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
3-(4-Methoxyphenyl)-1-(pyrrol-1-yl)propan-1-one 3-(4-Methoxyphenyl)-1-(pyrrol-1-yl)propan-1-one 448905-82-6 C14H15NO2
3α,6β-Ditigloyloxytropan-7β-ol 3α,6β-Ditigloyloxytropan-7β-ol 7159-86-6 C18H27NO5
DehydroforMouregine DehydroforMouregine 107633-69-2 C20H19NO4
Glycosolone Glycosolone 67879-81-6 C16H19NO3
Drahebenine Drahebenine 1399049-43-4 C13H16N2O2
Rauvotetraphylline D Rauvotetraphylline D 1422506-52-2 C24H26N2O3
Aglain B Aglain B 177262-32-7 C36H42N2O8
Daphnicyclidin H Daphnicyclidin H 385384-29-2 C23H29NO5
Mangochinine Mangochinine 209115-67-3 C19H22NO4+
(5α,12R,19α)-2,3-Didehydro-6α,7α-epoxyaspidospermidine-3-carboxylic acid methyl ester (5α,12R,19α)-2,3-Didehydro-6α,7α-epoxyaspidospermidine-3-carboxylic acid methyl ester 72058-36-7 C21H24N2O3
AristolactaM AIa AristolactaM AIa 97399-90-1 C16H11NO4
3-Chloro-4-hydroxypiperidin-2-one 3-Chloro-4-hydroxypiperidin-2-one 174204-83-2 C5H8ClNO2
4'-DeMethoxypiperlotine C 4'-DeMethoxypiperlotine C 807372-38-9 C15H19NO3
Cyclo(L-Leu-trans-4-hydroxy-L-Pro) Cyclo(L-Leu-trans-4-hydroxy-L-Pro) 115006-86-5 C11H18N2O3
Piperlotine D Piperlotine D 958296-13-4 C16H21NO4
Norglaucine hydrochloride Norglaucine hydrochloride 39945-41-0 C20H24ClNO4
Ravenine Ravenine 20105-22-0 C15H17NO2
Daphnicyclidin D Daphnicyclidin D 385384-24-7 C23H27NO4
3-Hydroxysarpagine 3-Hydroxysarpagine 857297-90-6 C19H22N2O3
11-HydroxyhuMantenine 11-HydroxyhuMantenine 122590-04-9 C21H26N2O4
Lauterine Lauterine 28200-65-9 C18H11NO4
Hybridaphniphylline A Hybridaphniphylline A 1467083-07-3 C37H47NO11
N-Methylcoclaurine N-Methylcoclaurine 5096-70-8 C18H21NO3
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methyl-, (3S,8aS)- (9CI) Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-methyl-, (3S,8aS)- (9CI) 36357-32-1 C8H12N2O2
spegatrine spegatrine 47326-53-4 C20H25N2O2+
16-Oxoprometaphanine 16-Oxoprometaphanine 58738-31-1 C20H23NO6
5-Methoxystrictamine 5-Methoxystrictamine 870995-64-5 C21H24N2O3
Neotuberostemone Neotuberostemone 954379-68-1 C22H31NO6
Oxoepistephamiersine Oxoepistephamiersine 51804-68-3 C21H25NO7
10-Acetoxyscandine 10-Acetoxyscandine 1432058-90-6 C23H24N2O5
Securitinine Securitinine 13861-71-7 C14H17NO3
N-benzyl-9Z,12Z,15Z-octadecatrienamide N-benzyl-9Z,12Z,15Z-octadecatrienamide 883715-18-2 C25H37NO
pericyclivine pericyclivine 975-77-9 C20H22N2O2
conquinamine conquinamine 464-86-8 C19H24N2O2
16-epi-isositsirikine 16-epi-isositsirikine 6519-27-3 C21H26N2O3
tubotaiwine tubotaiwine 6711-69-9 C20H24N2O2
asimilobine asimilobine 6871-21-2 C17H17NO2
Acetylcephalotaxine Acetylcephalotaxine 24274-60-0 C20H23NO5
Cassyfiline Cassyfiline 4030-51-7 C19H19NO5
Harmalidine Harmalidine 109794-97-0 C16H18N2O
Isotetrandrine N-2'-oxide Isotetrandrine N-2'-oxide 70191-83-2 C38H42N2O7
11-Hydroxygelsenicine 11-Hydroxygelsenicine 1195760-68-9 C19H22N2O4
Periglaucine B Periglaucine B 1025023-05-5 C20H23NO6
Griffithazanone A Griffithazanone A 240122-30-9 C14H11NO4
1-(3,4-DiMethoxycinnaMoyl)piperidine 1-(3,4-DiMethoxycinnaMoyl)piperidine 128261-84-7 C16H21NO3
2-(1H-Indole-3-carboxaMido)benzoic acid 2-(1H-Indole-3-carboxaMido)benzoic acid 171817-95-1 C16H12N2O3
2-Ethyl-2,6,6-triMethylpiperidin-4-one 2-Ethyl-2,6,6-triMethylpiperidin-4-one 133568-79-3 C10H19NO
(-)-CorluMine (-)-CorluMine 79082-64-7 C21H21NO6
Hybridaphniphylline B Hybridaphniphylline B 1467083-09-5 C37H47NO11
canadine canadine 5096-57-1 C20H21NO4
(+)-Cassythicine (+)-Cassythicine 5890-28-8 C19H19NO4
1-methoxyindole-3-carboxylic acid 1-methoxyindole-3-carboxylic acid 91913-76-7 C10H9NO3
ORTHO-NORNUCIFERINE ORTHO-NORNUCIFERINE 3153-55-7 C18H19NO2
4,8-Dimethoxyfuro[2,3-b]quinolin-7-ol 4,8-Dimethoxyfuro[2,3-b]quinolin-7-ol 5876-17-5 C13H11NO4
zarzissine zarzissine 160568-14-9 C5H5N5
4-METHOXY-1-METHYL-2(1H)-QUINOLINONE 4-METHOXY-1-METHYL-2(1H)-QUINOLINONE 32262-18-3 C11H11NO2
16-Epi-voacarpine 16-Epi-voacarpine 114027-38-2 C21H24N2O4
9-Methylfuro[2,3-b]quinolin-4(9H)-one 9-Methylfuro[2,3-b]quinolin-4(9H)-one 484-74-2 C12H9NO2
1-[2-(Dimethylamino)ethyl]-4-methoxyphenanthren-3-ol 1-[2-(Dimethylamino)ethyl]-4-methoxyphenanthren-3-ol 16625-57-3 C19H21NO2
11-Methoxyuncarine C 11-Methoxyuncarine C 61665-08-5 C22H26N2O5
Longistylumphylline A Longistylumphylline A 857672-34-5 C23H29NO3
Neostenine Neostenine 477953-07-4 C17H27NO2
Periglaucine A Periglaucine A 1025023-04-4 C20H23NO6
Cyclo(L-phenylalanyl-trans-4-hydroxy-L-proline) Cyclo(L-phenylalanyl-trans-4-hydroxy-L-proline) 118477-06-8 C14H16N2O3
10-Hydroxyneoline 10-Hydroxyneoline 132362-42-6 C24H39NO7
16-EpinorMacusine B 16-EpinorMacusine B 126640-98-0 C19H22N2O
Piperlotine C Piperlotine C 886989-88-4 C16H21NO4
Rauvotetraphylline B Rauvotetraphylline B 1422506-50-0 C31H37N3O6
Securinol A Securinol A 5008-48-0 C13H17NO3
pellitorine pellitorine 18836-52-7 C14H25NO
phenylalanyl-prolyl diketopiperazine phenylalanyl-prolyl diketopiperazine 26488-24-4 C14H16N2O2
Buxbodine B Buxbodine B 390362-51-3 C26H41NO2
N-Trans-Feruloyltyramine N-Trans-Feruloyltyramine 66648-43-9 C18H19NO4
(2S,βR)-β-Vinyl-1,2,3,4,6,7,12,12bβ-octahydroindolo[2,3-a]quinolizine-2-ethanol (2S,βR)-β-Vinyl-1,2,3,4,6,7,12,12bβ-octahydroindolo[2,3-a]quinolizine-2-ethanol 16049-28-8 C19H24N2O
(-)-3,9-Dihydro-2,3,3,9-tetramethylfuro[2,3-b]quinoline-4(2H)-one (-)-3,9-Dihydro-2,3,3,9-tetramethylfuro[2,3-b]quinoline-4(2H)-one 31520-95-3 C15H17NO2
17-Hydroxy-4α-methylsarpagan-4-ium 17-Hydroxy-4α-methylsarpagan-4-ium 6792-07-0 C20H25N2O+
(R)-Nornuciferine (R)-Nornuciferine 4846-19-9 C18H19NO2
KouMine N-oxide KouMine N-oxide 113900-75-7 C20H22N2O2
(19Z)-Sarpagan-17-ol (19Z)-Sarpagan-17-ol 124096-81-7 C19H22N2O
Rauvotetraphylline A Rauvotetraphylline A 1422506-49-7 C20H26N2O3
1-Methyl-2-nonylquinolin-4(1H)-one 1-Methyl-2-nonylquinolin-4(1H)-one 68353-24-2 C19H27NO
Aglain C Aglain C 177468-85-8 C36H42N2O8
2,2'-(1-Methyl-2,6-piperidinediyl)diacetophenon 2,2'-(1-Methyl-2,6-piperidinediyl)diacetophenon 579-21-5 C22H25NO2
Buxbodine D Buxbodine D 390362-53-5 C28H46N2O
sempervirin sempervirin 6882-99-1 C19H17N2+
4-Methoxyfuro[2,3-b]quinolin-8-ol 4-Methoxyfuro[2,3-b]quinolin-8-ol 2255-50-7 C12H9NO3
8β,10β-Epoxy-8-methoxy-2,3-[methylenebis(oxy)]hasubanan-6β,7β-diol 6-(4-hydroxy-3-methoxybenzoate) 8β,10β-Epoxy-8-methoxy-2,3-[methylenebis(oxy)]hasubanan-6β,7β-diol 6-(4-hydroxy-3-methoxybenzoate) 33116-33-5 C26H27NO9
(+)-Viroallosecurinine (+)-Viroallosecurinine 1857-30-3 C13H15NO2
4,7,8-Trimethoxy-3-(3-methyl-2-butenyl)quinolin-2(1H)-one 4,7,8-Trimethoxy-3-(3-methyl-2-butenyl)quinolin-2(1H)-one 38695-41-9 C17H21NO4
(16R)-18,19-Didehydro-17-hydroxycorynan-16-carboxylic acid methyl ester (16R)-18,19-Didehydro-17-hydroxycorynan-16-carboxylic acid methyl ester 1245-00-7 C21H26N2O3
Deoxycalyciphylline B Deoxycalyciphylline B 619326-74-8 C22H31NO2
Methyl demethoxycarbonylchafruticosinate Methyl demethoxycarbonylchafruticosinate 80151-89-9 C21H24N2O3
Pandamarilactonine B Pandamarilactonine B 303008-81-3 C18H23NO4
Paxiphylline E Paxiphylline E 1092555-03-7 C23H29NO5
pedatisectine F pedatisectine F 206757-32-6 C9H14N2O4
(2ξ,4ξ,5ξ,6ξ,18ξ)-Conopharyngine oxindole (2ξ,4ξ,5ξ,6ξ,18ξ)-Conopharyngine oxindole 16790-92-4 C23H30N2O5
16,17-Didehydro-19β-methyl-18-oxayohimban-16-carboxylic acid methyl ester 16,17-Didehydro-19β-methyl-18-oxayohimban-16-carboxylic acid methyl ester 25532-45-0 C21H24N2O3
(17R,19E)-19,20-Didehydro-1-demethylajmalan-17-ol (17R,19E)-19,20-Didehydro-1-demethylajmalan-17-ol 68160-76-9 C19H22N2O
2,2,6-Trimethyl-2,6-dihydro-5H-pyrano[3,2-c]quinoline-5-one 2,2,6-Trimethyl-2,6-dihydro-5H-pyrano[3,2-c]quinoline-5-one 50333-13-6 C15H15NO2
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