Compounds > taccalonolide a
Page last updated: 2024-11-08

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 SourceID
PubMed CID441685
CHEMBL ID1821838
CHEBI ID9388
MeSH IDM0452061

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.

ExcerptReferenceRelevance
"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

ExcerptReferenceRelevance
"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)

ClassDescription
withanolideAny 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 IDTitleYearJournalArticle
AID617639Antiproliferative activity against human HeLa cells after 48 hrs by SRB assay2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Identification and biological activities of new taccalonolide microtubule stabilizers.
AID1177715Antiproliferative activity against human HeLa cells by SRB assay2014Bioorganic & medicinal chemistry, Sep-15, Volume: 22, Issue:18
Taccalonolide microtubule stabilizers.
AID617633Cell 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 analysis2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Identification and biological activities of new taccalonolide microtubule stabilizers.
AID617736Toxicity 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%)2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Identification and biological activities of new taccalonolide microtubule stabilizers.
AID1349922Antiproliferative activity against human HeLa cells after 48 hrs by sulforhodamine B assay2018Journal 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.
AID617641Antitumor 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 control2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Identification and biological activities of new taccalonolide microtubule stabilizers.
AID617737Toxicity 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%)2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Identification and biological activities of new taccalonolide microtubule stabilizers.
AID1070877Cell cycle arrest in human HeLa cells assessed as accumulation at G2/M phase at 5 uM by flow cytometry2013Journal of natural products, Oct-25, Volume: 76, Issue:10
The bat flower: a source of microtubule-destabilizing and -stabilizing compounds with synergistic antiproliferative actions.
AID616231Inhibition of beta tubulin in human HeLa cells assessed asultiple abnormal mitotic spindle formation at 3.5 uM after 18 hrs by immunofluorescence analysis2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Identification and biological activities of new taccalonolide microtubule stabilizers.
AID617730Antitumor 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 control2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Identification and biological activities of new taccalonolide microtubule stabilizers.
AID616239Toxicity in B6C3F1 mouse allografted with mouse 16/C cells assessed as lethality at 56 mg/kg, iv2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Identification and biological activities of new taccalonolide microtubule stabilizers.
AID1070876Antimitotic activity in human HeLa cells assessed as abberent multiple spindle asters at 5 uM by indirect immunofluorescence assay relative to vehicle-treated control2013Journal of natural products, Oct-25, Volume: 76, Issue:10
The bat flower: a source of microtubule-destabilizing and -stabilizing compounds with synergistic antiproliferative actions.
AID617649Antitumor 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 control2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Identification and biological activities of new taccalonolide microtubule stabilizers.
AID617648Antitumor 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 control2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Identification and biological activities of new taccalonolide microtubule stabilizers.
AID762819Antiproliferative activity against human HeLa cells after 48 hrs by SRB assay2013Journal of natural products, Jul-26, Volume: 76, Issue:7
Hydrolysis reactions of the taccalonolides reveal structure-activity relationships.
AID617546Induction of interphase microtubule bundling in human HeLa cells at 3.5 uM after 18 hrs by indirect immunofluorescence analysis2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Identification and biological activities of new taccalonolide microtubule stabilizers.
AID617729Antitumor 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 control2011Journal of medicinal chemistry, Sep-08, Volume: 54, Issue:17
Identification and biological activities of new taccalonolide microtubule stabilizers.
AID617642Antitumor 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 control2011Journal 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)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (15.38)29.6817
2010's10 (76.92)24.3611
2020's1 (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.

MetricThis Compound (vs All)
Research Demand Index12.33 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.97 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.33)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (15.38%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (84.62%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
nocodazole
[no description available]		2.0610aromatic ketone;
benzimidazoles;
carbamate ester;
thiophenes		antimitotic;
antineoplastic agent;
microtubule-destabilising agent;
tubulin modulator
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		8.1850taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
sorafenib
[no description available]		2.2510(trifluoromethyl)benzenes;
aromatic ether;
monochlorobenzenes;
phenylureas;
pyridinecarboxamide		angiogenesis inhibitor;
anticoronaviral agent;
antineoplastic agent;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
ferroptosis inducer;
tyrosine kinase inhibitor
fosbretabulin
[no description available]		2.0810stilbenoid
laulimalide
laulimalide: isolated from Cacospongia mycofijiensis; structure in first source. laulimalide : A macrolide with formula C30H42O7 that is isolated from the marine sponges, Cacospongia mycofijiensis and Hyattella sp.		2.0610carboxylic ester;
epoxide;
macrolide;
secondary alcohol;
secondary allylic alcohol		animal metabolite;
antimitotic;
antineoplastic agent;
marine metabolite;
microtubule-stabilising agent
taccalonolide e
taccalonolide E: has microtubule-stabilizing activity; isolated from Tacca chantrieri; structure in first source		4.460
taccalonolide aj
taccalonolide AJ: isolated from plants of the genus Tacca; structure in first source		3.5920
ConditionIndicatedRelationship StrengthStudiesTrials
Experimental Mammary Neoplasms
[description not available]		02.0610
Hepatocellular Carcinoma
[description not available]		02.2510
Cancer of Liver
[description not available]		02.2510
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.2510
Liver Neoplasms
Tumors or cancer of the LIVER.		02.2510
Experimental Neoplasms
[description not available]		02.110
Breast Cancer
[description not available]		02.4420
Carcinoma, Epidermoid
[description not available]		02.0610
Cancer of Mouth
[description not available]		02.0610
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.4420
Carcinoma, Squamous Cell
A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)		02.0610
Mouth Neoplasms
Tumors or cancer of the MOUTH.		02.0610
Cancer of Ovary
[description not available]		02.0110
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		02.0110