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Alkaloids

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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:
Tryptophol
CAS:
526-55-6
MF:
C10H11NO
Structure:
Chemical Name:
(+)-Pilocarpine hydrochloride
CAS:
54-71-7
MF:
C11H17ClN2O2
Structure:
Chemical Name:
8-Chlorotheophylline
CAS:
85-18-7
MF:
C7H7ClN4O2
Structure:
Chemical Name:
Tropine
CAS:
120-29-6
MF:
C8H15NO
Structure:
Chemical Name:
CYTOCHALASIN D
CAS:
22144-77-0
MF:
C30H37NO6
Structure:
Chemical Name:
SANGUINARINE
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2447-54-3
MF:
C20H14NO4+
Structure:
Chemical Name:
2,2,6,6-Tetramethyl-4-piperidone hydrochloride
CAS:
33973-59-0
MF:
C9H18ClNO
Structure:
Chemical Name:
3-(2-Pyrrolidinyl)pyridine
CAS:
5746-86-1
MF:
C9H12N2
Structure:
Chemical Name:
Indole-3-carboxylic acid
CAS:
771-50-6
MF:
C9H7NO2
Structure:
Chemical Name:
Triacetonamine
CAS:
826-36-8
MF:
C9H17NO
Structure:
Chemical Name:
9-Aminocamptothecin
CAS:
91421-43-1
MF:
C20H17N3O4
Structure:
Chemical Name:
Oxindole
CAS:
59-48-3
MF:
C8H7NO
Structure:
Chemical Name:
BANISTERINE MONOHYDRATE
CAS:
442-51-3
MF:
C13H12N2O
Structure:
Chemical Name:
3-Methyl-7-propylxanthine
CAS:
55242-64-3
MF:
C9H12N4O2
Structure:
Chemical Name:
Gramine
CAS:
87-52-5
MF:
C11H14N2
Structure:
Chemical Name:
Vindoline
CAS:
2182-14-1
MF:
C25H32N2O6
Structure:
Chemical Name:
Trigonelline hydrochloride
CAS:
6138-41-6
MF:
C7H8ClNO2
Structure:
Chemical Name:
Methyl indole-3-carboxylate
CAS:
942-24-5
MF:
C10H9NO2
Structure:
Chemical Name:
CACOTHELINE
CAS:
561-20-6
MF:
C21H21N3O7
Structure:
Chemical Name:
(+)-MAGNOFLORINE IODIDE
CAS:
2141-09-5
MF:
C20H24INO4
Structure:
Chemical Name:
CORYNANTHINE
CAS:
483-10-3
MF:
C21H26N2O3
Structure:
Chemical Name:
SWAINSONINE
CAS:
72741-87-8
MF:
C8H15NO3
Structure:
Chemical Name:
DAURICINE
CAS:
524-17-4
MF:
C38H44N2O6
Structure:
Chemical Name:
VERATRIDINE
CAS:
71-62-5
MF:
C36H51NO11
Structure:
Chemical Name:
L-MIMOSINE
CAS:
500-44-7
MF:
C8H10N2O4
Structure:
Chemical Name:
TOMATINE
CAS:
17406-45-0
MF:
C50H83NO21
Structure:
Chemical Name:
Ryanodine
CAS:
15662-33-6
MF:
C25H35NO9
Structure:
Chemical Name:
Boldine
CAS:
476-70-0
MF:
C19H21NO4
Structure:
Chemical Name:
1-(3-CHLOROPROPYL)THEOBROMINE
CAS:
74409-52-2
MF:
C10H13ClN4O2
Structure:
Chemical Name:
LUMICHROME
CAS:
1086-80-2
MF:
C12H10N4O2
Structure:
Chemical Name:
SCOPOLAMINE METHYL NITRATE
CAS:
6106-46-3
MF:
C18H24N2O7
Structure:
Chemical Name:
HARRINGTONINE
CAS:
26833-85-2
MF:
C28H37NO9
Structure:
Chemical Name:
ALPHA-AMANITIN
CAS:
23109-05-9
MF:
C39H54N10O14S
Structure:
Chemical Name:
STRYCHNINE
CAS:
60-41-3
MF:
C21H22N2O2.1/2H2O4S
Structure:
Chemical Name:
SOLASONINE
CAS:
19121-58-5
MF:
C45H73NO16
Structure:
Chemical Name:
NICOTINE BI-L-(+)-TARTRATE
CAS:
2624-48-8
MF:
C18H26N2O12
Structure:
Chemical Name:
(-)-ANABASINE
CAS:
13078-04-1
MF:
C10H14N2
Structure:
Chemical Name:
SANGUINARINE CHLORIDE
CAS:
5578-73-4
MF:
C20H14ClNO4
Structure:
Chemical Name:
GELSEMINE
CAS:
509-15-9
MF:
C20H22N2O2
Structure:
Chemical Name:
(-)-LUPININE
CAS:
486-70-4
MF:
C10H19NO
Structure:
Chemical Name:
2-Propylpiperidine
CAS:
3238-60-6
MF:
C8H17N
Structure:
Chemical Name:
(+)-TUBOCURARINE CHLORIDE PENTAHYDRATE
CAS:
6989-98-6
MF:
C37H44Cl2N2O7
Structure:
Chemical Name:
D-Tetrahydropalmatine
CAS:
3520-14-7
MF:
C21H25NO4
Structure:
Chemical Name:
HYOSCYAMINE HYDROBROMIDE
CAS:
306-03-6
MF:
C17H24BrNO3
Structure:
Chemical Name:
ISOTETRANDRINE
CAS:
477-57-6
MF:
C38H42N2O6
Structure:
Chemical Name:
TABERSONINE
CAS:
4429-63-4
MF:
C21H24N2O2
Structure:
Chemical Name:
HORDENINE SULFATE
CAS:
622-64-0
MF:
C20H32N2O6S
Structure:
Chemical Name:
NICOTINE SULFATE
CAS:
65-30-5
MF:
C20H30N4O4S
Structure:
Chemical Name:
LOBELINE SULFATE
CAS:
134-64-5
MF:
C44H56N2O8S
Structure:
Chemical Name:
(-)-EBURNAMONINE
CAS:
4880-88-0
MF:
C19H22N2O
Structure:
Chemical Name:
HYOSCYAMINE SULFATE
CAS:
620-61-1
MF:
C34H48N2O10S
Structure:
Chemical Name:
MYOSMINE
CAS:
532-12-7
MF:
C9H10N2
Structure:
Chemical Name:
CASTANOSPERMINE
CAS:
79831-76-8
MF:
C8H15NO4
Structure:
Chemical Name:
HARMALINE
CAS:
304-21-2
MF:
C13H14N2O
Structure:
Chemical Name:
Seneciphylline
CAS:
480-81-9
MF:
C18H23NO5
Structure:
Chemical Name:
(+)-B-HYDRASTINE HCL
CAS:
5936-28-7
MF:
C21H22ClNO6
Structure:
Chemical Name:
CYCLO(-GLY-PRO)
CAS:
3705-27-9
MF:
C7H10N2O2
Chemical Name:
Moringa extract
Structure:
Chemical Name:
CALYCANTHINE
CAS:
595-05-1
MF:
C22H26N4
Structure:
Chemical Name:
Solamargine
CAS:
20311-51-7
MF:
C45H73NO15
Structure:
Chemical Name:
Dicentrin
CAS:
517-66-8
MF:
C20H21NO4
Structure:
Chemical Name:
BETONICINE
CAS:
515-25-3
MF:
C7H13NO3
Structure:
Chemical Name:
BULBOCAPNINE HYDROCHLORIDE
CAS:
632-47-3
MF:
C19H20ClNO4
Structure:
Chemical Name:
ISORHYNCHOPHYLLINE
CAS:
6859-01-4
MF:
C22H28N2O4
Structure:
Chemical Name:
HOMATROPINE HYDROCHLORIDE
CAS:
637-21-8
MF:
C16H22ClNO3
Structure:
Chemical Name:
6-METHOXY-2-BENZOXAZOLINONE
CAS:
532-91-2
MF:
C8H7NO3
Structure:
Chemical Name:
4-AMINO-4-METHYL-2-PENTANONE HYDROGENOXALATE
CAS:
625-04-7
MF:
C6H13NO
Structure:
Chemical Name:
TETRAHYDROALSTONINE
CAS:
6474-90-4
MF:
C21H24N2O3
Structure:
Chemical Name:
3,4-DIMETHOXYBENZAMIDE
CAS:
1521-41-1
MF:
C9H11NO3
Structure:
Chemical Name:
SYROSINGOPINE
CAS:
84-36-6
MF:
C35H42N2O11
Structure:
Chemical Name:
SCOPOLAMINE N-OXIDE HYDROBROMIDE
CAS:
6106-81-6
MF:
C17H22BrNO5
Structure:
Chemical Name:
RHOEADINE
CAS:
2718-25-4
MF:
C21H21NO6
Structure:
Chemical Name:
DIHYDROERGOTAMINE TARTRATE CRYSTALLINE
CAS:
5989-77-5
MF:
2C33H37N5O5.C4H6O6
Structure:
Chemical Name:
α-Chaconine
CAS:
20562-03-2
MF:
C45H73NO14
Structure:
Chemical Name:
daurisoline
CAS:
70553-76-3
MF:
C37H42N2O6
Structure:
Chemical Name:
INDACONITINE
CAS:
4491-19-4
MF:
C34H47NO10
Structure:
Chemical Name:
1-METHYL-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE
CAS:
525-40-6
MF:
C12H14N2
Structure:
Chemical Name:
(+/-)-EvodiaMine
CAS:
518-18-3
MF:
C19H17N3O
Structure:
Chemical Name:
INDOLE-3-GLYOXYLAMIDE
CAS:
5548-10-7
MF:
C10H8N2O2
Structure:
Chemical Name:
SENECIONINE
CAS:
130-01-8
MF:
C18H25NO5
Structure:
Chemical Name:
2-Piperidinoethanol
CAS:
3040-44-6
MF:
C7H15NO
Structure:
Chemical Name:
ELLIPTICINE
CAS:
519-23-3
MF:
C17H14N2
Structure:
Chemical Name:
2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one
CAS:
526-43-2
MF:
C19H17N3O2
Structure:
Chemical Name:
PIPERLONGUMINE
CAS:
20069-09-4
MF:
C17H19NO5
Structure:
Chemical Name:
2-(3-(4-hydroxyphenyl)propanamido)benzoic acid
CAS:
697235-49-7
MF:
C16H15NO4
Structure:
Chemical Name:
Tropolone
CAS:
533-75-5
MF:
C7H6O2
Structure:
Chemical Name:
ATROPINE METHYL NITRATE
CAS:
52-88-0
MF:
C18H26N2O6
Structure:
Chemical Name:
Notoginseng triterpenes
CAS:
88105-29-7
MF:
C47H80O17
Structure:
Chemical Name:
Sophocarpine
CAS:
6483-15-4
MF:
C15H22N2O
Structure:
Chemical Name:
songorine
CAS:
509-24-0
MF:
C22H31NO3
Structure:
Chemical Name:
2α,5α-Epoxy-1,2-dihydroakuammilan-17-oic acid methyl ester
CAS:
4684-32-6
MF:
C20H22N2O3
Structure:
Chemical Name:
SERPENTINE HYDROGEN TARTRATE
CAS:
18786-24-8
MF:
C25H26N2O9
Structure:
Chemical Name:
Vasicil
CAS:
5081-51-6
MF:
C11H12N2O2
Structure:
Chemical Name:
IBOGAINE
CAS:
83-74-9
MF:
C20H26N2O
Structure:
Chemical Name:
HYOSCYAMINE HYDROCHLORIDE
CAS:
5934-50-9
MF:
C17H24ClNO3
Structure:
Chemical Name:
A-ALLOCRYPTOPINE
CAS:
476-33-5
MF:
C21H23NO5
Structure:
Chemical Name:
BRUCINE SULFATE HEPTAHYDRATE
CAS:
60583-39-3
MF:
C46H68N4O19S
Structure:
Chemical Name:
SANGUINARINE NITRATE
CAS:
4752-86-7
MF:
C20H14N2O7
Structure:
Chemical Name:
BOLDINE DIMETHYL ETHER
CAS:
475-81-0
MF:
C21H25NO4
Structure:
Chemical Name:
Sophoramine
CAS:
6882-66-2
MF:
C15H20N2O