Compounds > schweinfurthin a
Page last updated: 2024-12-09

schweinfurthin a

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Description

schweinfurthin A: a geranyl stilbene from plant Macaranga schweinfurthii; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
MacarangagenusA plant genus. Members contain mappain.[MeSH]EuphorbiaceaeThe spurge family of flowering plants in the order Malpighiales. The family consists of annual and perennial herbs and woody shrubs or trees. Members contain securinine.[MeSH]

Cross-References

ID SourceID
PubMed CID643462
CHEMBL ID232644
SCHEMBL ID847068
MeSH IDM0301021

Synonyms (12)

Synonym
1h-xanthene-2,3,5-triol, 7-[(e)-2-[4-[(2e)-3,7-dimethyl-2,6-octadienyl]-3,5-dihydroxyphenyl]ethenyl]-2,3,4,4a,9,9a-hexahydro-1,1,4a-trimethyl-, (2s,3r,4ar,9ar)-
schweinfurthin a
(2s,3r,4ar,9ar)-7-((e)-2-{4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-3,5-dihydroxyphenyl}vinyl)-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1h-xanthene-2,3,5-triol
217476-92-1
inchi=1/c34h44o6/c1-20(2)8-7-9-21(3)10-13-25-26(35)15-23(16-27(25)36)12-11-22-14-24-18-30-33(4,5)32(39)29(38)19-34(30,6)40-31(24)28(37)17-22/h8,10-12,14-17,29-30,32,35-39h,7,9,13,18-19h2,1-6h3/b12-11+,21-10+/t29-,30-,32-,34-/m1/s
nsc-696119
nsc696119
1h-xanthene-2,5-triol, 2,3,4,4a,9,9a-hexahydro-1,1,4a-trimethyl- 7-[2-[3,5-dihydroxy-4-(5,7-dimethyl- 2,6-octadienyl)phenyl]ethenyl]-
CHEMBL232644
(2s,3r,4ar,9ar)-7-[(e)-2-[4-[(2e)-3,7-dimethylocta-2,6-dienyl]-3,5-dihydroxyphenyl]ethenyl]-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2h-xanthene-2,3,5-triol
SCHEMBL847068
DTXSID80349186

Research Excerpts

Overview

Schweinfurthin A is a prenylated stilbene natural product. It has previously shown specific inhibitory activity against brain and hematopoietic tumor lines.

ExcerptReferenceRelevance
"Schweinfurthin A (Sch A) is a natural product with a selective and strong anti-cancer effect. "( The anti-cancer compound Schweinfurthin A targets Osh2 and disrupts lipid metabolism in the yeast model.
Gao, M; Moosavi, B; Yang, GF; Zhu, XL, 2020)		2.3
"Schweinfurthin A is a prenylated stilbene natural product that has previously shown specific inhibitory activity against brain and hematopoietic tumor lines."( Schweinfurthin A selectively inhibits proliferation and Rho signaling in glioma and neurofibromatosis type 1 tumor cells in a NF1-GRD-dependent manner.
Beutler, JA; Gürsel, DB; Lipschultz, CA; Lockett, SJ; Reilly, KM; Turbyville, TJ; Tuskan, RG; Walrath, JC; Wiemer, DF, 2010)		2.52
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (72)

Assay IDTitleYearJournalArticle
AID403491Cytotoxicity against human SF539 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403502Cytotoxicity against human UACC62 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403467Cytotoxicity against human CCRF-CEM cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403513Cytotoxicity against human RXF393 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403490Cytotoxicity against human SF295 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403501Cytotoxicity against human UACC257 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403504Cytotoxicity against human OVCAR-3 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403474Cytotoxicity against human EKVX cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403505Cytotoxicity against human OVCAR4 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403521Cytotoxicity against human MDA-MB-231 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403524Cytotoxicity against human MDA-N cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403508Cytotoxicity against human SKOV3 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403485Cytotoxicity against human HCT15 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403476Cytotoxicity against human HOP92 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403462Cytotoxicity against human A549 cells after 1 hr compound washout1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403506Cytotoxicity against human OVCAR5 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403518Cytotoxicity against human DU145 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403523Cytotoxicity against human MDA-MB-435 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403477Cytotoxicity against human NCI-H226 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403472Cytotoxicity against human SR cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403493Cytotoxicity against human SNB75 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403483Cytotoxicity against human HCC2998 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403481Cytotoxicity against human NCI-H522 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403496Cytotoxicity against human MALME-3M cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403486Cytotoxicity against human HT-29 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403509Cytotoxicity against human 786-O cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403489Cytotoxicity against human SF268 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403512Cytotoxicity against human Caki1 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403478Cytotoxicity against human NCI-H23 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403464Cytotoxicity against human SF295 cells after 1 hr1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID427260Cytotoxicity against human SF539 cells after 44 hrs by MTT assay2009Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13
Synthesis and biological activity of a fluorescent schweinfurthin analogue.
AID403488Cytotoxicity against human SW620 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403498Cytotoxicity against human SK-MEL-2 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403526Cytotoxicity against human T47D cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403499Cytotoxicity against human SK-MEL-28 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403517Cytotoxicity against human PC3 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403470Cytotoxicity against human MOLT4 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403492Cytotoxicity against human SNB19 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403522Cytotoxicity against human Hs 578T cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403468Cytotoxicity against human HL60 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403510Cytotoxicity against human A498 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403503Cytotoxicity against human IGROV1 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403469Cytotoxicity against human K562 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403479Cytotoxicity against human NCI-H322M cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403471Cytotoxicity against human RPMI8226 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403511Cytotoxicity against human ACHN cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403519Cytotoxicity against human MCF7 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403473Cytotoxicity against human A549 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403520Cytotoxicity against human doxorubicin-resistant MCF7 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403507Cytotoxicity against human OVCAR8 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403494Cytotoxicity against human U251 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403497Cytotoxicity against human M14 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403482Cytotoxicity against human COLO205 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403514Cytotoxicity against human SN12C cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403500Cytotoxicity against human SK-MEL-5 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID527730Cytotoxicity against human NCI60 cells2010Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22
Biologically active biotin derivatives of schweinfurthin F.
AID427261Cytotoxicity against human SNB75 cells after 44 hrs by MTT assay2009Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13
Synthesis and biological activity of a fluorescent schweinfurthin analogue.
AID403525Cytotoxicity against human BT549 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403480Cytotoxicity against human NCI-H460 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403516Cytotoxicity against human UO31 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403465Cytotoxicity against human SF295 cells after 1 hr compound washout1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403515Cytotoxicity against human TK10 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403475Cytotoxicity against human HOP62 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403484Cytotoxicity against human HCT116 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID293633Growth inhibition of NCI60 cells after 48 hrs2007Bioorganic & medicinal chemistry letters, Feb-15, Volume: 17, Issue:4
Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F: differences of bioactivity in the enantiomeric series.
AID403495Cytotoxicity against human LOXIMVI cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403463Cytotoxicity against human A549 cells after 48 hrs1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID403487Cytotoxicity against human KM12 cells1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID427252Cytotoxicity against human SF295 cells after 44 hrs by MTT assay2009Bioorganic & medicinal chemistry, Jul-01, Volume: 17, Issue:13
Synthesis and biological activity of a fluorescent schweinfurthin analogue.
AID403461Cytotoxicity against human A549 cells after 1 hr1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
AID1464146Growth inhibition of human NCI60 cells by sulforhodamine B assay2017Bioorganic & medicinal chemistry, 10-15, Volume: 25, Issue:20
Synthesis of amide isosteres of schweinfurthin-based stilbenes.
AID403466Cytotoxicity against human SF295 cells after 48 hrs1998Journal of natural products, Dec, Volume: 61, Issue:12
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (11.11)18.2507
2000's2 (22.22)29.6817
2010's5 (55.56)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.62

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 Index12.62 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.92 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.62)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
25-hydroxycholesterol
[no description available]		2.061025-hydroxy steroid;
oxysterol		human metabolite
osw 1
OSW 1: RN given for the (3beta,16beta)-isomer		2.0610
y 27632
Y 27632: RN given for di-HCl salt; inhibits Rho-associated protein kinase; inhibits calcium sensitization to affect smooth muscle relaxation; structure in first source. Y-27632 : A monocarboxylic acid amide that is trans-[(1R)-1-aminoethyl]cyclohexanecarboxamide in which one of the nitrogens of the aminocarbony group is substituted by a pyridine nucleus. It has been shown to exhibit inhibitory activity against Rho-associated protein kinase (ROCK) enzyme.		2.0510aromatic amide
stilbenes
Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.		3.1550stilbene
schweinfurthin b
schweinfurthin B: a geranyl stilbene from plant Macaranga schweinfurthii; structure in first source		2.4220
vedelianin
vedelianin: Cytotoxic; from Macaranga tanarius; structure in first source. vedelianin : A stilbenoid derivative isolated from Macaranga alnifolia and Macaranga alnifolia and has been shown to exhibit cytotoxic activity.		2.0310cyclic ether;
organic heterotricyclic compound;
resorcinols;
stilbenoid		antineoplastic agent;
plant metabolite
beta-escin
[no description available]		2.0610
schweinfurthin f
schweinfurthin F: structure in first source. schweinfurthin F : A stilbenoid isolated from Macaranga alnifolia and has been shown to exhibit cytotoxic activity.		2.4520cyclic ether;
organic heterotricyclic compound;
resorcinols;
stilbenoid		metabolite
glycolipids
[no description available]		2.0610
ritterazine b
ritterazine B: ritterazine analog extracted from Ritterella tokioka, has been shown to be chemically similar to cephalostatin 1; structure in first source		2.0610
cephalostatin i
cephalostatin I: two steroid units are annulated to a 1,4-pyrazine ring; RN given for (3'R-(3'alpha(R*),4'alpha,4'abeta,6'balpha,8'abeta,11'aalpha,11'bbeta,13'alpha,13'aalpha,13'bbeta,14'beta,15'alpha(3*R*,5''S*),16'abeta,17'balpha,19'abeta,22'aalpha,22'bbeta,24'aR'*))-isomer; structure in first source		2.0610
ConditionIndicatedRelationship StrengthStudiesTrials
Adenocarcinoma, Basal Cell
[description not available]		02.0510
Cancer of Lung
[description not available]		02.0510
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		02.0510
Lung Neoplasms
Tumors or cancer of the LUNG.		02.0510
Benign Neoplasms, Brain
[description not available]		02.0510
Glial Cell Tumors
[description not available]		02.0510
Cafe-au-Lait Spots with Pulmonic Stenosis
[description not available]		02.0510
Brain Neoplasms
Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.		02.0510
Glioma
Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)		07.0510
Neurofibromatosis 1
An autosomal dominant inherited disorder (with a high frequency of spontaneous mutations) that features developmental changes in the nervous system, muscles, bones, and skin, most notably in tissue derived from the embryonic NEURAL CREST. Multiple hyperpigmented skin lesions and subcutaneous tumors are the hallmark of this disease. Peripheral and central nervous system neoplasms occur frequently, especially OPTIC NERVE GLIOMA and NEUROFIBROSARCOMA. NF1 is caused by mutations which inactivate the NF1 gene (GENES, NEUROFIBROMATOSIS 1) on chromosome 17q. The incidence of learning disabilities is also elevated in this condition. (From Adams et al., Principles of Neurology, 6th ed, pp1014-18) There is overlap of clinical features with NOONAN SYNDROME in a syndrome called neurofibromatosis-Noonan syndrome. Both the PTPN11 and NF1 gene products are involved in the SIGNAL TRANSDUCTION pathway of Ras (RAS PROTEINS).		02.0510
Benign Neoplasms
[description not available]		02.0610
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.0610