Compounds > asperulosidic acid

Page last updated: 2024-11-12

asperulosidic acid

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

Description

asperulosidic acid: from the fruit juice of Morinda citrifolia (noni), a plant originally grown in the Hawaiian and Tahitian islands, has long been used by islanders to treat diseases, including cancer; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Flora	Rank	Flora Definition	Family	Family Definition
Morinda	genus	A plant genus of the family RUBIACEAE. Members contain iridoid glycosides and ANTHRAQUINONES.[MeSH]	Rubiaceae	The Madder plant family of the order Gentianales (formerly Rubiales), subclass Asteridae, class Magnoliopsida includes important medicinal plants that provide QUININE; IPECAC; and COFFEE. They have opposite leaves and interpetiolar stipules.[MeSH]

Cross-References

ID Source	ID
PubMed CID	11968867
CHEMBL ID	460030
CHEBI ID	167730
SCHEMBL ID	422107
MeSH ID	M0395645

Synonyms (23)

Synonym
CHEBI:167730
(1s,4as,5s,7as)-7-(acetyloxymethyl)-5-hydroxy-1-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
ACON1_001484
MEGXP0_000737
NCGC00180458-01
asperulosidic acid
BRD-K47416262-001-01-9
25368-11-0
SCHEMBL422107
AC-34118
asperulosidic acid, >=90% (lc/ms-elsd)
asperuloside acid
NCGC00180458-02
CHEMBL460030 ,
bdbm50202632
AKOS037514940
cyclopenta(c)pyran-4-carboxylic acid, 7-((acetyloxy)methyl)-1-(.beta.-d-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-5-hydroxy-, (1s-(1.alpha.,4a.alpha.,5.beta.,7a.alpha.))-
cyclopenta(c)pyran-4-carboxylic acid, 7-((acetyloxy)methyl)-1-(.beta.-d-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-5-hydroxy-, (1s,4as,5s,7as)-
cyclopenta(c)pyran-4-carboxylic acid, 1.alpha.-(.beta.-d-glucopyranosyloxy)-1,4a.alpha.,5,7a.alpha.-tetrahydro-5.beta.-hydroxy-7-(hydroxymethyl)-, 7-acetate
HY-N6246
CS-0032781
DTXSID201315882
FS-7513

Research Excerpts

Overview

Asperulosidic acid (ASP) is a bioactive iridoid exerting broad pharmacological and medicinal properties.

Excerpt	Reference	Relevance
"Asperulosidic acid (ASP) is a bioactive iridoid exerting broad pharmacological and medicinal properties. "	( Asperulosidic Acid, a Bioactive Iridoid, Alleviates Placental Oxidative Stress and Inflammatory Responses in Gestational Diabetes Mellitus by Suppressing NF-κB and MAPK Signaling Pathways. Gai, S; Wu, Q; Zhang, H, 2022)	3.61

Pharmacokinetics

Excerpt	Reference	Relevance
" The aim of the study was to develop a novel and sensitive liquid chromatography-tandem mass spectrometry (LC/MS/MS) method for the simultaneous determination of the two isomeric iridoid glycosides and then evaluate their pharmacokinetic properties in rats."	( LC/MS/MS determination and pharmacokinetic study of iridoid glycosides monotropein and deacetylasperulosidic acid isomers in rat plasma after oral administration of Morinda officinalis extract. Deng, Z; Dong, J; Li, C; Song, X; Tian, J, 2016)	0.65
" The rats were administered orally at 1650 mg/kg MO and 25, 50 and 100 mg/kg MO iridoid glycosides (MOIGs) or intravenously at MOIG 25 mg/kg for pharmacokinetic study of MON and DA."	( Pharmacokinetics and tissue distribution of monotropein and deacetyl asperulosidic acid after oral administration of extracts from Morinda officinalis root in rats. Han, T; He, YQ; Hsu, HY; Lin, B; Qi, YP; Shen, Y; Song, HT; Wu, YB; Xin, HL; Zhang, JH; Zhang, Q; Zhang, QY; Zhao, L, 2018)	0.72
"Significant differences in the pharmacokinetic parameters were observed in male and female rats."	( Pharmacokinetics and tissue distribution of monotropein and deacetyl asperulosidic acid after oral administration of extracts from Morinda officinalis root in rats. Han, T; He, YQ; Hsu, HY; Lin, B; Qi, YP; Shen, Y; Song, HT; Wu, YB; Xin, HL; Zhang, JH; Zhang, Q; Zhang, QY; Zhao, L, 2018)	0.72

Bioavailability

Excerpt	Reference	Relevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."	( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)	0.51

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

Drug Classes (2)

Class	Description
glycoside	A glycosyl compound resulting from the attachment of a glycosyl group to a non-acyl group RO-, RS-, RSe-, etc. The bond between the glycosyl group and the non-acyl group is called a glycosidic bond. By extension, the terms N-glycosides and C-glycosides are used as class names for glycosylamines and for compounds having a glycosyl group attached to a hydrocarbyl group respectively. These terms are misnomers and should not be used. The preferred terms are glycosylamines and C-glycosyl compounds, respectively.
iridoid monoterpenoid	One of a class of monoterpenoids biosynthesized from isoprene and often intermediates in the biosynthesis of alkaloids. Iridoids usually consist of a cyclopentane ring fused to a six-membered oxygen heterocycle; cleavage of a bond in the cyclopentane ring gives rise to the subclass known as secoiridoids.
[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

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Pancreatic alpha-amylase	Sus scrofa (pig)	IC50 (µMol)	69.4000	1.3530	4.3108	8.9300	AID1327604
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (6)

Assay ID	Title	Year	Journal	Article
AID1346987	P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008	Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening	2020	SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1	Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347159	Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347160	Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346986	P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen	2019	Molecular pharmacology, 11, Volume: 96, Issue:5	A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1327604	Inhibition of hog pancreas alpha-amylase using starch as substrate preincubated for 10 mins followed by substrate addition measured after 10 mins by dinitrosalicylic acid color reagent-based UV-Vis spectrophotometric analysis	2016	Journal of natural products, 08-26, Volume: 79, Issue:8	α-Glucosidase and α-Amylase Inhibitors from Arcytophyllum thymifolium.
[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	3 (15.79)	29.6817
2010's	11 (57.89)	24.3611
2020's	5 (26.32)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.79

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	23.79 (24.57)
Research Supply Index	3.04 (2.92)
Research Growth Index	5.19 (4.65)
Search Engine Demand Index	23.28 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (23.79)

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	20 (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
dinitrochlorobenzene Dinitrochlorobenzene: A skin irritant that may cause dermatitis of both primary and allergic types. Contact sensitization with DNCB has been used as a measure of cellular immunity. DNCB is also used as a reagent for the detection and determination of pyridine compounds.. 1-chloro-2,4-dinitrobenzene : A C-nitro compound that is chlorobenzene carrying a nitro substituent at each of the 2- and 4-positions.	2.25	1	C-nitro compound; monochlorobenzenes	allergen; epitope; sensitiser
carbamates [no description available]	2.21	1	amino-acid anion
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	2.02	1	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2	1	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
acarbose [no description available]	2.13	1	tetrasaccharide derivative	EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; geroprotector; hypoglycemic agent
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.	3.31	6	D-glucopyranose	epitope; mouse metabolite
monotropein monotropein: isolated from the root of Morinda officinalis; structure in first source. monotropein : An iridoid monoterpenoid that is 1,4a,7,7a-tetrahydrocyclopenta[c]pyran substituted by a beta-D-glucopyranosyloxy group at position 1, a carboxylic acid group at position 4, and at position 7 by a hydroxy and hydroxymethyl groups respectively (the 1S,4aS,7R,7aS diastereomer).	7.17	1	beta-D-glucoside; cyclopentapyran; iridoid monoterpenoid; monocarboxylic acid; monosaccharide derivative	anti-inflammatory agent; metabolite
asperuloside asperuloside : A iridoid monoterpenoid glycoside isolated from Galium verum.	8.06	4	acetate ester; beta-D-glucoside; gamma-lactone; iridoid monoterpenoid; monosaccharide derivative	metabolite
scopolin [no description available]	2.02	1	beta-D-glucoside; coumarins; monosaccharide derivative	plant metabolite
geniposidic acid [no description available]	2.42	2	terpene glycoside
iridoids Iridoids: A type of MONOTERPENES, derived from geraniol. They have the general form of cyclopentanopyran, but in some cases, one of the rings is broken as in the case of secoiridoid. They are different from the similarly named iridals (TRITERPENES).	3.18	5
glycosides [no description available]	9.19	15
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	2.13	1	cinnamate ester; tannin	food component; plant metabolite
fraxetin fraxetin : A hydroxycoumarin that is 6-methoxycoumarin in which the hydrogens at positions 7 and 8 have been replaced by hydroxy groups.	2.13	1	aromatic ether; hydroxycoumarin	anti-inflammatory agent; antibacterial agent; antimicrobial agent; antioxidant; apoptosis inducer; apoptosis inhibitor; Arabidopsis thaliana metabolite; hepatoprotective agent; hypoglycemic agent
quercetin [no description available]	2.13	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
hyperoside quercetin 3-O-beta-D-galactopyranoside : A quercetin O-glycoside that is quercetin with a beta-D-galactosyl residue attached at position 3. Isolated from Artemisia capillaris, it exhibits hepatoprotective activity.	2.13	1	beta-D-galactoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	hepatoprotective agent; plant metabolite
rhamnetin rhamnetin: aglycone of xanthorhamnin; from Rhamnus. rhamnetin : A monomethoxyflavone that is quercetin methylated at position 7.	2.13	1	monomethoxyflavone; tetrahydroxyflavone	anti-inflammatory agent; antioxidant; metabolite
kaempferol-3-o-rutinoside kaempferol-3-O-rutinoside: isolated from the methanolic extract of the whole plants of Diodia teres through repeated silica gel and Sephadex LH-20 column chromatography; structure in first source. kaempferol-3-rutinoside : A kaempferol O-glucoside that is kaempferol attached to a rutinosyl [6-deoxy-alpha-L-mannosyl-(1->6)-beta-D-glucosyl] residue at position 3 via a glycosidic linkage. It has been isolated from the leaves of Solanum campaniforme.	2.02	1	disaccharide derivative; kaempferol O-glucoside; rutinoside; trihydroxyflavone	metabolite; plant metabolite; radical scavenger
quercetin 3-sambubioside quercetin 3-sambubioside: isolated from Actinidia arguta. quercetin 3-O-[beta-D-xylosyl-(1->2)-beta-D-glucoside] : A quercetin O-glucoside that is quercetin attached to a beta-D-sambubiosyl residue at position 3 via a glycosidc linkage.	2.13	1	disaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antioxidant; plant metabolite
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.02	1	benzenes; hydroxycoumarin; methyl ketone
epidermal growth factor Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.	2	1

Condition	Relationship Strength	Studies
Congenital Zika Syndrome [description not available]	2.25	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.63	2
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	2.25	1
Diabetes Mellitus, Gestational [description not available]	2.41	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.41	1
Diabetes, Gestational Diabetes mellitus induced by PREGNANCY but resolved at the end of pregnancy. It does not include previously diagnosed diabetics who become pregnant (PREGNANCY IN DIABETICS). Gestational diabetes usually develops in late pregnancy when insulin antagonistic hormones peaks leading to INSULIN RESISTANCE; GLUCOSE INTOLERANCE; and HYPERGLYCEMIA.	2.41	1
Eczema, Atopic [description not available]	2.69	2
Dermatitis, Atopic A chronic inflammatory genetically determined disease of the skin marked by increased ability to form reagin (IgE), with increased susceptibility to allergic rhinitis and asthma, and hereditary disposition to a lowered threshold for pruritus. It is manifested by lichenification, excoriation, and crusting, mainly on the flexural surfaces of the elbow and knee. In infants it is known as infantile eczema.	2.69	2
Dermatitis, Eczematous [description not available]	2.31	1
Eczema A pruritic papulovesicular dermatitis occurring as a reaction to many endogenous and exogenous agents (Dorland, 27th ed).	2.31	1
Cirrhosis [description not available]	2.21	1
Ureteral Obstruction Blockage in any part of the URETER causing obstruction of urine flow from the kidney to the URINARY BLADDER. The obstruction may be congenital, acquired, unilateral, bilateral, complete, partial, acute, or chronic. Depending on the degree and duration of the obstruction, clinical features vary greatly such as HYDRONEPHROSIS and obstructive nephropathy.	7.21	1
Fibrosis Any pathological condition where fibrous connective tissue invades any organ, usually as a consequence of inflammation or other injury.	7.21	1
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.21	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)	2.13	1
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	2	1
Cancer of Skin [description not available]	2	1
Skin Neoplasms Tumors or cancer of the SKIN.	2	1

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