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".
| 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 |