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]

Flora	Rank	Flora Definition	Family	Family Definition
Caesalpinia	genus	A 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]	Fabaceae	The 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 Source	ID
PubMed CID	9817274
CHEMBL ID	249002
SCHEMBL ID	2521583
MeSH ID	M000609704

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.

Excerpt	Reference	Relevance
"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 ID	Title	Year	Journal	Article
AID718314	Antioxidant activity assessed as nitric oxide free radical scavenging activity by UV-visible spectroscopy	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID310683	Antioxidant activity assessed as DPPH free radical scavenging activity	2007	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24	Synthesis and antioxidant properties of substituted 3-benzylidene-7-alkoxychroman-4-ones.
AID310684	Antioxidant activity in Wistar rat brain assessed as inhibition of lipid peroxidation	2007	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24	Synthesis and antioxidant properties of substituted 3-benzylidene-7-alkoxychroman-4-ones.
AID341720	Inhibition of FGFR2 at 10 uM by ELISA	2008	Journal 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.
AID718306	Antiinflammatory 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 immunoblot	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID341706	Inhibition of c-Met at 10 uM by ELISA	2008	Journal 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.
AID718310	Effect 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 immunoblot	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID718316	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide generation incubated for 24 hrs	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID341713	Inhibition of cKit at 10 uM by ELISA	2008	Journal 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.
AID718308	Antiinflammatory 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 immunoblot	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID718313	Cytotoxicity against mouse RAW264.7 cells at 50 uM incubated for 24 hrs in absence of LPS by MTT assay	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID341711	Inhibition of EGFR at 10 uM by ELISA	2008	Journal 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.
AID718312	Cytotoxicity against mouse RAW264.7 cells at 50 uM incubated for 24 hrs in presence of LPS by MTT assay	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID310685	Antioxidant activity at 100 ug by ferric reducing antioxidant power assay	2007	Bioorganic & medicinal chemistry letters, Dec-15, Volume: 17, Issue:24	Synthesis and antioxidant properties of substituted 3-benzylidene-7-alkoxychroman-4-ones.
AID341707	Inhibition of FGFR1 at 10 uM by ELISA	2008	Journal 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.
AID718311	Antiinflammatory 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 immunoblot	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID1434585	Inhibition of LPS-induced NO production in mouse RAW264.7 cells preincubated for 1 hr followed by LPS stimulation for 24 hrs by Griess assay	2017	Bioorganic & 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.
AID718315	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced TNFalpha production incubated for 24 hrs by ELISA	2012	Journal of natural products, Dec-28, Volume: 75, Issue:12	Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity.
AID341705	Inhibition of c-Src at 10 uM by ELISA	2008	Journal 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.
AID341709	Inhibition of KDR at 10 uM by ELISA	2008	Journal 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.
AID718307	Antiinflammatory 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 immunoblot	2012	Journal 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)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	2 (10.53)	29.6817
2010's	9 (47.37)	24.3611
2020's	8 (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.

Metric	This Compound (vs All)
Research Demand Index	27.10 (24.57)
Research Supply Index	3.00 (2.92)
Research Growth Index	5.43 (4.65)
Search Engine Demand Index	29.35 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (27.10)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	19 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
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.	7.41	1	acetamides; 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.	2.41	1	alanine 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]	2.03	1	chromanol; monocarboxylic acid; phenols	antioxidant; ferroptosis inhibitor; neuroprotective agent; radical scavenger; Wnt signalling inhibitor
celastrol [no description available]	2.07	1	monocarboxylic 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]	2.04	1	catechols	metabolite
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.	2.04	1	haematoxylin
isoliquiritigenin [no description available]	2.04	1	chalcones	antineoplastic 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.	7.13	1
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.	2.11	1	prostaglandins E	human 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.	2.07	1	dimethoxyflavone; trihydroxyflavone	EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor; metabolite
butein [no description available]	2.04	1	chalcones; 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'.	2.04	1	chalcones; 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.	2.04	1	catechols; 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.	2.04	1	chalcones; 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.	2.15	1	cysteinium	fundamental 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.	2.07	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent

Condition	Relationship Strength	Studies
Acute Liver Injury, Drug-Induced [description not available]	2.41	1
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.	2.41	1
Airflow Obstruction, Chronic [description not available]	3.52	4
Lung Injury, Acute [description not available]	3.52	4
Pulmonary Disease, Chronic Obstructive A disease of chronic diffuse irreversible airflow obstruction. Subcategories of COPD include CHRONIC BRONCHITIS and PULMONARY EMPHYSEMA.	3.52	4
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).	3.52	4
Injury, Myocardial Reperfusion [description not available]	3.18	4
Left Ventricular Dysfunction [description not available]	7.25	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.9	3
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.	2.25	1
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.31	1
Injury, Ischemia-Reperfusion [description not available]	2.31	1
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	7.31	1
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.	2.31	1
Innate Inflammatory Response [description not available]	2.15	1
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.	2.15	1
Rheumatoid Arthritis [description not available]	2.15	1
Bone Loss, Osteoclastic [description not available]	2.15	1
Age-Related Osteoporosis [description not available]	2.15	1
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.	2.15	1
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.	2.15	1
Anoxemia [description not available]	2.21	1
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	7.21	1
Adverse Drug Event [description not available]	2.13	1
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.13	1
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.	2.13	1
Asthma, Bronchial [description not available]	2.13	1
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).	7.13	1
B16 Melanoma [description not available]	2.07	1

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