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