theasinensin a profile

theasinensin A: a tea polyphenol formed from (-)-epigallocatechin gallate, suppresses antibiotic resistance of methicillin-resistant Staphylococcus aureus [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

theasinensin A : A biflavonoid that is obtained by coupling of two molecules of (-)-epigallocatechin 3-gallate resulting in a bond between positions C-2 of the hydroxyphenyl ring. It is a natural product found in oolong tea. [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]

ID Source	ID
PubMed CID	442543
CHEMBL ID	349197
CHEBI ID	9518
SCHEMBL ID	449649
MeSH ID	M0460494

Synonym
DIVK1C_006283
KBIO1_001227
SPECTRUM_000210 ,
SPECTRUM5_000886
BSPBIO_003359
theasinensin a
89064-31-3
C09972
bgcdg
theasinensin d
2',2'''-bisepigallocatechin digallate
benzoic acid, 3,4,5-trihydroxy-, (4,4',5,5',6,6'-hexahydroxy[1,1'-biphenyl]-2,2'-diyl)bis[(2r,3r)-3,4-dihydro-5,7-dihydroxy-2h-1-benzopyran-2,3-diyl] ester
[(2r,3r)-2-[2-[6-[(2r,3r)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-chroman-2-yl]-2,3,4-trihydroxy-phenyl]-3,4,5-trihydroxy-phenyl]-5,7-dihydroxy-chroman-3-yl] 3,4,5-trihydroxybenzoate
KBIOSS_000690
KBIO2_005826
KBIO3_002861
KBIOGR_001292
KBIO2_000690
KBIO2_003258
SPECTRUM4_000886
SPECTRUM3_001800
SPECTRUM2_000166
SPBIO_000031
SPECPLUS_000187 ,
NCGC00178119-01
2-(2-{6-[5,7-dihydroxy-3-(3,4,5-trihydroxyphenylcarbonyloxy)-(2r,3r)-3,4-dihydro-2h-2-chromenyl]-2,3,4-trihydroxyphenyl}-3,4,5-trihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxyphenylcarbonyloxy)-(2r,3r)-3,4-dihydro-2h-chromene
bdbm50240891
CHEMBL349197 ,
chebi:9518 ,
CCG-38377
SCHEMBL449649
2',2'-bisepigallocatechin digallate
DTXSID50331871
theasinensin a (d)
Q27108424

Excerpt	Reference	Relevance
"Theasinensin A (TSA) is a major group of catechin dimers mainly found in oolong tea and black tea. "	( Antimelanogenesis Effects of Theasinensin A. Cho, JY; Hong, YD; Hwang, KH; Jung, YJ; Kim, D; Kim, E; Kopalli, SR; Lim, HY; Park, SH; Sung, GH, 2021)	2.36

Excerpt	Reference	Relevance
"Due to low bioavailability of dietary phenolic compounds in small intestine, their metabolism by gut microbiota is gaining increasing attention."	( Insights in the Recalcitrance of Theasinensin A to Human Gut Microbial Degradation. Bruins, ME; de Bruijn, WJC; Liu, Z; Sanders, MG; Vincken, JP; Wang, S, 2021)	0.9

Role	Description
apoptosis inducer	Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
anti-inflammatory agent	Any compound that has anti-inflammatory effects.
hypoglycemic agent	A drug which lowers the blood glucose level.
hepatoprotective agent	Any compound that is able to prevent damage to the liver.
EC 3.2.1.20 (alpha-glucosidase) inhibitor	An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-glucosidase (EC 3.2.1.20).
melanin synthesis inhibitor	A depigmentation agent which inhibits the synthesis of melanin.
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
anticoronaviral agent	Any antiviral agent which inhibits the activity of coronaviruses.
[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]

Class	Description
proanthocyanidin	A flavonoid oligomer obtained by the the condensation of two or more units of hydroxyflavans.
gallate ester	A benzoate ester that is any ester resulting from the formal condensation of the carboxy group of gallic acid (3,4,5-trihydroxybenzoic acid) with an alcoholic or phenolic hydroxy group.
biflavonoid	A flavonoid oligomer that is obtained by the oxidative coupling of at least two units of aryl-substituted benzopyran rings or its substituted derivatives, resulting in the two ring systems being joined together by a single atom or bond.
[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	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Squalene monooxygenase	Rattus norvegicus (Norway rat)	IC50 (µMol)	0.1300	0.0610	2.3446	10.0000	AID357310
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Assay ID	Title	Year	Journal	Article
AID1159550	Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening	2015	Nature cell biology, Nov, Volume: 17, Issue:11	6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
AID977602	Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	2013	Molecular pharmacology, Jun, Volume: 83, Issue:6	Structure-based identification of OATP1B1/3 inhibitors.
AID977599	Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	2013	Molecular pharmacology, Jun, Volume: 83, Issue:6	Structure-based identification of OATP1B1/3 inhibitors.
AID357310	Inhibition of rat squalene epoxidase	2001	Journal of natural products, Aug, Volume: 64, Issue:8	Ellagitannins and hexahydroxydiphenoyl esters as inhibitors of vertebrate squalene epoxidase.
AID1159607	Screen for inhibitors of RMI FANCM (MM2) intereaction	2016	Journal of biomolecular screening, Jul, Volume: 21, Issue:6	A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	4 (13.79)	29.6817
2010's	18 (62.07)	24.3611
2020's	7 (24.14)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (3.45%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	28 (96.55%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
digallic acid digallic acid: structure given in first source	2.06	1	benzoate ester; gallate ester
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	2.95	4	trihydroxybenzoic acid	antineoplastic agent; antioxidant; apoptosis inducer; astringent; cyclooxygenase 2 inhibitor; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; geroprotector; human xenobiotic metabolite; plant metabolite
carbon tetrachloride Carbon Tetrachloride: A solvent for oils, fats, lacquers, varnishes, rubber waxes, and resins, and a starting material in the manufacturing of organic compounds. Poisoning by inhalation, ingestion or skin absorption is possible and may be fatal. (Merck Index, 11th ed). tetrachloromethane : A chlorocarbon that is methane in which all the hydrogens have been replaced by chloro groups.	7.15	1	chlorocarbon; chloromethanes	hepatotoxic agent; refrigerant
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	4.09	14	catechin	antioxidant; plant metabolite
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	2.31	1	indazole
podophyllotoxin Podophyllum: A genus of poisonous American herbs, family BERBERIDACEAE. The roots yield PODOPHYLLOTOXIN and other pharmacologically important agents. The plant was formerly used as a cholagogue and cathartic. It is different from the European mandrake, MANDRAGORA.	2.41	1	furonaphthodioxole; lignan; organic heterotetracyclic compound	antimitotic; antineoplastic agent; keratolytic drug; microtubule-destabilising agent; plant metabolite; tubulin modulator
hesperidin Hesperidin: A flavanone glycoside found in CITRUS fruit peels.. hesperidin : A disaccharide derivative that consists of hesperetin substituted by a 6-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.	7.11	1	3'-hydroxyflavanones; 4'-methoxyflavanones; dihydroxyflavanone; disaccharide derivative; flavanone glycoside; monomethoxyflavanone; rutinoside	mutagen
ethyl gallate ethyl gallate: used with osmium in procedure for mapping neuronal pathways. ethyl gallate : A gallate ester obtained by the formal condensation of gallic acid with ethanol.	2	1	gallate ester	plant metabolite
lauryl gallate [no description available]	2	1	gallate ester
octyl gallate [no description available]	2	1	gallate ester	food antioxidant; hypoglycemic agent; plant metabolite
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	3.42	7	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose pentagalloylglucose: pentahydroxy gallic acid ester of glucose; a phytogenic antineoplastic agent and antibacterial agent. 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose : A galloyl-beta-D-glucose compound having five galloyl groups in the 1-, 2-, 3-, 4- and 6-positions.	2	1	gallate ester; galloyl beta-D-glucose	anti-inflammatory agent; antineoplastic agent; geroprotector; hepatoprotective agent; plant metabolite; radiation protective agent; radical scavenger
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	2.31	1	1,2,3-triazole
corilagin corilagin: isolated from Geranii herba. corilagin : An ellagitannin with a hexahydroxydiphenoyl group bridging over the 3-O and 6-O of the glucose core.	2	1	ellagitannin; gallate ester	antihypertensive agent; antioxidant; EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor; non-steroidal anti-inflammatory drug
casuarictin sanguiin H 11: regulates chemotaxis of neutrophil; from plant, Sanguisorba officinalis; structure in first source	2	1	tannin
procyanidin b2-3,3'-di-o-gallate procyanidin B2-3,3'-di-O-gallate: structure in first source	2	1	flavonoid oligomer
p-2 P-2: reaction products of polymerized ascorbic acid with polymerized formaldehyde	2.05	1
1,2,6-tri-o-galloyl-beta-d-glucopyranose 1,2,6-tri-O-galloyl-beta-D-glucopyranose: from Terminalia chebula fruits, effective against multidrug-resistant uropathogens; structure in first source. 1,2,6-tris-O-galloyl-beta-D-glucose : A galloyl-beta-D-glucose compound having the galloyl groups in the 1-, 2- and 6-positions.	2	1	gallate ester; galloyl beta-D-glucose
afzelechin afzelechin: from Hovenia dulcis; structure in first source. afzelechin : A tetrahydroxyflavan that is (2S)-flavan substituted by hydroxy groups at positions 3, 5, 7 and 4' respectively.	2.17	1	catechin; tetrahydroxyflavan	EC 3.2.1.20 (alpha-glucosidase) inhibitor; plant metabolite
Chebulagic acid [no description available]	2	1	tannin
eugeniin eugeniin: structure in first source. eugeniin : An ellagitannin isolated from the dried flower buds of Eugenia caryophyllata. It exhibits alpha-glucosidase inhibitory activity and antiviral activity against acyclovir and phosphonoacetic acid (PAA)-resistant herpes simplex virus type 1 (HSV-1) as well as the wild-type HSV-1.	2	1	beta-D-glucoside; ellagitannin; gallate ester; lactone	anti-HSV-1 agent; antifungal agent; antineoplastic agent; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
Pedunculagin pedunculagin: from the walnut (Juglans regia) pellicle	2	1	tannin
decitabine [no description available]	2.31	1	2'-deoxyribonucleoside
squalene Addavax: an oil-water nanoemulsion and adjuvant containing squalene, Tween 80, and sorbitane trioleate	2	1	triterpene	human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
Geraniin [no description available]	2	1	tannin
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.1	1
ellagic acid [no description available]	2	1	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
furosin furosin: an ellagitannin from extract of leaves & stems of Phyllanthus sellowianus; structure given in first source	2	1
piperidines Piperidines: A family of hexahydropyridines.	2.41	1
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.	7.06	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
gsk-2816126 GSK-2816126: inhibits EZH2 methyltransferase; structure in first source	2.31	1	piperazines; pyridines
gsk343 GSK343: an EZH2 methyltransferase inhibitor. GSK343 : A member of the class of indazoles that is 1-isopropyl-1H-indazole-4-carboxamide in which the nitrogen of the carboxamide group is substituted by a (6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl group and in which the indazole ring is substituted at position 6 by a 2-(4-methylpiperazin-1-yl)pyridin-4-yl group. A highly potent and selective EZH2 inhibitor (IC50 = 4 nM).	2.31	1	aminopyridine; indazoles; N-alkylpiperazine; N-arylpiperazine; pyridone; secondary carboxamide	antineoplastic agent; apoptosis inducer; EC 2.1.1.43 (enhancer of zeste homolog 2) inhibitor
thearubigin thearubigin: from black tea leaves; a catechin oxidized product; a mixture of heterogenous polyphenols	2.1	1

Condition	Relationship Strength	Studies
Benign Neoplasms [description not available]	3.53	2
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.	3.53	2
Anemia, Fanconi [description not available]	2.13	1
Fanconi Anemia Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)	2.13	1
Cancer of Pancreas [description not available]	3.33	4
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).	3.33	4
B16 Melanoma [description not available]	2.31	1
Hepatocellular Carcinoma [description not available]	2.31	1
Cancer of Liver [description not available]	2.31	1
Experimental Neoplasms [description not available]	2.31	1
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.31	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.31	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.52	2
Cirrhosis, Liver [description not available]	2.15	1
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	2.15	1
Overweight A status with BODY WEIGHT that is above certain standards. In the scale of BODY MASS INDEX, overweight is defined as having a BMI of 25.0-29.9 kg/m2. Overweight may or may not be due to increases in body fat (ADIPOSE TISSUE), hence overweight does not equal over fat.	2.08	1
Hypertriglyceridemia A condition of elevated levels of TRIGLYCERIDES in the blood.	2.49	2
Diabetes Mellitus, Adult-Onset [description not available]	2.08	1
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.	2.08	1
Anasarca [description not available]	2.1	1
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.1	1
Herpes Simplex Virus Infection [description not available]	2.06	1
Herpes Simplex A group of acute infections caused by herpes simplex virus type 1 or type 2 that is characterized by the development of one or more small fluid-filled vesicles with a raised erythematous base on the skin or mucous membrane. It occurs as a primary infection or recurs due to a reactivation of a latent infection. (Dorland, 27th ed.)	2.06	1
Carcinoma, Epidermoid [description not available]	2.02	1
Cancer of Esophagus [description not available]	2.02	1
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	2.02	1
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	2.02	1

theasinensin a

Description

Cross-References

Synonyms (35)

Research Excerpts

Overview

Bioavailability

Roles (8)

Drug Classes (3)

Protein Targets (1)

Inhibition Measurements

Bioassays (5)

Research

Studies (29)

Market Indicators

Research Demand Index: 20.87

Study Types