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

psorospermin

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

Description

psorospermin: from Psorospermum febrifugum (Clusiaceae); some evidence it alkylates Gua N7 of DNA [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

psorospermin : An organic heterotetracyclic compound that is 1,2-dihydro-6H-furo[2,3-c]xanthene substituted by a hydroxy group at position 10, a methoxy group at position 5 nad a 2-methyloxiran-2-yl group at position 2. [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
Psorospermumgenus[no description available]Hypericaceae[no description available]
Psorospermum febrifugumspecies[no description available]Hypericaceae[no description available]

Cross-References

ID SourceID
PubMed CID126451
CHEMBL ID369474
CHEBI ID8617
SCHEMBL ID12312454
MeSH IDM0085027

Synonyms (14)

Synonym
74045-97-9
psorospermin
C10090 ,
AC1L2QCN ,
(2r)-10-hydroxy-5-methoxy-2-[(2r)-2-methyloxiran-2-yl]-1,2-dihydrofuro[2,3-c]xanthen-6-one
(2r)-10-hydroxy-5-methoxy-2-[(2r)-2-methyloxiran-2-yl]-1,2-dihydro-6h-furo[2,3-c]xanthen-6-one
chebi:8617 ,
CHEMBL369474 ,
psorospermine
6h-furo(2,3-c)xanthen-6-one, 1,2-dihydro-10-hydroxy-5-methoxy-2-(2-methyloxiranyl)-
SCHEMBL12312454
DTXSID60995463
10-hydroxy-5-methoxy-2-(2-methyloxiran-2-yl)-1,2-dihydro-6h-furo[2,3-c]xanthen-6-one
Q27108114

Research Excerpts

Overview

Psorospermin is a plant natural product that shows significant in vivo activity against P388 mouse leukemia. It has been shown to have activity against drug-resistant leukemia lines and AIDS-related lymphoma.

ExcerptReferenceRelevance
"Psorospermin is a natural product that has been shown to have activity against drug-resistant leukemia lines and AIDS-related lymphoma. "( Determination of the importance of the stereochemistry of psorospermin in topoisomerase II-induced alkylation of DNA and in vitro and in vivo biological activity.
Dexheimer, TS; Fellows, IM; Gleason-Guzman, M; Hurley, LH; Schwaebe, M; Vankayalapati, H; Whitten, JP, 2005)		2.02
"Psorospermin is a plant natural product that shows significant in vivo activity against P388 mouse leukemia. "( Topoisomerase II-mediated site-directed alkylation of DNA by psorospermin and its use in mapping other topoisomerase II poison binding sites.
Hurley, LH; Kwok, Y; Zeng, Q, 1998)		1.98
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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 (3)

ClassDescription
xanthonesAny member of the class of xanthenes based on a xanthone skeleton.
organic heterotetracyclic compound
epoxideAny cyclic ether in which the oxygen atom forms part of a 3-membered ring.
[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 (24)

Assay IDTitleYearJournalArticle
AID214557Inhibitory concentration against U937 lymphoma cancer cell line2003Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14
Design, synthesis, and evaluation of psorospermin/quinobenzoxazine hybrids as structurally novel antitumor agents.
AID398794Cytotoxicity against human KB cells
AID8427Inhibitory concentration against 8226 myeloma cancer cell line2003Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14
Design, synthesis, and evaluation of psorospermin/quinobenzoxazine hybrids as structurally novel antitumor agents.
AID335254Cytotoxicity against human MCF7 cells
AID422016In vivo cytotoxicity against mouse P388 cells at 8 mg/kg relative to control2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Antitumor psoropermum xanthones and sarcomelicope acridones: privileged structures implied in DNA alkylation.
AID247570Inhibitory concentration against HepG2 cell line2005Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8
Conformationally restricted analogues of psorospermin: design, synthesis, and bioactivity of natural-product-related bisfuranoxanthones.
AID247590Inhibitory concentration against COLO 320 cell line2005Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8
Conformationally restricted analogues of psorospermin: design, synthesis, and bioactivity of natural-product-related bisfuranoxanthones.
AID78557Inhibitory concentration against H522 (NSCLS) cancer cell line2003Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14
Design, synthesis, and evaluation of psorospermin/quinobenzoxazine hybrids as structurally novel antitumor agents.
AID398795Inhibition of mitosis in sea urchin egg at 1 uM
AID247557Inhibitory concentration against H522 cell line2005Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8
Conformationally restricted analogues of psorospermin: design, synthesis, and bioactivity of natural-product-related bisfuranoxanthones.
AID108085Inhibitory concentration against MIA PaCa pancreas cancer cell line2003Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14
Design, synthesis, and evaluation of psorospermin/quinobenzoxazine hybrids as structurally novel antitumor agents.
AID84454Inhibitory concentration against HT-29 colon cancer cell line2003Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14
Design, synthesis, and evaluation of psorospermin/quinobenzoxazine hybrids as structurally novel antitumor agents.
AID8428Inhibitory concentration against 8226/Dox40 (Dox-Re) cancer cell line2003Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14
Design, synthesis, and evaluation of psorospermin/quinobenzoxazine hybrids as structurally novel antitumor agents.
AID335252Cytotoxicity against human HT-29 cells
AID74857Inhibitory concentration against Granta lymphoma cancer cell line2003Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14
Design, synthesis, and evaluation of psorospermin/quinobenzoxazine hybrids as structurally novel antitumor agents.
AID247558Inhibitory concentration against HT-29 cell line2005Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8
Conformationally restricted analogues of psorospermin: design, synthesis, and bioactivity of natural-product-related bisfuranoxanthones.
AID398793In vivo antitumor activity against mouse P388 cells at 8 mg/kg
AID247591Inhibitory concentration against MIA PaCa cell line2005Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8
Conformationally restricted analogues of psorospermin: design, synthesis, and bioactivity of natural-product-related bisfuranoxanthones.
AID55810Inhibitory concentration against DU145 prostate cancer cell line2003Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14
Design, synthesis, and evaluation of psorospermin/quinobenzoxazine hybrids as structurally novel antitumor agents.
AID87781Inhibitory concentration against Hela cervix cancer cell line2003Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14
Design, synthesis, and evaluation of psorospermin/quinobenzoxazine hybrids as structurally novel antitumor agents.
AID335251Cytotoxicity against human A549 cells
AID103581Inhibitory concentration against MCF-7 breast cancer cell line2003Journal of medicinal chemistry, Jul-03, Volume: 46, Issue:14
Design, synthesis, and evaluation of psorospermin/quinobenzoxazine hybrids as structurally novel antitumor agents.
AID422015Cytotoxicity against human 9KB cells2009Journal of natural products, Mar-27, Volume: 72, Issue:3
Antitumor psoropermum xanthones and sarcomelicope acridones: privileged structures implied in DNA alkylation.
AID247559Inhibitory concentration against HeLa cell line2005Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8
Conformationally restricted analogues of psorospermin: design, synthesis, and bioactivity of natural-product-related bisfuranoxanthones.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (26.67)18.2507
2000's9 (60.00)29.6817
2010's2 (13.33)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%
Reviews3 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other15 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
urea
pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.		3.110isourea;
monocarboxylic acid amide;
one-carbon compound		Daphnia magna metabolite;
Escherichia coli metabolite;
fertilizer;
flour treatment agent;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
benzo(a)pyrene
Benzo(a)pyrene: A potent mutagen and carcinogen. It is a public health concern because of its possible effects on industrial workers, as an environmental pollutant, an as a component of tobacco smoke.. benzo[a]pyrene : An ortho- and peri-fused polycyclic arene consisting of five fused benzene rings.		2.0310ortho- and peri-fused polycyclic arenecarcinogenic agent;
mouse metabolite
norfloxacin
Norfloxacin: A synthetic fluoroquinolone (FLUOROQUINOLONES) with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin inhibits bacterial DNA GYRASE.. norfloxacin : A quinolinemonocarboxylic acid with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase.		210fluoroquinolone antibiotic;
N-arylpiperazine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone		antibacterial drug;
DNA synthesis inhibitor;
environmental contaminant;
xenobiotic
carbostyril
Quinolones: A group of derivatives of naphthyridine carboxylic acid, quinoline carboxylic acid, or NALIDIXIC ACID.. quinolin-2(1H)-one : A quinolone that is 1,2-dihydroquinoline substituted by an oxo group at position 2.		2.4120monohydroxyquinoline;
quinolone		bacterial xenobiotic metabolite
xanthenes
Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.		4.4870xanthene
deoxycytidine
[no description available]		2.0210pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
adenylyl imidodiphosphate
Adenylyl Imidodiphosphate: 5'-Adenylic acid, monoanhydride with imidodiphosphoric acid. An analog of ATP, in which the oxygen atom bridging the beta to the gamma phosphate is replaced by a nitrogen atom. It is a potent competitive inhibitor of soluble and membrane-bound mitochondrial ATPase and also inhibits ATP-dependent reactions of oxidative phosphorylation.		1.9910adenosine 5'-phosphate
gemcitabine
gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.		2.0210organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
DNA synthesis inhibitor;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
environmental contaminant;
immunosuppressive agent;
photosensitizing agent;
prodrug;
radiosensitizing agent;
xenobiotic
u 77779
bizelesin: structure given in first source		3.110
propamidine
propamidine: structure given in first source. propamidine : A polyether that is the bis(4-guanidinophenyl) ether of propane-1,3-diol. Used (as its isethionate salt) for the treatment of minor eye or eyelid infections, such as conjunctivitis and blepharitis.		3.110aromatic ether;
guanidines;
polyether		antimicrobial agent;
antiseptic drug
a 62176
A 62176: InChIKey: OLNJLTFSGFZCKE-JTQLQIEISA-N		2.4120
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		2.0410
acronine
Acronine: A pyrano-acridone alkaloid found in RUTACEAE plants.. acronycine : An alkaloid antineoplastic agent isolated from Acronychia baueri.		4.0640acridone derivatives;
alkaloid		antineoplastic agent;
metabolite
cc 1065
CC 1065: from Streptomyces zelensis; structure in second sourc		3.110
2,3,6,8-tetrahydroxy-1-(3-methylbut-2-enyl)-5-(2-methylbut-3-en-2-yl)-9h-xanthen-9-one
2,3,6,8-tetrahydroxy-1-(3-methylbut-2-enyl)-5-(2-methylbut-3-en-2-yl)-9H-xanthen-9-one: from the root bark of Cudrania tricuspidata; structure in first source. cudratricusxanthone A : A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 2, 3, 6 and 8, an isoprenyl group at position 1 and a 2-methylbut-3-en-2-yl group at position 5. It is isolated from the root barks of Cudrania tricuspidata and exhibits cytotoxicity towards human cancer cell lines.		3.1410polyphenol;
xanthones		anti-inflammatory agent;
antineoplastic agent;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
metabolite
chromomycins
Chromomycins: A complex of several closely related glycosidic antibiotics from Streptomyces griseus. The major component, CHROMOMYCIN A3, is used as a fluorescent stain of DNA where it attaches and inhibits RNA synthesis. It is also used as an antineoplastic agent, especially for solid tumors.. chromomycin : A family of antibiotics isolated from Streptomyces griseus.		3.110
guanine
[no description available]		1.99102-aminopurines;
oxopurine;
purine nucleobase		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Kahler Disease
[description not available]		02.0410
Multiple Myeloma
A malignancy of mature PLASMA CELLS engaging in monoclonal immunoglobulin production. It is characterized by hyperglobulinemia, excess Bence-Jones proteins (free monoclonal IMMUNOGLOBULIN LIGHT CHAINS) in the urine, skeletal destruction, bone pain, and fractures. Other features include ANEMIA; HYPERCALCEMIA; and RENAL INSUFFICIENCY.		02.0410
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.0210
Leucocythaemia
[description not available]		02.0210
Germinoblastoma
[description not available]		02.0210
Cancer of Pancreas
[description not available]		02.0210
Leukemia
A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)		02.0210
Lymphoma
A general term for various neoplastic diseases of the lymphoid tissue.		02.0210
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		02.0210
Ovine Diseases
[description not available]		0210
Acariasis
[description not available]		0210