Compounds > sappanone a
Page last updated: 2024-12-11

sappanone a

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

Description

sappanone A: melanogenesis inhibitor from Caesalpinia sappan; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
CaesalpiniagenusA plant genus of the family FABACEAE. The common name of Bird-Of-Paradise is also used for other plants such as Heliconia (HELICONIACEAE) and Strelitzia (STRELITZIACEAE) and some birds. The common name of Cat's-Claw is more often used with UNCARIA. The common name of Pernambuco also refers to a state in Brazil. Furanoditerpenoid lactones and caesalpin are produced by members of this genus.[MeSH]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

Cross-References

ID SourceID
PubMed CID9817274
CHEMBL ID249002
SCHEMBL ID2521583
MeSH IDM000609704

Synonyms (18)

Synonym
CHEMBL249002
sappanone a
SCHEMBL2521583
Q18355119
104778-14-5
(3e)-3-[(3,4-dihydroxyphenyl)methylene]-2,3-dihydro-7-hydroxy-4h-1-benzopyran-4-one
(3e)-3-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxychromen-4-one
MS-24041
HY-113556
CS-0062747
4h-1-benzopyran-4-one, 3-[(3,4-dihydroxyphenyl)methylene]-2,3-dihydro-7-hydroxy-, (3e)-
4h-1-benzopyran-4-one, 3-((3,4-dihydroxyphenyl)methylene)-2,3-dihydro-7-hydroxy-, (3e)-
4h-1-benzopyran-4-one, 3-((3,4-dihydroxyphenyl)methylene)-2,3-dihydro-7-hydroxy-
659e9z3j5x ,
3-((3,4-dihydroxyphenyl)methylene)-2,3-dihydro-7-hydroxy-4h-1-benzopyran-4-one
(3e)-3-((3,4-dihydroxyphenyl)methylene)-2,3-dihydro-7-hydroxy-4h-1-benzopyran-4-one
unii-659e9z3j5x
(3e)-3-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-3,4-dihydro-2h-1-benzopyran-4-one

Research Excerpts

Overview

Sappanone A (SA) is a homoisoflavonoid compound isolated from Caesalpinia sappan L. It may be a promising therapeutic agent to prevent the vicious cycle of COPD inflammation and oxidative stress.

ExcerptReferenceRelevance
"Sappanone A is a natural PDE4 inhibitor with dual anti-inflammatory and antioxidant activities from the traditional Chinese medicine Sumu, which may be a promising therapeutic agent to prevent the vicious cycle of COPD inflammation and oxidative stress."( Sappanone A: A natural PDE4 inhibitor with dual anti-inflammatory and antioxidant activities from the heartwood of Caesalpinia sappan L.
Che, HJ; Jia, YH; Li, TT; Wang, HF; Wang, JX; Wang, YL; Wang, YZ; Yang, K; Zuo, LF, 2023)		3.8
"Sappanone A (SA) is a homoisoflavonoid compound isolated from Caesalpinia sappan L. "( Beneficial effects of sappanone A on lifespan and thermotolerance in Caenorhabditis elegans.
Gao, Y; Li, G; Shan, D; Sun, Y; Wang, Q; Wang, S; Zeng, K; Zhang, T; Zhang, W; Zhao, J; Zhu, A, 2020)		2.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID718314Antioxidant activity assessed as nitric oxide free radical scavenging activity by UV-visible spectroscopy2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID310683Antioxidant activity assessed as DPPH free radical scavenging activity2007Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24
Synthesis and antioxidant properties of substituted 3-benzylidene-7-alkoxychroman-4-ones.
AID310684Antioxidant activity in Wistar rat brain assessed as inhibition of lipid peroxidation2007Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24
Synthesis and antioxidant properties of substituted 3-benzylidene-7-alkoxychroman-4-ones.
AID341720Inhibition of FGFR2 at 10 uM by ELISA2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening.
AID718306Antiinflammatory activity in mouse RAW264.7 cells assessed as reduction of LPS-induced IkappaBalpha resynthesis at 30 uM pre-treated for 30 mins before LPS challenge by immunoblot2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID341706Inhibition of c-Met at 10 uM by ELISA2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening.
AID718310Effect on alpha-tubulin protein expression in mouse RAW264.7 cells up to 10 uM pre-treated for 30 mins before LPS challenge for 18 hrs by immunoblot2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID718316Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide generation incubated for 24 hrs2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID341713Inhibition of cKit at 10 uM by ELISA2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening.
AID718308Antiinflammatory activity in mouse RAW264.7 cells assessed as reduction of LPS-induced IkappaBalpha degradation at 30 uM pre-treated for 30 mins before LPS challenge and measured after 15 mins by immunoblot2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID718313Cytotoxicity against mouse RAW264.7 cells at 50 uM incubated for 24 hrs in absence of LPS by MTT assay2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID341711Inhibition of EGFR at 10 uM by ELISA2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening.
AID718312Cytotoxicity against mouse RAW264.7 cells at 50 uM incubated for 24 hrs in presence of LPS by MTT assay2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID310685Antioxidant activity at 100 ug by ferric reducing antioxidant power assay2007Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24
Synthesis and antioxidant properties of substituted 3-benzylidene-7-alkoxychroman-4-ones.
AID341707Inhibition of FGFR1 at 10 uM by ELISA2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening.
AID718311Antiinflammatory activity in mouse RAW264.7 cells assessed as reduction of LPS-induced iNOS protein expression pre-treated for 30 mins before LPS challenge for 18 hrs by immunoblot2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID1434585Inhibition of LPS-induced NO production in mouse RAW264.7 cells preincubated for 1 hr followed by LPS stimulation for 24 hrs by Griess assay2017Bioorganic & medicinal chemistry letters, 02-01, Volume: 27, Issue:3
Lignan derivatives from Selaginella tamariscina and their nitric oxide inhibitory effects in LPS-stimulated RAW 264.7 cells.
AID718315Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced TNFalpha production incubated for 24 hrs by ELISA2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID341705Inhibition of c-Src at 10 uM by ELISA2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening.
AID341709Inhibition of KDR at 10 uM by ELISA2008Journal of medicinal chemistry, Aug-14, Volume: 51, Issue:15
Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening.
AID718307Antiinflammatory activity in mouse RAW264.7 cells assessed as reduction of LPS-induced IkappaBalpha degradation at 30 uM pre-treated for 30 mins before LPS challenge and measured after 5 mins by immunoblot2012Journal of natural products, Dec-28, Volume: 75, Issue:12
Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (19)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (10.53)29.6817
2010's9 (47.37)24.3611
2020's8 (42.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.10

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 Index27.10 (24.57)
Research Supply Index3.00 (2.92)
Research Growth Index5.43 (4.65)
Search Engine Demand Index29.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.10)

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%
Other19 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetaminophen
Acetaminophen: Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.		7.4110acetamides;
phenols		antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
cyclooxygenase 3 inhibitor;
environmental contaminant;
ferroptosis inducer;
geroprotector;
hepatotoxic agent;
human blood serum metabolite;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic
alanine
Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.		2.4110alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid
[no description available]		2.0310chromanol;
monocarboxylic acid;
phenols		antioxidant;
ferroptosis inhibitor;
neuroprotective agent;
radical scavenger;
Wnt signalling inhibitor
celastrol
[no description available]		2.0710monocarboxylic acid;
pentacyclic triterpenoid		anti-inflammatory drug;
antineoplastic agent;
antioxidant;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
Hsp90 inhibitor;
metabolite
protosappanin a
[no description available]		2.0410catecholsmetabolite
hematoxylin
haematoxylin : An organic heterotetracyclic compound 7,11b-dihydroindeno[2,1-c]chromene carrying five hydroxy substituents at positions 3, 4, 6a, 9 and 10. The most important and most used dye in histology, histochemistry, histopathology and in cytology.		2.0410haematoxylin
isoliquiritigenin
[no description available]		2.0410chalconesantineoplastic agent;
biological pigment;
EC 1.14.18.1 (tyrosinase) inhibitor;
GABA modulator;
geroprotector;
metabolite;
NMDA receptor antagonist
ovalbumin
Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.		7.1310
dinoprostone
prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.		2.1110prostaglandins Ehuman metabolite;
mouse metabolite;
oxytocic
3,7-dimethoxy-5,3',4'-trihydroxyflavone
3,7-dimethoxy-5,3',4'-trihydroxyflavone: isolated from Veronia eremophila; structure given in first source. 3',4',5-trihydroxy-3,7-dimethoxyflavone : A dimethoxyflavone that the 3,7-di-O-methyl derivative of quercetin.		2.0710dimethoxyflavone;
trihydroxyflavone		EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor;
metabolite
butein
[no description available]		2.0410chalcones;
polyphenol		antineoplastic agent;
antioxidant;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
geroprotector;
hypoglycemic agent;
plant metabolite;
radiosensitizing agent;
tyrosine kinase inhibitor
isobavachalcone
isobavachalcone: RN given for (E)-isomer; structure in first source. isobavachalcone : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4' and a prenyl group at position 3'.		2.0410chalcones;
polyphenol		antibacterial agent;
metabolite;
platelet aggregation inhibitor
sappanchalcone
sappanchalcone: RN given from Toxline; RN not in Chemline 3/85; structure given in first source. sappanchalcone : A member of the class of chalcones that consists of trans-chalcone substituted by hydroxy groups at positions 3, 4 and 4' and a methoxy group at position 2'. Isolated from Caesalpinia sappan, it exhibits neuroprotective and cytoprotective activity.		2.0410catechols;
chalcones;
monomethoxybenzene		anti-allergic agent;
anti-inflammatory agent;
antioxidant;
metabolite
3-deoxysappanchalcone
3-deoxysappanchalcone: Anti-allergic from the roots and heartwood of Caesalpinia sappan; structure in first source. 2'-O-methylisoliquiritigenin : A member of the class of chalcones that is isoliquiritigenin in which one of the hydroxy groups at position 2' is replaced by a methoxy group.		2.0410chalcones;
monomethoxybenzene;
phenols		metabolite
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		2.1510cysteiniumfundamental metabolite
ascorbic acid
Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.		2.0710ascorbic acid;
vitamin C		coenzyme;
cofactor;
flour treatment agent;
food antioxidant;
food colour retention agent;
geroprotector;
plant metabolite;
skin lightening agent
ConditionIndicatedRelationship StrengthStudiesTrials
Acute Liver Injury, Drug-Induced
[description not available]		02.4110
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		02.4110
Airflow Obstruction, Chronic
[description not available]		03.5240
Lung Injury, Acute
[description not available]		03.5240
Pulmonary Disease, Chronic Obstructive
A disease of chronic diffuse irreversible airflow obstruction. Subcategories of COPD include CHRONIC BRONCHITIS and PULMONARY EMPHYSEMA.		03.5240
Acute Lung Injury
A condition of lung damage that is characterized by bilateral pulmonary infiltrates (PULMONARY EDEMA) rich in NEUTROPHILS, and in the absence of clinical HEART FAILURE. This can represent a spectrum of pulmonary lesions, endothelial and epithelial, due to numerous factors (physical, chemical, or biological).		03.5240
Injury, Myocardial Reperfusion
[description not available]		03.1840
Left Ventricular Dysfunction
[description not available]		07.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.930
Ventricular Dysfunction, Left
A condition in which the LEFT VENTRICLE of the heart was functionally impaired. This condition usually leads to HEART FAILURE; MYOCARDIAL INFARCTION; and other cardiovascular complications. Diagnosis is made by measuring the diminished ejection fraction and a depressed level of motility of the left ventricular wall.		02.2510
Cerebral Infarction, Middle Cerebral Artery
[description not available]		02.3110
Injury, Ischemia-Reperfusion
[description not available]		02.3110
Reperfusion Injury
Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.		07.3110
Infarction, Middle Cerebral Artery
NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.		02.3110
Innate Inflammatory Response
[description not available]		02.1510
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.		02.1510
Rheumatoid Arthritis
[description not available]		02.1510
Bone Loss, Osteoclastic
[description not available]		02.1510
Age-Related Osteoporosis
[description not available]		02.1510
Arthritis, Rheumatoid
A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.		02.1510
Osteoporosis
Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.		02.1510
Anoxemia
[description not available]		02.2110
Hypoxia
Sub-optimal OXYGEN levels in the ambient air of living organisms.		07.2110
Adverse Drug Event
[description not available]		02.1310
Kidney Diseases
Pathological processes of the KIDNEY or its component tissues.		02.1310
Drug-Related Side Effects and Adverse Reactions
Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.		02.1310
Asthma, Bronchial
[description not available]		02.1310
Asthma
A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).		07.1310
B16 Melanoma
[description not available]		02.0710