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lignan
Any phenylpropanoid derived from phenylalanine via dimerization of substituted cinnamic alcohols, known as monolignols, to a dibenzylbutane skeleton. Note that while individual members of the class have names ending ...lignane, ...lignene, ...lignadiene, etc., the class names lignan, neolignan, etc., do not end with an "e".
ChEBI ID: 25036
Members (60)
| Member | Definition | Role |
|---|---|---|
| (+)-Eudesmin | (+)-Eudesmin | |
| (+)-lyoniresinol-3-alpha-O-beta-D-glucopyranoside | A lignan that is (+)-lyoniresinol substituted by a beta-D-glucopyranosyl moiety at position 3 via a glycosidic linkage. Isolated from the root barks of Stemmadenia minima and Lycium chinense, it exhibits antimicrobial activities. | (+)-lyoniresinol-3-alpha-O-beta-D-glucopyranoside |
| 2,3-bis(3'-hydroxybenzyl)butane-1,4-diol | 2,3-Bis(3-hydroxybenzyl)butane-1,4-diol | |
| 2,3-bis(3'-hydroxybenzyl)butyrolactone | Enterolactone | |
| 3,6-Bis(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan | 3,6-Bis(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan | |
| 4-[4-(4-hydroxy-3-methoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-2-methoxyphenyl hexopyranoside | 4-[4-(4-hydroxy-3-methoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-2-methoxyphenyl hexopyranoside | |
| 4'-demethyldesoxypodophyllotoxin | A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted at position 5 by a 4-hydroxy-3,5-dimethoxyphenyl group. | 4'-demethyldeoxypodophyllotoxin |
| 8-hydroxypinoresinol | 8-Hydroxypinoresinol | |
| aiphanol | A lignan that is (2R)-2,3-dihydro-1,4-benzodioxin-2-ylmethanol which is substituted by a 2-(3,5-dihydroxyphenyl)ethenyl group at position 6 and a 4-hydroxy-3,5-dimethoxyphenyl group at position 3. It is a stilbenolignan isolated from the seeds of Aiphanes aculeata and exhibits potent inhibitory efficacy against cyclooxygenase-1 and -2 (COX-1 and COX-2). | aiphanol |
| alpha-peltatin | An organic heterotetracyclic compound that is 4'-demethylpodophyllotoxin which is substituted by a hydroxy group at position 10 but which is lacking the hydroxy group at position 9. It is found as a glucoside in the rhizomes of Podophyllum peltatum. | alpha-peltatin |
| anthricin | A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted at position 5 by a 3,4,5-trimethoxyphenyl group. | deoxypodophyllotoxin |
| arctigenin | (-)-Arctigenin | |
| arctiin | Arctiin | |
| beta-peltatin | An organic heterotetracyclic compound that is alpha-peltatin in which the phenolic hydroxy group of the 4-hydroxy-3,5-dimethoxyphenyl substitutent had been converted into the corresponding methyl ether. | beta-peltatin |
| beta-peltatin a methyl ether | beta-Peltatin A methyl ether | |
| bursehernin | A butan-4-olide that is (-)-pluviatolide in which the phenolic hydroxy group has been converted to the corresponding methyl ether. | (-)-bursehernin |
| conidendrin | alpha-Conidendrin | |
| cubebin | A lignan that consists of tetrahydrofuran-2-ol substituted by two 1,3-benzodioxol-5-ylmethyl groups at positions 3 and 4 respectively (the 2S,3R,4R stereoisomer). It is isolated from the leaves of Piper nigrum and exhibits analgesic, anti-inflammatory, antimicrobial and trypanocidal activities. | (-)-cubebin |
| cycloolivil | Cycloolivil | |
| dihydrocubebin | A glycol that is butane-1,4-diol substituted at the 2- and 3-positions by (1,3-benzodioxol-5-yl)methyl groups (the R,R-configuration). | dihydrocubebin |
| diphyllin | Diphyllin | |
| galgravin | A member of the class of aryltetrahydrofurans carrying two 3,4-dimethoxyphenyl substituents at positions 2 and 5 as well as two methyl groups at positions 3 and 4. | galgravin |
| gmelinol | Gmelinol | |
| grandisin | Grandisin | |
| helioxanthin | A furonaphthodioxole that is furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-7(9H)-one substituted by a 1,3-benzodioxol-5-yl group at posiiton 10. It is a inhibitor of HBV, HCV and HSV-1 viruses. | helioxanthin |
| hetacillin | A lignan that consists of tetrahydrofuran substituted by a 3,4-dihydroxyphenyl group at position 2, a hydroxymethyl group at position 3 and a 4-hydroxy-3-methoxybenzyl group at position 4. It has been isolated from Taxus yunnanensis. | taxiresinol |
| hinokinin | A lignan that is dihydrofuran-2(3H)-one (gamma-butyrolactone) substituted by a 3,4-methylenedioxybenzyl group at positions 3 and 4 (the 3R,4R-diastereoisomer). | hinokinin |
| interiotherin b | A lignan with a dibenzocyclooctadiene skeleton attached to a fatty acid ester side chain. It is isolated from Kadsura interior and has been shown to exhibit anti-HIV activity. | interiotherin B |
| isolariciresinol | A lignan that is 5,6,7,8-tetrahydronaphthalen-2-ol substituted by hydroxymethyl groups at positions 6 and 7, a methoxy group at position 3 and a 4-hydroxy-3-methoxyphenyl group at position 8. It has been isolated from the roots of Rubia yunnanensis. | (+)-isolariciresinol |
| justicidin a | Justicidin A | |
| kobusin | A member of the class of furofurans that is tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-1,3-benzodioxole carrying an additional 3,4-dimethoxyphenyl substituent at position 4. | demethoxyaschantin |
| lariciresinol | A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer). | (+)-lariciresinol |
| LSM-20517 | LSM-20517 | |
| LSM-34734 | LSM-34734 | |
| lyoniresinol | A lignan that is tetralin substituted by a 4-hydroxy-3,5-dimethoxy group at position 4, hydroxymethyl groups at positions 2 and 3, methoxy groups at positions 5 and 7 and a hydroxy group at position 6. Isolated from Machilus robusta and Sinocalamus affinis, it exhibits antineoplastic activity. | (+)-lyoniresinol |
| macelignan | 4-[(2S,3R)-4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol | |
| magnosalin | Magnosalin | |
| manassantin b | A lignan isolated from Saururus cernuus and Saururus chinensis and has been shown to exhibit antineoplastic activity. | manassantin B |
| masoprocol | A tetrol that is butane which is substituted at positions 2 and 3 by 3,4-dihydroxybenzyl groups. Masoprocol, the meso-form found in the leaves of the creosote bush (Larrea divaricata), is a potent lipoxygenase inhibitor. | nordihydroguaiaretic acid |
| matairesinol | A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer). | (-)-matairesinol |
| medioresinol | A lignan that is tetrahydro-1H,3H-furo[3,4-c]furan substituted by a 4-hydroxy-3,5-dimethoxyphenyl group at position 1 and a 4-hydroxy-3-methoxyphenyl group at position 4. It has been isolated from the stems of Sinocalamus affinis. | (-)-medioresinol |
| meso-dihydroguaiaretic acid | A lignan that is 2,3-dimethylbutane substituted by 2-methoxyphenol groups at positions 1 and 4 respectively. It has been isolated from the bark of Machilus robusta. | meso-dihydroguaiaretic acid |
| mitopodozide | mitopodozide | |
| nortrachelogenin | Nortrachelogenin | |
| phyllanthin | Phyllanthin | |
| picropodophyllin | An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing 3,4,5-trimethoxyphenyl and hydroxy substituents. | picropodophyllotoxin |
| planinin | Fargesin | |
| plicatic acid | Plicatic acid | |
| pluviatolide | A butan-4-olide that is dihydrofuran-2(3H)-one which is substituted by a vanillyl group at position 3 and by a 3,4-methylenedioxybenzyl group at position 4 (the R,R stereoisomer). | (-)-pluviatolide |
| podophyllotoxin | An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing a 3,4,5-trimethoxyphenyl substituent. It is found in the roots and rhizomes of Podophyllum species and is used for the topical treatment of genital warts. | podophyllotoxin |
| pravastatin | Eleutheroside E | |
| savinin | A lignan that is dihydrofuran-2(3H)-one (gamma-butyrolactone) substituted by a 1,3-benzodioxol-5-ylmethylidene group at position 3 and a 1,3-benzodioxol-5-ylmethyl group at position 4 (the 3E,4R-isomer). It exhibits antiviral activity against SARS-CoV-2. | savinin |
| sesamin | A lignan that consists of tetrahydro-1H,3H-furo[3,4-c]furan substituted by 1,3-benzodioxole groups at positions 1 and 4 (the 1S,3aR,4S,6aR stereoisomer). Isolated from Cinnamomum camphora, it exhibits cytotoxic activity. | (+)-sesamin |
| syringaresinol | A lignan that is 7,9':7',9-diepoxylignane substituted by hydroxy groups at positions 4 and 4' and methoxy groups at positions 3, 3', 5 and 5' respectively. | syringaresinol |
| taiwanin c | A furonaphthodioxole that is furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one substituted by a 1,3-benzodioxol-5-yl group at position 5. It is a naturally occurring lignan extracted from Taiwania cryptomerioides and found to be a potential inhibitor of COX2 expression. | taiwanin C |
| terameprocol | terameprocol | |
| trachelogenin | Trachelogenin | |
| tracheloside | Tracheloside | |
| yangambin | Yangambin | |
| yatein | A member of the class of butan-4-olides carrying 3,4,5-trimethoxybenzyl and (1,3-benzodioxol-5-yl)methyl substituents at positions 3 and 4 respectively. | dihydroanhydropodorhizol |
Research
Studies (5,094)
| Timeframe | Studies, Drugs in This Class (%) | All Drugs % |
|---|---|---|
| pre-1990 | 1,337 (26.25) | 18.7374 |
| 1990's | 474 (9.31) | 18.2507 |
| 2000's | 1,031 (20.24) | 29.6817 |
| 2010's | 1,753 (34.41) | 24.3611 |
| 2020's | 499 (9.80) | 2.80 |
Study Types
| Publication Type | Studies, Drugs in This Class (%) | All Drugs (%) |
|---|---|---|
| Trials | 301 (4.91%) | 5.53% |
| Reviews | 360 (5.87%) | 6.00% |
| Case Studies | 142 (2.32%) | 4.05% |
| Observational | 4 (0.07%) | 0.25% |
| Other | 5,322 (86.83%) | 84.16% |