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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:
Decarine
CAS:
54354-62-0
MF:
C19H13NO4
Structure:
Chemical Name:
Glycozolinine
CAS:
5257-08-9
MF:
C13H11NO
Structure:
Chemical Name:
Neotuberostemonine
CAS:
143120-46-1
MF:
C22H33NO4
Structure:
Chemical Name:
N-Methyllindcarpine
CAS:
14028-97-8
MF:
C19H21NO4
Structure:
Chemical Name:
Pachyaximine A
CAS:
128255-08-3
MF:
C24H41NO
Structure:
Chemical Name:
Paniculidine C
CAS:
97399-95-6
MF:
C13H17NO
Structure:
Chemical Name:
Spiramine A
CAS:
114531-28-1
MF:
C24H33NO4
Structure:
Chemical Name:
1,4-Dihydro-1-methyl-4-oxo-3-pyridinecarbonitrile
CAS:
767-98-6
MF:
C7H6N2O
Structure:
Chemical Name:
Indole alkaloid
CAS:
642-18-2
MF:
C21H20N2O3
Structure:
Chemical Name:
10-Hydroxyscandine
CAS:
119188-47-5
MF:
C21H22N2O4
Structure:
Chemical Name:
2,7-Dihydrohomoerysotrine
CAS:
51095-85-3
MF:
C20H27NO3
Structure:
Chemical Name:
sambutoxin
CAS:
160047-56-3
MF:
C28H39NO4
Structure:
Chemical Name:
ARICINE
CAS:
482-91-7
MF:
C22H26N2O4
Structure:
Chemical Name:
5-Hydroxy-4-methoxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one
CAS:
18110-86-6
MF:
C15H10N2O3
Structure:
Chemical Name:
Daphnilongeranin C
CAS:
750649-07-1
MF:
C22H29NO3
Structure:
Chemical Name:
Methyl chafruticosinate
CAS:
14050-92-1
MF:
C23H26N2O5
Structure:
Chemical Name:
4-Hydroxycephalotaxine
CAS:
84567-08-8
MF:
C18H21NO5
Structure:
Chemical Name:
Antidesmone
CAS:
222629-77-8
MF:
C19H29NO3
Structure:
Chemical Name:
3'-Hydroxyrocaglamide
CAS:
189322-67-6
MF:
C29H31NO8
Structure:
Chemical Name:
Vandrikidine
CAS:
50656-92-3
MF:
C22H26N2O4
Structure:
Chemical Name:
10-Hydroxydihydroperaksine
CAS:
451478-47-0
MF:
C19H24N2O3
Structure:
Chemical Name:
GriffithinaM
CAS:
240122-32-1
MF:
C17H13NO4
Structure:
Chemical Name:
11-Hydroxyrankinidine
CAS:
122590-03-8
MF:
C20H24N2O4
Structure:
Chemical Name:
(R)-5,6,6a,7-Tetrahydro-1,2-dimethoxy-6,6-dimethyl-4H-dibenzo[de,g]quinolinium
CAS:
754919-24-9
MF:
C20H24NO2+
Structure:
Chemical Name:
16-epi-Nb-Methylvoacarpine
CAS:
865187-17-3
MF:
C22H26N2O4
Structure:
Chemical Name:
(6S,7R)-6,7-Dihydro-7-methyl-5H-cyclopenta[c]pyridin-6-ol
CAS:
17948-42-4
MF:
C9H11NO
Structure:
Chemical Name:
14-Benzoylneoline
CAS:
99633-05-3
MF:
C31H43NO7
Structure:
Chemical Name:
1-CinnaMoyl-3-hydroxypyrrolidine
CAS:
1344876-77-2
MF:
C13H15NO2
Structure:
Chemical Name:
3-Phenyl-1-(pyrrol-1-yl)propan-1-one
CAS:
112448-69-8
MF:
C13H13NO
Structure:
Chemical Name:
Neolinine
CAS:
112515-37-4
MF:
C23H37NO6
Structure:
Chemical Name:
Rauvoyunine C
CAS:
1211543-01-9
MF:
C32H36N2O9
Structure:
Chemical Name:
(Z)-1-Methyl-2-(undec-6-enyl)quinolin-4(1H)-one
CAS:
120693-49-4
MF:
C21H29NO
Structure:
Chemical Name:
Daphnicyclidin F
CAS:
385384-26-9
MF:
C23H27NO5
Structure:
Chemical Name:
Strictosidinic acid
CAS:
150148-81-5
MF:
C26H32N2O9
Structure:
Chemical Name:
Virosine B
CAS:
1052228-70-2
MF:
C13H17NO3
Structure:
Chemical Name:
20S-Hydroxyconopharyngine
CAS:
16790-93-5
MF:
C23H30N2O5
Structure:
Chemical Name:
Dimethyl toluene-2,6-dicarbamate
CAS:
20913-18-2
MF:
C11H14N2O4
Structure:
Chemical Name:
10-Hydroxy-16-epiaffinine
CAS:
82513-70-0
MF:
C20H24N2O3
Structure:
Chemical Name:
Piperlotine A
CAS:
389572-70-7
MF:
C14H17NO2
Structure:
Chemical Name:
Rauvoyunine B
CAS:
1414883-82-1
MF:
C23H26N2O6
Structure:
Chemical Name:
3'-Methoxyrocaglamide
CAS:
189322-69-8
MF:
C30H33NO8
Structure:
Chemical Name:
Aristolactam BIII
CAS:
53948-10-0
MF:
C18H15NO4
Structure:
Chemical Name:
Pandamarilactonine A
CAS:
303008-80-2
MF:
C18H23NO4
Structure:
Chemical Name:
Paxiphylline D
CAS:
1092555-02-6
MF:
C23H29NO4
Structure:
Chemical Name:
Scholaricine
CAS:
99694-90-3
MF:
C20H24N2O4
Structure:
Chemical Name:
Sessilifoline A
CAS:
929637-35-4
MF:
C22H31NO5
Structure:
Chemical Name:
Dihydroperaksine
CAS:
16100-84-8
MF:
C19H24N2O2
Structure:
Chemical Name:
N-(2-Hydroxy-4-Methoxyphenyl)acetaMide
CAS:
58469-06-0
MF:
C9H11NO3
Structure:
Chemical Name:
NSC 36549
CAS:
6935-99-5
MF:
C11H14N2O4
Structure:
Chemical Name:
1,2-Methylenedioxy-3,10,11-trimethoxyaporphine
CAS:
14050-90-9
MF:
C20H21NO5
Structure:
Chemical Name:
1-CinnaMoylpyrrole
CAS:
252248-89-8
MF:
C13H11NO
Structure:
Chemical Name:
SongoraMine
CAS:
23179-78-4
MF:
C22H29NO3
Structure:
Chemical Name:
Aglaxiflorin D
CAS:
269739-78-8
MF:
C36H42N2O9
Structure:
Chemical Name:
BisdehydroneotuberosteMonine
CAS:
160333-27-7
MF:
C22H29NO4
Structure:
Chemical Name:
Dihydrochelerythrine
CAS:
6880-91-7
MF:
C21H19NO4
Structure:
Chemical Name:
1-Methyl-2-undecyl-1,4-dihydroquinoline-4-one
CAS:
59443-02-6
MF:
C21H31NO
Structure:
Chemical Name:
(16R)-Dihydrositsirikine
CAS:
6519-26-2
MF:
C21H28N2O3
Structure:
Chemical Name:
11-Hydroxycodaphniphylline
CAS:
1186496-68-3
MF:
C30H47NO4
Structure:
Chemical Name:
4,R-ajmalicine N-oxide
CAS:
41590-29-8
MF:
C21H24N2O4
Structure:
Chemical Name:
Dehydroaglaiastatin
CAS:
155595-93-0
MF:
C31H28N2O6
Structure:
Chemical Name:
Serpentinic acid
CAS:
605-14-1
MF:
C20H19N2O3+
Structure:
Chemical Name:
N-Methoxyanhydrovobasinediol
CAS:
125180-42-9
MF:
C21H26N2O2
Structure:
Chemical Name:
Erysotrine
CAS:
27740-43-8
MF:
C19H23NO3
Structure:
Chemical Name:
Cyclo(L-Pro-L-Trp-)
CAS:
38136-70-8
MF:
C16H17N3O2
Structure:
Chemical Name:
(3R,8aS)-Octahydro-3-(1-methylethyl)pyrrolo[1,2-a]pyrazine-1,4-dione
CAS:
27483-18-7
MF:
C10H16N2O2
Structure:
Chemical Name:
14,15-Didehydroisoeburnamine
CAS:
50838-11-4
MF:
C19H22N2O
Structure:
Chemical Name:
Yunnandaphninine G
CAS:
1042143-83-8
MF:
C30H47NO3
Structure:
Chemical Name:
Rauvotetraphylline C
CAS:
1422506-51-1
MF:
C28H34N2O7
Structure:
Chemical Name:
Isopteleine
CAS:
2181-84-2
MF:
C13H11NO3
Structure:
Chemical Name:
Daphnicyclidin I
CAS:
1467083-10-8
MF:
C22H26N2O3
Structure:
Chemical Name:
STYLOPINE, (-)-(RG)(CALL)
CAS:
7461-02-1
MF:
C19H17NO4
Structure:
Chemical Name:
corydalmine
CAS:
30413-84-4
MF:
C20H23NO4
Structure:
Chemical Name:
humantenirine
CAS:
82375-30-2
MF:
C21H26N2O4
Structure:
Chemical Name:
lupanine
CAS:
550-90-3
MF:
C15H24N2O
Structure:
Chemical Name:
Canthin-6-one
CAS:
479-43-6
MF:
C14H8N2O
Structure:
Chemical Name:
(19Z)-Anhydrovobasinediol
CAS:
19452-84-7
MF:
C20H24N2O
Structure:
Chemical Name:
O-Methylpallidine【Corydalis】
CAS:
27510-33-4
MF:
C20H23NO4
Structure:
Chemical Name:
1-Ethyl-4-methoxy-9H-pyrido[3,4-b]indol-8-ol
CAS:
100234-62-6
MF:
C14H14N2O2
Structure:
Chemical Name:
11,12-De(methylenedioxy)danuphylline
CAS:
888482-17-5
MF:
C23H26N2O6
Structure:
Chemical Name:
1-Hydroxycanthin-6-one
CAS:
80787-59-3
MF:
C14H8N2O2
Structure:
Chemical Name:
Daphnezomine B
CAS:
247078-43-9
MF:
C23H37NO3
Structure:
Chemical Name:
Daphniyunnine B
CAS:
881388-88-1
MF:
C21H29NO3
Structure:
Chemical Name:
N-Demethylechitamine
CAS:
60048-88-6
MF:
C21H26N2O4
Structure:
Chemical Name:
DeMethylMurrayanine
CAS:
123497-84-7
MF:
C13H9NO2
Structure:
Chemical Name:
1-(4-MethoxycinnaMoyl)pyrrole
CAS:
736140-70-8
MF:
C14H13NO2
Structure:
Chemical Name:
7β-Hydroxyrutaecarpine
CAS:
163815-35-8
MF:
C18H13N3O2
Structure:
Chemical Name:
Pelirine
CAS:
30435-26-8
MF:
C21H26N2O3
Structure:
Chemical Name:
Rauvotetraphylline E
CAS:
1422506-53-3
MF:
C20H18N2O3
Structure:
Chemical Name:
Zanthobungeanine
CAS:
64190-94-9
MF:
C16H17NO3
Structure:
Chemical Name:
IsoMaculosidine
CAS:
518-96-7
MF:
C14H13NO4
Structure:
Chemical Name:
NorarMepavine
CAS:
3195-01-5
MF:
C18H21NO3
Structure:
Chemical Name:
PROTOPINE HYDROCHLORIDE
CAS:
6164-47-2
MF:
C20H20ClNO5
Structure:
Chemical Name:
(+)-alpha-isolupanine
CAS:
486-87-3
MF:
C15H24N2O
Structure:
Chemical Name:
Demethylcephalotaxinone
CAS:
51020-45-2
MF:
C17H17NO4
Structure:
Chemical Name:
Drupacine
CAS:
49686-57-9
MF:
C18H21NO5
Structure:
Chemical Name:
Fortuneine
CAS:
87340-25-8
MF:
C20H25NO3
Structure:
Chemical Name:
[5S,4E,(-)]-4-Ethylidene-1,3,4,5,6,7-hexahydro-6-methylene-2α,5-ethano-2H-azocino[4,3-b]indole
CAS:
2122-36-3
MF:
C18H20N2
Structure:
Chemical Name:
(+)-Xanthoplanine
CAS:
6872-88-4
MF:
C21H26NO4+
Structure:
Chemical Name:
(+)-Polyneuridine
CAS:
639-36-1
MF:
C21H24N2O3
Structure:
Chemical Name:
Cyclo[D-Leu-L-Pro-]
CAS:
36238-67-2
MF:
C11H18N2O2