obacunone

obacunoic acid, eta-lactone

CAS: 751-03-1 C26 H30 O7 MW: 454.51950000

Identification

Nameobacunone
CAS Number751-03-1
FDA UNIISearch
Molecular FormulaC26 H30 O7
Molecular Weight454.51950000
MDL NumberMFCD00075888
Nikkaji NumberJ37.085A

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Soluble in water, 30.54 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for obacunone usage levels up tonot for fragrance use.
Recommendation for obacunone flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

casimiroa edulis citrus limon leaf citrus reticulata phellodendron amurense bark

Synonyms

obacunoic acid, eta-lactone oxireno(4,4a)-2-benzopyrano(6,5-g)(2)benzoxepin-3,5,9(3aH,4bH,6H)-trione, 1-(3-furanyl)-1,6a,7,11a,11b,12,13,13a-octahydro-4b,7,7,11a,13a-pentamethyl-, (1S,3aS,4aR,4bR,6aR,11aR,11bR,11bR,13aS)- PubMed: Obacunone causes sustained expression of MKP-1 thus inactivating p38 MAPK to suppress pro-inflammatory mediators through intracellular MIF. PubMed: Identification of key amino acid residues in the hTGR5-nomilin interaction and construction of its binding model. PubMed: A novel UPLC-MS/MS method for simultaneous determination of 10 effective constituents in the Jixingshizhen preparation. PubMed: Pharmacokinetics and Pharmacodynamics of Promising Arginase Inhibitors. PubMed: Obacunone activates the Nrf2-dependent antioxidant responses. PubMed: Chemical Discrimination of Cortex Phellodendri amurensis and Cortex Phellodendri chinensis by Multivariate Analysis Approach. PubMed: Comparative metabolism of four limonoids in human liver microsomes using ultra-high-performance liquid chromatography coupled with high-resolution LTQ-Orbitrap mass spectrometry. PubMed: Developing an activity and absorption-based quality control platform for Chinese traditional medicine: Application to Zeng-Sheng-Ping(Antitumor B). PubMed: Dietary obacunone supplementation stimulates muscle hypertrophy, and suppresses hyperglycemia and obesity through the TGR5 and PPARγ pathway. PubMed: Non-targeted metabolite profiling of citrus juices as a tool for variety discrimination and metabolite flow analysis. PubMed: Cytotoxicity of obacunone and obacunone glucoside in human prostate cancer cells involves Akt-mediated programmed cell death. PubMed: Insight into reduction of obacunone, and their ester derivatives as insecticidal agents against Mythimna separata Walker. PubMed: Species-related difference between limonin and obacunone among five liver microsomes and zebrafish using ultra-high-performance liquid chromatography coupled with a LTQ-Orbitrap mass spectrometer. PubMed: [Chemical constituents from root bark of Dictamnus dasycarpus]. PubMed: Ultrafiltration liquid chromatography combined with high-speed countercurrent chromatography for screening and isolating potential α-glucosidase and xanthine oxidase inhibitors from Cortex Phellodendri. PubMed: Obacunone exhibits anti-proliferative and anti-aromatase activity in vitro by inhibiting the p38 MAPK signaling pathway in MCF-7 human breast adenocarcinoma cells. PubMed: Fingerprinting and simultaneous determination of alkaloids and limonins in Phellodendri amurensis cortex from different locations by high-performance liquid chromatography with diode array detection. PubMed: Endothelial nitric oxide synthase activation through obacunone-dependent arginase inhibition restored impaired endothelial function in ApoE-null mice. PubMed: [Analysis on component difference in Citrus reticulata before and after being processed with salt by UPLC-Q-TOF/MS]. PubMed: [Determination of obacunone and obaculactone in different processing products of Phellodendri amurensis cortex]. PubMed: Simultaneous determination of limonin, dictamnine, obacunone and fraxinellone in rat plasma by a validated UHPLC-MS/MS and its application to a pharmacokinetic study after oral administration of Cortex Dictamni extract. PubMed: Limonoids and their anti-proliferative and anti-aromatase properties in human breast cancer cells. PubMed: Obacunone represses Salmonella pathogenicity islands 1 and 2 in an envZ-dependent fashion. PubMed: Chemopreventive effect of a mixture of Chinese Herbs (antitumor B) on chemically induced oral carcinogenesis. PubMed: Structure-function relationships of citrus limonoids on p38 MAP kinase activity in human aortic smooth muscle cells. PubMed: Anti-obesity and anti-hyperglycemic effects of the dietary citrus limonoid nomilin in mice fed a high-fat diet. PubMed: Obacunone and obacunone glucoside inhibit human colon cancer (SW480) cells by the induction of apoptosis. PubMed: Apoptosis mediated cytotoxicity of citrus obacunone in human pancreatic cancer cells. PubMed: Simultaneous separation and identification of limonoids from citrus using liquid chromatography-collision-induced dissociation mass spectra. PubMed: Chemical fingerprint analysis of Phellodendri Amurensis Cortex by ultra performance LC/Q-TOF-MS methods combined with chemometrics. PubMed: [Simultaneous determination of jatrorrhizine, palmatine, berberine, and obacunone in Phellodendri Amurensis Cortex by RP-HPLC]. PubMed: Neuroprotective effects of constituents of the root bark of Dictamnus dasycarpus in mouse hippocampal cells. PubMed: Apigenin and naringenin suppress colon carcinogenesis through the aberrant crypt stage in azoxymethane-treated rats. PubMed: Grapefruit bioactive limonoids modulate E. coli O157:H7 TTSS and biofilm. PubMed: [Simultaneous determination of three active compounds in root barks of Dictamnus dasycarpus by RP-HPLC]. PubMed: Limonoids from Dictamnus dasycarpus protect against glutamate-induced toxicity in primary cultured rat cortical cells. PubMed: Neuroprotective limonoids of root bark of Dictamnus dasycarpus. PubMed: Antimalarial activity of anthothecol derived from Khaya anthotheca (Meliaceae). PubMed: Red Mexican grapefruit: a novel source for bioactive limonoids and their antioxidant activity. PubMed: Isolation of limonoids and alkaloids from Phellodendron amurense and their multidrug resistance (MDR) reversal activity. PubMed: Antiproliferative effects of citrus limonoids against human neuroblastoma and colonic adenocarcinoma cells. PubMed: Pressurized liquid extraction followed by high-performance liquid chromatography for determination of seven active compounds in Cortex Dictamni. PubMed: [Studies on chemical constituents in bark of dictamnus dasycarpus]. PubMed: Citrus limonoids induce apoptosis in human neuroblastoma cells and have radical scavenging activity. PubMed: Further studies on the anticancer activity of citrus limonoids. PubMed: Mass spectrometry and tandem mass spectrometry of citrus limonoids. PubMed: Electron ionization mass spectrometry of citrus limonoids. PubMed: Limonoids from Citrus reticulata. PubMed: [Research on the separation of limonoid glucosides by reversed-phase preparative high performance liquid chromatography]. PubMed: [Screening for limonoid glucosides in Citrus grandis L. Osbeck by high performance liquid chromatography-electrospray ionization/mass spectrometry]. PubMed: Citrus limonoids and their semisynthetic derivatives as antifeedant agents against Spodoptera frugiperda larvae. A structure-activity relationship study. PubMed: Differential inhibition of human cancer cell proliferation by citrus limonoids. PubMed: Limonoids from Nigerian Harrisonia abyssinica and their stimulatory activity against Striga hermonthica seeds. PubMed: Limonoids from Citrus sudachi. PubMed: Citrus limonoids obacunone and limonin inhibit azoxymethane-induced colon carcinogenesis in rats. PubMed: 7Beta-oxygenated limonoids from Trichilia elegans ssp. elegans. PubMed: Inhibition of azoxymethane-induced colon carcinogenesis in male F344 rats by the citrus limonoids obacunone and limonin. PubMed: Screening for limonoid glucosides in Citrus tangerina (Tanaka) Tseng by high-performance liquid chromatography-electrospray ionization mass spectrometry. PubMed: Potentiating effect of obacunone from Dictamnus dasycarpus on cytotoxicity of microtuble inhibitors, vincristine, vinblastine and taxol. PubMed: Isolation and characterization of new limonoid glycosides from Citrus unshiu peels. PubMed: Grapefruit component interacting with rat and human P450 CYP3A: possible involvement of non-flavonoid components in drug interaction. PubMed: Limonoids from Citrus reticulata and their moult inhibiting activity in mosquito Culex quinquefasciatus larvae. PubMed: Meliaceae and rutaceae limonoids as termite antifeedants evaluated usingReticulitermes speratus kolbe (Isoptera: Rhinotermitidae). PubMed: Isolation of limonin and obacunone from phellodendri cortex shorten the sleeping time induced in mice by alpha-chloralose-urethane. PubMed: A direct low temperature 1H and 19F nuclear magnetic resonance study of boron trifluoride complexes with 4-cholesten-3-one, 1(5beta)-androstene-3,17-dione, 5beta-androstane-3,17-dione, and obacunone.