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
Rosmarinic acid Rosmarinic acid 20283-92-5 C18H16O8
Honokiol Honokiol 35354-74-6 C18H18O2
Gomisin A Gomisin A 58546-54-6 C23H28O7
ChicoricAcid ChicoricAcid 6537-80-0 C22H18O12
ASARININ ASARININ 133-04-0 C20H18O6
MATAIRESINOL MATAIRESINOL 580-72-3 C20H22O6
SECOISOLARICIRESINOL SECOISOLARICIRESINOL 29388-59-8 C20H26O6
MANOOL MANOOL 596-85-0 C20H34O
(+)-ISOLARICIRESINOL (+)-ISOLARICIRESINOL 548-29-8 C20H24O6
magnolin magnolin 31008-18-1 C23H28O7
(+)-PINORESINOL (+)-PINORESINOL 487-36-5 C20H22O6
gomisin J gomisin J 66280-25-9 C22H28O6
(+)-LARICIRESINOL (+)-LARICIRESINOL 27003-73-2 C20H24O6
Methyl rosmarinate Methyl rosmarinate 99353-00-1 C19H18O8
4-[(3S)-1-(4-hydroxyphenyl)penta-1,4-dien-3-yl]phenol 4-[(3S)-1-(4-hydroxyphenyl)penta-1,4-dien-3-yl]phenol 17676-24-3 C17H16O2
(-)-NORTRACHELOGENIN (-)-NORTRACHELOGENIN 34444-37-6 C20H22O7
paulownin paulownin 13040-46-5 C20H18O7
gomisin D gomisin D 60546-10-3 C28H34O10
EUDESMINE EUDESMINE 526-06-7 C22H26O6
3-(4-Hydroxy-3-methoxyphenyl)propenoic acid 3-[2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-[[[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]oxy]methyl]-7-methoxybenzofuran-5-yl]propyl ester 3-(4-Hydroxy-3-methoxyphenyl)propenoic acid 3-[2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-[[[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]oxy]methyl]-7-methoxybenzofuran-5-yl]propyl ester 57296-22-7 C40H40O12
9,9'-Di-O-(E)-feruloylsecoisolariciresil 9,9'-Di-O-(E)-feruloylsecoisolariciresil 56973-66-1 C40H42O12
Angeloylisogomisin O Angeloylisogomisin O 83864-70-4 C28H34O8
Dehydroheliobuphthalmin Dehydroheliobuphthalmin 103001-05-4 C22H20O8
Meridil Meridil 120051-54-9 C20H18O7
Moluccanin Moluccanin 121700-26-3 C20H18O8
Lariciresinol acetate Lariciresinol acetate 79114-77-5 C22H26O7
5-Allyl-3-Methoxy-6-Methyl-7-(3,4,5-tri
Methoxyphenyl)bicyclo[3.2.1]oct-3-ene-2,8-dione 5-Allyl-3-Methoxy-6-Methyl-7-(3,4,5-tri Methoxyphenyl)bicyclo[3.2.1]oct-3-ene-2,8-dione 106894-43-3 C22H26O6
syringaresinol syringaresinol 1177-14-6 C22H26O8
Olivil Olivil 2955-23-9 C20H24O7
4',9,9'-Trihydroxy-3'-methoxy-
3,7'-epoxy-4,8'-oxyneolignan 4',9,9'-Trihydroxy-3'-methoxy- 3,7'-epoxy-4,8'-oxyneolignan 144881-21-0 C19H22O6
5'-Demethylaquillochin 5'-Demethylaquillochin 305364-91-4 C20H18O9
Hedyotisol A Hedyotisol A 95732-59-5 C42H50O16
Nyasicol Nyasicol 111518-95-7 C17H16O6
threo-Guaiacylglycerol beta-coniferyl ether threo-Guaiacylglycerol beta-coniferyl ether 869799-76-8 C20H24O7
HYPOPHYLLANTHIN HYPOPHYLLANTHIN 33676-00-5 C24H30O7
PHYLLANTHIN PHYLLANTHIN 10351-88-9 C24H34O6
R(+)-Gomisin M1 R(+)-Gomisin M1 82467-50-3 C22H26O6
Maglifloenone Maglifloenone 82427-77-8 C22H26O6
Hedyotisol B Hedyotisol B 95839-45-5 C42H50O16
(1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2β,3α-dimethanol (1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-6,8-dimethoxy-7-hydroxy-1,2,3,4-tetrahydronaphthalene-2β,3α-dimethanol 14464-90-5 C22H28O8
Dihydroguaiaretic acid Dihydroguaiaretic acid 66322-34-7 C20H26O4
Desoxypodophyllotoxin Desoxypodophyllotoxin 19186-35-7 C22H22O7
GOMISIN N GOMISIN N 69176-52-9 C23H28O6
[[(3S)-3aα,4,6,6aα-Tetrahydro-1H,3H-furo[3,4-c]furan]-3α,6α-diyl]bis(2,6-dimethoxy-4,1-phenylene)bis(β-D-glucopyranoside) [[(3S)-3aα,4,6,6aα-Tetrahydro-1H,3H-furo[3,4-c]furan]-3α,6α-diyl]bis(2,6-dimethoxy-4,1-phenylene)bis(β-D-glucopyranoside) 573-44-4 C34H46O18
CONOCARPAN CONOCARPAN 221666-27-9 C18H18O2
Moluccanin diacetate Moluccanin diacetate 121700-27-4 C24H22O10
Phyllostadimer A Phyllostadimer A 638203-32-4 C42H50O16
PINORESINOL PINORESINOL 4263-88-1 C20H22O6
DIMETHYLMATAIRESINOL DIMETHYLMATAIRESINOL 25488-59-9 C22H26O6
acuminatin acuminatin 41744-39-2 C21H24O4
(+/-)-MATAIRESINOL (+/-)-MATAIRESINOL 148409-36-3 C20H22O6
alfa-Conidendrin alfa-Conidendrin 85699-62-3 C20H20O6
Gomisin M2 Gomisin M2 82425-45-4 C22H26O6
Tupichilignan A Tupichilignan A 69586-96-5 C22H26O7
ISOTAXIRESINOL ISOTAXIRESINOL 26194-57-0 C19H22O6
[[(1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-3α-(hydroxymethyl)-6,8-dimethoxy-7-hydroxytetralin-2β-yl]methyl]β-D-xylopyranoside [[(1S)-1α-(3,5-Dimethoxy-4-hydroxyphenyl)-3α-(hydroxymethyl)-6,8-dimethoxy-7-hydroxytetralin-2β-yl]methyl]β-D-xylopyranoside 34425-25-7 C27H36O12
3-[4-β-D-Glucopyranosyloxy-5-methoxy-3-[2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethyl]phenyl]-2-propen-1-ol 3-[4-β-D-Glucopyranosyloxy-5-methoxy-3-[2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethyl]phenyl]-2-propen-1-ol 126176-79-2 C26H34O11
5-Acetoxymatairesil dimethyl ether 5-Acetoxymatairesil dimethyl ether 74892-45-8 C24H28O8
9-O-Feruloyl-5,5'-dimethoxylariciresil 9-O-Feruloyl-5,5'-dimethoxylariciresil 166322-14-1 C32H36O11
Cedrusin Cedrusin 75775-36-9 C19H22O6
Lariciresil dimethyl ether Lariciresil dimethyl ether 67560-68-3 C22H28O6
4-[(S,E)-1-[(S)-1,2-Dihydroxyethyl]-3-(4-hydroxyphenyl)-2-propenyl]-1,2-benzenediol 4-[(S,E)-1-[(S)-1,2-Dihydroxyethyl]-3-(4-hydroxyphenyl)-2-propenyl]-1,2-benzenediol 18194-29-1 C17H18O5
Niranthin Niranthin 50656-77-4 C24H32O7
(2S,3S,4E)-3,5-Bis(4-hydroxyphenyl)-4-pentene-1,2-diol (2S,3S,4E)-3,5-Bis(4-hydroxyphenyl)-4-pentene-1,2-diol 7288-11-1 C17H18O4
[(2R,3R)-4-(3,5-Dimethoxy-4-hydroxyphenyl)-3-(hydroxymethyl)-2-(3,5-dimethoxy-4-hydroxybenzyl)butyl]β-D-xylopyranoside [(2R,3R)-4-(3,5-Dimethoxy-4-hydroxyphenyl)-3-(hydroxymethyl)-2-(3,5-dimethoxy-4-hydroxybenzyl)butyl]β-D-xylopyranoside 126882-53-9 C27H38O12
(+)-Piresil diacetate (+)-Piresil diacetate 32971-25-8 C24H26O8
9,9'-O-isopropyllidene-isolariciresil 9,9'-O-isopropyllidene-isolariciresil 252333-71-4 C23H28O6
Dimeric coniferyl acetate Dimeric coniferyl acetate 184046-40-0 C24H26O8
Hierochin D Hierochin D 155759-02-7 C19H20O6
(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
licarin A licarin A 51020-86-1 C20H22O4
Angeloylgomisin H Angeloylgomisin H 66056-22-2 C28H36O8
5,5'-Dimethoxylariciresil 4-O-glucoside 5,5'-Dimethoxylariciresil 4-O-glucoside 154418-16-3 C28H38O13
Fraxiresil 1-O-glucoside Fraxiresil 1-O-glucoside 89199-94-0 C27H34O13
Isogomisin O Isogomisin O 83916-76-1 C23H28O7
Olivil Monoacetate Olivil Monoacetate 1016974-78-9 C8H14O5
Agatharesinol acetonide Agatharesinol acetonide 800389-33-7 C20H22O4
SequoseMpervirin B SequoseMpervirin B 864719-17-5 C18H20O5
(-)-Pinoresinol 4-O-glucoside (-)-Pinoresinol 4-O-glucoside 41607-20-9 C26H32O11
Dehydrocostuslactone Dehydrocostuslactone 74299-48-2 C15H18O2
hancinone C hancinone C 111843-10-8 C23H28O6
(-)-PINORESINOL (-)-PINORESINOL 81446-29-9 C20H22O6
7-Oxohikinin 7-Oxohikinin 130837-92-2 C20H16O7
Dadahol A Dadahol A 405281-76-7 C39H38O12
Dunnial Dunnial 139726-29-7 C27H26O3
Fragransin A2 Fragransin A2 112652-46-7 C20H24O5
savinin savinin 493-95-8 C20H16O6
5-(2-Propenyl)-1,1'-biphenyl-2,2',5'-triol 5-(2-Propenyl)-1,1'-biphenyl-2,2',5'-triol 87562-14-9 C15H14O3
Acetylepipodophyllotoxin Acetylepipodophyllotoxin 1180-35-4 C24H24O9
gamma-Diasarone gamma-Diasarone 80434-33-9 C24H32O6
Kaerophyllin Kaerophyllin 75590-33-9 C21H20O6
Lancifolin C Lancifolin C 74048-71-8 C22H28O5
(+)-Lyoniresinol 9'-O-glucoside (+)-Lyoniresinol 9'-O-glucoside 87585-32-8 C28H38O13
cleomiscosin A cleomiscosin A 76948-72-6 C20H18O8
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