Page last updated: 2024-09-27

dioncophylline a

Description

dioncophylline A: derived from the tropical vine Triphyophyllum peltatum; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

dioncophylline A : An isoquinoline alkaloid that is the biaryl resulting from substitution of the hydrogen at the 7-position of (1R,3R)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol by a 4,5-dimethoxy-2-methylnaphthalen-1-yl group. It is a naphthylisoquinoline alkaloid isolated from the roots and stem barks of Triphyophyllum peltatum and exhibits antifungal, antimalarial, antineoplastic and molluscicidal activites. [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
Triphyophyllumgenus[no description available]DioncophyllaceaeA plant family of the order Violales, subclass Dilleniidae class Magnoliopsida. Members contain naphthylisoquinolines which inhibit PLASMODIUM.[MeSH]
Triphyophyllum peltatumspecies[no description available]DioncophyllaceaeA plant family of the order Violales, subclass Dilleniidae class Magnoliopsida. Members contain naphthylisoquinolines which inhibit PLASMODIUM.[MeSH]

Cross-References

ID SourceID
PubMed CID443773
CHEMBL ID410597
CHEBI ID31504
CHEBI ID66272
MeSH IDM0272527

Synonyms (8)

Synonym
7-(4,5-dimethoxy-2-methylnaphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol
dioncophylline a
60142-17-8
chebi:31504 ,
CHEMBL410597
(1r,3r)-7-(4,5-dimethoxy-2-methylnaphthalen-1-yl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol
CHEBI:66272
DTXSID20975569

Roles (4)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
antifungal agentAn antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
molluscicideA substance used to destroy pests of the phylum Mollusca.
[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 (6)

ClassDescription
isoquinolinesA class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives.
naphthalenesAny benzenoid aromatic compound having a skeleton composed of two ortho-fused benzene rings.
isoquinoline alkaloidAny alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.
methylnaphthalenesAny naphthalene carrying one or more methyl substituents.
methoxynaphthaleneAny alkyloxynaphthalene bearing one or more methoxy substituents.
isoquinolinesA class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives.
biarylAn organic aromatic compound whose structure contains two aromatic rings or ring systems, joined to each other by a single bond.
[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 (15)

Assay IDTitleYearJournalArticle
AID403248Insecticidal activity against Spodoptera littoralis larvae assessed per gram of fresh weight of diet administered through artificial diet measured after 6 days1997Journal of natural products, Apr, Volume: 60, Issue:4
Dioncophylline A as a growth-retarding agent against the herbivorous insect Spodoptera littoralis: structure-activity relationships.
AID1483958Induction of apoptosis in human INA-6 cells after 3 days by V-FITC/ propidium iodide staining-based flow cytometric analysis2017Journal of natural products, 02-24, Volume: 80, Issue:2
Dioncophyllines C
AID304045Cytotoxicity against rat L6 cells2007Journal of medicinal chemistry, Nov-29, Volume: 50, Issue:24
Synthesis and pharmacological evaluation of fluorescent and photoactivatable analogues of antiplasmodial naphthylisoquinolines.
AID1483962Resistance index, ratio of IC50 for human CEM/ADR5000 cells to IC50 for human CCRF-CEM cells2017Journal of natural products, 02-24, Volume: 80, Issue:2
Dioncophyllines C
AID278848Cytotoxicity index, IC50 for J774.1 macrophages over IC50 for Leishmania major promastigotes2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Activities of naphthylisoquinoline alkaloids and synthetic analogs against Leishmania major.
AID1483960Growth inhibition of human CCRF-CEM cells at 10 uM by resazurin assay relative to control2017Journal of natural products, 02-24, Volume: 80, Issue:2
Dioncophyllines C
AID278847Cytotoxicity against J774.1 macrophages after 48 hrs2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Activities of naphthylisoquinoline alkaloids and synthetic analogs against Leishmania major.
AID1483961Growth inhibition of human CCRF-CEM cells by resazurin assay2017Journal of natural products, 02-24, Volume: 80, Issue:2
Dioncophyllines C
AID304046Inhibition of Plasmodium falciparum recombinant cysteine protease falcipain-22007Journal of medicinal chemistry, Nov-29, Volume: 50, Issue:24
Synthesis and pharmacological evaluation of fluorescent and photoactivatable analogues of antiplasmodial naphthylisoquinolines.
AID683706Antimalarial activity against liver stages of Plasmodium berghei in human HepG2 cells assessed as growth inhibition at 10 ug/mL2012Journal of medicinal chemistry, Feb-09, Volume: 55, Issue:3
Targeting the liver stage of malaria parasites: a yet unmet goal.
AID1541173Antiprotozoal activity against asexual erythrocytic form of chloroquine-sensitive Plasmodium falciparum NF54 clone A1A9 assessed as growth inhibition incubated for 42 hrs by [3H]-hypoxanthine incorporation assay
AID1314110Antitrypanosomal activity against Trypanosoma brucei brucei TC2212016Bioorganic & medicinal chemistry letters, 08-15, Volume: 26, Issue:16
New naphthalene derivatives and isoquinoline alkaloids from Ancistrocladus cochinchinensis with their anti-proliferative activity on human cancer cells.
AID1483963Growth inhibition of human multi-drug resistant CEM/ADR5000 cells by resazurin assay2017Journal of natural products, 02-24, Volume: 80, Issue:2
Dioncophyllines C
AID304044Antiplasmodial activity against Plasmodium falciparum in human red blood cells after 4 hrs2007Journal of medicinal chemistry, Nov-29, Volume: 50, Issue:24
Synthesis and pharmacological evaluation of fluorescent and photoactivatable analogues of antiplasmodial naphthylisoquinolines.
AID278846Cytotoxicity against cloned virulent Leishmania major promastigotes MHOM/IL/81/FE/BN1 after 48 hrs2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Activities of naphthylisoquinoline alkaloids and synthetic analogs against Leishmania major.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (23.53)18.2507
2000's6 (35.29)29.6817
2010's7 (41.18)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (11.76%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (88.24%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Pharmacokinetics (1)

ArticleYear
Biotransformation and pharmacokinetics of the antiplasmodial naphthylisoquinoline alkaloid dioncophylline A.
Xenobiotica; the fate of foreign compounds in biological systems, Volume: 36, Issue: 9
2006
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (1)

ArticleYear
Biotransformation and pharmacokinetics of the antiplasmodial naphthylisoquinoline alkaloid dioncophylline A.
Xenobiotica; the fate of foreign compounds in biological systems, Volume: 36, Issue: 9
2006
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (1)

ArticleYear
Naphthylisoquinoline alkaloids against malaria: evaluation of the curative potentials of dioncophylline C and dioncopeltine A against Plasmodium berghei in vivo.
Antimicrobial agents and chemotherapy, Volume: 41, Issue: 11
1997
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]