol | [66] | |
| Luotonin A; luotonin B | [73] | |
| Luotonin E; luotonin F | [74] | |
| Vasicol | [75] | |
| Harmine; vasicine; vasicinone; harmaline | [76] | |
|
| ||
| Flowers | Harmine; peganine | [77] |
| Proline; lysine; asparagine; 4-hydroxyisoleucine; sucrose; vasicine; choline; phosphorylcholine | [44] | |
|
| ||
| Whole plant | 1-Octadecene; 6,10,14-trimethyl-2-pentadecanone; [5]-15-heptadecenal; oxacyclohexadecan-2-one; 1,2,2,6,8-pentamethyl-7-oxabicyclo[4.3.1]dec-8-en-10-one; hexadecane-1,2-diol; eicosan-3-ol; tetradecanoic acid; 12-methyl tetradecanoic acid; pentadecanoic acid; 5,9,13-trimethyl tetradecanoic acid; tridecanoic acid; 2-methyl-octadecanoic acid; heptadecanoic acid; [5]-9-dodecenoic acid; (Z)-9-hexadecenoic acid; (Z,Z,Z)-9,12,15-octadecatrienoic acid | [78] |
| Harmine; harmaline | [77] | |
| Deoxyvasicine; deoxyvasicinone | [72] | |
|
| ||
| Leaves | Trigonelline; formic acid; vasicinone; vasicine; harmaline; harmine; maleic acid; sucrose; α-glucose; β-glucose; malic acid; proline; asparagine; betaine; choline; phosphorylcholine; succinic acid; 4-hydroxyisoleucine; acetic acid; alanine; threonine; valine; isoleucine; malic acid; lysine | [79] |
| Isoleucine; valine; alanine; betaine; maleic acid; proline; lysine; asparagine; 4-hydroxyisoleucine; acetic acid; sucrose; vasicine; choline; phosphorylcholine | [44] | |
| Aspartate; threonine; serine; glutamate; glycine; alanine; valine; methionine; isoleucine; leucine; tyrosine; phenylalanine; lysine; histidine; arginine; proline; cystine | [73] | |
|
| ||
| Stem | Lysine; succinic acid; malic acid; vasicinone; proline; asparagine; 4-hydroxyisoleucine; asparagine; sucrose; vasicine; choline; phosphorylcholine | [44] |
|
| ||
| Areal part | 10-Vasicinol; 11-vasicinol; 4-vasicinol; 6-vasicinol; vasicine-glu; vasicine-2glu; vasicine-2glu; methylation-acetylation-vasicine; methylation-acetylation-vasicine; vasicinol-glu; vasicinone-glu; vasicinone-2glu; vasicinone-2glu; pegaline; diosmetin+3glu+rha+ac; acacetin+glu+rha; diosmetin+glu+rha | [75] |
| 2-Ethoxylpropane; 3-hydroxy-3-methyl-2-butanol; methylcyclopentane; 2-methylhexane; 3-methylhexane; 1-ethoxy-2-methylpropane; heptane; methylcyclohexane; 2,4-dimethylhexane; 1-octen-3-ol; 2-methylheptane; 3-methylheptane; hexanol; cis-1,3-dimethylcyclohexane; 2-octanol; octane; cis-1,4-dimethylcyclohexane; [5]-2-hexanol; 1,3-dimethylbenzene; benzaldehyde; 6-methyl-5-heptane-2-one; [8]-[5]-5-ethyl-2(5H)-furanone; 3,5,5-trimethyl-2-cyclohexene-1-one; 12-heptadecyn-1-ol; benzenamine; N-phenyl-formamide; geranylacetone; 1,2,3,3,4-pentamethylcyclopenene; 5,6,7,7α-tetratydro-4,4,7α-trimethyl-2(4H)-benzenofranone; 6,10,14-trimethyl-2-pentadecanone; 3,7,11,15-tetramethyl-2-hexadecen-1-ol; dodecanoic acid; hexadecanoic acid | [80] | |
| Liriodendrin; trans-ferulic acid β-D-glucopyranoside; (6S,7E,9R)-6,9-dihydroxymegastigma-4,7-dien-3-one-9-O-β-D-glucopyranoside (or roseoside); (3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol-3-O-β-D-glucopyranoside | [81] | |
| Deoxypeganidine; peganidine; peganol; quinoline; pegamine; hemicellulose; gentisate-2,5-diglucoside | [72] | |
|
| ||
| Fruits | α-Glucose; choline; proline; lysine; asparagine; 4-hydroxyisoleucine; acetic acid; sucrose; vasicine; choline; phosphorylcholine | [44] |
| Harmine; peganine; harmaline | [77] | |
|
| ||
| Testa | 4-Hydroxyisoleucine; asparagine; proline; vasicine | [44] |
|
| ||
| Floral nectar | Harmalol; harmine; fructose; glucose; sucrose; aspartic acid; glutamic acid; serine; glutamine; glycine; histidine; alanine; proline; tyrosine; valine; phenylalanine | [82] |
|
| ||
| Peganum multisectum (Maxim.) Bobrov | 2-Methylquinoline; 9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta [b] quinoline; vasicinone; harmine; peganine; deoxypeganine; deoxyvasicinone; harmane | [83] |
| Vasicine | [84] | |
| (S/R)-Vasicinone | [10] | |
| Harmol; harmane; harmine; harmaline; harmalol | [66] | |
| Peganetin; deacetylpeganetin; 7,4′-dihydroxy-3′-methoxy-5-O-rutinoside | [85] | |
| Aspartate; threonine; serine; glutamate; glycine; alanine; valine; methionine; isoleucine; leucine; tyrosine; phenylalanine; lysine; histidine; arginine; proline; cystine | [73] | |
| 2-Ethoxylpropane; 3-hydroxy-3-methyl-2-butanol; methylcyclopentane; 2-methylhexane; 3-methylhexane; 1-ethoxy-2-methylpropane; heptane; methylcyclohexane; 2,4-dimethylhexane; 1-octen-3-ol; 2-methylheptane; 3-methylheptane; hexanol; cis-1,3-dimethylcyclohexane; 2-octanol; octane; cis-1,4-dimethylcyclohexane; [5]-2-hexanol; 1,3-dimethylbenzene; benzaldehyde; 6-methyl-5-heptane-2-one; [8]-[5]-5-ethyl-2(5H)-furanone; 3,5,5-trimethyl-2-cyclohexene-1-one; 12-heptadecyn-1-ol; benzenamine; N-phenyl-formamide; geranylacetone; 1,2,3,3,4-pentamethylcyclopenene; 5,6,7,7α-tetrahydro-4,4,7α-trimethyl-2(4H)-benzenofranone; 6,10,14-trimethyl-2-pentadecanone; 3,7,11,15-tetramethyl-2-hexadecen-1-ol | [80] | |
| Deoxyvasicine; deoxyvasicinone | [72] | |
|
| ||
| Peganum nigellastrum Bunge | Vasicine | [64] |
| (S/R)-Vasicinone | [10] | |
| Diosmetin 7-O-β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl(1→2)-[α-L-rhamnopyranosyl (1→6)]-β-D-glucopyranoside | [86] | |
| Nigellastrine I; nigellastrine II; harmol; harmane; harmine; harmaline; harmalol | [66] | |
| Dihydrosinapyl ferulate; dihydroconiferyl ferulate | [36] | |
| 3α,27-Dihydroxylup-20(29)-en-28-oic acid methyl ester; 3α-acetoxyolean-12-ene-27,28-dioic acid 28-methyl ester; 3-oxotirucalla-7,24-dien-21-oic acid; 3α-acetoxy-27-hydroxylup-20(29)-en-28-oic acid methyl ester; betulinic acid; 3-O-acetylbetulinic acid; 3-epibetulinc acid; 3-O-acetylepibetulinic acid | [87] | |
| Acacetin; peganetin; deacetylpeganetin | [85] | |
| Aspartate; threonine; serine; glutamate; glycine; alanine; valine; methionine; isoleucine; leucine; tyrosine; phenylalanine; lysine; histidine; arginine; proline; cystine | [73] | |
| 2-Ethoxylpropane; 3-hydroxy-3-methyl-2-butanol; methylcyclopentane; 2-methylhexane; 3-methylhexane; 1-ethoxy-2-methylpropane; heptane; methylcyclohexane; 2,4-dimethylhexane; 1-octen-3-ol; 2-methylheptane; 3-methylheptane; hexanol; cis-1,3-dimethylcyclohexane; 2-octanol; octane; cis-1,4-dimethylcyclohexane; [5]-2-hexanol; 1,3-dimethylbenzene; benzaldehyde; 6-methyl-5-heptane-2-one; [8]-[5]-5-ethyl-2(5H)-furanone; 3,5,5-trimethyl-2-cyclohexene-1-one; 12-heptadecyn-1-ol; benzenamine; N-phenyl-formamide; geranylacetone; 1,2,3,3,4-pentamethylcyclopenene; 5,6,7,7α-tetrahydro-4,4,7α-trimethyl-2(4H)-benzenofranone; 6,10,14-trimethyl-2-pentadecanone; 3,7,11,15-tetramethyl-2-hexadecen-1-ol; | [80] | |
| Deoxyvasicine; deoxyvasicinone | [72] | |