Compounds > epipodophyllotoxin
Page last updated: 2024-12-07

epipodophyllotoxin

Epipodophyllotoxin is a natural product isolated from the rhizomes of the plant Podophyllum peltatum (Mayapple). It exhibits potent anti-cancer activity by inhibiting topoisomerase II, an enzyme essential for DNA replication and repair. Its mechanism of action involves trapping the enzyme in a DNA-cleaved complex, preventing further DNA replication and ultimately leading to cell death. Epipodophyllotoxin is the precursor for the semi-synthetic drugs etoposide and teniposide, which are used clinically to treat various cancers, including lung cancer, testicular cancer, and leukemia. The study of epipodophyllotoxin and its derivatives has been instrumental in understanding the role of topoisomerase II in cancer cell growth and proliferation, leading to the development of several anti-cancer agents. Furthermore, ongoing research focuses on the development of new epipodophyllotoxin analogs with enhanced efficacy and reduced side effects, aiming to improve cancer treatment outcomes.'

Cross-References

ID SourceID
PubMed CID105111
CHEMBL ID282256
SCHEMBL ID5792464
MeSH IDM0017088

Synonyms (20)

Synonym
brn 0099162
furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5r-(5-alpha,5a-beta,8a-alpha,9-beta))-
furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5r,5ar,8ar,9s)-
epipodophyllotoxin
CHEMBL282256
(5s,5ar,8ar,9r)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
4375-07-9
SCHEMBL5792464
(10r,11r,15r,16s)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1(9),2,7-trien-12-one
(-)-epipodophyllotoxin
Q3589174
MS-27170
(5r)-5beta-(3,4,5-trimethoxyphenyl)-7alpha-(hydroxymethyl)-8alpha-hydroxy-5,6,7,8-tetrahydronaphtho[2,3-d]-1,3-dioxole-6beta-carboxylic acid 6,7-lactone
furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5ah)-one,5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-,(5r,5ar,8ar,9s)-
E80546
DTXSID10859440
(10r,11r,15r,16s)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one
EN300-20599945
CS-0134999
HY-N7654
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID398417Cytotoxicity against human HT-29 cells1995Journal of natural products, Jun, Volume: 58, Issue:6
Methyl ethers of podophyllotoxin-related cyclolignans.
AID83615In vitro cytotoxicity against the HT-29 (human colon carcinoma) neoplastic cell line2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Synthesis and cytotoxicity of hydrophobic esters of podophyllotoxins.
AID699782Growth inhibition of human HT-29 cells after 72 hrs by SRB assay2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Synthesis and antimitotic and tubulin interaction profiles of novel pinacol derivatives of podophyllotoxins.
AID398415Cytotoxicity against mouse P388 cells1995Journal of natural products, Jun, Volume: 58, Issue:6
Methyl ethers of podophyllotoxin-related cyclolignans.
AID404065Antiviral activity against HSV1 infected in human primary amnion cells assessed as inhibition of virus-induced pathogenic effect1998Journal of natural products, Nov, Volume: 61, Issue:11
Antiviral activity of lignans.
AID403984Therapeutic index, ratio of MTC for human primary amnion cells to lowest drug level causing inhibition of HSV11998Journal of natural products, Nov, Volume: 61, Issue:11
Antiviral activity of lignans.
AID404066Cytotoxicity against human primary amnion cells assessed as morphological changes by microscopic examination1998Journal of natural products, Nov, Volume: 61, Issue:11
Antiviral activity of lignans.
AID398416Cytotoxicity against human A549 cells1995Journal of natural products, Jun, Volume: 58, Issue:6
Methyl ethers of podophyllotoxin-related cyclolignans.
AID221407Compound was tested for Immunosuppression activity by mixed lymphocyte reaction (MLR) in murine splenocytes of mice1996Journal of medicinal chemistry, Jul-05, Volume: 39, Issue:14
Immunosuppressive cyclolignans.
AID140793Compound was tested for Cytotoxic activity by lymphocyte viability assay.1996Journal of medicinal chemistry, Jul-05, Volume: 39, Issue:14
Immunosuppressive cyclolignans.
AID152273In vitro cytotoxicity against the P-388 (from DBA/2 mouse) neoplastic cell line2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Synthesis and cytotoxicity of hydrophobic esters of podophyllotoxins.
AID235867Non cytotoxic IM activity index which is the ratio of IC50 of LcV to IC50 of MLR1996Journal of medicinal chemistry, Jul-05, Volume: 39, Issue:14
Immunosuppressive cyclolignans.
AID699781Growth inhibition of human A549 cells after 72 hrs by SRB assay2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Synthesis and antimitotic and tubulin interaction profiles of novel pinacol derivatives of podophyllotoxins.
AID9039In vitro cytotoxicity against the A-549 (human lung carcinoma) neoplastic cell line2004Bioorganic & medicinal chemistry letters, Mar-08, Volume: 14, Issue:5
Synthesis and cytotoxicity of hydrophobic esters of podophyllotoxins.
AID1123832Inhibition of chicken brain microtubule polymerization after 30 mins1979Journal of medicinal chemistry, Mar, Volume: 22, Issue:3
Conformational analysis of podophyllotoxin and its congeners. Structure--activity relationship in microtubule assembly.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (16.67)18.7374
1990's3 (50.00)18.2507
2000's1 (16.67)29.6817
2010's1 (16.67)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 43.28

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index43.28 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.71 (4.65)
Search Engine Demand Index57.69 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (43.28)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
podophyllotoxin
Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.		4.3460furonaphthodioxole;
lignan;
organic heterotetracyclic compound		antimitotic;
antineoplastic agent;
keratolytic drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator
etoposide
[no description available]		3.5120beta-D-glucoside;
furonaphthodioxole;
organic heterotetracyclic compound		antineoplastic agent;
DNA synthesis inhibitor
arctigenin
arctigenin: precursor to catechols; in many plants		3.0910lignan
picropodophyllin
picropodophyllin: isolated from American May apple (Podophyllum); inhibits IGF-I autophosphorylation without interfering with tyrosine kinase activity. picropodophyllotoxin : An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing 3,4,5-trimethoxyphenyl and hydroxy substituents.		440furonaphthodioxole;
lignan;
organic heterotetracyclic compound		antineoplastic agent;
insulin-like growth factor receptor 1 antagonist;
plant metabolite;
tyrosine kinase inhibitor
beta-peltatin
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.		3.4920furonaphthodioxole;
gamma-lactone;
lignan;
organic heterotetracyclic compound;
phenols		antineoplastic agent;
plant metabolite
alpha-peltatin
alpha-peltatin: RN given for (5R-(5alpha,5beta,8aalpha))-isomer. 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.		3.4920furonaphthodioxole;
gamma-lactone;
lignan;
organic heterotetracyclic compound;
phenols		antineoplastic agent;
metabolite
diphyllin
diphyllin: extract of Cleistanthus collinus (Roxb), a highly poisonous plant; do not confuse with diphyllin or diphylline which is the main heading AMINOPHYLLINE; do not confuse with the theophylline derivative DYPHYLLINE		3.0910lignan
4'-demethylpodophyllotoxin
4'-demethylpodophyllotoxin : An organic heterotetracyclic compound that is podophyllotoxin in which the methyl ether group at position 4 of the trimethoxyphenyl group has been cleaved to afford the corresponding phenol.		3.0910furonaphthodioxole;
organic heterotetracyclic compound;
phenols		metabolite
4'-demethylepipodophyllotoxin
4'-demethylepipodophyllotoxin: structure in first source. 4'-demethylepipodophyllotoxin : An organic heterotetracyclic compound that is the 9- epimer of 4'-demethylpodophyllotoxin.		3.0910furonaphthodioxole;
organic heterotetracyclic compound;
phenols		antineoplastic agent
beta-peltatin a methyl ether
beta-peltatin A methyl ether: isolated from Mexican plant Bursera fagaroides; antitumor agent of podophyllotoxin (III) class; RN given refers to (5alpha,5beta,8aalpha)-isomer		3.0910lactone;
lignan
justicidin a
justicidins: from Justica procumbens		3.0910lignan
4'-demethyldesoxypodophyllotoxin
4'-demethyldesoxypodophyllotoxin: from the root of Bursera tonkinensis Guillaum; structure in first source. 4'-demethyldeoxypodophyllotoxin : 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.		1.9910furonaphthodioxole;
gamma-lactone;
lignan;
methoxybenzenes;
phenols		antineoplastic agent;
antioxidant;
immunosuppressive agent;
plant metabolite
rubschisandrin
rubschisandrin: isolated from kernels of Schisandra rubriflora; structure given in first source		3.0910tannin
anthricin
anthricin: antitumor constituent from Anthriscus sylvestris (L.) Hoffm; structure in first source. deoxypodophyllotoxin : 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.		3.4720furonaphthodioxole;
gamma-lactone;
lignan;
methoxybenzenes		antineoplastic agent;
apoptosis inducer;
plant metabolite
schizandrin c
schizandrin C: from Schizandra chinensis Baill & Fructus schisandrae; protects liver from carbon tetrachloride injury;		3.0910tannin
doxorubicin hydrochloride
[no description available]		2.0710anthracycline
trachelogenin
trachelogenin: structure in first source		3.0910lignan
retrojusticidin b
retrojusticidin B: isolated from Phyllanthus myrtifolius; structure in first source		3.0910
gomisin j
gomisin J: a lignan from Schizandra fruits		3.0910
cyclosporine
ramihyphin A: one of the metabolites produced by Fusarium sp. S-435; RN given refers to cpd with unknown MF		1.9910homodetic cyclic peptideanti-asthmatic drug;
anticoronaviral agent;
antifungal agent;
antirheumatic drug;
carcinogenic agent;
dermatologic drug;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
geroprotector;
immunosuppressive agent;
metabolite
gomisin-g
[no description available]		3.0910
ConditionIndicatedRelationship StrengthStudiesTrials
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