Page last updated: 2024-12-08
taccalonolide a
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Market Indicators
Description
taccalonolide A: has microtubule stabilizing activity; isolated from Tacca chantrieri; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 441685 |
| CHEMBL ID | 1821838 |
| CHEBI ID | 9388 |
| MeSH ID | M0452061 |
Synonyms (17)
| Synonym |
|---|
| C08635 , |
| 108885-68-3 |
| taccalonolide a |
| AC1L9BGV , |
| CHEMBL1821838 , |
| chebi:9388 , |
| PTTJLTMUKRRHAT-VJAKQJMOSA-N |
| 5,7-dihydroxy-1,5,5a,11a,13a-pentamethyl-4,8-dioxo-4,5,5a,5b,6,6a,6b,7,8,8a,9,9a,10a,11,11a,11b,12,13,13a,13b-icosahydro-1h-oxireno[6',7']naphtho[1',2':7,8]fluoreno[2,1-b]furan-6,11,12,13-tetrayl tetraacetate |
| DTXSID80910895 |
| AKOS037515195 |
| Q27108373 |
| CS-0022618 |
| HY-N2416 |
| MS-31170 |
| 16,24-cycloergost-22-en-26-oicacid, 1,11,12,15-tetrakis(acetyloxy)-2,3-epoxy-7,23,25-trihydroxy-6-oxo-, g-lactone, (1a,2a,3a,5a,7b,11a,12a,15a,16b,24b,25s)- |
| A904550 |
| [(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 |
Research Excerpts
Overview
Taccalonolide A is a microtubule stabilizer that has cellular effects almost identical to paclitaxel. However, it does not enhance purified tubulin polymerization or bind tubulin/microtubules.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Taccalonolide A is a microtubule stabilizer that has cellular effects almost identical to paclitaxel. However, biochemical studies show that, unlike paclitaxel, taccalonolide A does not enhance purified tubulin polymerization or bind tubulin/microtubules. Mechanistic studies aimed at understanding the nature of the differences between taccalonolide A and paclitaxel were conducted. Our results show that taccalonolide A causes bundling of interphase microtubules at concentrations that cause antiproliferative effects. In contrast, the concentration of paclitaxel that initiates microtubule bundling is 31-fold higher than its IC 50. Taccalonolide A's effects are further differentiated from paclitaxel in that it is unable to enhance the polymerization of tubulin in cellular extracts. This finding extends previous biochemical results with purified brain tubulin to demonstrate that taccalonolide A requires more than tubulin and a full complement of cytosolic proteins to cause microtubule stabilization. Reversibility studies were conducted and show that the cellular effects of taccalonolide A persist after drug washout. In contrast, other microtubule stabilizers, including paclitaxel and laulimalide, demonstrate a much higher degree of cellular reversibility in both short-term proliferation and long-term clonogenic assays. The propensity of taccalonolide A to alter interphase microtubules at antiproliferative concentrations as well as its high degree of cellular persistence may explain why taccalonolide A is more potent in vivo than would be expected from cellular studies. The close linkage between the microtubule bundling and antiproliferative effects of taccalonolide A is of interest given the recent hypothesis that the effects of microtubule targeting agents on interphase microtubules might play a prominent role in their clinical anticancer efficacy." | ( Cellular studies reveal mechanistic differences between taccalonolide A and paclitaxel. Mooberry, SL; Risinger, AL, 2011) | 2.06 |
Effects
| Excerpt | Reference | Relevance |
|---|---|---|
| "Taccalonolide A has been reported to have anti-tumour efficiency. " | ( Anti-hepatoma effect of taccalonolide A through suppression of sonic hedgehog pathway. He, Z; Tian, H, 2020) | 2.31 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Drug Classes (1)
| Class | Description |
|---|---|
| withanolide | Any steroid lactone that is a C28 steroid with a modified side chain forming a lactone ring and its substituted derivatives. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
Bioassays (18)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID617639 | Antiproliferative activity against human HeLa cells after 48 hrs by SRB assay | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Identification and biological activities of new taccalonolide microtubule stabilizers. |
| AID1177715 | Antiproliferative activity against human HeLa cells by SRB assay | 2014 | Bioorganic & medicinal chemistry, Sep-15, Volume: 22, Issue:18 | Taccalonolide microtubule stabilizers. |
| AID617633 | Cell cycle arrest in human HeLa cells assessed as accumulation of cells at G2/M phase at 3.5 uM after 18 hrs by flow cytometric analysis | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Identification and biological activities of new taccalonolide microtubule stabilizers. |
| AID617736 | Toxicity in B6C3F1 mouse allografted with mouse 16/C cells assessed as mean body weight loss at 56 mg/kg, iv administered on days 1,4,6 and day 8 or 9 (Rvb = -2.2%) | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Identification and biological activities of new taccalonolide microtubule stabilizers. |
| AID1349922 | Antiproliferative activity against human HeLa cells after 48 hrs by sulforhodamine B assay | 2018 | Journal of natural products, 03-23, Volume: 81, Issue:3 | Taccalonolide Microtubule Stabilizers Generated Using Semisynthesis Define the Effects of Mono Acyloxy Moieties at C-7 or C-15 and Disubstitutions at C-7 and C-25. |
| AID617641 | Antitumor activity against mouse 16/C cells allografted in mouse B6C3F1 assessed as decrease in tumor mass at 56 mg/kg, iv administered on days 1,4,6 and day 8 or 9 relative to control | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Identification and biological activities of new taccalonolide microtubule stabilizers. |
| AID617737 | Toxicity in B6C3F1 mouse allografted with mouse 16/C cells assessed as mean body weight loss at 40 mg/kg, iv administered on days 1,4,6 and day 8 or 9 (Rvb = -2.2%) | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Identification and biological activities of new taccalonolide microtubule stabilizers. |
| AID1070877 | Cell cycle arrest in human HeLa cells assessed as accumulation at G2/M phase at 5 uM by flow cytometry | 2013 | Journal of natural products, Oct-25, Volume: 76, Issue:10 | The bat flower: a source of microtubule-destabilizing and -stabilizing compounds with synergistic antiproliferative actions. |
| AID616231 | Inhibition of beta tubulin in human HeLa cells assessed asultiple abnormal mitotic spindle formation at 3.5 uM after 18 hrs by immunofluorescence analysis | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Identification and biological activities of new taccalonolide microtubule stabilizers. |
| AID617730 | Antitumor activity against mouse 16/C cells allografted in mouse B6C3F1 assessed as gross log cell killing at 40 mg/kg, iv administered on days 1,4,6 and day 8 or 9 relative to control | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Identification and biological activities of new taccalonolide microtubule stabilizers. |
| AID616239 | Toxicity in B6C3F1 mouse allografted with mouse 16/C cells assessed as lethality at 56 mg/kg, iv | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Identification and biological activities of new taccalonolide microtubule stabilizers. |
| AID1070876 | Antimitotic activity in human HeLa cells assessed as abberent multiple spindle asters at 5 uM by indirect immunofluorescence assay relative to vehicle-treated control | 2013 | Journal of natural products, Oct-25, Volume: 76, Issue:10 | The bat flower: a source of microtubule-destabilizing and -stabilizing compounds with synergistic antiproliferative actions. |
| AID617649 | Antitumor activity against mouse 16/C cells allografted in mouse B6C3F1 assessed as delay in tumor growth at 40 mg/kg, iv administered on days 1,4,6 and day 8 or 9 relative to control | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Identification and biological activities of new taccalonolide microtubule stabilizers. |
| AID617648 | Antitumor activity against mouse 16/C cells allografted in mouse B6C3F1 assessed as delay in tumor growth at 56 mg/kg, iv administered on days 1,4,6 and day 8 or 9 relative to control | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Identification and biological activities of new taccalonolide microtubule stabilizers. |
| AID762819 | Antiproliferative activity against human HeLa cells after 48 hrs by SRB assay | 2013 | Journal of natural products, Jul-26, Volume: 76, Issue:7 | Hydrolysis reactions of the taccalonolides reveal structure-activity relationships. |
| AID617546 | Induction of interphase microtubule bundling in human HeLa cells at 3.5 uM after 18 hrs by indirect immunofluorescence analysis | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Identification and biological activities of new taccalonolide microtubule stabilizers. |
| AID617729 | Antitumor activity against mouse 16/C cells allografted in mouse B6C3F1 assessed as gross log cell killing at 56 mg/kg, iv administered on days 1,4,6 and day 8 or 9 relative to control | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Identification and biological activities of new taccalonolide microtubule stabilizers. |
| AID617642 | Antitumor activity against mouse 16/C cells allografted in mouse B6C3F1 assessed as decrease in tumor mass at 40 mg/kg, iv administered on days 1,4,6 and day 8 or 9 relative to control | 2011 | Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17 | Identification and biological activities of new taccalonolide microtubule stabilizers. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (13)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 2 (15.38) | 29.6817 |
| 2010's | 10 (76.92) | 24.3611 |
| 2020's | 1 (7.69) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
Market Indicators
Research Demand Index: 12.33
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (12.33) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 2 (15.38%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 11 (84.62%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||