Page last updated: 2024-12-08

eurycomanone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

eurycomanone: from Eurycoma longifolia; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

eurycomanone : A quassinoid isolated from Eurycoma longifolia and has been shown to exhibit antineoplastic and antimalarial activties. [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]

FloraRankFlora DefinitionFamilyFamily Definition
EurycomagenusA plant genus of the family SIMAROUBACEAE. Members contain quassinoids. There is Malaysian folk use of these plants for male virility.[MeSH]SimaroubaceaeA plant family of the order Sapindales, subclass Rosidae, class Magnoliopsida. Leaves are alternate and compound. Most have small flowers, bitter bark, and fleshy fruits that are sometimes winged. Members contain QUASSINS.[MeSH]
Eurycoma longifoliaspecies[no description available]SimaroubaceaeA plant family of the order Sapindales, subclass Rosidae, class Magnoliopsida. Leaves are alternate and compound. Most have small flowers, bitter bark, and fleshy fruits that are sometimes winged. Members contain QUASSINS.[MeSH]
EurycomagenusA plant genus of the family SIMAROUBACEAE. Members contain quassinoids. There is Malaysian folk use of these plants for male virility.[MeSH]SimaroubaceaeA plant family of the order Sapindales, subclass Rosidae, class Magnoliopsida. Leaves are alternate and compound. Most have small flowers, bitter bark, and fleshy fruits that are sometimes winged. Members contain QUASSINS.[MeSH]

Cross-References

ID SourceID
PubMed CID49798945
CHEMBL ID1171981
CHEBI ID65887
PubMed CID433873
MeSH IDM0493261

Synonyms (15)

Synonym
pasakbumin-a
CHEMBL1171981
chebi:65887 ,
picrasa-3,13(21)-diene-2,16-dione,11,2o-epoxy-1,11,12,14,15-pentahydroxy-,(1beta,11beta,12alpha,15beta)-,dihydrate
(1beta,11beta,12alpha,15beta)-1,11,12,14,15-pentahydroxy-11,20-epoxypicrasa-3,13(21)-diene-2,16-dione
Q27134379
nsc339187
quassinoid fr eurycoma longifolia
nsc-339187
eurycomanone
(1r,2r,3ar,3a1r,4r,6ar,7as,11s,11as,11br)-1,2,3a,4,11-pentahydroxy-8,11a-dimethyl-3-methylene-2,3,3a,4,7,7a,11,11a-octahydro-1h-1,3a1-(epoxymethano)dibenzo[de,g]chromene-5,10(6ah,11bh)-dione
BCP32936
pasakbumin a;pasakbumin-a
FT-0776748
(1r,4r,5r,7r,8r,11r,13s,17s,18s,19r)-4,5,7,8,17-pentahydroxy-14,18-dimethyl-6-methylidene-3,10-dioxapentacyclo[9.8.0.0^{1,7.0^{4,19.0^{13,18]nonadec-14-ene-9,16-dione

Research Excerpts

Treatment

ExcerptReferenceRelevance
"The treatment with eurycomanone reduced the abundance expression of the lung cancer markers, heterogeneous nuclear ribonucleoprotein (hnRNP) A2/B1, p53 tumor suppressor protein and other cancer-associated genes including prohibitin (PHB), annexin 1 (ANX1) and endoplasmic reticulum protein 28 (ERp28) but not the house keeping genes."( Eurycomanone suppresses expression of lung cancer cell tumor markers, prohibitin, annexin 1 and endoplasmic reticulum protein 28.
AbuBakar, S; Chan, KL; Cheong, WF; Shu, MH; Teh, CH; Wong, PF, 2012
)
2.14

Pharmacokinetics

ExcerptReferenceRelevance
"A validated HPLC analysis of eurycomanone (1), a bioactive quassinoid, in rat plasma following oral and intravenous administration of Eurycoma longifolia Jack extract was developed for pharmacokinetic and bioavailability studies."( Bioavailability and pharmacokinetic studies of eurycomanone from Eurycoma longifolia.
Chan, KL; Choy, WP; Low, BS; Ng, BH; Yuen, KH, 2005
)
0.88
"Despite the better pharmacokinetic profile of DHY, EN remains the main chemical contributor to plant bioactivity."( Comparing the pharmacokinetics of 13α,21-dihydroeurycomanone and eurycomanone exclusively enriched in Eurycoma longifolia extracts and their spermatogenesis enhancement in andrographolide-induced oligospermia in rats.
Chan, KL; Chung, WJ; Lee, CY, 2021
)
0.88

Bioavailability

ExcerptReferenceRelevance
"A validated HPLC analysis of eurycomanone (1), a bioactive quassinoid, in rat plasma following oral and intravenous administration of Eurycoma longifolia Jack extract was developed for pharmacokinetic and bioavailability studies."( Bioavailability and pharmacokinetic studies of eurycomanone from Eurycoma longifolia.
Chan, KL; Choy, WP; Low, BS; Ng, BH; Yuen, KH, 2005
)
0.88
" longifolia, its bioavailability (AUC0-∞) decreased by 29% while C(max) was reduced by 42% and T(max) was significantly prolonged by almost 86%."( Modification of propranolol's bioavailability by Eurycoma longifolia water-based extract.
Amrah, S; Gan, SH; Ismail, R; Ismail, Z; Salman, SA; Wahab, MS; Yuen, KH, 2010
)
0.36
" DHY showed better oral bioavailability (1."( Comparing the pharmacokinetics of 13α,21-dihydroeurycomanone and eurycomanone exclusively enriched in Eurycoma longifolia extracts and their spermatogenesis enhancement in andrographolide-induced oligospermia in rats.
Chan, KL; Chung, WJ; Lee, CY, 2021
)
0.88
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimalarialA drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
[role 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]

Drug Classes (9)

ClassDescription
quassinoidMembers of the class of triterpenoid, mostly isolated as bitter principles of the Simaroubaceae family. They are chemically regarded as degraded triterpenes and can be categorized into groups with C18, C19, C20, C22 and C25 skeletons.
delta-lactoneA lactone having a six-membered lactone ring.
cyclic etherAny ether in which the oxygen atom forms part of a ring.
enoneAn alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position.
organic heteropentacyclic compound
secondary alcoholA secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it.
tertiary alcoholA tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it.
pentolA polyol with five hydroxy groups.
secondary alpha-hydroxy ketoneAn alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing one hydrogen and one organyl group. Secondary alpha-hydroxy ketones are also known as acyloins, and are formally derived from reductive coupling of two carboxylic acid groups.
[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 (33)

Assay IDTitleYearJournalArticle
AID1918729Antiviral activity against SARS-CoV-2 infected in African green monkey Vero cells assessed as inhibition of viral growth incubated for 2 days by ELISA analysis2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID338761Cytotoxicity against human fibrosarcoma cells
AID338762Cytotoxicity against human melanoma cells
AID338767Antimalarial activity against Plasmodium falciparum D6 in human erythrocytes after 24 hrs by [3H]hypoxanthine uptake
AID1918734Cytotoxicity against human HepG2 cells assessed as reduction in cell viability incubated for 48 hrs by PrestoBlue reagent based assay2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID1918728Selectivity index, ratio of CC50 for cytotoxicity against human HCT-8 cells to IC50 for antiviral activity against HCoV-OC43 infected in human HCT-8 cells2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID1185873Cytotoxicity against human A549 cells assessed as cell viability at 100 uM by SRB assay2014Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16
Five new quassinoids and cytotoxic constituents from the roots of Eurycoma longifolia.
AID492425Antimalarial activity against Plasmodium falciparum2009Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9
Antimalarials from nature.
AID1918732Cytotoxicity against human Calu-3 cells assessed as reduction in cell viability incubated for 48 hrs by PrestoBlue reagent based assay2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID338766Cytotoxicity against mouse P388 cells
AID1070422Inhibition of NF-kappaB activity in TNF-alpha stimulated human HEK-293/NF-kB-luc cells at 30 uM incubated for 30 mins prior to TNF-alpha challenge for 4 hrs by luciferase reporter gene assay2014Journal of natural products, Mar-28, Volume: 77, Issue:3
NF-κB inhibitors from Eurycoma longifolia.
AID338760Cytotoxicity against human KBV1 cells
AID1918724Antiviral activity against HCoV-OC43 infected in human HCT-8 cells assessed as inhibition of viral growth at 10 uM incubated for 4 days by ELISA analysis relative to control2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID1185875Cytotoxicity against human HeLa cells assessed as cell viability at 10 uM by SRB assay2014Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16
Five new quassinoids and cytotoxic constituents from the roots of Eurycoma longifolia.
AID338765Cytotoxicity against human colon cancer cells
AID1918730Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability incubated for 48 hrs by PrestoBlue reagent based assay2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID338759Cytotoxicity against human KB cells
AID1918727Cytotoxicity against human HCT-8 cells assessed as redcution in cell viability incubated for 96 hrs by PrestoBlue reagent based assay2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID1918733Cytotoxicity against human MRC5 cells assessed as reduction in cell viability incubated for 48 hrs by PrestoBlue reagent based assay2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID1070420Growth inhibition of TNF-alpha stimulated human HEK-293/NF-kB-luc cells assessed as cell viability at 30 uM incubated for 30 mins prior to TNF-alpha challenge for 4 hrs by CellTracker Green CMFDA staining2014Journal of natural products, Mar-28, Volume: 77, Issue:3
NF-κB inhibitors from Eurycoma longifolia.
AID1070421Inhibition of NF-kappaB activity in TNF-alpha stimulated human HEK-293/NF-kB-luc cells incubated for 30 mins prior to TNF-alpha challenge for 4 hrs by luciferase reporter gene assay2014Journal of natural products, Mar-28, Volume: 77, Issue:3
NF-κB inhibitors from Eurycoma longifolia.
AID1070419Acute toxicity in po dosed mouse2014Journal of natural products, Mar-28, Volume: 77, Issue:3
NF-κB inhibitors from Eurycoma longifolia.
AID1185876Cytotoxicity against human HeLa cells assessed as cell viability at 100 uM by SRB assay2014Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16
Five new quassinoids and cytotoxic constituents from the roots of Eurycoma longifolia.
AID1918731Selectivity index, ratio of CC50 for cytotoxicity against African green monkey Vero cells to IC50 for antiviral activity against SARS-CoV-2 infected in African green monkey Vero cells2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID1918725Cytotoxicity against human HCT-8 cells assessed as redcution in cell viability at 10 uM incubated for 96 hrs by PrestoBlue reagent based assay relative to control2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID1185872Cytotoxicity against human A549 cells assessed as cell viability at 10 uM by SRB assay2014Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16
Five new quassinoids and cytotoxic constituents from the roots of Eurycoma longifolia.
AID338764Cytotoxicity against human breast cancer cells
AID338763Cytotoxicity against human lung cancer cells
AID1185871Cytotoxicity against human A549 cells assessed as cell viability at 1 uM by SRB assay2014Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16
Five new quassinoids and cytotoxic constituents from the roots of Eurycoma longifolia.
AID1918726Antiviral activity against HCoV-OC43 infected in human HCT-8 cells assessed as inhibition of viral growth incubated for 4 days by ELISA analysis2022Journal of natural products, 12-23, Volume: 85, Issue:12
Evaluating the
AID338768Antimalarial activity against Plasmodium falciparum W2 in human erythrocytes after 24 hrs by [3H]hypoxanthine uptake
AID1185874Cytotoxicity against human HeLa cells assessed as cell viability at 1 uM by SRB assay2014Bioorganic & medicinal chemistry letters, Aug-15, Volume: 24, Issue:16
Five new quassinoids and cytotoxic constituents from the roots of Eurycoma longifolia.
AID1070418Toxicity against brine shrimp2014Journal of natural products, Mar-28, Volume: 77, Issue:3
NF-κB inhibitors from Eurycoma longifolia.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (6.90)29.6817
2010's20 (68.97)24.3611
2020's7 (24.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.11

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

MetricThis Compound (vs All)
Research Demand Index31.11 (24.57)
Research Supply Index3.30 (2.92)
Research Growth Index5.62 (4.65)
Search Engine Demand Index70.78 (26.88)
Search Engine Supply Index4.00 (0.95)

This Compound (31.11)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials1 (4.00%)5.53%
Reviews1 (20.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
Other24 (96.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]