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28957-04-2

28957-04-2 | Kaur-16-en-15-one, 7,20-epoxy-1,6,7,14-tetrahydroxy-, (1α,6β,7α,14R)-

CAS No: 28957-04-2 Catalog No: AG002UZH MDL No:MFCD00221762

Product Description

Catalog Number:
AG002UZH
Chemical Name:
Kaur-16-en-15-one, 7,20-epoxy-1,6,7,14-tetrahydroxy-, (1α,6β,7α,14R)-
CAS Number:
28957-04-2
Molecular Formula:
C20H28O6
Molecular Weight:
364.4327
MDL Number:
MFCD00221762
IUPAC Name:
(1S,2S,5S,8R,9S,10S,11R,15S,18R)-9,10,15,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.15,8.01,11.02,8]octadecan-7-one
InChI:
InChI=1S/C20H28O6/c1-9-10-4-5-11-18-8-26-20(25,19(11,14(9)22)15(10)23)16(24)13(18)17(2,3)7-6-12(18)21/h10-13,15-16,21,23-25H,1,4-8H2,2-3H3/t10-,11-,12-,13+,15+,16-,18+,19-,20+/m0/s1
InChI Key:
SDHTXBWLVGWJFT-XKCURVIJSA-N
SMILES:
C=C1[C@@H]2CC[C@H]3[C@@](C1=O)([C@@H]2O)[C@]1(O)OC[C@]23[C@@H](O)CCC([C@@H]2[C@@H]1O)(C)C
UNII:
0APJ98UCLQ

Properties

Complexity:
717  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Defined Bond Stereocenter Count:
0
Exact Mass:
364.189g/mol
Formal Charge:
0
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
364.438g/mol
Monoisotopic Mass:
364.189g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
107A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.1  

Literature

Title Journal
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Inhibition of RNA transportation induces glioma cell apoptosis via downregulation of RanGAP1 expression. Chemico-biological interactions 20150505
Interaction of oridonin with human serum albumin by isothermal titration calorimetry and spectroscopic techniques. Chemico-biological interactions 20150505
The tyrphostin AG1478 augments oridonin-induced A431 cell apoptosis by blockage of JNK MAPK and enhancement of oxidative stress. Free radical research 20121101
Nitric oxide augments oridonin-induced efferocytosis by human histocytic lymphoma U937 cells via autophagy and the NF-κB-COX-2-IL-1β pathway. Free radical research 20121001
Oridonin enhances antitumor activity of gemcitabine in pancreatic cancer through MAPK-p38 signaling pathway. International journal of oncology 20120901
Oridonin induces apoptosis and autophagy in murine fibrosarcoma L929 cells partly via NO-ERK-p53 positive-feedback loop signaling pathway. Acta pharmacologica Sinica 20120801
Synthesis and biological evaluation of novel furozan-based nitric oxide-releasing derivatives of oridonin as potential anti-tumor agents. Molecules (Basel, Switzerland) 20120618
The conversion of oridonin to spirolactone-type or enmein-type diterpenoid: synthesis and biological evaluation of ent-6,7-seco-oridonin derivatives as novel potential anticancer agents. European journal of medicinal chemistry 20120601
[Longikaurin A induces apoptosis of multiple myeloma H929 cells]. Zhongguo shi yan xue ye xue za zhi 20120601
[Anti-tumor effect of tanshinone II A, tetrandrine, honokiol, curcumin, oridonin and paeonol on leukemia cell lines]. Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition 20120501
Oridonin induces apoptosis and senescence by increasing hydrogen peroxide and glutathione depletion in colorectal cancer cells. International journal of molecular medicine 20120401
In vitro and in vivo evaluation of oridonin-loaded long circulating nanostructured lipid carriers. International journal of biological macromolecules 20120401
Targeting of AML1-ETO in t(8;21) leukemia by oridonin generates a tumor suppressor-like protein. Science translational medicine 20120328
Study on the autophagy of prostate cancer PC-3 cells induced by oridonin. Anatomical record (Hoboken, N.J. : 2007) 20120301
Autophagy enhanced phagocytosis of apoptotic cells by oridonin-treated human histocytic lymphoma U937 cells. Archives of biochemistry and biophysics 20120201
Biodegradable self-assembled MPEG-PCL micelles for hydrophobic oridonin delivery in vitro. Journal of biomedical nanotechnology 20120201
Synergistic antitumor activity of oridonin and arsenic trioxide on hepatocellular carcinoma cells. International journal of oncology 20120101
Autophagy counteracts apoptosis in human multiple myeloma cells exposed to oridonin in vitro via regulating intracellular ROS and SIRT1. Acta pharmacologica Sinica 20120101
RGD-modified poly(D,L-lactic acid) nanoparticles enhance tumor targeting of oridonin. International journal of nanomedicine 20120101
Oridonin nanosuspension was more effective than free oridonin on G2/M cell cycle arrest and apoptosis in the human pancreatic cancer PANC-1 cell line. International journal of nanomedicine 20120101
Optimisation of an ultrasound-assisted extraction followed by RP-HPLC separation for the simultaneous determination of oleanolic acid, ursolic acid and oridonin content in Rabdosia rubescens. Phytochemical analysis : PCA 20120101
Oridonin up-regulates expression of P21 and induces autophagy and apoptosis in human prostate cancer cells. International journal of biological sciences 20120101
Galactose-decorated pH-responsive nanogels for hepatoma-targeted delivery of oridonin. Biomacromolecules 20111212
[Study on pharmacokinetics of oridonin in mice]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20111201
Oridonin nanosuspension enhances anti-tumor efficacy in SMMC-7721 cells and H22 tumor bearing mice. Colloids and surfaces. B, Biointerfaces 20111015
Reactive oxygen species contribute to oridonin-induced apoptosis and autophagy in human cervical carcinoma HeLa cells. Acta pharmacologica Sinica 20111001
Isolation and purification of oridonin from the whole plant of Isodon rubescens by high-speed counter-current chromatography. Molecules (Basel, Switzerland) 20110914
Sensitization to TRAIL-induced apoptosis in human neuroblastoma SK-N-AS cells by NF-κB inhibitors is dependent on reactive oxygen species (ROS). Journal of neuro-oncology 20110901
Oridonin induced the apoptosis of PC-3 cells and its mechanism. Zhong nan da xue xue bao. Yi xue ban = Journal of Central South University. Medical sciences 20110801
Stimulation of suicidal erythrocyte death by oridonin. Archives of biochemistry and biophysics 20110701
Synthesis and revision of stereochemistry of rubescensin S. Organic & biomolecular chemistry 20110621
Development and in-vivo assessment of the bioavailability of oridonin solid dispersions by the gas anti-solvent technique. International journal of pharmaceutics 20110615
Proteomic and functional analyses reveal the potential involvement of endoplasmic reticulum stress and α-CP1 in the anticancer activities of oridonin in HepG2 cells. Integrative cancer therapies 20110601
Chitosan-g-poly(N-isopropylacrylamide) based nanogels for tumor extracellular targeting. International journal of pharmaceutics 20110516
Growth inhibition and induction of apoptosis in MCF-7 breast cancer cells by oridonin nanosuspension. Drug delivery 20110501
Oridonin: An active diterpenoid targeting cell cycle arrest, apoptotic and autophagic pathways for cancer therapeutics. The international journal of biochemistry & cell biology 20110501
Combined activity of oridonin and wogonin in advanced-stage ovarian cancer cells: sensitivity of ovarian cancer cells to phyto-active chemicals. Cell biology and toxicology 20110401
Downregulation of AP-1 gene expression is an initial event in the oridonin-mediated inhibition of colorectal cancer: studies in vitro and in vivo. Journal of gastroenterology and hepatology 20110401
Proteomic identification of proteins involved in the anticancer activities of oridonin in HepG2 cells. Phytomedicine : international journal of phytotherapy and phytopharmacology 20110115
A novel analysis method for diterpenoids in rat plasma by liquid chromatography-electrospray ionization mass spectrometry. Analytical biochemistry 20101201
[Autophagy of prostate cancer PC-3 cells under the induction of oridonin]. Zhonghua yi xue za zhi 20101116
Oridonin induces G2/M cell cycle arrest and apoptosis through MAPK and p53 signaling pathways in HepG2 cells. Oncology reports 20100901
Inhibition of EGFR signaling augments oridonin-induced apoptosis in human laryngeal cancer cells via enhancing oxidative stress coincident with activation of both the intrinsic and extrinsic apoptotic pathways. Cancer letters 20100828
Induction of G(2)/M phase arrest and apoptosis by oridonin in human laryngeal carcinoma cells. Journal of natural products 20100625
Preparation and characteristics of oridonin-loaded nanostructured lipid carriers as a controlled-release delivery system. Journal of microencapsulation 20100501
Apoptosis inducing and differentiation enhancement effect of oridonin on the all-trans-retinoic acid-sensitive and -resistant acute promyelocytic leukemia cells. International journal of laboratory hematology 20100201
Sigma-1 receptors regulate Bcl-2 expression by reactive oxygen species-dependent transcriptional regulation of nuclear factor kappaB. The Journal of pharmacology and experimental therapeutics 20100201
Effects of oridonin nanosuspension on cell proliferation and apoptosis of human prostatic carcinoma PC-3 cell line. International journal of nanomedicine 20100101
Oridonin induces apoptosis and senescence in colorectal cancer cells by increasing histone hyperacetylation and regulation of p16, p21, p27 and c-myc. BMC cancer 20100101
[Empirical study of oridonin-induced gastric cancer cells MKN45 apoptosis]. Zhonghua wei chang wai ke za zhi = Chinese journal of gastrointestinal surgery 20091101
Oridonin induces G2/M arrest and apoptosis via activating ERK-p53 apoptotic pathway and inhibiting PTK-Ras-Raf-JNK survival pathway in murine fibrosarcoma L929 cells. Archives of biochemistry and biophysics 20091001
[Preparation and characterization of oridonin submicron emulsions]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20091001
In vitro and in vivo antitumor activity of oridonin nanosuspension. International journal of pharmaceutics 20090908
NF-kappab facilitates oridonin-induced apoptosis and autophagy in HT1080 cells through a p53-mediated pathway. Archives of biochemistry and biophysics 20090901
Effects and mechanism of oridonin on pulmonary hypertension induced by chronic hypoxia-hypercapnia in rats. Chinese medical journal 20090620
Molecular mechanisms of oridonin-induced apoptosis and autophagy in murine fibrosarcoma L929 cells. Autophagy 20090401
Multiple-modulation effects of Oridonin on the production of proinflammatory cytokines and neurotrophic factors in LPS-activated microglia. International immunopharmacology 20090301
Autophagy inhibits reactive oxygen species-mediated apoptosis via activating p38-nuclear factor-kappa B survival pathways in oridonin-treated murine fibrosarcoma L929 cells. The FEBS journal 20090301
Involvement of PKC signal pathways in oridonin-induced autophagy in HeLa cells: a protective mechanism against apoptosis. Biochemical and biophysical research communications 20090109
Optimization and in situ intestinal absorption of self-microemulsifying drug delivery system of oridonin. International journal of pharmaceutics 20090105
[Study on stability of oridonin solution]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090101
The effect of stealth liposomes on pharmacokinetics, tissue distribution and anti-tumor activity of oridonin. PDA journal of pharmaceutical science and technology 20090101
Oridonin confers protection against arsenic-induced toxicity through activation of the Nrf2-mediated defensive response. Environmental health perspectives 20080901
Caspase inhibition augmented oridonin-induced cell death in murine fibrosarcoma l929 by enhancing reactive oxygen species generation. Journal of pharmacological sciences 20080901
[Release kinetics of oridonin self-microemulsifying drug delivery system in vitro]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080901
Synthesis and biological evaluation of novel 1-O- and 14-O-derivatives of oridonin as potential anticancer drug candidates. Bioorganic & medicinal chemistry letters 20080815
Reactive oxygen species mediate oridonin-induced HepG2 apoptosis through p53, MAPK, and mitochondrial signaling pathways. Journal of pharmacological sciences 20080801
Apoptosis-suppressing and autophagy-promoting effects of calpain on oridonin-induced L929 cell death. Archives of biochemistry and biophysics 20080715
Oridonin-loaded poly(epsilon-caprolactone)-poly(ethylene oxide)-poly(epsilon-caprolactone) copolymer nanoparticles: preparation, characterization, and antitumor activity on mice with transplanted hepatoma. Journal of drug targeting 20080701
An HPLC method for determination of oridonin in rabbits using isopsoralen as an internal standard and its application to pharmacokinetic studies for oridonin-loaded nanoparticles. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080615
Characterization and in vivo evaluation of an inclusion complex of oridonin and 2-hydroxypropyl-beta-cyclodextrin. Drug development and industrial pharmacy 20080601
Preparation and evaluation of self-microemulsifying drug delivery system of oridonin. International journal of pharmaceutics 20080501
Studies on pharmacokinetics and tissue distribution of oridonin nanosuspensions. International journal of pharmaceutics 20080501
Oridonin promotes CD4+/CD25+ Treg differentiation, modulates Th1/Th2 balance and induces HO-1 in rat splenic lymphocytes. Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20080401
Down-regulation of androgen-receptor and PSA by phytochemicals. International journal of oncology 20080201
[Inhibitory effect of Oridonin injection on heterotransplanted gastric adenocarcinoma in nude mice and its mechanism]. Zhonghua zhong liu za zhi [Chinese journal of oncology] 20080201
Oridonin induces human epidermoid carcinoma A431 cell apoptosis through tyrosine kinase and mitochondrial pathway. Journal of Asian natural products research 20080101
Oridonin induces human melanoma A375-S2 cell death partially through inhibiting insulin-like growth factor 1 receptor signaling. Journal of Asian natural products research 20080101
Oridonin induced autophagy in human cervical carcinoma HeLa cells through Ras, JNK, and P38 regulation. Journal of pharmacological sciences 20071201
Preparation and characterization of an oridonin nanosuspension for solubility and dissolution velocity enhancement. Drug development and industrial pharmacy 20071201
Oridonin induces apoptosis via PI3K/Akt pathway in cervical carcinoma HeLa cell line. Acta pharmacologica Sinica 20071101
Authentication and chemical study of isodonis herba and isodonis extracts. Chemical & pharmaceutical bulletin 20071101
[Determination of oridonin and rosemarinic acid in Rabdosia rubescens by HPLC]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20071101
[Effects of Oridonin on proliferation in human nasopharyngeal carcinoma line CNE 2 in vitro]. Zhonghua er bi yan hou tou jing wai ke za zhi = Chinese journal of otorhinolaryngology head and neck surgery 20071001
Inactivation of ras and changes of mitochondrial membrane potential contribute to oridonin-induced autophagy in a431 cells. Journal of pharmacological sciences 20070901
Studies on the cell-immunosuppressive mechanism of Oridonin from Isodon serra. International immunopharmacology 20070701
P53-mediated cell cycle arrest and apoptosis through a caspase-3- independent, but caspase-9-dependent pathway in oridonin-treated MCF-7 human breast cancer cells. Acta pharmacologica Sinica 20070701
Effects of oridonin on proliferation of HT29 human colon carcinoma cell lines both in vitro and in vivo in mice. Die Pharmazie 20070601
Autophagy preceded apoptosis in oridonin-treated human breast cancer MCF-7 cells. Biological & pharmaceutical bulletin 20070501
Oridonin, a diterpenoid extracted from medicinal herbs, targets AML1-ETO fusion protein and shows potent antitumor activity with low adverse effects on t(8;21) leukemia in vitro and in vivo. Blood 20070415
Back to the future of oridonin: again, compound from medicinal herb shows potent antileukemia efficacies in vitro and in vivo. Cell research 20070401
Effective two-dimensional counter-current chromatographic method for simultaneous isolation and purification of oridonin and ponicidin from the crude extract of Rabdosia rubescens. Journal of chromatography. A 20070330
Oridonin induced apoptosis through Akt and MAPKs signaling pathways in human osteosarcoma cells. Cancer biology & therapy 20070201
Oridonin inhibited the tyrosine kinase activity and induced apoptosis in human epidermoid carcinoma A431 cells. Biological & pharmaceutical bulletin 20070201
Studies on the oridonin-loaded poly(D,L-lactic acid) nanoparticles in vitro and in vivo. International journal of biological macromolecules 20070130
Determination of oridonin in rat plasma by reverse-phase high-performance liquid chromatography. Journal of pharmaceutical and biomedical analysis 20070117
Oridonin-induced A431 cell apoptosis partially through blockage of the Ras/Raf/ERK signal pathway. Journal of pharmacological sciences 20070101
[Mechanism of downregulation of apoptosis by autophagy induced by oridonin in HeLa cells]. Yao xue xue bao = Acta pharmaceutica Sinica 20070101
Pharmacokinetic behaviors and oral bioavailability of oridonin in rat plasma. Acta pharmacologica Sinica 20061201
Fibroblast growth factor-2 suppresses oridonin-induced L929 apoptosis through extracellular signal-regulated kinase-dependent and phosphatidylinositol 3-kinase-independent pathway. Journal of pharmacological sciences 20061101
[Change of Bcl-2 expression and telomerase during apoptosis induced by oridonin on human hepatocelluar carcinoma cells]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20061101
Fas/FasL signaling allows extracelluar-signal regulated kinase to regulate cytochrome c release in oridonin-induced apoptotic U937 cells. Biological & pharmaceutical bulletin 20060901
A rapid HPLC/ESI-MS method for the quantitative determination of oridonin in rat plasma. Die Pharmazie 20060901
Augmentation of oridonin-induced apoptosis observed with reduced autophagy. Journal of pharmacological sciences 20060701
Celastrol, a triterpene extracted from the Chinese 'Thunder of God Vine,' is a potent proteasome inhibitor and suppresses human prostate cancer growth in nude mice. Cancer research 20060501
Roles of Ras and extracellular signal-regulated kinase-dependent IkappaBalpha degradation in oridonin-enhanced phagocytosis of apoptotic cells by human macrophage-like U937 cells. International immunopharmacology 20060201
Antiproliferation effects of oridonin on HPB-ALL cells and its mechanisms of action. American journal of hematology 20060201
Isolation and purification of oridonin from Rabdosia rubescens using upright counter-current chromatography. Journal of separation science 20060201
The effects of oridonin on cell growth, cell cycle, cell migration and differentiation in melanoma cells. Journal of ethnopharmacology 20060116
A comparison of the signal pathways between the TNF alpha- and oridonin-induced murine L929 fibrosarcoma cell death. Acta medica Okayama 20051201
[Oridonin induced U937 cell apoptosis through ERK pathway]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20051201
Differential control of growth, cell cycle progression, and expression of NF-kappaB in human breast cancer cells MCF-7, MCF-10A, and MDA-MB-231 by ponicidin and oridonin, diterpenoids from the chinese herb Rabdosia rubescens. Biochemical and biophysical research communications 20051111
Bcl-2 up-regulation and P-p53 down-regulation account for the low sensitivity of murine L929 fibrosarcoma cells to oridonin-induced apoptosis. Biological & pharmaceutical bulletin 20051101
Activation of phosphoinositide 3-kinase, protein kinase C, and extracellular signal-regulated kinase is required for oridonin-enhanced phagocytosis of apoptotic bodies in human macrophage-like U937 cells. Journal of pharmacological sciences 20050801
[The tissue distribution in mice and pharmacokinetics in rabbits of oridonin-solid lipid nanoparticles]. Yao xue xue bao = Acta pharmaceutica Sinica 20050601
Oridonin, a diterpenoid purified from Rabdosia rubescens, inhibits the proliferation of cells from lymphoid malignancies in association with blockade of the NF-kappa B signal pathways. Molecular cancer therapeutics 20050401
Apoptotic effect of oridonin on NB4 cells and its mechanism. Leukemia & lymphoma 20050401
The cytostatic and cytotoxic effects of oridonin (Rubescenin), a diterpenoid from Rabdosia rubescens, on tumor cells of different lineage. International journal of oncology 20050301
Oridonin enhances phagocytosis of UV-irradiated apoptotic U937 cells. Biological & pharmaceutical bulletin 20050301
Oridonin-induced apoptosis in leukemia K562 cells and its mechanism. Neoplasma 20050101
Antiproliferation effects of oridonin on HL-60 cells. Annals of hematology 20041101
[Regulation of telomerase activity and cell cycle of K562 cells by oridonin]. Yao xue xue bao = Acta pharmaceutica Sinica 20041101
Oridonin induces a caspase-independent but mitochondria- and MAPK-dependent cell death in the murine fibrosarcoma cell line L929. Biological & pharmaceutical bulletin 20041001
Cytochrome c release from oridonin-treated apoptotic A375-S2 cells is dependent on p53 and extracellular signal-regulated kinase activation. Journal of pharmacological sciences 20041001
Oridonin induced A375-S2 cell apoptosis via bax-regulated caspase pathway activation, dependent on the cytochrome c/caspase-9 apoptosome. Journal of Asian natural products research 20040601
Anti-proliferation effect of oridonin on HL-60 cells and its mechanism. Chinese medical sciences journal = Chung-kuo i hsueh k'o hsueh tsa chih 20040601
Oridonin induces apoptosis of HeLa cells via altering expression of Bcl-2/Bax and activating caspase-3/ICAD pathway. Acta pharmacologica Sinica 20040501
Ponicidin and oridonin are responsible for the antiangiogenic activity of Rabdosia rubescens, a constituent of the herbal supplement PC SPES. Journal of natural products 20040101
Anti-proliferative effects of oridonin on SPC-A-1 cells and its mechanism of action. The Journal of international medical research 20040101
Oridonin induces growth inhibition and apoptosis of a variety of human cancer cells. International journal of oncology 20031001
Taibaijaponicains C and D: two new diterpenoids from Isodon japonica. Planta medica 20020501
Antibacterial activity of trichorabdal A from Rabdosia trichocarpa against Helicobacter pylori. Zentralblatt fur Bakteriologie : international journal of medical microbiology 19970601

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