Page last updated: 2024-12-08

spinosin

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

Description

spinosin: isolated from seeds of Ziziph spinosa; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

spinosin : A flavone C-glycoside that is flavone substituted by hydroxy groups at positions 5 and 4', a methoxy group at position 7 and a 2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl residue at position 6 via a C-glycosidic linkage. [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]

Cross-References

ID Source	ID
PubMed CID	155692
CHEBI ID	81360
SCHEMBL ID	2980651
MeSH ID	M0156600

Synonyms (26)

Synonym
spinosin
6-[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
72063-39-9
C17834
6-(2-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4h-1-benzopyran-4-one
4h-1-benzopyran-4-one, 6-(2-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-
S9134
AKOS015897169
SCHEMBL2980651
(1s)-1,5-anhydro-2-o-beta-d-glucopyranosyl-1-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-4h-1-benzopyran-6-yl]-d-glucitol
flavoayamenin
2''-o-glycosylswertisin
CHEBI:81360
DTXSID50222396
Q-100793
AC-31296
mfcd09754430
Q27155298
HY-N0651
6-((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)tetrahydro-2h-pyran-2-yl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4h-chromen-4-one
BS-17968
HMS3886F18
CCG-270216
CS-0009676
A866326
P2887

Research Excerpts

Overview

Spinosin is a C-glycoside flavonoid isolated from the seeds of Zizyphus jujuba var.

Excerpt	Reference	Relevance
"Spinosin is a C-glycoside flavonoid isolated from the seeds of Zizyphus jujuba var. "	( Ameliorating effect of spinosin, a C-glycoside flavonoid, on scopolamine-induced memory impairment in mice. Ahn, YJ; Jang, DS; Jo, YW; Jung, IH; Kang, SS; Kim, JS; Kwon, G; Lee, HE; Lee, SY; Park, SJ; Ryu, JH; Woo, H, 2014)	2.16

Treatment

Excerpt	Reference	Relevance
"Treatments of spinosin and 6'''‑feruloylspinosin led to the reduction of glycogen synthase kinase‑3β (GSK3β) phosphorylation at Tyr216, and the increase of peroxisome proliferator‑activated receptor γ coactivator (PGC)‑1α and its downstream signaling proteins, including nuclear factor (erythroid‑derived 2)‑like 2 (Nrf2) and hemeoxygenase1 (HO‑1)."	( Spinosin and 6'''‑Feruloylspinosin protect the heart against acute myocardial ischemia and reperfusion in rats. Cheng, S; Gu, M; Gu, Y; He, P; Jia, Y; Liu, X; Lyu, C; Xu, Y, 2019)	2.3

Pharmacokinetics

Excerpt	Reference	Relevance
" The main pharmacokinetic parameters T(0."	( Pharmacokinetics and tissue distribution of spinosin after intravenous administration in rats. Dai, YH; Deng, YL; Li, Y; Li, YJ; Yu, YL, 2007)	0.6
" The validated method has been successfully applied to comparing pharmacokinetic profiles of analytes in rat plasma."	( A UFLC-MS/MS method for simultaneous quantitation of spinosin, mangiferin and ferulic acid in rat plasma: application to a comparative pharmacokinetic study in normal and insomnic rats. Bi, K; Chen, X; He, B; Jia, Y; Li, Q; Lv, C; Xiao, F; Xu, H; Zhao, L, 2012)	0.63
"To study the pharmacokinetic effect of different combined administration with monarch drug Ziziphi Spinosae Semen on its main components in rats."	( [Pharmacokinetic effect of combined administration on spinosin and ferulic acid in monarch drug Ziziphi Spinosae Semen kernel]. Chen, XJ; Fang, MF; Gao, R; Li, S; Wang, SX; Wang, XF, 2015)	0.67

Bioavailability

Excerpt	Reference	Relevance
"The results showed that the absorption rate constant (0."	( The preparation and investigation of spinosin-phospholipid complex self-microemulsifying drug delivery system based on the absorption characteristics of spinosin. Lai, C; Song, P; Xie, J; Zhang, Y, 2019)	0.79

Dosage Studied

Excerpt	Relevance	Reference
"The aim of this research was to investigate the intestinal absorption characteristics and mechanisms of spinosin (SPI), and a new dosage form was prepared to increase the intestinal absorption of SPI."	( The preparation and investigation of spinosin-phospholipid complex self-microemulsifying drug delivery system based on the absorption characteristics of spinosin. Lai, C; Song, P; Xie, J; Zhang, Y, 2019)	1

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

Role	Description
plant metabolite	Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
anxiolytic drug	Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.
[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 (3)

Class	Description
flavone C-glycoside	Any C-glycosyl compound arising formally from the elimination of water from a glycosidic hydroxy group and an H atom bound to a flavone skeleton, thus creating a C-C bond.
dihydroxyflavone	Any hydroxyflavone in which two ring hydrogens are replaced by hydroxy substituents.
monomethoxyflavone	Any methoxyflavone with a single methoxy substituent.
[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]

Research

Studies (39)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (2.56)	18.7374
1990's	0 (0.00)	18.2507
2000's	7 (17.95)	29.6817
2010's	22 (56.41)	24.3611
2020's	9 (23.08)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.25

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	32.25 (24.57)
Research Supply Index	3.69 (2.92)
Research Growth Index	4.89 (4.65)
Search Engine Demand Index	42.09 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (32.25)

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	39 (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
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	2.11	1	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
5-hydroxytryptophan 5-Hydroxytryptophan: The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.. 5-hydroxytryptophan : A tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5.	2.04	1	hydroxytryptophan	human metabolite; neurotransmitter
gallic acid gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.	2.31	1	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
8-hydroxy-2-(di-n-propylamino)tetralin 8-Hydroxy-2-(di-n-propylamino)tetralin: A serotonin 1A-receptor agonist that is used experimentally to test the effects of serotonin.. 8-OH-DPAT : A tetralin substituted at positions 1 and 7 by hydroxy and dipropylamino groups respectively	2.47	2	phenols; tertiary amino compound; tetralins	serotonergic antagonist
donepezil Donepezil: An indan and piperidine derivative that acts as a selective and reversible inhibitor of ACETYLCHOLINESTERASE. Donepezil is highly selective for the central nervous system and is used in the management of mild to moderate DEMENTIA in ALZHEIMER DISEASE.. donepezil : A racemate comprising equimolar amounts of (R)- and (S)-donepezil. A centrally acting reversible acetylcholinesterase inhibitor, its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine.. 2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxyindan-1-one : A member of the class of indanones that is 5,6-dimethoxyindan-1-one which is substituted at position 2 by an (N-benzylpiperidin-4-yl)methyl group.	7.25	1	aromatic ether; indanones; piperidines; racemate	EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; nootropic agent
flumazenil Flumazenil: A potent benzodiazepine receptor antagonist. Since it reverses the sedative and other actions of benzodiazepines, it has been suggested as an antidote to benzodiazepine overdoses.. flumazenil : An organic heterotricyclic compound that is 5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted at positions 3, 5, 6, and 8 by ethoxycarbonyl, methyl, oxo, and fluoro groups, respectively. It is used as an antidote to benzodiazepine overdose.	2.11	1	ethyl ester; imidazobenzodiazepine; organofluorine compound	antidote to benzodiazepine poisoning; GABA antagonist
fenclonine Fenclonine: A selective and irreversible inhibitor of tryptophan hydroxylase, a rate-limiting enzyme in the biosynthesis of serotonin (5-HYDROXYTRYPTAMINE). Fenclonine acts pharmacologically to deplete endogenous levels of serotonin.	2.04	1	phenylalanine derivative
4-(2'-methoxyphenyl)-1-(2'-(n-(2''-pyridinyl)-4-iodobenzamido)ethyl)piperazine 4-(2'-methoxyphenyl)-1-(2'-(N-(2''-pyridinyl)-4-iodobenzamido)ethyl)piperazine: a 5-HT(1A) ligand; structure in first source	2.47	2
pentobarbital Pentobarbital: A short-acting barbiturate that is effective as a sedative and hypnotic (but not as an anti-anxiety) agent and is usually given orally. It is prescribed more frequently for sleep induction than for sedation but, like similar agents, may lose its effectiveness by the second week of continued administration. (From AMA Drug Evaluations Annual, 1994, p236). pentobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and sec-pentyl groups.	2.75	3	barbiturates	GABAA receptor agonist
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	2.04	1	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
protocatechualdehyde protocatechualdehyde: found in wheat grains, wheat seedlings, & other plants; RN given refers to parent cpd; see also rancinamycins; structure	2.17	1	dihydroxybenzaldehyde
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.	2.31	1	catechin	antioxidant; plant metabolite
alpha-aminopyridine alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.	2.47	2
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	2.04	1
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	2.04	1	D-glucopyranose	epitope; mouse metabolite
magnoflorine magnoflorine: opium alkaloid having the aporphine configuration; RN given refers to parent cpd(S)-isomer; structure. (S)-magnoflorine : An aporphine alkaloid that is (S)-corytuberine in which the nitrogen has been quaternised by an additional methyl group.	2.57	2	aporphine alkaloid; quaternary ammonium ion	plant metabolite
swertisin swertisin: from Wilbrandia ebracteata; structure in first source. swertisin : A flavone C-glycoside that is 7-O-methylapigenin in which the hydrogen at position 6 has been replaced by a beta-D-glucosyl residue.	2.82	3	dihydroxyflavone; flavone C-glycoside; monomethoxyflavone; monosaccharide derivative; polyphenol	adenosine A1 receptor antagonist; anti-inflammatory agent; antioxidant; hypoglycemic agent; plant metabolite
ceanothic acid ceanothic acid: isolated from Ceanothus americanus; structure in first source	2.1	1
isovitexin [no description available]	2.46	2	C-glycosyl compound; trihydroxyflavone	EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.17	1
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	2.17	1
ferulic acid ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.	2.49	2	ferulic acids	anti-inflammatory agent; antioxidant; apoptosis inhibitor; cardioprotective agent; MALDI matrix material; plant metabolite
schizandrin schizandrin: a dibenzocyclooctadiene lignan; schizandra is the plant name	2.17	1
glycosides [no description available]	2.97	4
quercetin [no description available]	2.31	1	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	3.01	4	trihydroxyflavone	antineoplastic agent; metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.31	1	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
mangiferin shamimin: isolated from the leaves of Bombax ceiba; structure in first source	7.07	1	C-glycosyl compound; xanthones	anti-inflammatory agent; antioxidant; hypoglycemic agent; plant metabolite
puerarin [no description available]	2.13	1	C-glycosyl compound; isoflavonoid
salvianolic acid B salvianolic acid B: isolated from Salvia miltiorrhiza. salvianolic acid B : A member of the class of 1-benzofurans that is an antioxidant and free radical scavenging compound extracted from S. miltiorrhiza	2.17	1	1-benzofurans; catechols; dicarboxylic acid; enoate ester; polyphenol	anti-inflammatory agent; antidepressant; antineoplastic agent; antioxidant; apoptosis inducer; autophagy inhibitor; cardioprotective agent; hepatoprotective agent; hypoglycemic agent; neuroprotective agent; osteogenesis regulator; plant metabolite
beta-escin [no description available]	2.52	2
scopolamine hydrobromide [no description available]	2.1	1
6-o-desmethyl donepezil 6-O-desmethyl donepezil: structure in first source	7.25	1	piperidines
jujuboside b jujuboside B: from seeds of Ziziphus jujuba; structure in first source	2.15	1	triterpenoid
piperidines Piperidines: A family of hexahydropyridines.	2.25	1
jujuboside a [no description available]	7.52	2	triterpenoid
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	2.07	1

Condition	Relationship Strength	Studies
Acute Confusional Senile Dementia [description not available]	2.6	1
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	2.6	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.63	2
Injury, Myocardial Reperfusion [description not available]	2.21	1
Heart Disease, Ischemic [description not available]	2.21	1
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	7.21	1
Innate Inflammatory Response [description not available]	2.25	1
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	7.25	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.	2.25	1
Colitis-Associated Cancer [description not available]	2.25	1
Cancer of Colon [description not available]	2.25	1
Colonic Neoplasms Tumors or cancer of the COLON.	2.25	1
Age-Related Memory Disorders [description not available]	2.1	1
Memory Disorders Disturbances in registering an impression, in the retention of an acquired impression, or in the recall of an impression. Memory impairments are associated with DEMENTIA; CRANIOCEREBRAL TRAUMA; ENCEPHALITIS; ALCOHOLISM (see also ALCOHOL AMNESTIC DISORDER); SCHIZOPHRENIA; and other conditions.	2.1	1
Anxiety Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.	2.11	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.43	2
Chronic Insomnia [description not available]	2.47	2
Sleep Initiation and Maintenance Disorders Disorders characterized by impairment of the ability to initiate or maintain sleep. This may occur as a primary disorder or in association with another medical or psychiatric condition.	2.47	2
Hypothermia, Accidental [description not available]	2.07	1
Hypothermia Lower than normal body temperature, especially in warm-blooded animals.	2.07	1

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