Classification Term: 168392

Withanolides and derivatives [ST0116] (ontology term: 7df0496344442a2a33d91e518df7b391)

Withanolides and derivatives [ST0116]

found 65 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Sterols [ST01]

Child Taxonomies: There is no child term of current ontology term.

Taccalonolide A

[(1S,2S,3R,5S,7S,9S,10R,11R,12S,13S,14R,15R,16S,17S,22S,23S,24R,25R)-10,14,25-triacetyloxy-3,22-dihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.02,12.05,11.07,9.016,24.019,23]pentacos-18-en-13-yl] acetate

C36H46O14 (702.2887)


Taccalonolide A is a withanolide. Taccalonolide A is a natural product found in Tacca plantaginea and Tacca chantrieri with data available. Taccalonolide A is a microtubule stabilizer, which is a steroid isolated from Tacca chantrieri, with cytotoxic and antimalarial activities[1][2]. Taccalonolide A causes G2-M accumulation, Bcl-2 phosphorylation and initiation of apoptosis[1]. Taccalonolide A is effective in vitro against cell lines that overexpress P-glycoprotein (Pgp) and multidrug resistance protein 7 (MRP7), with an IC50 of 622 nM for SK-OV-3 cells[3].

   

Withaferin A

(4S,4aR,5aR,6aS,6bS,9R,9aS,11aS,11bR)-4-hydroxy-9-((S)-1-((R)-5-(hydroxymethyl)-4-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-9a,11b-dimethyl-5a,6,6a,6b,7,8,9,9a,10,11,11a,11b-dodecahydrocyclopenta[1,2]phenanthro[8a,9-b]oxiren-1(4H)-one

C28H38O6 (470.2668)


Withaferin A is a withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity. It has a role as an antineoplastic agent and an apoptosis inducer. It is a delta-lactone, a 4-hydroxy steroid, an enone, an ergostanoid, a secondary alcohol, a withanolide, a 27-hydroxy steroid, a primary alcohol and an epoxy steroid. Ashwagandha is a popular Ayurvedic herb used as a general tonic, to increase energy and reduce stress. Ashwagandha has not been implicated in causing serum enzyme elevations during therapy, but recently has been implicated in rare cases of clinically apparent liver injury. Withaferin A is a natural product found in Vassobia breviflora, Withania somnifera, and other organisms with data available. A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physalis longifolia, it exhibits cytotoxic activity. Withaferin A is a steroidal lactone isolated from Withania somnifera, inhibits NF-kB activation and targets vimentin, with potent antiinflammatory and anticancer activities. Withaferin A is an inhibitor of endothelial protein C receptor (EPCR) shedding. Withaferin A is a steroidal lactone isolated from Withania somnifera, inhibits NF-kB activation and targets vimentin, with potent antiinflammatory and anticancer activities. Withaferin A is an inhibitor of endothelial protein C receptor (EPCR) shedding.

   

Taccalonolide B

[(1S,2S,3R,5S,7S,9S,10R,11R,12S,13S,14R,15R,16S,17S,22S,23S,24R,25R)-10,14-diacetyloxy-3,22,25-trihydroxy-11,15,17,22,23-pentamethyl-4,21-dioxo-8,20-dioxaheptacyclo[13.10.0.02,12.05,11.07,9.016,24.019,23]pentacos-18-en-13-yl] acetate

C34H44O13 (660.2782)


Taccalonolide B is a natural product found in Tacca plantaginea and Tacca chantrieri with data available. Taccalonolide B is microtubule stabilizer isolated from Tacca plantaginea, with antitumor activity. Taccalonolide B is effective in vitro against cell lines that overexpress P-glycoprotein (Pgp) and multidrug-resistance protein (MRP7). Taccalonolide B inhibits growth of SK-OV-3 cells with an IC50 of 208 nM[1][2]. Taccalonolide B is microtubule stabilizer isolated from Tacca plantaginea, with antitumor activity. Taccalonolide B is effective in vitro against cell lines that overexpress P-glycoprotein (Pgp) and multidrug-resistance protein (MRP7). Taccalonolide B inhibits growth of SK-OV-3 cells with an IC50 of 208 nM[1][2].

   

Withanoside X

27-O-beta-D-glucopyranosylpubesenolide 3-O-beta-D-glucopyranoside

C40H62O15 (782.4089)


   

Withanoside IX

27-O-beta-D-glucopyranosyl (1-6)-beta-D-glucopyranosylpubesenolide 3-O-beta-D-glucopyranosyl (1-6)-beta-D-glucopyranoside

C52H82O25 (1106.5145)


   

Withanoside XI

(20R,22R)-1alpha,3beta,20,27-tetrahydroxywitha-5,24-dienolide 3-O-beta-D-glucopyranoside

C34H52O11 (636.3509)


   

Withanoside VIII

27-O-beta-D-glucopyranosylpubesenolide 3-O-beta-D-glucopyranosyl (1-6)-beta-D-glucopyranoside

C46H72O20 (944.4617)


   

physachenolide D

1-oxo-18-acetoxy-14alpha,17beta,20S-trihydroxy-witha-1,5,24-trienolide

C30H40O8 (528.2723)


   

physachenolide E

1-oxo-18-acetoxy-5alpha,6beta,17beta,20S-tetrahydroxy-witha-1,14,24-trienolide

C30H40O9 (544.2672)


   

physachenolide A

1-oxo-18-acetoxy-5alpha,6beta,14alpha,17beta,20S-pentahydroxy-witha-1,24-dienolide

C30H42O10 (562.2778)


   

Withanolide A

(1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one

C28H38O6 (470.2668)


Withanolide A is a withanolide. withanolide A is a natural product found in Withania somnifera, Withania coagulans, and Discopodium penninervium with data available.

   

Physachenolide C

1-oxo-5beta,6beta-epoxy--18-acetoxy-14alpha,17beta,20S-trihydroxy-witha-1,24-dienolide

C30H40O9 (544.2672)


   

NCI60_001790

(1S,2R,6S,7R,9R,11R,12R,15S,16S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one

C28H38O8 (502.2567)


4beta-Hydroxywithanolide E is a withanolide. 4beta-Hydroxywithanolide E is a natural product found in Physalis peruviana, Physalis viscosa, and Physalis cinerascens with data available.

   

Physapubenolide

15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-13-yl acetate

C30H40O8 (528.2723)


   

Withaperuvin C

6-(1-hydroxy-1-{8,11,14-trihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-4,6-dien-14-yl}ethyl)-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one

C28H38O7 (486.2617)


   

Physalolactone B

14-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-3-yl acetate

C30H44O6 (500.3138)


   

Physagulin A

15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-12-hydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadeca-4,14-dien-13-yl acetate

C30H38O7 (510.2617)


   

ST 28:5;O3

(22E,24R)-9alpha,15beta-dihydroxyergosta-4,6,8(14),22-tetraene-3-one

C28H40O3 (424.2977)


   

ST 28:5;O5

(22E,24R)-4alpha,5alpha-epoxyergosta-9alpha,14alpha-dihydroxy-7,22-diene-3,6-dione

C28H40O5 (456.2876)


   

ST 27:4;O3

(25R)-5alpha,8alpha-epidioxy-24R,26-cyclo-cholest-6,22E-dien-3beta-ol

C27H40O3 (412.2977)


D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D045930 - Anabolic Agents D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D000728 - Androgens C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C2360 - Anabolic Steroid

   

ST 28:6;O7

5alpha,12alpha,15beta-trihydroxy-6alpha,7alpha-epoxy-1-oxo-22R-witha-2,24-dienolide

C28H38O7 (486.2617)


   

ST 28:6;O3

3-oxo-witha-1,4,24-trienolide

C28H38O3 (422.2821)


   

ST 29:7;O5

3-oxo-18-acetoxywitha-1,4,24-trienolide

C29H38O5 (466.2719)


   

ST 27:5;O3

28-nor-3-oxo-witha-1,4-dienolide

C27H38O3 (410.2821)


   

ST 28:6;O5

28-nor-3-oxo-18-acetoxy-witha-1,4-dienolide

C28H38O5 (454.2719)


   

ST 29:5;O5

28-nor-3-oxo-11alpha-acetoxy-with-4-enolide

C29H42O5 (470.3032)


   

ST 28:5;O8

(1S,2R,6S,7R,9R,11S,12S,14S,15R,16S)-15-[(1R,2R)-1-[(2R,3R,4R)-3,4-Dimethyl-5-oxooxolan-2-yl]-1,2-dihydroxypropan-2-yl]-6,14-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one

C28H40O8 (504.2723)


   

Physalolactone

17S,20S,22R-6alpha-chloro-4beta,5beta,17beta,14alpha,20alpha-pentahydroxy-1-oxo-ergosta-2,24-dienolide

C28H39O8Cl (538.2333)


   

Physalolactone C

17S,20S,22R-6alpha-chloro-4beta,5beta,17beta,20alpha-tetrahydroxy-1-oxo-ergosta-2,14,24-trienolide

C28H37O7Cl (520.2228)


   

Withanolide

(1S,2R,6S,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one

C28H38O6 (470.2668)


A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 22 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Tubocapsicum anomalum and Withania somnifera, it exhibits cytotoxic activity. Withanolides, which are extracted from Withania somnifera, are employed in the treatment of arthritis and are known to be potent inhibitors of angiogenesis, inflammation and oxidative stress. Withanolides can indeed inhibit the activation of NF-κB and NF-κB-regulated gene expression, which could explain their anti-arthritic actions. W. somnifera root powder has suppressive effect on arthritis by reducing amplification and propagation of the inflammatory response, without causing any gastric damage. (PMID: 17475558, 3248848, 17084827) [HMDB]

   

Withanolide

(3aS,5aR,9bR)-5a,9-dimethyl-3-methylene-4,5,6,7,8,9b-hexahydro-3aH-benzo[g]benzofuran-2-one

C28H38O6 (470.2668)


   

Withaperuvin B

17S,20S,22R-4beta,5beta,6alpha,17beta,20alpha-pentahydroxy-1-oxo-ergosta-2,14,24-trienolide

C28H38O8 (502.2567)


   

Exodeconolide E

16alpha-acetoxy-7alpha-hydroxy-24,25-epoxy-1-oxowitha-2,5-dien-26,22-olide

C30H40O7 (512.2774)


   

Exodeconolide F

14,15-dihydroxy-1-oxowitha-2,5,24-trien-26,22-olide

C28H38O5 (454.2719)


   

Exodeconolide D

16alpha-acetoxy-7alpha-hydroxy-22,26:24,25-diepoxy-26-hydroxyergost-2,5-dien-1-one

C30H42O7 (514.293)


   

FA 28:8;O5

(20S,22R)-3a,6a-epoxy-4beta,5beta,27-trihydroxy-1-oxowitha-24-enolide

C28H40O7 (488.2774)


   

Zenkersterone

2beta,3beta,14alpha 20R-tetrahydroxy-26(22)-olid-5beta-ergost-7-en-6-one

C28H42O8 (506.288)


   

Acutifolactone

(22R,24S,25S)-5alpha-hydroxy-7alpha,8alpha;24alpha,25alpha-diepoxy-1,12,16-trioxowitha-2,17(20)-dienolide

C28H32O8 (496.2097)


   

Withaperuvin

17S,20S,22R-4beta,5beta,6alpha,14alpha,17beta,20alpha-hexahydroxy-1-oxo-ergosta-2,24-dienolide

C28H40O9 (520.2672)


   

ST 28:6;O3

(22R)-3,26-Dioxo-22,26-epoxyergosta-1,4,24-trien-18-al

C28H36O4 (436.2613)


   

Nicansteroidin A

15alpha-acetoxy-5beta,6beta-epoxy-14beta,17beta,24beta-trihydroxy-1-oxo-witha-2,25(27)-dien-26,22-olide

C30H40O9 (544.2672)


   

Nicansteroidin B

15alpha-acetoxy-5beta,6beta-epoxy-14beta,17beta,24alpha-trihydroxy-1-oxo-witha-2,25(27)-dien-26,22-olide

C30H40O9 (544.2672)


   

Nicansteroidin C

15alpha-acetoxy-6beta,14beta-dihydroxy-1-oxo-2alpha,5alpha-dioxy-witha3,16,24-trien-26,22-olide

C30H38O9 (542.2516)


   

Nicansteroidin D

15alpha-acetoxy-16beta,17beta-epoxy-6beta,14beta-dihydroxy-1-oxo-2alpha,5alpha-dioxy-witha3,24-dien-26,22-olide

C30H38O10 (558.2465)


   

Physagulide I

15alpha-acetoxy-5beta,6beta-epoxy-14beta,17beta-dihydroxy-1-oxo-witha2,24-dien-26,22-olide

C30H40O8 (528.2723)


   

Physagulin K

15alpha-acetoxy-5alpha,6beta,14beta,17beta-tetrahydroxy-1-oxo-witha2,24-dien-26,22-olide

C30H42O9 (546.2829)


   

Withaminimin

15alpha-acetoxy-5alpha,6beta,14alpha-trihydroxy-1-oxo-witha2,16,24-trien-26,22-olide

C30H40O8 (528.2723)


   

Physagulin B

15alpha-acetoxy-5alpha-chloro-6beta,14alpha-dihydroxy-1-oxo-witha2,16,24-trien-26,22-olide

C30H39O7Cl (546.2384)


   

Physagulin D

1alpha,3beta,27-trihydroxywitha-5,24-dienolide 3-O-beta-D-glucopyranoside

C34H52O11 (636.3509)


   

Physagulin J

15alpha-acetoxy-5alpha,6beta,14beta,trihydroxy-1-oxo-witha2,24-dien-26,22-olide

C30H42O8 (530.288)


   

15alpha-acetoxy-5alpha-chloro-6beta,14beta,dihydroxy-1-oxo-witha2,24-dien-26,22-olide

15alpha-acetoxy-5alpha-chloro-6beta,14beta,dihydroxy-1-oxo-witha2,24-dien-26,22-olide

C30H41O7Cl (548.2541)


   

Physagulin C

15alpha-acetoxy-16beta,17beta-epoxy-5alpha-6beta,14beta,trihydroxy-1-oxo-witha2,24-dien-26,22-olide

C30H40O9 (544.2672)


   

Physagulin F

15alpha-acetoxy-5beta,6beta:16beta,17beta-diepoxy-4beta14beta,dihydroxy-1-oxo-witha2,24-dien-26,22-olide

C30H38O9 (542.2516)


   

Withacnistin

5beta,6beta:22R,26-diepoxyergosta-18-acetoxy-4beta-hydroxy-2,24-diene-1,26-dione

C30H40O7 (512.2774)


   

Withalongolide A

5beta,6beta:22R,26-diepoxyergosta-4beta,19,27-trihydroxy-2,24-diene-1,26-dione

C28H38O7 (486.2617)


A withanolide that is withaferin A substituted by a hydroxy group at position 19. Isolated from Physalis longifolia, it exhibits antineoplastic activitiy.

   

Withalongolide B

5beta,6beta:22R,26-diepoxyergosta-27-acetoxy-4beta,19-dihydroxy-2,24-diene-1,26-dione

C28H38O6 (470.2668)


A withanolide that is 27-deoxywithaferin A substituted by a hydroxy group at position 19. Isolated from Physalis longifolia, it exhibits antineoplastic activity.

   

Withalongolide C

5beta,6beta:22R,26-diepoxyergosta-4beta,11beta,19,27-tetrahydroxy-2,24-diene-1,26-dione

C28H38O8 (502.2567)


   

Sinubrasolide L

(24S,25R)-3-oxo-witha-1,4-dienolide

C28H40O3 (424.2977)


   

Physachenolide B

1-oxo-18-acetoxy-5alpha,6beta,14alpha,17beta,20S,28-hexahydroxy-witha-1,24-dienolide

C30H42O11 (578.2727)


   

Mantuoluoside D

(20S,22R)-1alpha,3beta,7alpha-trihydroxy-witha-5,24-dienolide 27-O-beta-D-glucopyranoside

C34H52O11 (636.3509)


   

Mantuoluoside E

(20S,22R)-1alpha,3beta,7beta-trihydroxy-witha-5,24-dienolide 27-O-beta-D-glucopyranoside

C34H52O11 (636.3509)


   

Mantuoluoside F

(20S,22R)-1alpha,7beta,28-trihydroxy-witha-5,24-dienolide 3-O-beta-D-glucopyranoside

C34H52O11 (636.3509)


   

Mantuoluoside G

(20S,22R)-1alpha,28-dihydroxy-7beta-methoxy-witha-5,24-dienolide 3-O-beta-D- glucopyranoside

C35H54O11 (650.3666)


   

Mantuoluoside H

(20S,22R)-1alpha,28-dihydroxy-alpha-methoxy-witha-5,24-dienolide 3-O-beta-D- glucopyranoside

C35H54O11 (650.3666)


   

ST 29:5;O8

2beta,3beta,14alpha,20R,27-pentahydroxy-27-methyl-witha-24-enolide

C29H42O8 (518.288)