Alkaloids

Alkaloid is a kind of nitrogen-containing natural compound of physiological function with the majority of them containing complicated heterocyclic structures and a few of them being non-nitrogen heterocyclic organic amine. They generally have similar properties of the alkaline. Some kinds of natural derived vitamins, amino acids and peptides, although also belonging to nitrogen-containing compound, but generally are not classified into the range of alkaloids. In fact the word “alkaloid” still has not yet strict and precise definition to now.

Alkaloid is widely distributed in nature, especially in the plant kingdom. There are also some kinds found in animal kingdom such as the bufotenine found in toad, the hypoxanthine found in the earthworm. According to statistics, it has been found of alkaloids from at least 140 species of plants, especially in poppy, Menispermaceae, Solanaceae, Leguminosae, oleander, Ranunculaceae and barberry Branch. In general, alkaloids are mostly distributed in dicots with less being contained in monocots. There are rarely kinds of alkaloids found in gymnosperms and ferns or even lower plants. Alkaloid-containing plants often contain a variety of alkaloids of similar chemical structure. Plants have close family & genus relationship often contains alkaloids of similar structure while some being the same.

There are several ways of classifications of alkaloids, plant sources, the chemical structure or physiological effect can all be taken as classification references with the later one being more reasonable. Common types include pyrroles, pyridines, quinolines, isoquinolines, indoles, imidazoles, purines, tropane, terpenes, steroids and organic amines. Some people have divided alkaloids into 59 kinds, illustrating the complexity of their structure.

Alkaloids, except for a very few kinds which are liquid at room temperature, mostly appears as crystalline solid. They are generally colorless with bitterness, optically active and mostly left-handed. They exhibit alkalinity with the strength of the alkalinity exhibiting a significant relationship with the molecular structure especially the binding state of the nitrogen atoms. Quaternary ammonium alkaloids exhibit strong alkalinity with tertiary amines and secondary amines alkaloids being moderate or weak alkaline. Some kinds of alkaloids molecules contain phenol groups or carboxyl groups, thus having amphoteric property. The plants alkaloids can mostly bind with organic acid into salt or have condensation reaction with sugar to become glycosides. A few kinds of alkaloids having weak alkalinity exist in their free states. Alkaloid salts, after alkalization or alkaloid glycosides, after hydrolysis can obtain free alkaloid. Most kinds of alkaloids are insoluble or poorly soluble in water, soluble in organic solvents such as benzene, chloroform, ether, acetone, ethanol, and forming salt after being dissolved in dilute acid. Alkaloid salts are more soluble in water and alcohol, insoluble or poorly soluble in organic solvents. Alkaloids can react with some kinds of reagents, such as potassium iodide, bismuth, mercury, potassium iodide, iodine-potassium iodide to form precipitates of different colors. This precipitation reaction is often applied to identify specific alkaloids.

There are many ways for extracting alkaloid. Generally, we can first use water, acid water or alcohol to extract the crushed samples; the extract was concentrated; use organic solvent to extract out the total alkaloids after alkalization. Or first send the crushed sample to alkalization; further apply organic solvent to extract the total alkaloids. The total alkaloids can be further separated through various methods such as chromatography, preparative derivatives. There are few sublimated or volatile alkaloids which can be purified through water steam distillation or sublimation purification.

Though the alkaloid content is very small inside plants, they have intimate relationship with humans. Mankind has long been recognized that some alkaloid-containing plants or crude extracts can be used for treatment of disease or being used as poisoning drugs. Since 1806 when Serturner had isolated morphine from the opium poppy, there have been over 6000 kinds of alkaloids extracted from plants and animals. Among them, nearly 100 kinds have been used or tested in clinical application. Many kinds of alkaloids are effective medicine, such as the berberine contained in Ranunculaceae rhizome has anti-bacterial as well as anti-inflammatory effect; the reserpine in Rauwolfia can lower blood pressure; the galantamine of Lycoris has efficacy in treating post-polio syndrome. The morphine contained in the poppy peel is a kind of famous analgesics; quinine alkaline is a valuable antipyretic drug; Cephalotaxine and vinblastine are effective cancer medicine; colchicine (alkaline) mutagenesis can produce polyploid. Some kinds of alkaloids can be used to make pesticides of agricultural purpose. It has been also isolated in vertebrates and invertebrates of alkaloids, among which, the alkaloids contained in some animals are related to their intake of plant. The alkaloids found in toads, newts and some kinds of fishes are real animal metabolites.

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Structure Chemical Name CAS MF
6-Acetonyldihydrochelerythrine 6-Acetonyldihydrochelerythrine 22864-92-2 C24H23NO5
(2β,5α,12β,19α)-4β-(Acetyloxy)-6,7-didehydro-3β-hydroxy-1-methylaspidospermidine-3-carboxylic acid methyl ester (2β,5α,12β,19α)-4β-(Acetyloxy)-6,7-didehydro-3β-hydroxy-1-methylaspidospermidine-3-carboxylic acid methyl ester 5231-60-7 C24H30N2O5
[7aS,(+)]-6,7,7a,8-Tetrahydro-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline [7aS,(+)]-6,7,7a,8-Tetrahydro-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline 2030-53-7 C18H17NO2
1,2,7,8,13,13bβ,14,14aα-Octahydro-1β-vinyl-2α-(β-D-glucopyranosyloxy)-5H-indolo[2,3-a]pyrano[3,4-g]quinolizine-5-one 1,2,7,8,13,13bβ,14,14aα-Octahydro-1β-vinyl-2α-(β-D-glucopyranosyloxy)-5H-indolo[2,3-a]pyrano[3,4-g]quinolizine-5-one 23141-25-5 C26H30N2O8
odorinol odorinol 72755-22-7 C18H24N2O3
humantenmine humantenmine 82354-38-9 C19H22N2O3
crebanine crebanine 25127-29-1 C20H21NO4
Seneciphylline N-oxide Seneciphylline N-oxide 38710-26-8 C18H23NO6
Vasicilone Vasicilone 84847-50-7 C11H10N2O3
AUSTRALINE HYDROCHLORIDE AUSTRALINE HYDROCHLORIDE 118396-02-4 C8H15NO4
echitamine echitamine 6871-44-9 C22H29N2O4
Pseudopalmatine Pseudopalmatine 19716-66-6 C21H22NO4+
cannabisin F cannabisin F 163136-19-4 C36H36N2O8
CORYCAVINE CORYCAVINE 521-85-7 C21H21NO5
3-methyl-9H-carbazol-2-ol 3-methyl-9H-carbazol-2-ol 24224-30-4 C13H11NO
(3β,20α)-16,17-Didehydro-19α-methyl-18-oxayohimban-16-carboxylic acid methyl ester (3β,20α)-16,17-Didehydro-19α-methyl-18-oxayohimban-16-carboxylic acid methyl ester 642-17-1 C21H24N2O3
(+)-Normacusine B (+)-Normacusine B 604-99-9 C19H22N2O
NORFLUOROCURARINE NORFLUOROCURARINE 6880-54-2 C19H20N2O
SINOACUTINE SINOACUTINE 4090-18-0 C19H21NO4
1,4-Dihydro-1,2-dimethyl-4-oxo -3-quilinecarboxylic acid 1,4-Dihydro-1,2-dimethyl-4-oxo -3-quilinecarboxylic acid 73281-83-1 C12H11NO3
4,5-Dimethoxycanthin-6-one 4,5-Dimethoxycanthin-6-one 18110-87-7 C16H12N2O3
Methyl 3-carbazolecarboxylate Methyl 3-carbazolecarboxylate 97931-41-4 C14H11NO2
N-Methylcalycinine N-Methylcalycinine 86537-66-8 C19H19NO4
Paniculidine B Paniculidine B 97399-94-5 C14H19NO2
N1-MethoxyMethyl picrinine N1-MethoxyMethyl picrinine 1158845-78-3 C22H26N2O4
Clauszoline M Clauszoline M 187110-72-1 C13H9NO3
GrossaMide GrossaMide 80510-06-1 C36H36N2O8
ISOTHEBAINE ISOTHEBAINE 568-21-8 C19H21NO3
1-(1-Methyl-2-piperidinyl)acetone 1-(1-Methyl-2-piperidinyl)acetone 18747-42-7 C9H17NO
humantenine humantenine 82375-29-9 C21H26N2O3
pseurotin pseurotin 58523-30-1 C22H25NO8
2,3-trimethylene-4-quinazolone 2,3-trimethylene-4-quinazolone 530-53-0 C11H10N2O
BRUCINE BRUCINE 5892-11-5 C23H26N2O4
Indole-3-acrylic acid methyl ester Indole-3-acrylic acid methyl ester 19626-92-7 C12H11NO2
Phenylalanine betaine Phenylalanine betaine 56755-22-7 C12H17NO2
N-FeruloyloctopaMine N-FeruloyloctopaMine 66648-44-0 C18H19NO5
6-Oxochelerythrine 6-Oxochelerythrine 28342-33-8 C21H17NO5
C-Homoerythrinan, 1,2-didehydro-6,7-epoxy-3,15,16-trimethoxy-, (3alpha ,6xi)- C-Homoerythrinan, 1,2-didehydro-6,7-epoxy-3,15,16-trimethoxy-, (3alpha ,6xi)- 39024-12-9 C20H25NO4
Gelsemine, 1-methoxy- Gelsemine, 1-methoxy- 38990-03-3 C21H24N2O3
corytuberine corytuberine 517-56-6 C19H21NO4
oblongine oblongine 60008-01-7 C19H24NO3+
LOCHNERINE LOCHNERINE 522-47-4 C20H24N2O2
1-[3-(3,4-dimethoxyphenyl)prop-2-enoyl]piperidin-2-one 1-[3-(3,4-dimethoxyphenyl)prop-2-enoyl]piperidin-2-one 130263-10-4 C16H17NO4
(7S)-8β,10β-Epoxy-3,4,7,8-tetramethoxy-17-methylhasubanan-6-one (7S)-8β,10β-Epoxy-3,4,7,8-tetramethoxy-17-methylhasubanan-6-one 52389-15-8 C21H27NO6
(+)-Erythristemine (+)-Erythristemine 28619-41-2 C20H25NO4
Norcepharadione B Norcepharadione B 57576-41-7 C18H13NO4
(Z)-Akuammidine (Z)-Akuammidine 113973-31-2 C21H24N2O3
6-Acetonyldihydrosanguinarine 6-Acetonyldihydrosanguinarine 37687-34-6 C23H19NO5
Daphmacropodine Daphmacropodine 39729-21-0 C32H51NO4
Daphniyunnine A Daphniyunnine A 881388-87-0 C23H31NO3
Deoxyisocalyciphylline B Deoxyisocalyciphylline B 619326-75-9 C22H31NO2
4-Methoxy-1-Methoxycarbonyl-beta-carboline 4-Methoxy-1-Methoxycarbonyl-beta-carboline 60807-25-2 C14H12N2O3
HexadecanaMide, N-(phenylMethyl)- HexadecanaMide, N-(phenylMethyl)- 74058-71-2 C23H39NO
HOLOCALIN(P) HOLOCALIN(P) 101-93-9 C18H22N2O2
(16R)-17-Acetoxyakuammilan-16-carboxylic acid methyl ester (16R)-17-Acetoxyakuammilan-16-carboxylic acid methyl ester 1897-26-3 C23H26N2O4
(12aβ,14aS)-13,14-Dihydro-8α-methyl-6aα,8aα-methano-11H,12aH-benzo[k]pyrrolo[3,2,1-mn][1,8]phenanthroline-6,7(5H,8H)-dione (12aβ,14aS)-13,14-Dihydro-8α-methyl-6aα,8aα-methano-11H,12aH-benzo[k]pyrrolo[3,2,1-mn][1,8]phenanthroline-6,7(5H,8H)-dione 28645-27-4 C20H20N2O2
1-Ethyl-4-methoxy-9H-pyrido[3,4-b]indole 1-Ethyl-4-methoxy-9H-pyrido[3,4-b]indole 26585-14-8 C14H14N2O
[7S,(+)]-6,7,7a,8-Tetrahydro-7-methyl-5H-bis[1,3]benzodioxolo[6,5,4-de:5',6'-g]quinoline [7S,(+)]-6,7,7a,8-Tetrahydro-7-methyl-5H-bis[1,3]benzodioxolo[6,5,4-de:5',6'-g]quinoline 2466-42-4 C19H17NO4
Caboxine A Caboxine A 53851-13-1 C22H26N2O5
Calyciphylline A Calyciphylline A 596799-30-3 C23H31NO4
Clausine Z Clausine Z 866111-14-0 C13H9NO3
1-Methyl-2-tridecylquinolin-4(1H)-one 1-Methyl-2-tridecylquinolin-4(1H)-one 15266-35-0 C23H35NO
Aristolactam AIIIa Aristolactam AIIIa 97399-91-2 C16H11NO4
SENECIPHYLLIN SENECIPHYLLIN 19776-79-5 C10H16O4
gardneramine gardneramine 34274-91-4 C23H28N2O5
vomicine vomicine 125-15-5 C22H24N2O4
(5S)-4-[(E)-Ethylidene]-1,3,4,5,6,7-hexahydro-6-hydroxymethyl-6β-methoxycarbonyl-2α,5-ethano-2H-azocino[4,3-b]indole 2-oxide (5S)-4-[(E)-Ethylidene]-1,3,4,5,6,7-hexahydro-6-hydroxymethyl-6β-methoxycarbonyl-2α,5-ethano-2H-azocino[4,3-b]indole 2-oxide 126594-73-8 C20H24N2O4
1-Vinyl-4-methoxy-β-carboline 1-Vinyl-4-methoxy-β-carboline 26585-13-7 C14H12N2O
(-)-N-Methylsedridine (-)-N-Methylsedridine 41447-15-8 C9H19NO
11-Hydroxytabersonine 11-Hydroxytabersonine 22149-28-6 C21H24N2O3
1-Methyl-2-pentyl-4(1H)-quiline 1-Methyl-2-pentyl-4(1H)-quiline 22048-98-2 C15H19NO
7-Isopentenyloxy-gamma-fagarine 7-Isopentenyloxy-gamma-fagarine 23417-92-7 C18H19NO4
Dehydrocrenatidine Dehydrocrenatidine 65236-62-6 C15H14N2O2
Dihydrooxoepistephamiersine Dihydrooxoepistephamiersine 51804-69-4 C21H27NO7
Erythrartine Erythrartine 51666-26-3 C19H23NO4
Neosophoramine Neosophoramine 52932-74-8 C15H20N2O
Picrasidine S Picrasidine S 112503-87-4 C30H29N4O4
Prostephanaberrine Prostephanaberrine 105608-27-3 C19H21NO5
Alstolenine Alstolenine 85769-33-1 C31H34N2O7
PiperolactaM C PiperolactaM C 116064-76-7 C18H15NO4
N-cis-FeruloyltyraMine N-cis-FeruloyltyraMine 80510-09-4 C18H19NO4
8a-(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)-2,3,8,8a-tetrahydro-3aH-furo[2,3-b]indol-3a-ol 8a-(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)-2,3,8,8a-tetrahydro-3aH-furo[2,3-b]indol-3a-ol 464-85-7 C19H24N2O2
(17R,19E,21alpha)-17-acetoxy-1,2,19,20-tetradehydro-1-demethylajmalan-21-yl beta-D-glucopyranoside (17R,19E,21alpha)-17-acetoxy-1,2,19,20-tetradehydro-1-demethylajmalan-21-yl beta-D-glucopyranoside 31282-07-2 C27H32N2O8
C-Homoerythrinan, 1,2-didehydro-6,7-epoxy-3,15,16-trimethoxy-, (3beta, 6xi)- C-Homoerythrinan, 1,2-didehydro-6,7-epoxy-3,15,16-trimethoxy-, (3beta, 6xi)- 39024-15-2 C20H25NO4
aristololactam BII aristololactam BII 53948-09-7 C17H13NO3
Clausine I Clausine I 182261-94-5 C14H11NO3
(+)-Erysotramidine (+)-Erysotramidine 52358-58-4 C19H21NO4
Neochinulin A Neochinulin A 51551-29-2 C19H21N3O2
1-Ethenyl-4-methoxy-9H-pyrido[3,4-b]indol-8-ol 1-Ethenyl-4-methoxy-9H-pyrido[3,4-b]indol-8-ol 100234-59-1 C14H12N2O2
6,7-Didehydro-8β,10β-epoxy-3,4,7-trimethoxy-17-methylhasubanan-8-ol 6,7-Didehydro-8β,10β-epoxy-3,4,7-trimethoxy-17-methylhasubanan-8-ol 6858-85-1 C20H25NO5
(1R)-1β-Ethenyl-2α-(β-D-glucopyranosyloxy)-1,2,7,8,13,13bα,14,14aα-octahydro-5H-indolo[2,3-a]pyrano[3,4-g]quinolizine-5-one (1R)-1β-Ethenyl-2α-(β-D-glucopyranosyloxy)-1,2,7,8,13,13bα,14,14aα-octahydro-5H-indolo[2,3-a]pyrano[3,4-g]quinolizine-5-one 23141-27-7 C26H30N2O8
1,3-Dihydroxy-4-methoxy-10-methylacridin-9(10H)-one 1,3-Dihydroxy-4-methoxy-10-methylacridin-9(10H)-one 1189362-86-4 C15H13NO4
6-Acetonyl-N-methyl-dihydrodecarine 6-Acetonyl-N-methyl-dihydrodecarine 1253740-09-8 C23H21NO5
Ervamycine Ervamycine 27773-39-3 C22H26N2O3
N-trans-Feruloyl-3-methoxytyramine N-trans-Feruloyl-3-methoxytyramine 78510-19-7 C19H21NO5
N-p-CouMaroyloctopaMine N-p-CouMaroyloctopaMine 66648-45-1 C17H17NO4
Agrocybenine Agrocybenine 178764-92-6 C12H18N2O
CYCLO(-PHE-PRO) CYCLO(-PHE-PRO) 3705-26-8 C14H16N2O2
[7S-(7alpha,7bbeta,10abeta)]-N-(5,6,7,7b,8,10a-hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl)acetamide [7S-(7alpha,7bbeta,10abeta)]-N-(5,6,7,7b,8,10a-hexahydro-1,2,3,9-tetramethoxy-8-oxobenzo[a]cyclopenta[3,4]cyclobuta[1,2-c]cyclohepten-7-yl)acetamide 6901-13-9 C22H25NO6
5H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline-5,6(7H)-dione, 7-methy l- 5H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline-5,6(7H)-dione, 7-methy l- 55610-01-0 C18H11NO4
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