Compounds > palbinone
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palbinone

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Description

palbinone: terpenoid isolated from the roots of Paeonia albiflora; structure given in first source; showed strong inhibitory activity against 3-alpha-hydroxysteroid dehydrogenase [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
PaeoniagenusA plant genus of the family Paeoniaceae, order Dilleniales, subclass Dilleniidae, class Magnoliopsida. These perennial herbs are up to 2 m (6') tall. Leaves are alternate and are divided into three lobes, each lobe being further divided into three smaller lobes. The large flowers are symmetrical, bisexual, have 5 sepals, 5 petals (sometimes 10), and many stamens.[MeSH]Paeoniaceae[no description available]

Cross-References

ID SourceID
PubMed CID9841735
CHEBI ID69584
MeSH IDM0216001

Synonyms (16)

Synonym
139954-00-0
palbinone
chebi:69584 ,
txg6f287lt ,
18-norandrosta-11,13(17)-diene-15,16-dione, 3,17-dihydroxy-4,4,8,14-tetramethyl-, (3beta,5alpha)-
(-)-palbinone
Q27137926
FS-8612
18-norandrosta-11,13(17)-diene-15,16-dione, 3,17-dihydroxy-4,4,8,14-tetramethyl-, (3.beta.,5.alpha.)-
(3s,5r,8r,9r,10s,14s)-3,17-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9-hexahydro-1h-cyclopenta(a)phenanthrene-15,16-dione
(3.beta.,5.alpha.)-3,17-dihydroxy-4,4,8,14-tetramethyl-18-norandrosta-11,13(17)-diene-15,16-dione
CS-0023289
(3s,5r,8r,9r,10s,14s)-3,17-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9-hexahydro-1h-cyclopenta[a]phenanthrene-15,16-dione
HY-N3115
(3s,5r,8r,9r,10s,14s)-3,17-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9-hexahydro1h-cyclopenta[a]phenanthrene-15,16-dione
AKOS040733950
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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 (1)

ClassDescription
16-oxo steroidAny oxo steroid carrying an oxo group at position 16.
[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]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Aldo-keto reductase family 1 member B1Rattus norvegicus (Norway rat)IC50 (µMol)11.40000.00041.877310.0000AID470242
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID437581Increase in glycogen synthesis in human HepG2 cells assessed as incorporation of [14C]glucose in to cellular glycogen pools at 10 uM after 60 mins in presence of 33 mM glucose2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells.
AID437574Induction of GSK3-beta phosphorylation in human HepG2 cells by Western blot analysis in presence of 33 mM glucose2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells.
AID470243Inhibition of advanced glycation end product formation after 14 day in phosphate buffer at pH7.4 by spectrofluorimetry2009Journal of natural products, Aug, Volume: 72, Issue:8
Inhibitors of aldose reductase and formation of advanced glycation end-products in moutan cortex (Paeonia suffruticosa).
AID437583Induction of acetyl-coA carboxylase phosphorylation in human HepG2 cells by Western blot analysis in presence of 33 mM glucose2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells.
AID437584Increase in glycogen synthesis in human HepG2 cells assessed as incorporation of [14C]glucose in to cellular glycogen pools at 1 uM after 60 mins in presence of 33 mM glucose2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells.
AID437575Cytotoxicity against human HepG2 cells assessed as cell survival at 5 uM after 24 hrs by MTT assay2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells.
AID437577Cytotoxicity against human HepG2 cells assessed as cell survival at 20 uM after 24 hrs by MTT assay2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells.
AID623337Cytotoxicity against human M14 cells at 1 to 50 uM after 48 hrs by MTT assay2011Journal of natural products, Oct-28, Volume: 74, Issue:10
Triterpenoid constituents from the roots of Paeonia rockii ssp. rockii.
AID437579Induction of AMPK phosphorylation in human HepG2 cells at 10 uM by Western blot analysis in presence of 33 mM glucose2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells.
AID437580Induction of GSK3-beta phosphorylation in human HepG2 cells at 10 uM by Western blot analysis in presence of 33 mM glucose2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells.
AID437582Induction of glucose uptake in human HepG2 cells at 10 uM in presence of 33 mM 2-[14C]-DOG by scintillation counting2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells.
AID437576Cytotoxicity against human HepG2 cells assessed as cell survival at 10 uM after 24 hrs by MTT assay2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells.
AID437573Induction of AMPK phosphorylation in human HepG2 cells by Western blot analysis in presence of 33 mM glucose2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells.
AID437585Induction of glucose uptake in human HepG2 cells in presence of 33 mM 2-[14C]-DOG by scintillation counting2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells.
AID437578Cytotoxicity against human HepG2 cells assessed as cell survival at 100 uM after 24 hrs by MTT assay2009Bioorganic & medicinal chemistry letters, Oct-01, Volume: 19, Issue:19
Palbinone and triterpenes from Moutan Cortex (Paeonia suffruticosa, Paeoniaceae) stimulate glucose uptake and glycogen synthesis via activation of AMPK in insulin-resistant human HepG2 Cells.
AID470242Inhibition of Sprague-Dawley rat lens aldose reductase by spectrofluorimetry2009Journal of natural products, Aug, Volume: 72, Issue:8
Inhibitors of aldose reductase and formation of advanced glycation end-products in moutan cortex (Paeonia suffruticosa).
[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-19900 (0.00)18.7374
1990's1 (16.67)18.2507
2000's2 (33.33)29.6817
2010's2 (33.33)24.3611
2020's1 (16.67)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%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
benzoic acid
Benzoic Acid: A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.. benzoic acid : A compound comprising a benzene ring core carrying a carboxylic acid substituent.. aromatic carboxylic acid : Any carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.		2.0610benzoic acidsalgal metabolite;
antimicrobial food preservative;
drug allergen;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor;
human xenobiotic metabolite;
plant metabolite
pimagedine
pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.		2.0510guanidines;
one-carbon compound		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
EC 1.4.3.4 (monoamine oxidase) inhibitor
oleanolic acid
[no description available]		2.4620hydroxy monocarboxylic acid;
pentacyclic triterpenoid		plant metabolite
paeonol
paeonol: structure		2.4620methoxybenzenes;
phenols		metabolite
ursolic acid
[no description available]		2.0510hydroxy monocarboxylic acid;
pentacyclic triterpenoid		geroprotector;
plant metabolite
betulinic acid
[no description available]		2.4620hydroxy monocarboxylic acid;
pentacyclic triterpenoid		anti-HIV agent;
anti-inflammatory agent;
antimalarial;
antineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
plant metabolite
hederagenin
[no description available]		2.0610dihydroxy monocarboxylic acid;
pentacyclic triterpenoid;
sapogenin		plant metabolite
tetramethylene glutaric acid
[no description available]		2.0510
sitosterol, (3beta)-isomer
Sobatum: tradename; active fraction of Solanum trilobatum; reduces side-effects of radiation-induced toxicity. sitosterol : A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3.		2.05103beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
C29-steroid;
phytosterols;
stigmastane sterol		anticholesteremic drug;
antioxidant;
mouse metabolite;
plant metabolite;
sterol methyltransferase inhibitor
glycogen
glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.		7.0510
lyoniside
daucosterol : A steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa.		2.0510beta-D-glucoside;
monosaccharide derivative;
steroid saponin		plant metabolite
23-hydroxybetulinic acid
23-hydroxybetulinic acid: structure in first source		2.0610triterpenoidmetabolite
peoniflorin
[no description available]		2.0510
benzoylpaeoniflorin
benzoylpaeoniflorin: from Paeonia lactiflora		2.4620
galloylpaeoniflorin
galloylpaeoniflorin: an acylated monoterpene glucoside from paeony root; structure in first source		2.0510
ConditionIndicatedRelationship StrengthStudiesTrials
Diabetes Mellitus, Adult-Onset
[description not available]		02.0510
Insulin Sensitivity
[description not available]		02.0510
Diabetes Mellitus, Type 2
A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.		02.0510
Insulin Resistance
Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.		02.0510
Innate Inflammatory Response
[description not available]		02.2510
Diabetic Retinopathy
Disease of the RETINA as a complication of DIABETES MELLITUS. It is characterized by the progressive microvascular complications, such as ANEURYSM, interretinal EDEMA, and intraocular PATHOLOGIC NEOVASCULARIZATION.		07.2510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.2510