monotropein profile

Monotropein is a naturally occurring iridoid glycoside found in various plants, including Monotropa uniflora (Indian Pipe). It is characterized by its unique structure, consisting of a cyclopentanopyran ring system attached to a glucose moiety. Monotropein is known for its various pharmacological activities, including anti-inflammatory, antioxidant, and neuroprotective effects. It has been reported to inhibit the production of pro-inflammatory cytokines and reactive oxygen species, suggesting its potential therapeutic applications in inflammatory diseases. The compound's biological activity has attracted significant research interest, particularly in the areas of medicine and pharmaceuticals. Studies are ongoing to further explore its potential therapeutic benefits and investigate its mechanisms of action. Monotropein's synthesis is a complex process that often involves the extraction and purification of the compound from plant sources. However, researchers are exploring alternative synthetic approaches to produce monotropein in a more sustainable and cost-effective manner.'

monotropein: isolated from the root of Morinda officinalis; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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). [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]

Related Flora

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]

ID Source	ID
PubMed CID	73466
CHEBI ID	6988
SCHEMBL ID	422339
MeSH ID	M0494633

Synonym
nsc-88926
nsc-291303
monotropein
C09788
LMPR0102070012
(1s,4as,7r,7as)-1-(beta-d-glucopyranosyloxy)-7-hydroxy-7-(hydroxymethyl)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
CHEBI:6988 ,
nsc 291303
nsc 88926
unii-0y61m84o2t
cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-d-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, (1s-(1alpha,4aalpha,7beta,7aalpha))-
0y61m84o2t ,
AKOS015897158
S5471
monotropein [mi]
cyclopenta(c)pyran-4-carboxylic acid, 1-(.beta.-d-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, (1s-(1.alpha.,4a.alpha.,7.beta.,7a.alpha.))-
cyclopenta(c)pyran-4-carboxylic acid, 1-(.beta.-d-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, (1s,4as,7r,7as)-
SCHEMBL422339
(1s,4as,7r,7as)-7-hydroxy-7-(hydroxymethyl)-1-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
Q-100689
(1s,4as,7r,7as)-1-(beta-d-glucopyranosyloxy)-7-hydroxy-7-(hydroxymethyl)-1,4a,7,7a-tetrahydrocyclopenta(c)pyran-4-carboxylic acid
cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-d-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, (1s,4as,7r,7as)-
monotropein, >=98% (hplc)
HY-N0648
Q27107380
CCG-268524
CS-0009674
BS-49948
AC-34713

Excerpt	Reference	Relevance
"Monotropein (Mon) is a kind of iridoid glycoside plant secondary metabolite primarily present in some edible and medicinal plants. "	( Monotropein Protects against Inflammatory Bone Loss and Suppresses Osteoclast Formation and Bone Resorption by Inhibiting NFATc1 via NF-κB and Akt/GSK-3β Pathway. He, Y; Hu, S; Qin, L; Shen, Y; Song, Z; Zhang, Q; Zhao, Z, 2022)	3.61
"Monotropein is a natural iridoid glycoside enriched in Morinda officinalis and has been used for medicinal purposes in China. "	( Monotropein isolated from the roots of Morinda officinalis increases osteoblastic bone formation and prevents bone loss in ovariectomized mice. Liu, W; Qin, L; Xin, H; Yang, H; Zhang, N; Zhang, Q; Zhang, Z, 2016)	3.32

Excerpt	Reference	Relevance
"Monotropein was found to inhibit the expressions of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), tumor necrosis factor-α (TNF-α), and interleukin-1β (IL-1β) mRNA in LPS-induced RAW 264.7 macrophages."	( Monotropein isolated from the roots of Morinda officinalis ameliorates proinflammatory mediators in RAW 264.7 macrophages and dextran sulfate sodium (DSS)-induced colitis via NF-κB inactivation. Baek, NI; Cho, YW; Chung, KS; Jang, D; Lee, KT; Park, HJ; Seo, KH; Shin, JS; Yun, KJ, 2013)	2.55

Excerpt	Reference	Relevance
"Treatment with monotropein decreased the DNA binding activity of nuclear factor-κB (NF-κB)."	( Monotropein isolated from the roots of Morinda officinalis ameliorates proinflammatory mediators in RAW 264.7 macrophages and dextran sulfate sodium (DSS)-induced colitis via NF-κB inactivation. Baek, NI; Cho, YW; Chung, KS; Jang, D; Lee, KT; Park, HJ; Seo, KH; Shin, JS; Yun, KJ, 2013)	2.17
"Pretreatment with monotropein (at 20, 30 mg/kg/d, p.o.) significantly reduced stretching episodes and prolonged action time in mice."	( Antinociceptive anti-inflammatory effect of Monotropein isolated from the root of Morinda officinalis. Choi, J; Choi, MY; Jung, HJ; Lee, KT; Nam, JH; Park, HJ; Park, SK, 2005)	0.91

Excerpt	Reference	Relevance
" 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)	0.74
"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)	0.74

Role	Description
metabolite	Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
anti-inflammatory agent	Any compound that has anti-inflammatory effects.
[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
cyclopentapyran
monocarboxylic acid	An oxoacid containing a single carboxy group.
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.
beta-D-glucoside	Any D-glucoside in which the anomeric centre has beta-configuration.
monosaccharide derivative	A carbohydrate derivative that is formally obtained from a monosaccharide.
[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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	3 (15.00)	29.6817
2010's	9 (45.00)	24.3611
2020's	8 (40.00)	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	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
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2.17	1	alkyl hydroperoxide	antibacterial agent; oxidising agent
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.25	1	dialdehyde	biomarker
uvaol uvaol: from Vauquelinia corymbosa (Rosaceae)	2.03	1	triterpenoid	metabolite
chimaphilin chimaphilin: isolated from Chimaphila umbellata; structure given in first source	2.03	1	1,4-naphthoquinones
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).	4.39	18
glycosides [no description available]	2.17	1
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.03	1
quercetin [no description available]	2.21	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
astragalin kaempferol-3-O-glucoside: isolated from the pit of Mahkota dewa; structure in first source. kaempferol 3-O-beta-D-glucoside : A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage.	7.21	1	beta-D-glucoside; kaempferol O-glucoside; monosaccharide derivative; trihydroxyflavone	plant metabolite; trypanocidal drug
spiraeoside spiraeoside: from flowers of Filipendula ulmaria (L.); structure given in first source. quercetin 4'-O-beta-D-glucopyranoside : A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 4'.	7.21	1	beta-D-glucoside; flavonols; monosaccharide derivative; quercetin O-glucoside; tetrahydroxyflavone	antineoplastic agent; antioxidant; plant metabolite
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	2.08	1	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
asperulosidic acid 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	7.17	1	glycoside; iridoid monoterpenoid

Condition	Relationship Strength	Studies
Atrophy, Muscle [description not available]	2.41	1
Muscular Atrophy Derangement in size and number of muscle fibers occurring with aging, reduction in blood supply, or following immobilization, prolonged weightlessness, malnutrition, and particularly in denervation.	2.41	1
Bone Loss, Osteoclastic [description not available]	2.66	2
Arrhythmia [description not available]	4.21	9
Innate Inflammatory Response [description not available]	4.33	12
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	4.21	9
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.	4.33	12
Ventricular Fibrillation A potentially lethal cardiac arrhythmia that is characterized by uncoordinated extremely rapid firing of electrical impulses (400-600/min) in HEART VENTRICLES. Such asynchronous ventricular quivering or fibrillation prevents any effective cardiac output and results in unconsciousness (SYNCOPE). It is one of the major electrocardiographic patterns seen with CARDIAC ARREST.	4.21	9
Blood Poisoning [description not available]	2.6	1
Lung Injury, Acute [description not available]	2.6	1
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	7.6	1
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).	7.6	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.21	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.1	4
Varicocele A condition characterized by the dilated tortuous veins of the SPERMATIC CORD with a marked left-sided predominance. Adverse effect on male fertility occurs when varicocele leads to an increased scrotal (and testicular) temperature and reduced testicular volume.	2.21	1
Acute Kidney Failure [description not available]	2.25	1
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	7.25	1
Chronic Illness [description not available]	2.25	1
Liver Dysfunction [description not available]	2.25	1
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	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.	2.54	2
Liver Diseases Pathological processes of the LIVER.	2.25	1
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	2.25	1
Surgical Incision [description not available]	2.17	1
Age-Related Osteoporosis [description not available]	2.55	2
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.	2.55	2
Arthritis, Degenerative [description not available]	2.1	1
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	7.1	1

monotropein

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Roles (2)

Drug Classes (5)

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Research Demand Index: 27.90

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