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maslinic acid
olean-12-en-28-oic acid, 2,3-dihydroxy-, (2alpha,3beta)-

Supplier Sponsors

CAS Number: 4373-41-5Picture of molecule3D/inchi
FDA UNII: E233J88OHQ
Nikkaji Web:J22.580K
MDL:MFCD00049293
XlogP3-AA:6.50 (est)
Molecular Weight:472.70936000
Formula:C30 H48 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:antioxidants
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 570.00 °C. @ 760.00 mm Hg (est)
Flash Point: 595.00 °F. TCC ( 312.60 °C. ) (est)
logP (o/w): 7.870 (est)
Soluble in:
 water, 0.00396 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: antioxidants
skin conditioning
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Maslinic acid 98%
BOC Sciences
For experimental / research use only.
Maslinic acid >98%
Odor: characteristic
Use: Maslinic acid is a pentacyclic triterpene found in a variety of natural sources. It exerts a wide range of biological activities, such as antitumor, antidiabetic, antioxidant, cardioprotective, neuroprotective, antiparasitic and growth-stimulating.
Carbosynth
For experimental / research use only.
Crategolic acid
Glentham Life Sciences
Maslinic acid
Santa Cruz Biotechnology
For experimental / research use only.
Maslinic Acid
Sigma-Aldrich: Sigma
For experimental / research use only.
Maslinic Acid ≥98% (HPLC)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
antioxidants
Recommendation for maslinic acid usage levels up to:
 not for fragrance use.
 
Recommendation for maslinic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :73659
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Chemidplus:0004373415
 
References:
 (4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):73659
Pubchem (sid):135033519
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C16939
HMDB (The Human Metabolome Database):HMDB02392
FooDB:FDB013041
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 clove fruit
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 clove oil
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 clove seed
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 guava fruit
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 guava leaf
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 guava leaf oil
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 loquat leaf
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 olive
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 olive fruit
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 olive hull husk
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 olive skin wax
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 pomegranate
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 pomegranate flower
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 sage leaf
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 savory winter savory plant
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Synonyms:
 crategolic acid
(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
 maslic acid
 maslinicacid
 olean-12-en-28-oic acid, 2,3-dihydroxy-,
 olean-12-en-28-oic acid, 2,3-dihydroxy-, (2alpha,3beta)-
 

Articles:

PubMed:Maslinic Acid Induces Mitochondrial Apoptosis and Suppresses HIF-1α Expression in A549 Lung Cancer Cells under Normoxic and Hypoxic Conditions.
PubMed:In vitro effects of triterpenic acids from olive leaf extracts on the mitochondrial membrane potential of promastigote stage of Leishmania spp.
PubMed:Protective effects of maslinic acid against alcohol-induced acute liver injury in mice.
PubMed:Antibacterial oleanane-type triterpenoids from pericarps of Akebia trifoliata.
PubMed:Maslinic acid, a natural phytoalexin-type triterpene from olives--a promising nutraceutical?
PubMed:Maslinic acid activates mitochondria-dependent apoptotic pathway in cardiac carcinoma.
PubMed:Population pharmacokinetics of maslinic acid, a triterpene from olives, after intravenous and oral administration in rats.
PubMed:Solid-phase library synthesis of bi-functional derivatives of oleanolic and maslinic acids and their cytotoxicity on three cancer cell lines.
PubMed:Phytochemistry and bioactivity of aromatic and medicinal plants from the genus Agastache (Lamiaceae).
PubMed:Maslinic acid modulates glycogen metabolism by enhancing the insulin signaling pathway and inhibiting glycogen phosphorylase.
PubMed:Maslinic acid induced apoptosis in bladder cancer cells through activating p38 MAPK signaling pathway.
PubMed:Maslinic acid protects vascular smooth muscle cells from oxidative stress through Akt/Nrf2/HO-1 pathway.
PubMed:Oleanolic and maslinic acid sensitize soft tissue sarcoma cells to doxorubicin by inhibiting the multidrug resistance protein MRP-1, but not P-glycoprotein.
PubMed:Semi-synthesis of acylated triterpenes from olive-oil industry wastes for the development of anticancer and anti-HIV agents.
PubMed:Membrane damaging activity of a maslinic acid analog.
PubMed:Four new triterpenoids isolated from the resin of Garcinia hanburyi.
PubMed:Antioxidant effects of maslinic acid in livers, hearts and kidneys of streptozotocin-induced diabetic rats: effects on kidney function.
PubMed:Bioactive properties of the main triterpenes found in olives, virgin olive oil, and leaves of Olea europaea.
PubMed:Effects of Syzygium aromaticum-derived triterpenes on postprandial blood glucose in streptozotocin-induced diabetic rats following carbohydrate challenge.
PubMed:Towards cytotoxic and selective derivatives of maslinic acid.
PubMed:Esters and amides of maslinic acid trigger apoptosis in human tumor cells and alter their mode of action with respect to the substitution pattern at C-28.
PubMed:Maslinic acid and its in vitro anti-neoplastic effects.
PubMed:Liquid chromatography-mass spectrometry determination in plasma of maslinic acid, a bioactive compound from Olea europaea L.
PubMed:Antitumour activity on extrinsic apoptotic targets of the triterpenoid maslinic acid in p53-deficient Caco-2 adenocarcinoma cells.
PubMed:Biotransformation of oleanolic and maslinic acids by Rhizomucor miehei.
PubMed:Time course of pentacyclic triterpenoids from fruits and leaves of olive tree (Olea europaea L.) cv. Picual and cv. Cornezuelo during ripening.
PubMed:[Chemical constituents of Rabdosia japonica var. glaucocalyx and their anti-complementary activity].
PubMed:Antiallodynic and analgesic effects of maslinic acid, a pentacyclic triterpenoid from Olea europaea.
PubMed:[Protective effect of maslinic acid preconditioning against oxygen-glucose deprivation- induced injuries in embryonic rat cortical neurons].
PubMed:Maslinic acid-enriched diet decreases intestinal tumorigenesis in Apc(Min/+) mice through transcriptomic and metabolomic reprogramming.
PubMed:Maslinic acid, a triterpenic anti-tumoural agent, interferes with cytoskeleton protein expression in HT29 human colon-cancer cells.
PubMed:Anti-Proliferative Activities and Apoptosis Induction by Triterpenes Derived from Eriobotrya japonica in Human Leukemia Cell Lines.
PubMed:Chemical constituents of flowers and fruits of Rabdosia excisa.
PubMed:Assessment of the safety of maslinic acid, a bioactive compound from Olea europaea L.
PubMed:Simultaneous determination of seven major triterpenoids in Pyrola decorata H. Andres by LC-MS method.
PubMed:[Non-anthraquinones constituents from the roots of Knoxia valerianoides].
PubMed:A simple GC-MS method for the screening of betulinic, corosolic, maslinic, oleanolic and ursolic acid contents in commercial botanicals used as food supplement ingredients.
PubMed:Determination of maslinic acid, a pentacyclic triterpene from olives, in rat plasma by high-performance liquid chromatography.
PubMed:[Chemical constituents from Sambucus chinensis].
PubMed:Maslinic acid protects against isoproterenol-induced cardiotoxicity in albino Wistar rats.
PubMed:Bioavailability, distribution, and antioxidative effects of selected triterpenes in mice.
PubMed:Suppressive effect of maslinic acid on PMA-induced protein kinase C in human B-lymphoblastoid cells.
PubMed:Efficacy of bioactive compounds from extra virgin olive oil to modulate atherosclerosis development.
PubMed:Maslinic acid inhibits the metastatic capacity of DU145 human prostate cancer cells: possible mediation via hypoxia-inducible factor-1α signalling.
PubMed:New terpenes from Salvia palaestina Benth. and Salvia syriaca L. growing wild in Jordan.
PubMed:Nonsterol Triterpenoids as Major Constituents of Olea europaea.
PubMed:A new triterpenoid from the rhizomes of Nelumbo nucifera.
PubMed:[Study on the triterpenoids from the fruits of Ligustrum lucidum].
PubMed:Unusual isomeric corniculatolides from mangrove, Aegiceras corniculatum.
PubMed:Towards an efficient protocol for the determination of triterpenic acids in olive fruit: a comparative study of drying and extraction methods.
PubMed:[Chemical constituents of Swertia hispidicalyx].
PubMed:Targeting inflammatory pathways by triterpenoids for prevention and treatment of cancer.
PubMed:[Chemical constituents about the stem of Rabdosia excisa].
PubMed:Maslinic acid derivatives induce significant apoptosis in b16f10 murine melanoma cells.
PubMed:Anti-inflammatory effects of maslinic acid, a natural triterpene, in cultured cortical astrocytes via suppression of nuclear factor-kappa B.
PubMed:Proteomic analysis of the molecular response of Raji cells to maslinic acid treatment.
PubMed:Maslinic acid, a natural triterpenoid compound from Olea europaea, protects cortical neurons against oxygen-glucose deprivation-induced injury.
PubMed:[Studies on the chemical constituents from the leave of Paulownia tomentosa].
PubMed:Maslinic acid, a natural inhibitor of glycogen phosphorylase, reduces cerebral ischemic injury in hyperglycemic rats by GLT-1 up-regulation.
PubMed:Proteomics in the liver of gilthead sea bream (Sparus aurata) to elucidate the cellular response induced by the intake of maslinic acid.
PubMed:Effect of olive pomace extracts on hyperlipidaemia.
PubMed:Identification and determination of carboxylic acids in food samples using 2-(2-(anthracen-10-yl)-1H-phenanthro[9,10-d]imidazol-1-yl)ethyl 4-methylbenzenesulfonate (APIETS) as labeling reagent by HPLC with FLD and APCI/MS.
PubMed:Multi-targeted activity of maslinic acid as an antimalarial natural compound.
PubMed:Simultaneous qualitative and quantitative analysis of triterpenic acids, saponins and flavonoids in the leaves of two Ziziphus species by HPLC-PDA-MS/ELSD.
PubMed:The natural triterpene maslinic acid induces apoptosis in HT29 colon cancer cells by a JNK-p53-dependent mechanism.
PubMed:Parasitostatic effect of maslinic acid. II. Survival increase and immune protection in lethal Plasmodium yoelii-infected mice.
PubMed:[Triterpenoids and triterpenoid saponins of Viscum liquidambaricolum].
PubMed:Parasitostatic effect of maslinic acid. I. Growth arrest of Plasmodium falciparum intraerythrocytic stages.
PubMed:Development of a new HPLC method with precolumn fluorescent derivatization for rapid, selective and sensitive detection of triterpenic acids in fruits.
PubMed:Triterpenoid saponins from Symplocos lancifolia.
PubMed:Maslinic acid induces apoptosis in salivary gland adenoid cystic carcinoma cells by Ca2+-evoked p38 signaling pathway.
PubMed:Phenylpropanoids from the stem bark of Jacaranda mimosaefolia.
PubMed:Antiangiogenic potential of three triterpenic acids in human liver cancer cells.
PubMed:Antioxidant, antiproliferative, and pro-apoptotic capacities of pentacyclic triterpenes found in the skin of olives on MCF-7 human breast cancer cells and their effects on DNA damage.
PubMed:Astrocytic glutamate transporter-dependent neuroprotection against glutamate toxicity: an in vitro study of maslinic acid.
PubMed:[Studies on the chemical constituents of Ficus microcarpa].
PubMed:Pentacyclic triterpenoids and ceramide mediate the vasorelaxant activity of Vitex cienkowskii via involvement of NO/cGMP pathway in isolated rat aortic rings.
PubMed:Maslinic acid suppresses osteoclastogenesis and prevents ovariectomy-induced bone loss by regulating RANKL-mediated NF-κB and MAPK signaling pathways.
PubMed:Isolation and identification of intestinal CYP3A inhibitors from cranberry (Vaccinium macrocarpon) using human intestinal microsomes.
PubMed:Pharmacological manipulation of brain glycogenolysis as a therapeutic approach to cerebral ischemia.
PubMed:Chemical constituents with free-radical-scavenging activities from the stem of Microcos paniculata.
PubMed:Pentacyclic triterpenoids from olive fruit and leaf.
PubMed:Cancer chemopreventive activity of maslinic acid: suppression of COX-2 expression and inhibition of NF-κB and AP-1 activation in Raji cells.
PubMed:Antioxidant and antiatherogenic activities of pentacyclic triterpenic diols and acids.
PubMed:Anticoccidial activity of maslinic acid against infection with Eimeria tenella in chickens.
PubMed:Chemopreventive properties of phytosterols and maslinic acid extracted from Coleus tuberosus in inhibiting the expression of EBV early-antigen in Raji cells.
PubMed:Action of a pentacyclic triterpenoid, maslinic acid, against Toxoplasma gondii.
PubMed:Maslinic acid potentiates the anti-tumor activity of tumor necrosis factor alpha by inhibiting NF-kappaB signaling pathway.
PubMed:Two new secoiridoid glycosides from the leaves of Olea europaea L.
PubMed:Bioactive compounds with added value prepared from terpenes contained in solid wastes from the olive oil industry.
PubMed:Different pathways for the deoxygenation of the A-ring of natural triterpene compounds.
PubMed:[Chemical constituents of roots of Boehmeria nivea].
PubMed:[Determination of triterpenoid acids in leaves of Eriobotrya japonica collected at in different seasons].
PubMed:Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B.
PubMed:Transformed cell suspension culture of Galphimia glauca producing sedative nor-friedelanes.
PubMed:Fruit quality and olive leaf and stone addition affect Picual virgin olive oil triterpenic content.
PubMed:Triterpenic content and chemometric analysis of virgin olive oils from forty olive cultivars.
PubMed:Effects of maslinic acid, a natural triterpene, on glycogen metabolism in cultured cortical astrocytes.
PubMed:[Chemical constituents from herbs of Swertia mileensis].
PubMed:Novel binding studies of human serum albumin with trans-feruloyl maslinic acid.
PubMed:[Studies on the triterpenes from loquat leaf (Eriobotrya japonica)].
PubMed:Solution- and solid-phase synthesis and anti-HIV activity of maslinic acid derivatives containing amino acids and peptides.
PubMed:Triterpene acids isolated from Lagerstroemia speciosa leaves as alpha-glucosidase inhibitors.
PubMed:Triterpenoic acids of Prunella vulgaris var. lilacina and their cytotoxic activities in vitro.
PubMed:Apolipoprotein E determines the hepatic transcriptional profile of dietary maslinic acid in mice.
PubMed:Medicinal flowers. XXIII. New taraxastane-type triterpene, punicanolic acid, with tumor necrosis factor-alpha inhibitory activity from the flowers of Punica granatum.
PubMed:Practical synthesis of bredemolic acid, a natural inhibitor of glycogen phosphorylase.
PubMed:Maslinic acid, a natural triterpene from Olea europaea L., induces apoptosis in HT29 human colon-cancer cells via the mitochondrial apoptotic pathway.
PubMed:Anti-inflammatory and antioxidant activities and constituents of Platostoma africanum P. Beauv.
PubMed:Evaluation of gastroprotective activity of Plinia edulis (Vell.) Sobral (Myrtaceae) leaves in rats.
PubMed:Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystallographic studies.
PubMed:Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells.
PubMed:Aldose-reductase- and protein-glycation-inhibitory principles from the whole plant of Duchesnea chrysantha.
PubMed:Bioactivity-guided isolation of the active compounds from Rosa nutkana and quantitative analysis of ascorbic acid by HPLC.
PubMed:Maslinic acid reduces blood glucose in KK-Ay mice.
PubMed:Maslinic acid added to the diet increases growth and protein-turnover rates in the white muscle of rainbow trout (Oncorhynchus mykiss).
PubMed:Antielastase and free radical scavenging activities of compounds from the stems of Cornus kousa.
PubMed:Tyrosinase inhibitory pentacyclic triterpenes and analgesic and spasmolytic activities of methanol extracts of Rhododendron collettianum.
PubMed:Inhibition of DNA topoisomerase I and growth inhibition of human cancer cell lines by an oleanane from Junellia aspera (Verbenaceae).
PubMed:Triterpenoids isolated from apple peels have potent antiproliferative activity and may be partially responsible for apple's anticancer activity.
PubMed:Production of triterpene acids by cell suspension cultures of Olea europaea.
PubMed:Acidic triterpenes compromise growth and survival of astrocytoma cell lines by regulating reactive oxygen species accumulation.
PubMed:Remote hydroxylation of methyl groups by regioselective cyclopalladation. Partial synthesis of hyptatic acid-A.
PubMed:Formation of triterpenoids throughout Olea europaea fruit ontogeny.
PubMed:Modulation of cytokine secretion by pentacyclic triterpenes from olive pomace oil in human mononuclear cells.
PubMed:[Triterpenes from herb of Potentilla chinesis].
PubMed:Triterpenoids from Hippophae rhamnoides L. and their nitric oxide production-inhibitory and DPPH radical-scavenging activities.
PubMed:New glycosides from Tetracentron sinense and their cytotoxic activity.
PubMed:(2Alpha,3beta)-2,3-dihydroxyolean-12-en-28-oic acid, a new natural triterpene from Olea europea, induces caspase dependent apoptosis selectively in colon adenocarcinoma cells.
PubMed:Olive fruit extracts inhibit proliferation and induce apoptosis in HT-29 human colon cancer cells.
PubMed:Maslinic acid as a feed additive to stimulate growth and hepatic protein-turnover rates in rainbow trout (Onchorhynchus mykiss).
PubMed:Secondary metabolites from the wood bark of Durio zibethinus and Durio kutejensis.
PubMed:Constituents of the flowers of Punica granatum.
PubMed:Diterpenes from Leucas aspera inhibiting prostaglandin-induced contractions.
PubMed:An efficient chemical method for separation of corsolic acid from its isomeric maslinic acid.
PubMed:New triterpenoids isolated from the root bark of Ulmus pumila L.
PubMed:Production of triterpenoids in liquid-cultivated hairy roots of Galphimia glauca.
PubMed:Triterpenic compounds from "orujo" olive oil elicit vasorelaxation in aorta from spontaneously hypertensive rats.
PubMed:Supressive effect of maslinic acid from pomace olive oil on oxidative stress and cytokine production in stimulated murine macrophages.
PubMed:Pentacyclic triterpenes. Part 2: Synthesis and biological evaluation of maslinic acid derivatives as glycogen phosphorylase inhibitors.
PubMed:Pentacyclic triterpenes. Part 1: the first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases.
PubMed:Triterpenoids from the flower of Campsis grandiflora K. Schum. as human acyl-CoA: cholesterol acyltransferase inhibitors.
PubMed:[Studies on chemical constituents in fruit of Rubus chingii].
PubMed:Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta.
PubMed:Anti-complementary activity of triterpenoides from fruits of Zizyphus jujuba.
PubMed:Antitumor-promoting constituents from Chaenomeles sinensis KOEHNE and their activities in JB6 mouse epidermal cells.
PubMed:Antioxidant activity of maslinic acid, a triterpene derivative obtained from Olea europaea.
PubMed:Epoxides, cyclic sulfites, and sulfate from natural pentacyclic triterpenoids: theoretical calculations and chemical transformations.
PubMed:Production of bioactive triterpenes by Eriobotrya japonica calli.
PubMed:Phytochemical study and anti-inflammatory properties of Lampaya hieronymi Schum. ex Moldenke.
PubMed:Antimicrobial triterpenoids from Licania heteromorpha.
PubMed:Cytotoxic triterpenes from stem bark of Physocarpus intermedius.
PubMed:Two glycosides from the stem bark of Tetracentron sinense.
PubMed:Flavonoids and terpenoids from Luma gayana (Barn.) Burret.
PubMed:DNA polymerase beta inhibitors from Tetracera boiviniana.
PubMed:Anti-HIV triterpene acids from Geum japonicum.
PubMed:Antiviral activity of new triterpenic derivatives.
PubMed:Screening of plant constituents for effect on glucose transport activity in Ehrlich ascites tumour cells.
PubMed:[Studies on the chemical constituents from roots of Agastache rugosa].
PubMed:Triterpene saponins from Cylicodiscus gabunensis.
PubMed:Cytotoxic triterpenes from a Chinese medicine, Goreishi.
 
Notes:
isolated from the stem bark of physocarpus intermedius. Maslinic acid is a compound derived from dry olive-pomace oil (an olive skin wax) which is a byproduct of olive oil extraction. It is a member of the group of triterpenes known as oleananes.; Maslinic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Maslinic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. (PMID: 17292619)
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