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Deoxyshikonin

$359

  • Brand : BIOFRON

  • Catalogue Number : BD-P0041

  • Specification : 98.0%(HPLC)

  • CAS number : 43043-74-9

  • Formula : C16H16O4

  • Molecular Weight : 272.3

  • PUBCHEM ID : 98914

  • Volume : 20mg

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Catalogue Number

BD-P0041

Analysis Method

Specification

98.0%(HPLC)

Storage

-20℃

Molecular Weight

272.3

Appearance

Powder

Botanical Source

This product is isolated and purified from the roots of Lithosperraum erythrorhizon Sieb. et Zucc.

Structure Type

Category

SMILES

CC(=CCCC1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)C

Synonyms

5,8-dihydroxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione

IUPAC Name

Applications

Antibacterial and cytotoxic activities of naphthoquinone pigments from Onosma visianii Clem.[Pubmed: 28435429 ]Wound healing effects of deoxyshikonin isolated from Jawoongo: In vitro and in vivo studies.[Pubmed: 27725239 ]J Ethnopharmacol. 2017 Mar 6;199:128-137. Jawoongo is a traditional drug ointment (with a traditional botanic formula) used for the treatment of burns and wounds in Korea. One of the components of Jawoongo is Lithospermi Radix (LR, the dried root of Lithospermum erythrorhizon Siebold & Zucc., also known as Zicao or Gromwell), which contains Deoxyshikonin and its derivatives. The aim of the present study was to investigate the effects of Deoxyshikonin on wound healing. METHODS AND RESULTS: The effects of LR extract and Deoxyshikonin on tube formation and migration were measured in human umbilical vein vascular endothelial cells (HUVEC) and HaCaT cells, respectively. We evaluated protein expression of mitogen-activated protein kinase (MAPK) activation by Western blotting. The wound healing effects of Deoxyshikonin was assessed in a mouse model of cutaneous wounds. The results showed that Deoxyshikonin enhanced tube formation in HUVEC and migration in HaCaT cells. From the western blot analysis, we found that Deoxyshikonin stimulated the phosphorylation of p38 and extracellular signal-regulated kinase (ERK) in HaCaT cells. Moreover, 20μm Deoxyshikonin-treated groups showed accelerated wound closure compared with the controls in a mouse model of cutaneous wounds. CONCLUSIONS: In conclusion, the current data indicate that Deoxyshikonin treatment elevated tube formation in HUVECs, and that Deoxyshikonin-induced proliferation and migration in HaCaT cells were mediated by the activation of ERK and p38 MAPKs, respectively. Collectively, these data suggest that Deoxyshikonin in Jawoongo must be an active compound for may be wound healing.EXCLI J. 2017 Feb 16;16:73-88. In this study, the antibacterial and cytotoxic activities of isolated compounds from the roots of Onosma visianii were investigated. METHODS AND RESULTS:By using different chromatographic techniques and appropriate spectroscopic methods, the seven naphthoquinones were described: Deoxyshikonin ( 1 ), isobutyrylshikonin ( 2 ), α-methylbutyrylshikonin ( 3 ), acetylshikonin ( 4 ), β-hydroxyisovalerylshikonin ( 5 ), 5,8-O-dimethyl isobutyrylshikonin ( 6 ) and 5,8-O-dimethyl Deoxyshikonin ( 7 ). Among the tested compounds, 3 and 4 exhibited the highest antibacterial activities toward all tested bacterial species (MIC50 and MIC90 for gram positive bacteria: 6.40 μg/mL-12.79 μg/mL and 6.82 μg/mL-13.60 μg/mL, respectively; for gram negative bacteria: 4.27 μg/mL-8.53 μg/mL and 4.77 μg/mL-9.54 μg/mL, respectively). Also, naphthoquinones 3 and 4 exhibited strong cytotoxic activity against MDA-MB-231 cells (IC50 values 86.0 μg/mL and 80.2 μg/mL, respectively), while compounds 1 , 3 , 4 and 5 significantly decreased viability of HCT116 cells (IC50 values of 97.8 μg/mL, 15.2 μg/mL, 24.6 μg/mL and 30.9 μg/mL, respectively). CONCLUSIONS:Our results indicated that all tested naphthoquinone pigments are potential candidates for clinical uses as antibacterial and cytotoxic agents.

Density

1.3±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

272.5±26.6 °C

Boiling Point

503.7±50.0 °C at 760 mmHg

Melting Point

91ºC

InChl

InChl Key

VOMDIEGPEURZJO-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:43043-74-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

31230505

Abstract

Context: Shikonins, a series of natural occurring naphthoquinones extracted from Arnebia euchroma (Royle) Jonst. (Boraginaceae), have antitumor activities and low toxicity. Objective: To illuminate potential activity and mechanism of shikonins against colorectal cancer (CRC). Materials and methods: Five shikonins were isolated from A. euchroma, and elucidated by extensive spectroscopic analysis. Anti-proliferative activities of shikonins (0-100 μg/mL) on human colorectal cells were evaluated by MTT and CCK-8 for 24 or 48 h. Cell apoptosis and cycle distribution were examined by FCM analysis. The expression of PI3K/Akt/mTOR pathway mRNAs and proteins was analysed by RT-PCR and Western blot, respectively. Cell viability, cell apoptosis, cell cycle and protein expression were measured, when co-treated with PI3K/Akt/mTOR pathway inhibitors. The in vivo activity of deoxyshikonin was evaluated using xenograft tumour model. Results: Deoxyshikonin and another four shikonins were isolated and identified. Deoxyshikonin exhibited anti-proliferative activity with IC50 of 10.97 μM against HT29 cells. Moreover, the percentage of early apoptotic cells and G0/G1 cells increased from 1 to 29% and 44 to 67% with 0-50 μg/mL deoxyshikonin, respectively. Deoxyshikonin also down-regulated the expression of PI3K, p-PI3K, Akt, p-Akt308 and mTOR proteins in HT29 and DLD-1 cells. Moreover, LY294002, NVP-BEZ235 and MK-2206 can make deoxyshikonin more cell proliferation inhibited, cell cycle arrested at G0/G1 and apoptosis promoted. In vivo study, the weight of tumour tissues at deoxyshikonin groups was significantly reduced compared with the control group, and PI3K, p-PI3K, Akt, p-Akt308 and mTOR expression was decreased. Discussion and conclusions: We can conclude that deoxyshikonin isolated from Arnebia euchroma inhibited CRC through the PI3K/Akt/mTOR pathway.

KEYWORDS

Shikonin; apoptosis; cell cycle; proliferation.

Title

Deoxyshikonin isolated from Arnebia euchroma inhibits colorectal cancer by down-regulating the PI3K/Akt/mTOR pathway

Author

Yuzhen Zhu 1, Yu Zhong 2, Xun Long 3, Zhu Zhu 4, Yu Zhou 5, Hua Ye 1, Xiaobin Zeng 6 7, Xuebao Zheng 1 8

Publish date

2019 Dec

PMID

30965550

Abstract

Wounds are a largely unrecognized, spiraling epidemic that affect millions of people world-wide […].

Title

New Innovations in Wound Healing and Repair

Author

Allison J Cowin 1

Publish date

2019 Apr 8

PMID

30463303

Abstract

Shiunko ointment is composed of five ingredients including Lithospermi Radix (LR), Angelicae Gigantis Radix, sesame seed oil, beeswax, and swine oil. It is externally applied as a treatment for a wide range of skin conditions such as eczema, psoriasis, hair loss, burns, topical wounds, and atopic dermatitis. Deoxyshikonin is the major angiogenic compound extracted from LR. In this study, we investigated the efficacy of LR extract and deoxyshikonin on impaired wound healing in streptozotocin (STZ)-induced diabetic mice. Treatment with LR extract elevated tube formation in human umbilical vein endothelial cells (HUVECs) and exerted antioxidant activity. An open skin wound was produced on the backs of diabetic mice and was then topically treated with deoxyshikonin or vehicle. In addition, deoxyshikonin promoted tube formation in high glucose conditions exposed to HUVECs, and which may be regulated by increased VEGFR2 expression and phosphorylation of Akt and p38. Our results demonstrate that deoxyshikonin application promoted wound repair in STZ-induced diabetic mice. Collectively, these data suggest that deoxyshikonin is an active ingredient of LR, thereby contributing to wound healing in patients with diabetes.

KEYWORDS

Shiunko; deoxyshikonin; tube formation; wound healing.

Title

Beneficial Effects of Deoxyshikonin on Delayed Wound Healing in Diabetic Mice

Author

Jun Yeon Park 1, Myoung-Sook Shin 2, Gwi Seo Hwang 3, Noriko Yamabe 4, Jeong-Eun Yoo 5, Ki Sung Kang 6, Jin-Chul Kim 7, Jeong Gun Lee 8, Jungyeob Ham 9, Hye Lim Lee 10

Publish date

2018 Nov 20