Lignans

Lignans are natural organic compounds by a class of 2 or 3 molecules of benzene in different forms of polymerization, mainly located in the angiosperms and gymnosperms. It can be divided into two categories: The lignan is composed of two molecules of benzene and its derivatives through its side chain polymerization of β-bit. The new lignan is a molecular propyl benzene side chain, connected with benzene ring of another molecule, or the two part of the oxygen atom connected compound. The sesquilignan is a compound of three molecules of phenyl group. A compound condensed by the flavone or chalcone wiht allyl benzene derivatives, called flavonolignan or xanthonolignan. After lignan condensed by two molecule of phenylpropyl β-carbon, oxygen-containing groups of γ- carbon on the side chain can be substituted tetrahydrofuran / Hemiacetal / Lactone tetralin / cyclooctene structure formed by dehydration condensation. So lignans can be divided into more types. Such as monoe-poxy lignan, lignanolide, cycloli-gnan, etc. From the plant kingdom has been allocated more than 200 lignans, more than 100 new lignans. Chinese medicine Ciwujia, Schisandra, the brother Wang, burdock, Polygala, forsythia, Trachelospermum jasminoides, safflower, asarum, contain lignans.

In plants, lignans in the form of free or glucoside, most are optically active, almost all, and are mostly colorless crystals in free form, some of the new lignans as an oil. Lignans are soluble in organic solvents, sparingly soluble or insoluble in water. The solubility of glycosides in alcohols or water is larger, and can be hydrolyzed by acid. Extract lignans aforetime first proposed total lignans with methanol or ethanol, and then separate the single component by chromatography or fractional crystallization.

Most lignans components can be color in case of concentrated sulfuric acid. If the molecule of lignans contains a number of phenolic hydroxyl group, Such as ferric chloride reagents, alkaline reagents diazotized sulfanilic, can able to react with the phenolic reagent showed different colors. Some of the lignans can react with the five antimony chloride solution and carbon tetrachloride, such as, with podophyllotoxin reaction is brown,  with alpha - peltatin is purple.

Many lignans component may have stereoisomers due to the saturated cyclic moiety. It has been found in some lignans unstable in traditional Chinese medicine, and it is easy to isomerization, changed into its solid isomer, influenced by acid or alkali. For example podophylloxin has significant anti-cancer effect, which is easily transformed into Picrop-odophyllin in alkaline solution; if affected by phosphorus trichloride, C1-OH translocation generated Epi-podophyllotoxin, and picrop-odophyllin and its derivatives had no anti-cancer activity.

We have found that lignans have a variety of activity, such as anti-cancer, anti-fungal, insecticidal, l white blood cells, lower alanine aminotransferase, liver, cough, diarrhea, etc. However, it is not used as a medicine. Derivatives of podophyllotoxin lignans useful as anti-cancer agents, lignans in Schisandra chinensis is known as lowering alanineaminotransferase , for the treatment of hepatitis.

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Structure Chemical Name CAS MF
(1S,3aR)-1β,7-Dimethoxy-4β-(3-methoxy-4-hydroxyphenyl)-1,3,3aβ,4,9,9aα-hexahydronaphtho[2,3-c]furan-6-ol (1S,3aR)-1β,7-Dimethoxy-4β-(3-methoxy-4-hydroxyphenyl)-1,3,3aβ,4,9,9aα-hexahydronaphtho[2,3-c]furan-6-ol 101312-79-2 C21H24O6
2-(4-Hydroxy-3-methoxyphenyl)
-7-methoxy-5-benzofuranpropal 2-(4-Hydroxy-3-methoxyphenyl) -7-methoxy-5-benzofuranpropal 144735-57-9 C19H20O5
9-O-Acetyl-4,4'-di-O-methyllariciresil 9-O-Acetyl-4,4'-di-O-methyllariciresil 73354-15-1 C24H30O7
Balaphonin Balaphonin 118916-57-7 C20H20O6
Nyasicoside Nyasicoside 111518-94-6 C23H26O11
Simonsil Simonsil 155709-40-3 C27H26O3
Vitexdoin A Vitexdoin A 1186021-77-1 C19H18O6
Olivil Monoacetate Olivil Monoacetate 1016974-78-9 C22H26O8
Agatharesinol acetonide Agatharesinol acetonide 800389-33-7 C20H22O4
SequoseMpervirin B SequoseMpervirin B 864719-17-5 C18H20O5
Fraxiresil 1-O-glucoside Fraxiresil 1-O-glucoside 89199-94-0 C27H34O13
Isogomisin O Isogomisin O 83916-76-1 C23H28O7
5,5'-Dimethoxylariciresil 4-O-glucoside 5,5'-Dimethoxylariciresil 4-O-glucoside 154418-16-3 C28H38O13
licarin A licarin A 51020-86-1 C20H22O4
Angeloylgomisin H Angeloylgomisin H 66056-22-2 C28H36O8
Futoquinol Futoquinol 28178-92-9 C21H22O5
nirandin A nirandin A 62163-24-0 C22H26O6
9-O-Feruloyllariciresil 9-O-Feruloyllariciresil 60337-67-9 C30H32O9
(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one (3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one 40456-50-6 C22H24O7
Yangambin Yangambin 13060-14-5 C24H30O8
Angeloylgomisin O Angeloylgomisin O 83864-69-1 C28H34O8
4-[Tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-hydroxymethylfuran-2-yl]-1,2-benzenediol 4-[Tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-hydroxymethylfuran-2-yl]-1,2-benzenediol 40951-69-7 C19H22O6
Tetrahydro-4-(1,3-benzodioxol-5-ylmethyl)-2-(4-hydroxy-3-methoxyphenyl)-3-furanmethanol Tetrahydro-4-(1,3-benzodioxol-5-ylmethyl)-2-(4-hydroxy-3-methoxyphenyl)-3-furanmethanol 54854-91-0 C20H22O6
2',4'-Dihydroxy-3,7':4,8'-diepoxylign-7-ene 2',4'-Dihydroxy-3,7':4,8'-diepoxylign-7-ene 666250-52-8 C18H18O4
erythro-Guaiacylglycerol β-dihydroconiferyl ether erythro-Guaiacylglycerol β-dihydroconiferyl ether 135820-77-8 C20H26O7
epiyangambin epiyangambin 24192-64-1 C24H30O8
(-)-Denudatin B (-)-Denudatin B 87402-88-8 C21H24O5
5-(2,3-Dihydroxypropyl)-5'-allylbiphenyl-2,2'-diol 5-(2,3-Dihydroxypropyl)-5'-allylbiphenyl-2,2'-diol 93673-81-5 C18H20O4
4,9,9'-Trihydroxy-3,3'-
diMethoxy-8,4'-oxyneolignan 4,9,9'-Trihydroxy-3,3'- diMethoxy-8,4'-oxyneolignan 53505-68-3 C20H26O6
Bis-5,5-nortrachelogenin Bis-5,5-nortrachelogenin 870480-56-1 C40H42O14
erythro-Guaiacylglycerol β-sinapyl ether erythro-Guaiacylglycerol β-sinapyl ether 877875-96-2 C21H26O8
DihydrosesaMin DihydrosesaMin 83708-70-7 C20H20O6
2-Epi-3a-epiburchellin 2-Epi-3a-epiburchellin 57457-99-5 C20H20O5
Isosalicifolin Isosalicifolin 156974-99-1 C20H20O6
4-O-DeMethylkadsurenin D 4-O-DeMethylkadsurenin D 127179-70-8 C20H22O5
5'-Methoxylariciresinol 5'-Methoxylariciresinol 105256-12-0 C21H26O7
Episyringaresinol Episyringaresinol 51152-20-6 C22H26O8
Spathulatol Spathulatol 1373888-27-7 C30H34O9
(-)Gomisin L1 (-)Gomisin L1 82425-43-2 C22H26O6
Gomisin S Gomisin S 119239-49-5 C23H30O7
burchellin burchellin 38276-59-4 C20H20O5
Fargesone A Fargesone A 116424-69-2 C21H24O6
Isomaglone Isomaglone 155709-41-4 C18H18O3
SequoseMpervirin D SequoseMpervirin D 864719-19-7 C21H24O5
Curlignan Curlignan 220736-54-9 C19H20O7
Isokadsurenin D Isokadsurenin D 147976-35-0 C21H24O5
DeMethylcarolignan E DeMethylcarolignan E 873694-46-3 C39H40O13
(5R,6S,7S,13aS,16R,17R)-5,6,7,8-Tetrahydro-17-hydroxy-1,2,3-trimethoxy-6,7,16,17-tetramethyl-5,13-(epoxybutanoxy)benzo[3,4]cycloocta[1,2-f][1,3]benzodioxol-18-one (5R,6S,7S,13aS,16R,17R)-5,6,7,8-Tetrahydro-17-hydroxy-1,2,3-trimethoxy-6,7,16,17-tetramethyl-5,13-(epoxybutanoxy)benzo[3,4]cycloocta[1,2-f][1,3]benzodioxol-18-one 72960-21-5 C28H34O9
5,5'-Dimethoxylariciresil 5,5'-Dimethoxylariciresil 116498-58-9 C22H28O8
De-4'-O-methylyangambin De-4'-O-methylyangambin 149250-48-6 C23H28O8
Longifloroside A Longifloroside A 175556-08-8 C27H34O11
Isotaxiresinol 9,9'-acetonide Isotaxiresinol 9,9'-acetonide 252333-72-5 C22H26O6
(+)-Isolariciresinol 9'-O-glucoside (+)-Isolariciresinol 9'-O-glucoside 63358-12-3 C26H34O11
3a-Epiburchellin 3a-Epiburchellin 155551-61-4 C20H20O5
wallichinine D wallichinine D 125292-97-9 C22H26O5
dehydrodiconiferyl alcohol dehydrodiconiferyl alcohol 4263-87-0 C20H22O6
4-[2-(1,3-Benzodioxol-5-yl)-1-methylethyl]-4,5-dimethoxy-2-(2-propenyl)-2,5-cyclohexadien-1-one 4-[2-(1,3-Benzodioxol-5-yl)-1-methylethyl]-4,5-dimethoxy-2-(2-propenyl)-2,5-cyclohexadien-1-one 62499-71-2 C21H24O5
2,2'-Dihydroxy-5'-(2-propenyl)-1,1'-biphenyl-5-carbaldehyde 2,2'-Dihydroxy-5'-(2-propenyl)-1,1'-biphenyl-5-carbaldehyde 93753-33-4 C16H14O3
(3R)-3β,4α-Bis(3-methoxy-4-hydroxybenzyl)-3-hydroxytetrahydrofuran-2-one (3R)-3β,4α-Bis(3-methoxy-4-hydroxybenzyl)-3-hydroxytetrahydrofuran-2-one 61521-74-2 C20H22O7
Massoniaside B Massoniaside B 188300-19-8 C25H32O10
Nitidanin Nitidanin 171674-89-8 C21H24O8
(+)-Conocarpan acetate (+)-Conocarpan acetate 56319-04-1 C20H20O3
(+)-Regiomontanin (+)-Regiomontanin 52151-92-5 C20H20O6
Denudanolide A Denudanolide A 288259-72-3 C20H20O6
Nyasicol 1,2-acetonide Nyasicol 1,2-acetonide 1432057-64-1 C20H20O6
2,3-Di(3',4'-Methylenedioxybenzyl)
-2-buten-4-olide 2,3-Di(3',4'-Methylenedioxybenzyl) -2-buten-4-olide 137809-97-3 C20H16O6
Fargesone B Fargesone B 116424-70-5 C21H24O6
Dihydrodehydrodiconiferyl alcohol Dihydrodehydrodiconiferyl alcohol 126253-41-6 C20H24O6
Piperenone Piperenone 57625-31-7 C22H28O6
1-Hydroxypinoresinol 1-O-glucoside 1-Hydroxypinoresinol 1-O-glucoside 81495-71-8 C26H32O12
erythro-Guaiacylglycerol
-β-O-4'-dehydrodisinapyl ether erythro-Guaiacylglycerol -β-O-4'-dehydrodisinapyl ether 613684-55-2 C31H36O11
Futoenone Futoenone 19913-01-0 C20H20O5
Prenylpiperitol Prenylpiperitol 157659-20-6 C25H28O6
Metasequirin D Metasequirin D 1264694-96-3 C19H22O6
6-Hydroxy-4-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-3,4-dihydro-2-naphthaldehyde 6-Hydroxy-4-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-3,4-dihydro-2-naphthaldehyde 357645-16-0 C20H20O6
Isodihydrofutoquinol A Isodihydrofutoquinol A 62560-95-6 C21H24O5
Secoisolariciresinol Monoglucoside Secoisolariciresinol Monoglucoside 63320-67-2 C26H36O11
(-)-Syringaresinol (-)-Syringaresinol 6216-81-5 C22H26O8
(+)-Cycloolivil (+)-Cycloolivil 3064-05-9 C20H24O7
(5R)-6β,7β-Dimethyl-1,2,3,12-tetramethoxy-10,11-methylenedioxy(5,6,7,8-tetrahydrodibenzo[a,c]cyclooctene)-5β,6α-diol 5-[(E)-2-methyl-2-butenoate] (5R)-6β,7β-Dimethyl-1,2,3,12-tetramethoxy-10,11-methylenedioxy(5,6,7,8-tetrahydrodibenzo[a,c]cyclooctene)-5β,6α-diol 5-[(E)-2-methyl-2-butenoate] 69176-51-8 C28H34O9
5-(2,3-Dihydroxypropyl)-3'-(2-propenyl)-1,1'-biphenyl-2,4'-diol 5-(2,3-Dihydroxypropyl)-3'-(2-propenyl)-1,1'-biphenyl-2,4'-diol 93697-42-8 C18H20O4
erythro-Guaiacylglycerol beta-coniferyl ether erythro-Guaiacylglycerol beta-coniferyl ether 890317-92-7 C20H24O7
SesarteMin SesarteMin 77394-27-5 C23H26O8
Magnolianin Magnolianin 147663-91-0 C54H50O8
7-O-Acetyl-4-O-demethylpolysyphorin 7-O-Acetyl-4-O-demethylpolysyphorin 89706-39-8 C24H30O8
Epinortrachelogenin Epinortrachelogenin 125072-69-7 C20H22O7
1,6-Dihydro-4,7'-epoxy-1-Methoxy-
3',4'-Methylenedioxy-6-oxo-3,8'-lignan 1,6-Dihydro-4,7'-epoxy-1-Methoxy- 3',4'-Methylenedioxy-6-oxo-3,8'-lignan 67920-48-3 C20H20O5
Kadsurenin D Kadsurenin D 140669-89-2 C21H24O5
4-O-DeMethylisokadsurenin D 4-O-DeMethylisokadsurenin D 89104-59-6 C20H22O5
4,4'-Dihydroxy-3,3',9-triMethoxy-9,9'-epoxylignan 4,4'-Dihydroxy-3,3',9-triMethoxy-9,9'-epoxylignan 1206464-65-4 C21H26O6
threo-7-O-Methylguaiacylglycerol
 β-coniferyl ether threo-7-O-Methylguaiacylglycerol β-coniferyl ether 150333-85-0 C21H26O7
Gomisin K1 Gomisin K1 75629-20-8 C23H30O6
Angeloylgomisin Q Angeloylgomisin Q 72561-28-5 C29H38O9
Cleomiscosin C Cleomiscosin C 84575-10-0 C21H20O9
(2S)-2α-(1,3-Benzodioxole-5-yl)-3β-methyl-5α-methoxy-5-allyl-2,3,5,6-tetrahydrobenzofuran-6-one (2S)-2α-(1,3-Benzodioxole-5-yl)-3β-methyl-5α-methoxy-5-allyl-2,3,5,6-tetrahydrobenzofuran-6-one 57430-03-2 C20H20O5
Isodunnial Isodunnial 139726-30-0 C27H26O3
Kadsurin A Kadsurin A 99340-07-5 C21H24O6
Denudadione C Denudadione C 61240-34-4 C20H20O5
(1S,2R,3R)-1,2,3,4-Tetrahydro-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxy-2,3-naphthalenedimethanol (1S,2R,3R)-1,2,3,4-Tetrahydro-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-6,8-dimethoxy-2,3-naphthalenedimethanol 136082-41-2 C21H26O7
Schizandriside Schizandriside 71222-06-5 C25H32O10
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