obacunone
obacunoic acid, eta-lactone
Identification
| Name | obacunone |
| CAS Number | 751-03-1 |
| FDA UNII | Search |
| Molecular Formula | C26 H30 O7 |
| Molecular Weight | 454.51950000 |
| MDL Number | MFCD00075888 |
| Nikkaji Number | J37.085A |
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 Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for obacunone usage levels up to | not for fragrance use. |
| Recommendation for obacunone flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
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.