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shikonin
1,4-naphthalenedione, 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-

Supplier Sponsors

Name:5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
CAS Number: 517-89-5Picture of molecule3D/inchi
FDA UNII: 3IK6592UBW
Nikkaji Web:J13.981E
Beilstein Number:2058010
MDL:MFCD00016668
XlogP3-AA:3.00 (est)
Molecular Weight:288.29952000
Formula:C16 H16 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 567.40 °C. @ 760.00 mm Hg (est)
Flash Point: 592.00 °F. TCC ( 311.00 °C. ) (est)
logP (o/w): 4.350 (est)
Soluble in:
 water, 160.9 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Shikonin 98%
BOC Sciences
For experimental / research use only.
Shikonin >98%
Odor: characteristic
Use: Source from roots of Lithosperraum erythrorhizon Sieb. et Zucc. antineoplastic
Coompo
For experimental / research use only.
Shikonin from Plants ≥98%
EMD Millipore
For experimental / research use only.
Shikonin
Nacalai USA
For experimental / research use only.
Shikonin
Santa Cruz Biotechnology
For experimental / research use only.
Shikonin ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
Shikonin ≥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:
intraperitoneal-mouse LD50 20 mg/kg
BEHAVIORAL: ATAXIA BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 73, Pg. 193, 1977.

oral-mouse LD50 > 1000 mg/kg
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 73, Pg. 193, 1977.

intravenous-rabbit LD50 16 mg/kg
Pakistan Journal of Pharmacology. Vol. 3(1-2), Pg. 43, 1986.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for shikonin usage levels up to:
 not for fragrance use.
 
Recommendation for shikonin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :479503
National Institute of Allergy and Infectious Diseases:Data
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
Chemidplus:0000517895
 
References:
 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):479503
Pubchem (sid):134976484
 
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):C17412
HMDB (The Human Metabolome Database):Search
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
 gromwell purple gromwell
Search Trop Picture
 
Synonyms:
isoarnebin 4
5,8-dihydroxy-2-((R)-1-hydroxy-4-methyl-pent-3-enyl)-[1,4]naphthoquinone
(+)-5,8-8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone
(R)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione
(R)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthalenedione
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthoquinone
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-naphthoquinone
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]naphthalene-1,4-dione
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
2-((1R)-1-hydroxy-4-methylpent-3-enyl)-5,8-dihydroxynaphthalene-1,4-dione
1,4-naphthalenedione, 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-
1,4-naphthalenedione, 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-pentenyl]-
 tokyo violet
 

Articles:

PubMed:In vitro induction of erythrocyte phosphatidylserine translocation by the natural naphthoquinone shikonin.
PubMed:Novel ShikoninDerivatives Targeting Tubulin as Anti-cancer Agents.
PubMed:Shikonin-loaded antibody-armed nanoparticles for targeted therapy of ovarian cancer.
PubMed:Shikonin blocks migration and invasion of human breast cancer cells through inhibition of matrix metalloproteinase-9 activation.
PubMed:Acetylshikonin induces apoptosis of hepatitis B virus X protein-expressing human hepatocellular carcinoma cells via endoplasmic reticulum stress.
PubMed:Self-reporter shikonin-Act-loaded solid lipid nanoparticle: Formulation, physicochemical characterization and geno/cytotoxicity evaluation.
PubMed:An oxidative stress mechanism of shikonin in human glioma cells.
PubMed:Sensitizing the therapeutic efficacy of taxol with shikonin in human breast cancer cells.
PubMed:Effect of Salicylic Acid on the Activity of PAL and PHB Geranyltransferase and Shikonin Derivatives Production in Cell Suspension Cultures of Arnebia euchroma (Royle) Johnst-a Medicinally Important Plant Species.
PubMed:Sterically stabilized liposomes as a potent carrier for shikonin.
PubMed:Shikonin targets cytosolic thioredoxin reductase to induce ROS-mediated apoptosis in human promyelocytic leukemia HL-60 cells.
PubMed:Shikonin inhibits the growth of human prostate cancer cells via modulation of the androgen receptor.
PubMed:Shikonin suppresses tumor growth and synergizes with gemcitabine in a pancreatic cancer xenograft model: Involvement of NF-κB signaling pathway.
PubMed:Shikonin suppresses IL-17-induced VEGF expression via blockage of JAK2/STAT3 pathway.
PubMed:Shikonin reduces endometriosis by inhibiting RANTES secretion and mononuclear macrophage chemotaxis.
PubMed:Shikonin time-dependently induced necrosis or apoptosis in gastric cancer cells via generation of reactive oxygen species.
PubMed:Shikonin inhibits the lipopolysaccharide-induced release of HMGB1 in RAW264.7 cells via IFN and NF-κB signaling pathways.
PubMed:Liquid perfluorodecalin application for in situ extraction and enhanced naphthoquinones production in Arnebia euchroma cell suspension cultures.
PubMed:Shikonin induces cell cycle arrest in human gastric cancer (AGS) by early growth response 1 (Egr1)-mediated p21 gene expression.
PubMed:Onosma L.: A review of phytochemistry and ethnopharmacology.
PubMed:Quantitative determination of alkannins and shikonins in endemic Mediterranean Alkanna species.
PubMed:Shikonin shortens the circadian period: possible involvement of Top2 inhibition.
PubMed:Biopolymeric film containing bioactive naphthoquinone (shikonin) in combined therapy of inflammatory destructive lesions in the buccal mucosa.
PubMed:The anti-tumor effect of shikonin on osteosarcoma by inducing RIP1 and RIP3 dependent necroptosis.
PubMed:Topoisomerase I inhibitors, shikonin and topotecan, inhibit growth and induce apoptosis of glioma cells and glioma stem cells.
PubMed:Acetylshikonin, a Novel AChE Inhibitor, Inhibits Apoptosis via Upregulation of Heme Oxygenase-1 Expression in SH-SY5Y Cells.
PubMed:Improved cosmetic activity by optimizing the Lithospermum erythrorhizon extraction process.
PubMed:Protective effect of shikonin in experimental ischemic stroke: attenuated TLR4, p-p38MAPK, NF-κB, TNF-α and MMP-9 expression, up-regulated claudin-5 expression, ameliorated BBB permeability.
PubMed:[Studies on flash extraction methods of Arnebia euchroma].
PubMed:Long-term systemic toxicity of shikonin derivatives in Wistar rats.
PubMed:Pharmacological properties of shikonin - a review of literature since 2002.
PubMed:Synthesis and biological evaluation of heterocyclic carboxylic acyl shikonin derivatives.
PubMed:Shikonin inhibits thyroid cancer cell growth and invasiveness through targeting major signaling pathways.
PubMed:The apoptotic effect of shikonin on human papillary thyroid carcinoma cells through mitochondrial pathway.
PubMed:Molecularly imprinted polymers for the isolation of bioactive naphthoquinones from plant extracts.
PubMed:[Growth and accumulation of shikonin compounds of two kinds of cells in suspension culture of Arnebia euchroma].
PubMed:Shikonin suppresses ERK 1/2 phosphorylation during the early stages of adipocyte differentiation in 3T3-L1 cells.
PubMed:Design and synthesis of fluoroacylshikonin as an anticancer agent.
PubMed:Shikonin suppresses the migratory ability of hepatocellular carcinoma cells.
PubMed:Integration of Different "-omics" Technologies Identifies Inhibition of the IGF1R-Akt-mTOR Signaling Cascade Involved in the Cytotoxic Effect of Shikonin against Leukemia Cells.
PubMed:The Phytochemical Shikonin Stimulates Epithelial-Mesenchymal Transition (EMT) in Skin Wound Healing.
PubMed:Shikonin kills glioma cells through necroptosis mediated by RIP-1.
PubMed:The molecular mechanisms and gene expression profiling for shikonin-induced apoptotic and necroptotic cell death in U937 cells.
PubMed:Shikonin Suppresses Human T Lymphocyte Activation through Inhibition of IKK β Activity and JNK Phosphorylation.
PubMed:Enhancement of Lymphangiogenesis In Vitro via the Regulations of HIF-1α Expression and Nuclear Translocation by Deoxyshikonin.
PubMed:Shikonin promotes intestinal wound healing in vitro via induction of TGF-β release in IEC-18 cells.
PubMed:[Influence of fungal elicitor and macroporous resin on shikonin accumulation in hairy roots of Arnebia euchroma (Royle) Johnst].
PubMed:Shikonin exerts anti-inflammatory effects in a murine model of lipopolysaccharide-induced acute lung injury by inhibiting the nuclear factor-kappaB signaling pathway.
PubMed:Traditional chinese medicine remedy to jury: the pharmacological basis for the use of shikonin as an anticancer therapy.
PubMed:Shikonin protects dopaminergic cell line PC12 against 6-hydroxydopamine-mediated neurotoxicity via both glutathione-dependent and independent pathways and by inhibiting apoptosis.
PubMed:Shikonin attenuates lung cancer cell adhesion to extracellular matrix and metastasis by inhibiting integrin β1 expression and the ERK1/2 signaling pathway.
PubMed:Reactive oxygen species-mediated activation of the Akt/ASK1/p38 signaling cascade and p21(Cip1) downregulation are required for shikonin-induced apoptosis.
PubMed:Homogeneous purification and characterization of LePGT1--a membrane-bound aromatic substrate prenyltransferase involved in secondary metabolism of Lithospermum erythrorhizon.
PubMed:Inhibition of in vitro leukotriene B4 biosynthesis in human neutrophil granulocytes and docking studies of natural quinones.
PubMed:Shikonin, a natural product from the root of Lithospermum erythrorhizon, is a cytotoxic DNA-binding agent.
PubMed:Beneficial effect of shikonin on experimental colitis induced by dextran sulfate sodium in BALB/c mice.
PubMed:Anticancer agent shikonin is an incompetent inducer of cancer drug resistance.
PubMed:Optimization of shikonin homogenate extraction from Arnebia euchroma using response surface methodology.
PubMed:Shikonin induces programmed necrosis-like cell death through the formation of receptor interacting protein 1 and 3 complex.
PubMed:PKM2 inhibitor shikonin suppresses TPA-induced mitochondrial malfunction and proliferation of skin epidermal JB6 cells.
PubMed:Shikonin ameliorates cerulein-induced acute pancreatitis in mice.
PubMed:Preparation, cellular uptake and angiogenic suppression of shikonin-containing liposomes in vitro and in vivo.
PubMed:Shikonin attenuates lipopolysaccharide-induced acute lung injury in mice.
PubMed:Inhibitory effect of Shikonin on Candida albicans growth.
PubMed:The critical role of redox homeostasis in shikonin-induced HL-60 cell differentiation via unique modulation of the Nrf2/ARE pathway.
PubMed:Shikonin directly targets mitochondria and causes mitochondrial dysfunction in cancer cells.
PubMed:Design, synthesis and biological evaluation of cinnamic acyl shikonin derivatives.
PubMed:Effect of l-phenylalanine on PAL activity and production of naphthoquinone pigments in suspension cultures of Arnebia euchroma (Royle) Johnst.
PubMed:The molecular basis of wound healing processes induced by lithospermi radix: a proteomics and biochemical analysis.
PubMed:Addition of β-lactoglobulin produces water-soluble shikonin.
PubMed:In vitro and in vivo anticancer effects of Lithospermum erythrorhizon extract on B16F10 murine melanoma.
PubMed:Mesh-loosening quantification of inhibition of angiogenic tube formation through image analysis.
PubMed:Effect of β,β-Dimethylacrylshikonin on Inhibition of Human Colorectal Cancer Cell Growth in Vitro and in Vivo.
PubMed:Quinones derived from plant secondary metabolites as anti-cancer agents.
PubMed:[Mechanisms of (2-methyl-n-butyl) shikonin induced apoptosis of gastric cancer SGC-7901 cells].
PubMed:Lithospermum erythrorhizon suppresses high-fat diet-induced obesity, and acetylshikonin, a main compound of Lithospermum erythrorhizon, inhibits adipocyte differentiation.
PubMed:[Compare the composition and content of Arnebiae radix and the stem residues].
PubMed:Nec-1 Enhances Shikonin-Induced Apoptosis in Leukemia Cells by Inhibition of RIP-1 and ERK1/2.
PubMed:Shikonin and its derivatives: a patent review.
PubMed:[Antitumor effect research progress of shikonin and its derivatives].
PubMed:Ionization of shikonin derivatives using negative-ion electrospray mass spectrometry: [M-H]- versus [M + e]•-.
PubMed:[Effects of shikonin on the proliferation and apoptosis of HL-60 cells].
PubMed:Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells.
PubMed:Shikonin induces immunogenic cell death in tumor cells and enhances dendritic cell-based cancer vaccine.
PubMed:Shikonin enhances efficacy of a gene-based cancer vaccine via induction of RANTES.
PubMed:Novel multiple apoptotic mechanism of shikonin in human glioma cells.
PubMed:On-line continuous sampling dynamic microwave-assisted extraction coupled with high performance liquid chromatographic separation for the determination of lignans in Wuweizi and naphthoquinones in Zicao.
PubMed:Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases.
PubMed:Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin.
PubMed:Chemical inducers of heat shock proteins derived from medicinal plants and cytoprotective genes response.
PubMed:A protocol for detecting and scavenging gas-phase free radicals in mainstream cigarette smoke.
PubMed:Redox and non-redox mechanism of in vitro cyclooxygenase inhibition by natural quinones.
PubMed:[Rationality for dynamic detection of shikonin of Arnerbia euchroma in industrial process].
PubMed:Shikonin, a Chinese plant-derived naphthoquinone, induces apoptosis in hepatocellular carcinoma cells through reactive oxygen species: A potential new treatment for hepatocellular carcinoma.
PubMed:Glutathione-S-transferase enhances proliferation-migration and protects against shikonin-induced cell death in breast cancer cells.
PubMed:Compounds from Arnebia euchroma and their related anti-HCV and antibacterial activities.
PubMed:Chimeric advanced drug delivery nano systems (chi-aDDnSs) for shikonin combining dendritic and liposomal technology.
PubMed:Screening for novel quorum-sensing inhibitors to interfere with the formation of Pseudomonas aeruginosa biofilm.
PubMed:Shikonin increases glucose uptake in skeletal muscle cells and improves plasma glucose levels in diabetic Goto-Kakizaki rats.
PubMed:[Study on dynamic changes and stability of effective components of Arnerbia euchroma].
PubMed:Shikonin inhibited mitogen-activated IL-4 and IL-5 production on EL-4 cells through downregulation of GATA-3 and c-Maf induction.
PubMed:Structure/antileishmanial activity relationship study of naphthoquinones and dependency of the mode of action on the substitution patterns.
PubMed:Anti-cancer natural products isolated from chinese medicinal herbs.
PubMed:Detailed investigations on the solid cell culture and antimicrobial activities of the Iranian Arnebia euchroma.
PubMed:Theoretical investigation of the radical scavenging activity of shikonin and acylshikonin derivatives.
PubMed:Synthesis and antitumour activity of β-hydroxyisovalerylshikonin analogues.
PubMed:Cancer therapeutic agents targeting hypoxia-inducible factor-1.
PubMed:Semi-synthesis and antitumor activity of 6-isomers of 5, 8-O-dimethyl acylshikonin derivatives.
PubMed:Determination of the active constituents in Arnebia euchroma (Royle) Johnst. by ionic liquid-based ultrasonic-assisted extraction high-performance liquid chromatography.
PubMed:Modeling of hyperbranched polyesters as hosts for the multifunctional bioactive agent Shikonin.
PubMed:Shikonin derivatives protect immune organs from damage and promote immune responses in vivo in tumour-bearing mice.
PubMed:Shikonin and its analogs inhibit cancer cell glycolysis by targeting tumor pyruvate kinase-M2.
PubMed:Evaluation of the effectiveness of an ointment based on Alkannins/Shikonins on second intention wound healing in the dog.
PubMed:Assessment of shikonin for potential estrogenic activity by dual-luciferase reporter based bioluminescent measurements in vitro.
PubMed:Anti-adenovirus activities of shikonin, a component of Chinese herbal medicine in vitro.
PubMed:Shikonin extracted from medicinal Chinese herbs exerts anti-inflammatory effect via proteasome inhibition.
PubMed:Electrospun fiber mats containing shikonin and derivatives with potential biomedical applications.
PubMed:LeERF-1, a novel AP2/ERF family gene within the B3 subcluster, is down-regulated by light signals in Lithospermum erythrorhizon.
PubMed:Comparative study on enantiomeric excess of main akannin/shikonin derivatives isolated from the roots of three endemic Boraginaceae plants in China.
PubMed:DNA damage induced by shikonin in the presence of Cu(II) ions: potential mechanism of its activity to apoptotic cell death.
PubMed:Tigloylshikonin, a new minor Shikonin derivative, from the roots and the commercial root extract of lithospermum erythrorhizon.
PubMed:Shikonin inhibits the proliferation and induces the apoptosis of human HepG2 cells.
PubMed:Shikonin inhibits adipogenesis by modulation of the WNT/β-catenin pathway.
PubMed:[Simultaneous determination of five active components in compound preparation of Dangguishuan by high-performance liquid chromatography].
PubMed:Unexpected applications of secondary metabolites.
PubMed:Expression of 3-hydroxy-3-methylglutaryl-CoA reductase, p-hydroxybenzoate-m-geranyltransferase and genes of phenylpropanoid pathway exhibits positive correlation with shikonins content in arnebia [Arnebia euchroma (Royle) Johnston].
PubMed:Shikonin inhibits tumor invasion via down-regulation of NF-κB-mediated MMP-9 expression in human ACC-M cells.
PubMed:Physico-chemical factors influencing the shikonin derivatives production in cell suspension cultures of Arnebia euchroma (Royle) Johnston, a medicinally important plant species.
PubMed:Semi-synthesis and anti-tumor activity of 5,8-O-dimethyl acylshikonin derivatives.
PubMed:Differential functional genomic effects of anti-inflammatory phytocompounds on immune signaling.
PubMed:The efficacy of shikonin on cartilage protection in a mouse model of rheumatoid arthritis.
PubMed:Shikonin inhibits maturation of bone marrow-derived dendritic cells and suppresses allergic airway inflammation in a murine model of asthma.
PubMed:Callus culture of Echium italicum L. towards production of a shikonin derivative.
PubMed:Inhibition of estrogen signaling activates the NRF2 pathway in breast cancer.
PubMed:Shikonin protects mouse brain against cerebral ischemia/reperfusion injury through its antioxidant activity.
PubMed:Shikonin induces apoptosis through reactive oxygen species/extracellular signal-regulated kinase pathway in osteosarcoma cells.
PubMed:Solid-phase extraction for purification of alkannin/shikonin samples and isolation of monomeric and dimeric fractions.
PubMed:[Novel compounds increasing chaperone Hsp70 expression and their biological activity].
PubMed:Shikonin reduces oedema induced by phorbol ester by interfering with IkappaBalpha degradation thus inhibiting translocation of NF-kappaB to the nucleus.
PubMed:Synthesis and antitumor activity of new shikonin glycosides.
PubMed:[Role of NF-kappaB pathway in shikonin induced apoptosis in oral squamous cell carcinoma Tca-8113 cells].
PubMed:Shikonin directly inhibits nitric oxide synthases: possible targets that affect thoracic aorta relaxation response and nitric oxide release from RAW 264.7 macrophages.
PubMed:Targeting tumor proteasome with traditional Chinese medicine.
PubMed:Effect of hydroxy substituent on the prooxidant action of naphthoquinone compounds.
PubMed:[Shikonin down-regulates CXCR4 expression and inhibits CXCL12-induced migratory responses in colorectal carcinoma cell line SW480].
PubMed:Bothriodumin, a shikonin derivative from Bothriospermum secundum Maxim.
PubMed:A novel antiestrogen agent Shikonin inhibits estrogen-dependent gene transcription in human breast cancer cells.
PubMed:Effects of shikonin isolated from zicao on lupus nephritis in NZB/W F1 mice.
PubMed:Simultaneous densitometric determination of shikonin, acetylshikonin, and beta-acetoxyisovaleryl-shikonin in ultrasonic-assisted extracts of four Arnebia species using reversed-phase thin layer chromatography.
PubMed:Electrospun shikonin-loaded PCL/PTMC composite fiber mats with potential biomedical applications.
PubMed:Shikonin inhibits fat accumulation in 3T3-L1 adipocytes.
PubMed:In vitro and in vivo antitumor effects of acetylshikonin isolated from Arnebia euchroma (Royle) Johnst (Ruanzicao) cell suspension cultures.
PubMed:Shikonin, an ingredient of Lithospermum erythrorhizon, down-regulates the expression of steroid sulfatase genes in breast cancer cells.
PubMed:Functional characterization of LePGT1, a membrane-bound prenyltransferase involved in the geranylation of p-hydroxybenzoic acid.
PubMed:Necrostatin-1 reverts shikonin-induced necroptosis to apoptosis.
PubMed:Identification of shikonin and its ester derivatives from the roots of Echium italicum L.
PubMed:Mechanism of inhibition of tumor angiogenesis by beta-hydroxyisovalerylshikonin.
PubMed:Shikonin exerts antitumor activity via proteasome inhibition and cell death induction in vitro and in vivo.
PubMed:Synthesis and biological activity of novel shikonin analogues.
PubMed:Alkannins and shikonins: a new class of wound healing agents.
PubMed:Naturally-occurring shikonin analogues--a class of necroptotic inducers that circumvent cancer drug resistance.
PubMed:Nitric oxide regulates shikonin formation in suspension-cultured Onosma paniculatum cells.
PubMed:Larvicidal activity of naturally occurring naphthoquinones and derivatives against the West Nile virus vector Culex pipiens.
PubMed:Synthesis and antitumor activity of 6- and 2-(1-substituted-thio-4-methylpent-3-enyl)-5,8-dimethoxynaphthalene-1,4-diones.
PubMed:Shikonin, acetylshikonin, and isobutyroylshikonin inhibit VEGF-induced angiogenesis and suppress tumor growth in lewis lung carcinoma-bearing mice.
PubMed:Modulation of orphan nuclear receptor Nur77-mediated apoptotic pathway by acetylshikonin and analogues.
PubMed:Red pigment from Lithospermum erythrorhizon by supercritical CO2 extraction.
PubMed:Shikonin derivatives inhibited LPS-induced NOS in RAW 264.7 cells via downregulation of MAPK/NF-kappaB signaling.
PubMed:Shikonin inhibits IgE-mediated histamine release by human basophils and Syk kinase activity.
PubMed:Preparative isolation and purification of alkannin/shikonin derivatives from natural products by high-speed counter-current chromatography.
PubMed:Dual role of shikonin in early and late stages of collagen type II arthritis.
PubMed:Induction of apoptosis by shikonin through a ROS/JNK-mediated process in Bcr/Abl-positive chronic myelogenous leukemia (CML) cells.
PubMed:Shikonins attenuate microglial inflammatory responses by inhibition of ERK, Akt, and NF-kappaB: neuroprotective implications.
PubMed:Immunomodulatory effects of phytocompounds characterized by in vivo transgenic human GM-CSF promoter activity in skin tissues.
PubMed:[Shikonin inhibits the proliferation of human airway smooth muscle cells].
PubMed:Alkannin/shikonin mixture from roots of Onosma echioides (L.) L.: extraction method study and quantification.
PubMed:Isolation and purification of acetylshikonin and beta-acetoxyisovalerylshikonin from cell suspension cultures of Arnebia euchroma (Royle) Johnston using rapid preparative HPLC.
PubMed:Expression analysis of light-regulated genes isolated from a full-length-enriched cDNA library of Onosma paniculatum cell cultures.
PubMed:Shikonin-induced apoptosis involves caspase-3 activity in a human bladder cancer cell line (T24).
PubMed:Growth inhibition and induction of apoptosis in human oral squamous cell carcinoma Tca-8113 cell lines by Shikonin was partly through the inactivation of NF-kappaB pathway.
PubMed:Bypassing cancer drug resistance by activating multiple death pathways--a proposal from the study of circumventing cancer drug resistance by induction of necroptosis.
PubMed:Simultaneous determination of monomeric and oligomeric alkannins and shikonins by high-performance liquid chromatography-diode array detection-mass spectrometry.
PubMed:Shikonin analogue (SA) 93/637 induces apoptosis by activation of caspase-3 in U937 cells.
PubMed:Comparison of the cytotoxic activities of naturally occurring hydroxyanthraquinones and hydroxynaphthoquinones.
PubMed:Pharmacogenomics of a traditional Japanese herbal medicine (Kampo) for cancer therapy.
PubMed:Simultaneous determination of naphthoquinone derivatives in Boraginaceous herbs by high-performance liquid chromatography.
PubMed:Targeting the weak point of cancer by induction of necroptosis.
PubMed:Microencapsulation of extract containing shikonin using gelatin-acacia coacervation method: a formaldehyde-free approach.
PubMed:Shikonin circumvents cancer drug resistance by induction of a necroptotic death.
PubMed:Protection of human keratinocytes from UVB-induced inflammation using root extract of Lithospermum erythrorhizon.
PubMed:DMNQ S-64 induces apoptosis via caspase activation and cyclooxygenase-2 inhibition in human nonsmall lung cancer cells.
PubMed:Inhibition of tumor necrosis factor-alpha through selective blockade of Pre-mRNA splicing by shikonin.
PubMed:A new EGFR inhibitor induces apoptosis in colon cancer cells.
PubMed:Human ACAT inhibitory effects of shikonin derivatives from Lithospermum erythrorhizon.
PubMed:Effect of shikonin on human breast cancer cells proliferation and apoptosis in vitro.
PubMed:Analysis of alkannin derivatives from Alkanna species by high-performance liquid chromatography/photodiode array/mass spectrometry.
PubMed:A naphthoquinone derivative, shikonin, has insulin-like actions by inhibiting both phosphatase and tensin homolog deleted on chromosome 10 and tyrosine phosphatases.
PubMed:The shikonin derivatives and pyrrolizidine alkaloids in hairy root cultures of Lithospermum canescens (Michx.) Lehm.
PubMed:Cell growth and shikonin production of Arnebia euchroma in a periodically submerged airlift bioreactor.
PubMed:SH-7, a new synthesized shikonin derivative, exerting its potent antitumor activities as a topoisomerase inhibitor.
PubMed:Evaluation of the anti-inflammatory and cytotoxic activities of naphthazarine derivatives from Onosma leptantha.
PubMed:[Antitumor effect and mechanism of shikonin derivative SYUNZ-7].
PubMed:Fibroblast growth stimulation by extracts and compounds of Onosma argentatum roots.
PubMed:[Effect of shikonin, a phytocompound from Lithospermum erythrorhizon, on rat vascular smooth muscle cells proliferation and apoptosis in vitro].
PubMed:[Determination of shikonin derivatives in gromwell by reversed-phase high performance liquid chromatography].
PubMed:Presence of peroxyradicals in cigarette smoke and the scavenging effect of shikonin, a naphthoquinone pigment.
PubMed:Monoamine oxidase inhibitory naphthoquinones from the roots of Lithospermum erythrorhizon.
PubMed:Phosphorylated extracellular signal-regulated kinase up-regulated p53 expression in shikonin-induced HeLa cell apoptosis.
PubMed:Radical scavenging activity of Alkanna tinctoria root extracts and their main constituents, hydroxynaphthoquinones.
PubMed:Ethylene induced shikonin biosynthesis in shoot culture of Lithospermum erythrorhizon.
PubMed:Structure determination of oligomeric alkannin and shikonin derivatives.
PubMed:[Cytochrome P450 enzymes in biosyntheses of some plant secondary metabolites].
PubMed:[Biosynthesis of naphthoquinoine pigments in plants from Boraginaceae family in nature and in vitro culture].
PubMed:Separation methods of quinonoid constituents of plants used in Oriental traditional medicines.
PubMed:Induction of apoptosis by shikonin through coordinative modulation of the Bcl-2 family, p27, and p53, release of cytochrome c, and sequential activation of caspases in human colorectal carcinoma cells.
PubMed:Study on the enantiomeric ratio of the pharmaceutical substances alkannin and shikonin.
PubMed:Study on polymerization of the pharmaceutical substances isohexenylnaphthazarins.
PubMed:Study on isohexenylnaphthazarins polymerization in alkaline media.
PubMed:Immunomodulatory effect of shikonin derivatives isolated from Lithospermum canescens on cellular and humoral immunity in Balb/c mice.
PubMed:[Production of shikonin by cell cultures of Lithospermum erythrorhizon].
PubMed:(S)-2,3-Di-O-geranylgeranylglyceryl phosphate synthase from the thermoacidophilic archaeon Sulfolobus solfataricus. Molecular cloning and characterization of a membrane-intrinsic prenyltransferase involved in the biosynthesis of archaeal ether-linked membrane lipids.
PubMed:Shikonin inhibits the growth and N-acetylation of 2-aminofluorene in Helicobacter pylori from ulcer patients.
PubMed:Shikonin regulates HeLa cell death via caspase-3 activation and blockage of DNA synthesis.
PubMed:Encapsulation of isohexenylnaphthazarins in cyclodextrins.
PubMed:The inhibition of N-acetyltransferase activity and gene expression in human bladder cancer cells (T24) by shikonin.
PubMed:p53-mediated cell cycle arrest and apoptosis induced by shikonin via a caspase-9-dependent mechanism in human malignant melanoma A375-S2 cells.
PubMed:Impairment of vascular function of rat thoracic aorta in an endothelium-dependent manner by shikonin/alkannin and derivatives isolated from roots of Macrotomia euchroma.
PubMed:Preparative high-speed counter-current chromatography for purification of shikonin from the Chinese medicinal plant Lithospermum erythrorhizon.
PubMed:Enhancement of wound healing by shikonin analogue 93/637 in normal and impaired healing.
PubMed:Involvement of reactive oxygen species, but not mitochondrial permeability transition in the apoptotic induction of human SK-Hep-1 hepatoma cells by shikonin.
PubMed:Shikonins, phytocompounds from Lithospermum erythrorhizon, inhibit the transcriptional activation of human tumor necrosis factor alpha promoter in vivo.
PubMed:Shikonin modulates cell proliferation by inhibiting epidermal growth factor receptor signaling in human epidermoid carcinoma cells.
PubMed:A shikonin derivative, beta-hydroxyisovalerylshikonin, is an ATP-non-competitive inhibitor of protein tyrosine kinases.
PubMed:Shikonin, a component of chinese herbal medicine, inhibits chemokine receptor function and suppresses human immunodeficiency virus type 1.
PubMed:Synthesis and release studies of shikonin-containing microcapsules prepared by the solvent evaporation method.
PubMed:Anti-inflammatory activity of shikonin derivatives from Arnebia hispidissima.
PubMed:Biological activity of some naturally occurring resins, gums and pigments against in vitro LDL oxidation.
PubMed:Molecular cloning and characterization of a cDNA encoding a novel apoplastic protein preferentially expressed in a shikonin-producing callus strain of Lithospermum erythrorhizon.
PubMed:Beta-hydroxyisovalerylshikonin is a novel and potent inhibitor of protein tyrosine kinases.
PubMed:Antimicrobial activities of naphthazarins from Arnebia euchroma.
PubMed:Alkannin and shikonin: effect on free radical processes and on inflammation - a preliminary pharmacochemical investigation.
PubMed:High level expression of chorismate pyruvate-lyase (UbiC) and HMG-CoA reductase in hairy root cultures of Lithospermum erythrorhizon.
PubMed:Regulation of lithospermic acid B and shikonin production in Lithospermum erythrorhizon cell suspension cultures.
PubMed:Cellular pharmacology studies of shikonin derivatives.
PubMed:Direct reaction between shikonin and thiols induces apoptosis in HL60 cells.
PubMed:In vitro antifungal activity of naphthoquinone derivatives.
PubMed:Shikonin derivatives: synthesis and inhibition of human telomerase.
PubMed:Inhibitory effects of quinones on RNase H activity associated with HIV-1 reverse transcriptase.
PubMed:A new efficient route for multigram asymmetric synthesis of alkannin and shikonin.
PubMed:Shikonin stimulates glucose uptake in 3T3-L1 adipocytes via an insulin-independent tyrosine kinase pathway.
PubMed:Enhancement of shikonin production in single- and two-phase suspension cultures of Lithospermum erythrorhizon cells using low-energy ultrasound.
PubMed:Geranyl diphosphate:4-hydroxybenzoate geranyltransferase from Lithospermum erythrorhizon. Cloning and characterization of a ket enzyme in shikonin biosynthesis.
PubMed:Development and use of a gene promoter-based screen to identify novel inhibitors of cyclooxygenase-2 transcription.
PubMed:Cinnamoyl shikonin.
PubMed:Antitumor activities of a newly synthesized shikonin derivative, 2-hyim-DMNQ-S-33.
PubMed:New naphthoquinones from Arnebia hispidissima roots.
PubMed:Granulomatous tissue formation of shikon and shikonin by air pouch method.
PubMed:Shikonin production by p-fluorophenylalanine resistant cells of Lithospermum erythrorhizon.
PubMed:Shikonin, a component of antiinflammatory Chinese herbal medicine, selectively blocks chemokine binding to CC chemokine receptor-1.
PubMed:A novel dark-inducible protein, LeDI-2, and its involvement in root-specific secondary metabolism in Lithospermum erythrorhizon.
PubMed:Reaction of beta-alkannin (shikonin) with reactive oxygen species: detection of beta-alkannin free radicals.
PubMed:Genetic engineering on shikonin biosynthesis: expression of the bacterial ubiA gene in Lithospermum erythrorhizon.
PubMed:Inhibition of growth and regulation of IGFs and VEGF in human prostate cancer cell lines by shikonin analogue 93/637 (SA).
PubMed:Simultaneous analysis of shikimate-derived secondary metabolites in Lithospermum erythrorhizon cell suspension cultures by high-performance liquid chromatography.
PubMed:Caffeic acid oligomers in Lithospermum erythrorhizon cell suspension cultures.
PubMed:[Changes in productivity of plant cells as result of cultivation under the space flight conditions].
PubMed:Geranylhydroquinone 3"-hydroxylase, a cytochrome P-450 monooxygenase from Lithospermum erythrorhizon cell suspension cultures.
PubMed:Physical stability of shikonin derivatives from the roots of Lithospermum erythrorhizon cultivated in Korea.
PubMed:Effect of Brassinolide on Growth and Shikonin Formation in Cultured Onosma paniculatum Cells.
PubMed:Exogenous quinones inhibit photosynthetic electron transfer in Chloroflexus aurantiacus by specific quenching of the excited bacteriochlorophyll c antenna.
PubMed:Propionylshikonin from the roots of Lithospermum erythrorhizon.
PubMed:Shikonin, an ingredient of Lithospermum erythrorhizon induced apoptosis in HL60 human premyelocytic leukemia cell line.
PubMed:Studies on in vitro metabolism of shikonin.
PubMed:Genetic engineering of shikonin biosynthesis hairy root cultures of Lithospermum erythrorhizon transformed with the bacterial ubiC gene.
PubMed:Cell-specific production and antimicrobial activity of naphthoquinones in roots of lithospermum erythrorhizon
PubMed:[Effect of shikonin and alkannin on hydroxyl radical generation system concerned with iron ion].
PubMed:beta-hydroxyisovalerylshikonin inhibits the cell growth of various cancer cell lines and induces apoptosis in leukemia HL-60 cells through a mechanism different from those of Fas and etoposide.
PubMed:Enantiomeric ratio of shikonin derivatives as a possible key for the determination of the origin of lithospermi radix.
PubMed:Inhibition of topoisomerase I by naphthoquinone derivatives.
PubMed:Evaluation of shikonin on granulation tissue formation compared with carrageenan.
PubMed:4-Hydroxybenzoate 3-geranyltransferase from Lithospermum erythrorhizon: purification of a plant membrane-bound prenyltransferase.
PubMed:Shikonin, an ingredient of Lithospermum erythrorhizon, inhibits angiogenesis in vivo and in vitro.
PubMed:Study of the accelerating effect of shikonin and alkannin on the proliferation of granulation tissue in rats.
PubMed:Regulatory role of microsomal 3-hydroxy-3-methylglutaryl-coenzyme A reductase for shikonin biosynthesis in Lithospermum erythrorhizon cell suspension cultures.
PubMed:cDNA cloning and gene expression of phenylalanine ammonia-lyase in Lithospermum erythrorhizon.
PubMed:Study on baths with crude drug. III. The effect of ligustici chuanxiong rhizoma extract on the percutaneous absorption of some natural compounds.
PubMed:Inhibition on platelet activation by shikonin derivatives isolated from Arnebia euchroma.
PubMed:Acylshikonin analogues: synthesis and inhibition of DNA topoisomerase-I.
PubMed:[Effect of the interaction of tannins with coexisting substances. VIII. Inhibitory effect of tannins on discoloration of natural pigments].
PubMed:Shikonin production by extractive cultivation in transformed-suspension and hairy root cultures of Lithospermum erythrorhizon.
PubMed:Accelerative effect of shikonin, alkannin and acetylshikonin on the proliferation of granulation tissue in rats.
PubMed:[The antiinflammatory activity of shikonin and its inhibitory effect on leukotriene B4 biosynthesis].
PubMed:Inhibition of platelet aggregation by shikonin derivatives isolated from Arnebia euchroma.
PubMed:Improvement of shikonin productivity in Lithospermum erythrorhizon cell culture by alternating carbon and nitrogen feeding strategy.
PubMed:Comparative study on the accelerative effect of "koushikon" and "nanshikon" and their constituents on proliferation of granuloma tissue in rats.
PubMed:[Studies on CD spectra of derivatives of shikonin and alkannin].
PubMed:Modifying effects of fungal and herb metabolites on azoxymethane-induced intestinal carcinogenesis in rats.
PubMed:Induction of topoisomerase II-mediated DNA cleavage by the plant naphthoquinones plumbagin and shikonin.
PubMed:Human in vivo percutaneous absorptiometry using the laser-photoacoustic method.
PubMed:Biochemical and electrophoretical studies of the effect of some chemosterilants on theenzymes of aedes aegypti (L.) larvae.
PubMed:Enzyme activity and shikonin production in Lithospermum erythrorhizon cell cultures.
PubMed:[Effect of shikonin and its derivatives, pentaacetylated shikonin (MDS-004) on granuloma formation and delayed-type allergy in experimental animals].
PubMed:[Clinical trial on the effects of shikonin mixture on later stage lung cancer].
PubMed:Shikonin production and secretion by hairy root cultures of Lithospermum erythrorhizon.
PubMed:[Quality of Chinese drug zicao].
PubMed:Enhanced shikonin production from Lithospermum erythrorhizon by in situ extraction and calcium alginate immobilization.
PubMed:Induction of shikonin biosynthesis by endogenous polysaccharides in Lithospermum erythrorhizon cell suspension cultures.
PubMed:[Detection of the anti-cancer biological effect of naphthoquinone pigment-LIII].
PubMed:[Evaluation on equivalence of pharmacological properties between natural crude drugs and their cultured cells based on their components. Accelerative effect of lithospermi radix and inhibitory effect of coptidis rhizoma on proliferation of granulation tissue].
PubMed:In vitro percutaneous absorptiometry by simultaneous measurement using the photoacoustic method and absorbance.
PubMed:Betanin Production and Release In Vitro from Suspension Cultures of Beta vulgaris.
PubMed:Partial purification and properties of geranyl pyrophosphate synthase from Lithospermum erythrorhizon cell cultures.
PubMed:Studies on inhibitors of skin tumor promotion, VI. Inhibitory effects of quinones on Epstein-Barr virus activation.
PubMed:New Aspects of Shikonin Biosynthesis: Geranyl Pyrophosphate Synthase and Origin of p-Hydroxybenzoic Acid.
PubMed:[A study on absorption, distribution and excretion of 3H-shikonin in mice].
PubMed:Isolation of deoxyshikonin, an antidermatophytic principle from Lithospermum erythrorhizon cell cultures.
PubMed:[Tissue cultures of Lithospermum erythrorhizon and biosynthesis of shikonin derivatives].
PubMed:[Application of supercritical fluid extraction to components of crude drugs and plants. III. Extraction of pigments from lithospermum root and licorice root].
PubMed:Production of shikonin derivatives by cell suspension cultures of Lithospermum erythrorhizon : VI. Production of shikonin derivatives by a two-layer culture containing an organic solvent.
PubMed:Regulation of shikonin production by glutamine in Lithospermum erythrorhizon cell cultures.
PubMed:Production of shikonin derivatives by cell suspension cultures of Lithospermum erythrorhizon : V. Differences in the production between callus and suspension cultures.
PubMed:A comparative study on anti-inflammatory activities of the enantiomers, shikonin and alkannin.
PubMed:Intracellular Localization and Secretion of Naphthoquinone Pigments in Cell Cultures of Lithospermum erythrorhizon.
PubMed:Production of shikonin derivatives by cell suspension cultures of Lithospermum erythrorhizon. III. Comparison of shikonin derivatives of cultured cells and ko-shikon.
PubMed:Production of shikonin derivatives by cell suspension cultures of Lithospermum erythrorhizon : II. A new Medium for the production of shikonin derivatives.
PubMed:Production of shikonin derivatives by cell suspension cultures of Lithospermum erythrorhizon : I. Effects of nitrogen sources on the production of shikonin derivatives.
PubMed:Antitumor activity of shikonin, alkannin and their derivatives. II. X-ray analysis of cyclo-alkannin leucoacetate, tautomerism of alkannin and cyclo-alkannin and antitumor activity of alkannin derivatives.
PubMed:[Biological characteristics of the gromwell (Lithospermum erythrorhizon Sieb. et Zucc.) and its content of shikonin when grown in Moscow Province].
PubMed:Effect of tepa, shikonin and ecdysone on the alkaline phosphatase in the larvae Aedes aegypti (L.).
PubMed:Antitumor activity of shikonin and its derivatives.
PubMed:[Pharmacological studies of Shikon and Tooki. (2) Pharmacological effects of the pigment components, Shikonin and acetylshikonin].
PubMed:[Photocolorimetric determination of shikonin].
 
Notes:
a naphthazarin; has antineoplastic and angiogenesis inhibiting activities.
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