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
calyxamine B calyxamine B 150710-72-8 C12H21NO
(16R)-2α,5α-Epoxy-16-formyl-1,2-dihydroakuammilan-17-oic acid methyl ester (16R)-2α,5α-Epoxy-16-formyl-1,2-dihydroakuammilan-17-oic acid methyl ester 20045-06-1 C21H22N2O4
(+)-CORYPALMINE (+)-CORYPALMINE 6018-40-2 C20H23NO4
methyl (16alpha,17beta)-17-hydroxyyohimban-16-carboxylate methyl (16alpha,17beta)-17-hydroxyyohimban-16-carboxylate 549-84-8 C21H26N2O3
EUDESMINE EUDESMINE 522-11-2 C18H21NO6
Nicotine ditartrate Nicotine ditartrate 65-31-6 C18H26N2O12
DEHYDROEVODIAMINE HYDROCHLORIDE DEHYDROEVODIAMINE HYDROCHLORIDE 75853-60-0 C19H16N3O.Cl
b-Carboline-1-propanoic acid b-Carboline-1-propanoic acid 89915-39-9 C14H12N2O2
23-[(1R,4R,5S)-1,4-Dimethyl-2,8-dioxabicyclo[3.2.1]oct-4-yl]daphnan-23-one 23-[(1R,4R,5S)-1,4-Dimethyl-2,8-dioxabicyclo[3.2.1]oct-4-yl]daphnan-23-one 14694-15-6 C30H47NO3
talatisamine talatisamine 20501-56-8 C24H39NO5
N-benzoylphenylalanylphenylalinol acetate N-benzoylphenylalanylphenylalinol acetate 56121-42-7 C27H28N2O4
5,6-dihydro-1H-pyridin-2-one 5,6-dihydro-1H-pyridin-2-one 6052-73-9 C5H7NO
LAUROLITSINE LAUROLITSINE 5890-18-6 C18H19NO4
4H-Dibenzo(de,g)quinolin-9-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-6 -methyl-, (S)- 4H-Dibenzo(de,g)quinolin-9-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-6 -methyl-, (S)- 2169-44-0 C20H23NO4
BRUCINE SULFATE BRUCINE SULFATE 4845-99-2 C23H28N2O8S
ECHINULIN ECHINULIN 1859-87-6 C29H39N3O2
5-hydroxy-2-pyrrolidone 5-hydroxy-2-pyrrolidone 62312-55-4 C4H7NO2
ODORINE ODORINE 72755-20-5 C18H24N2O2
6,7-DIMETHOXY-1-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE 6,7-DIMETHOXY-1-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE 883-87-4 C12H18ClNO2
ALLOCRYPTOPINE ALLOCRYPTOPINE 24240-04-8 C21H23NO5
ENNIATIN B ENNIATIN B 917-13-5 C33H57N3O9
NICOTINE SULFATE NICOTINE SULFATE 6505-86-8 C20H30N4O4S
stephanine stephanine 517-63-5 C19H19NO3
Aristolactam FI Aristolactam FI 112501-42-5 C16H11NO3
PILOSINE PILOSINE 13640-28-3 C16H18N2O3
CORALYNE CHLORIDE HYDRATE, 98+% CORALYNE CHLORIDE HYDRATE, 98+% 38989-38-7 C22H22ClNO4
VERATRINE HYDROCHLORIDE VERATRINE HYDROCHLORIDE 17666-25-0 C32H50ClNO9
[7(S)-(1alpha,.2beta,4beta,5alpha,7beta)]-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl (hydroxymethyl)phenylacetate [7(S)-(1alpha,.2beta,4beta,5alpha,7beta)]-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl (hydroxymethyl)phenylacetate 4684-28-0 C16H19NO4
gamma-fagarine gamma-fagarine 524-15-2 C13H11NO3
koumine koumine 1358-76-5 C20H22N2O
TMC-58B TMC-58B 58115-31-4 C25H26N2O3
BRUCINE DIHYDRATE BRUCINE DIHYDRATE 145428-94-0 C23H30N2O6
TOMATIDINE TOMATIDINE 77-59-8 C27H45NO2
Corynoxine Corynoxine 6877-32-3 C22H28N2O4
liriodenine liriodenine 475-75-2 C17H9NO3
O-METHYLDAURICINE O-METHYLDAURICINE 2202-17-7 C39H46N2O6
APOHYOSCINE APOHYOSCINE 535-26-2 C17H19NO3
SEMPERVIRINE NITRATE SEMPERVIRINE NITRATE 549-92-8 C19H13N3O3
VASICINONE VASICINONE 486-64-6 C11H10N2O2
MITRAGYNINE PICRATE MITRAGYNINE PICRATE 4098-40-2 C23H30N2O4
alpha-yohimbine alpha-yohimbine 131-03-3 C21H26N2O3
rotundine rotundine 483-14-7 C21H25NO4
skimmianine skimmianine 83-95-4 C14H13NO4
Cophylline Cophylline 142741-24-0 C44H50N4O10
N-p-trans-Coumaroyltyramine N-p-trans-Coumaroyltyramine 36417-86-4 C17H17NO3
DESOXYPEGANINE HYDROCHLORIDE DESOXYPEGANINE HYDROCHLORIDE 61939-05-7 C11H13ClN2
(+)-CORYDALINE (+)-CORYDALINE 476-69-7 C20H23NO4
5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7-dihydro-9,10-dime thoxy-7-methyl- 5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7-dihydro-9,10-dime thoxy-7-methyl- 77784-22-6 C20H19NO4
coclaurine coclaurine 486-39-5 C17H19NO3
SARPAGINE SARPAGINE 482-68-8 C19H22N2O2
SCOULERIN SCOULERIN 6451-73-6 C19H21NO4
(+)-BULBOCAPNINE (+)-BULBOCAPNINE 298-45-3 C19H19NO4
FUMITREMORGIN C FUMITREMORGIN C 118974-02-0 C22H25N3O3
ROCAGLAMIDE ROCAGLAMIDE 84573-16-0 C29H31NO7
3-hydroxy-3-acetonyl-2-oxindole 3-hydroxy-3-acetonyl-2-oxindole 33417-17-3 C11H11NO3
clausine D clausine D 142846-95-5 C18H17NO2
leuconolam leuconolam 93710-27-1 C19H22N2O3
(+)-Scandine (+)-Scandine 24314-59-8 C21H22N2O3
3-(4,8-Dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-1-(9H-pyrido[3,4-b]indol-1-yl)-1-propanone 3-(4,8-Dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-1-(9H-pyrido[3,4-b]indol-1-yl)-1-propanone 82652-20-8 C27H22N4O3
Dihydrocinchonamine Dihydrocinchonamine 10283-68-8 C19H26N2O
Conopharyngine Conopharyngine 76-98-2 C23H30N2O4
Serpentinine Serpentinine 36519-42-3 C42H45N4O5+
(+)-N-Methylallosedridine (+)-N-Methylallosedridine 41447-16-9 C9H19NO
14,15-Didehydrovincamenine 14,15-Didehydrovincamenine 112219-48-4 C19H20N2
16-O-Methyl-14,15-didehydroisovincal 16-O-Methyl-14,15-didehydroisovincal 112237-71-5 C20H24N2O
Isocarapanaubine Isocarapanaubine 17391-09-2 C23H28N2O6
Paniculidine A Paniculidine A 97399-93-4 C14H17NO2
Picrasidine T Picrasidine T 113808-03-0 C28H25N4O4+
2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 69804-59-7 C8H7NO4
Vinorine Vinorine 34020-07-0 C21H22N2O2
HuMantenidine HuMantenidine 114027-39-3 C19H22N2O4
ANISOTROPINE METHYLBROMIDE ANISOTROPINE METHYLBROMIDE 80-50-2 C17H32BrNO2
(S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol (S)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol 485-19-8 C19H23NO4
PERAKINE PERAKINE 4382-56-3 C21H22N2O3
PTEROLACTAM PTEROLACTAM 38072-88-7 C5H9NO2
1-cinnamoylpyrrolidine 1-cinnamoylpyrrolidine 52438-21-8 C13H15NO
enniatin B1 enniatin B1 19914-20-6 C34H59N3O9
(3β,20α)-17α-Hydroxyyohimban-16β-carboxylic acid methyl ester (3β,20α)-17α-Hydroxyyohimban-16β-carboxylic acid methyl ester 483-09-0 C21H26N2O3
(16R)-17-(Acetoxy)-2α,5α-epoxy-1,2-dihydroakuammilan-16-carboxylic acid methyl ester (16R)-17-(Acetoxy)-2α,5α-epoxy-1,2-dihydroakuammilan-16-carboxylic acid methyl ester 2671-32-1 C23H26N2O5
(5S)-4-[(E)-Ethylidene]-1,3,4,5,6,7-hexahydro-6-hydroxymethyl-2α,5-ethano-2H-azocino[4,3-b]indole-6β-carboxylic acid methyl ester (5S)-4-[(E)-Ethylidene]-1,3,4,5,6,7-hexahydro-6-hydroxymethyl-2α,5-ethano-2H-azocino[4,3-b]indole-6β-carboxylic acid methyl ester 3368-87-4 C20H24N2O3
Methyl β-carboline-1-carboxylate Methyl β-carboline-1-carboxylate 3464-66-2 C13H10N2O2
6β-Acetoxy-15,23-dideoxy-19,23-epoxyajaconine 6β-Acetoxy-15,23-dideoxy-19,23-epoxyajaconine 21040-64-2 C24H33NO4
1-Hydroxyrutaecarpine 1-Hydroxyrutaecarpine 53600-24-1 C18H13N3O2
2,4,6,6-Tetramethyl-3(6H)-pyridine 2,4,6,6-Tetramethyl-3(6H)-pyridine 203524-64-5 C9H13NO
3-Furfuryl 2-pyrrolecarboxylate 3-Furfuryl 2-pyrrolecarboxylate 119767-00-9 C10H9NO3
Axillaridine A Axillaridine A 128255-16-3 C30H42N2O2
Cephalocyclidin A Cephalocyclidin A 421583-14-4 C17H19NO5
Daphnilongeranin A Daphnilongeranin A 874201-05-5 C23H29NO4
Litseglutine B Litseglutine B 25368-01-8 C20H23NO4
N1,N10-Bis(p-coumaroyl)spermidine N1,N10-Bis(p-coumaroyl)spermidine 114916-05-1 C25H31N3O4
Alstoyunine E Alstoyunine E 1188932-15-1 C21H22N2O3
1-Methoxyindoleacetonitrile 1-Methoxyindoleacetonitrile 30536-48-2 C11H10N2O
seneciphyllinine seneciphyllinine 90341-45-0 C20H25NO6
ARISTOLACTAM-AII ARISTOLACTAM-AII 53948-07-5 C16H11NO3
PERAKSINE PERAKSINE 15527-80-7 C19H22N2O2
1,2-Dihydro-1-methyl-2β,16-(epoxymethano)akuammilan-17-oic acid methyl ester 1,2-Dihydro-1-methyl-2β,16-(epoxymethano)akuammilan-17-oic acid methyl ester 2447-70-3 C22H26N2O3
Daphmacrine Daphmacrine 19775-48-5 C32H49NO4
Daphnilongeridine Daphnilongeridine 922522-15-4 C32H51NO4
Dihydroepistephamiersine 6-acetate Dihydroepistephamiersine 6-acetate 57361-74-7 C23H31NO7
N-p-coumaroyl-N'-caffeoylputrescine N-p-coumaroyl-N'-caffeoylputrescine 1138156-77-0 C22H24N2O5
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