Product name: Deoxyshikonin
Synonym name:
Catalogue No.: BP3119
Cas No.: 43043-74-9
Formula: C16H16O4
Mol Weight: 272.3
Botanical Source:
Physical Description: Powder
Type of Compound: Quinones
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
The product could be supplied from milligrams to grams. Inquire for bulk scale.
We provide solution to improve the water-solubility of compounds, thereby facilitating the variety of activity tests and clinic uses.
For Reference Standard and R&D, Not for Human Use Directly.
Description:
Deoxyshikonin and dodecyl gallate show significantly synergic antimicrobial activity with penicillin in vivo and in vitro, and can effectively reduce nasopharyngeal and lung colonization caused by different penicillin-resistant pneumococcal serotypes. Deoxyshikonin exerts very good radical scavenging activities toward ABTS+ but shows moderate inhibition of DPPH·, and shows cytotoxic activities. Deoxyshikonin may be a new drug candidate for wound healing and treatment of lymphatic diseases.
References:
Evid Based Complement Alternat Med. 2013;2013:148297.
Enhancement of Lymphangiogenesis In Vitro via the Regulations of HIF-1α Expression and Nuclear Translocation by Deoxyshikonin.
The objectives of this study were to determine the effects of Deoxyshikonin on lymphangiogenesis.
METHODS AND RESULTS:
Deoxyshikonin enhanced the ability of human dermal lymphatic microvascular endothelial cells (HMVEC-dLy) to undergo time-dependent in vitro cord formation. Interestingly, an opposite result was observed in cells treated with shikonin. The increased cord formation ability following Deoxyshikonin treatment correlated with increased VEGF-C mRNA expression to higher levels than seen for VEGF-A and VEGF-D mRNA expression. We also found that Deoxyshikonin regulated cord formation of HMVEC-dLy by increasing the HIF-1 α mRNA level, HIF-1 α protein level, and the accumulation of HIF-1 α in the nucleus. Knockdown of the HIF-1 α gene by transfection with siHIF-1 α decreased VEGF-C mRNA expression and cord formation ability in HMVEC-dLy. Deoxyshikonin treatment could not recover VEGF-C mRNA expression and cord formation ability in HIF-1 α knockdown cells. This indicated that Deoxyshikonin induction of VEGF-C mRNA expression and cord formation in HMVEC-dLy on Matrigel occurred mainly via HIF-1 α regulation. We also found that Deoxyshikonin promoted wound healing in vitro by the induction of HMVEC-dLy migration into the wound gap. This study describes a new effect of Deoxyshikonin, namely, the promotion of cord formation by human endothelial cells via the regulation of HIF-1 α .
CONCLUSIONS:
The findings suggest that Deoxyshikonin may be a new drug candidate for wound healing and treatment of lymphatic diseases.
Front Microbiol. 2015 May 20;6:479.
Antibacterial effects of Traditional Chinese Medicine monomers against Streptococcus pneumoniae via inhibiting pneumococcal histidine kinase (VicK).
Two-component systems (TCSs) have the potential to be an effective target of the antimicrobials, and thus received much attention in recent years. VicK/VicR is one of TCSs in Streptococcus pneumoniae (S. pneumoniae), which is essential for pneumococcal survival. We have previously obtained several Traditional Chinese Medicine monomers using a computer-based screening.
METHODS AND RESULTS:
In this study, either alone or in combination with penicillin, their antimicrobial activities were evaluated based on in vivo and in vitro assays. The results showed that the MICs of 5'-(Methylthio)-5'-deoxyadenosine, octanal 2, 4-dinitrophenylhydrazone, Deoxyshikonin, kavahin, and dodecyl gallate against S. pneumoniae were 37.1, 38.5, 17, 68.5, and 21 μg/mL, respectively. Time-killing assays showed that these compounds elicited bactericidal effects against S. pneumoniae D39 strain, which led to a 6-log reduction in CFU after exposure to compounds at four times of the MIC for 24 h. The five compounds inhibited the growth of Streptococcus pyogenes, Streptococcus mitis, Streptococcus mutans or Streptococcus pseudopneumoniae, meanwhile, Deoxyshikonin and dodecyl gallate displayed strong inhibitory activities against Staphylococcus aureus. These compounds showed no obvious cytotoxicity effects on Vero cells. Survival time of the mice infected by S. pneumoniae strains was prolonged by the treatment with the compounds. Importantly, all of the five compounds exerted antimicrobial effects against multidrug-resistant clinical strains of S. pneumoniae. Moreover, even at sub-MIC concentration, they inhibited cell division and biofilm formation. The five compounds all have enhancement effect on penicillin. Deoxyshikonin and dodecyl gallate showed significantly synergic antimicrobial activity with penicillin in vivo and in vitro, and effectively reduced nasopharyngeal and lung colonization caused by different penicillin-resistant pneumococcal serotypes. In addition, the two compounds also showed synergic antimicrobial activity with erythromycin and tetracycline.
CONCLUSIONS:
Taken together, our results suggest that these novel VicK inhibitors may be promising compounds against the pneumococcus, including penicillin-resistant strains.
Food Chemistry, 2008 , 106 (1) :2-10.
Antioxidants from a Chinese medicinal herb - Lithospermum erythrorhizon
Seven compounds, Deoxyshikonin (1), β,β-dimethylacrylshikonin (2), isobutylshikonin (3), shikonin (4), 5,8-dihydroxy-2-(1-methoxy-4-methyl-3-pentenyl)-1,4-naphthalenedione (5), β-sitosterol (6) and a mixture of two caffeic acid esters [7 (7a,7b)] were isolated from Lithospermum erythrorhizon Sieb et. Zucc. and identified by spectroscopic methods. Among them, compound 5 was isolated from this plant species for the first time.
METHODS AND RESULTS:
The antioxidant activities of the seven compounds were compared and evaluated through Rancimat method, reducing power and radical scavenging activity. Results showed that, except compound 6, another 6 compounds all exhibited obvious antioxidant activities against four different methods. Compounds 4 and 7 exerted much more potent antioxidant effects on retarding the lard oxidation than that of BHT and both were found to exhibit strong reducing power. Their antioxidant activities, assessed by Rancimat method and reducing power, decreased in the following order, respectively: compound 7 > 4 > BHT > 2 > 3 > 5 > 1 > 6 and compound 7 > BHT > 4 > 2 approximately 3 approximately 5 > 1> 6. In addition, compounds 1-5 all exerted very good radical scavenging activities toward ABTS+ but showed moderate inhibition of DPPH·, while compound 7 presented as a powerful radical scavenger against both ABTS·+ and DPPH·.
CONCLUSIONS:
Thus, our results suggested that L. erythrorhizon could be a promising rich source of natural antioxidants.
HPLC of Deoxyshikonin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
74.6000
3.6555
3.3328
.1300
5.6559
24.1274
Low
90.1448
2.8183
Yes
Yes
No
No
Yes
Yes
0.6
Yes
Yes
Yes
Yes
Naphthoquinone compounds are an important class of active molecules in natural products, widely distributed in plants such as the purple grass family and persimmon family. They have attracted much attention for their significant pharmacological activities such as anti-inflammatory, antibacterial, anti-tumor, and wound healing promotion. Deoxyshikonin, as one of the core active ingredients of the purple grass genus, is a derivative of shikonin. Its CAS number is 43043-74-9, and its molecular formula is C16H16O4. In recent years, with the deepening of molecular pharmacology research, deoxyriboflavin has shown a complex and multi-directional pharmacological activity spectrum that exceeds traditional understanding. It not only retains the classic antibacterial and wound healing properties of the shikonin family, but has also been revealed to have unique roles in regulating the tumor microenvironment, inhibiting tumor growth and metastasis, such as inhibiting colorectal cancer progression through the PI3K/Akt/mTOR pathway. At the same time, its dual role in promoting angiogenesis - promoting the expression of angiogenic factors in normal endothelial cells for tissue repair, and exhibiting anti-tumor effects in tumor models - highlights its environmental and target dependence. This article aims to systematically review the chemical properties, plant sources, multidimensional pharmacological activities, molecular mechanisms of action, pharmacological potential, and clinical application prospects of deoxyriboflavin, in order to provide comprehensive academic references for the in-depth research and development of this compound.
Deoxypurpurin is a naphthoquinone pigment with a chemical structure centered around 1,4-naphthoquinone as the parent nucleus. It is connected to a hydroxyl group at positions C-5 and C-8, and a 1-methylbutenyl side chain at position C-2. Compared with purpurin, the hydroxyl group at the end of its side chain is replaced by a hydrogen atom, hence the name "deoxygenation". This structural difference has a significant impact on its physicochemical properties and biological activity.
Its molecular weight is 272.30 g/mol. The calculated lipid water partition coefficient (LogP) is 3.66, indicating that the compound has good lipophilicity, which is consistent with its good solubility in organic solvents, but also suggests its low solubility in water (about 0.13 mg/mL). The topological polar surface area (TPSA) is 74.6 Å ², which is relatively small and conducive to transmembrane transport. Based on these parameters, it is preliminarily predicted that its ability to cross the blood-brain barrier is low, which to some extent limits its direct effects on central nervous system related diseases, but may also reduce the potential risk of neurotoxicity. Preliminary safety screening shows that it has no significant inhibitory effect on hERG potassium channels, indicating a low risk of cardiac toxicity; The Ames test result is 0.6, indicating a weak risk of mutagenicity. These basic pharmacological parameters provide a preliminary physicochemical and safety baseline for the subsequent development of deoxyriboflavin.
Deoxystrobin mainly comes from various plants in the Boraginaceae family, such as Lithospermum and Onosma, among which the traditional Chinese medicine Lithospermum erythrorhizon is the most famous. In the roots of these plants, deoxy shikonin often coexists with various naphthoquinone derivatives such as shikonin, acetyl shikonin, and β, β - dimethylacryloyl shikonin, forming the basis of their medicinal substances.
The traditional extraction method mainly utilizes its lipophilicity, using organic solvents for reflux extraction or cold soaking. Common solvents include petroleum ether, ethyl acetate, acetone, ethanol, etc. In order to improve extraction efficiency and selectivity, modern separation techniques have been widely applied in its preparation process. Ultrasound assisted extraction (UAE) and microwave-assisted extraction (MAE) can effectively shorten extraction time and improve yield. The crude extract after extraction is usually separated and purified by silica gel column chromatography, preparative high-performance liquid chromatography (HPLC) and other methods to obtain high-purity deoxyriboflavin monomer. In recent years, the development of biosynthetic pathway analysis and synthetic biology technology has also provided new possibilities for the modeling production of deoxyriboflavin and its derivatives through microbial fermentation, which is expected to solve the problems of limited plant resources and complex extraction processes.
Deoxypurpurin has a wide and diverse pharmacological activity, mainly covering the following aspects:
Antibacterial activity Deoxypurpurin inherits the powerful antibacterial ability of naphthoquinone compounds. Research has confirmed that it has significant inhibitory activity against Gram positive bacteria, especially drug-resistant strains such as methicillin-resistant Staphylococcus aureus (MRSA). The MIC value for Streptococcus pneumoniae can reach 17 μ g/mL, demonstrating its potential as a novel antibacterial lead compound. Its antibacterial mechanism may be related to interfering with bacterial cell membrane integrity, inhibiting energy metabolism, or interacting with bacterial DNA.
Promoting wound healing and anti-inflammatory effects This is the core pharmacological basis of the traditional application of purple grass. In the skin trauma model, deoxyriboflavin promotes healing through multi-target synergistic effects:a) Upregulate the expression of vascular endothelial growth factor A (VEGFA), basic fibroblast growth factor 2 (FGF2), and promote granulation tissue formation and angiogenesis;b) Regulating extracellular matrix metabolism, such as promoting the synthesis of type I collagen (COL1A1), inhibiting the overexpression of matrix metalloproteinase-9 (MMP9), and upregulating its inhibitor TIMP1 to maintain tissue remodeling balance;c) The anti-inflammatory effect may be achieved by inducing the anti-inflammatory cytokine IL-10 and regulating the expression of inducible nitric oxide synthase (NOS2) and arginase 1 (ARG1), balancing the inflammatory response and tissue repair process.
Antitumor activity Deoxystrobin has shown significant anti-tumor potential, especially in colorectal cancer (CRC) where it has been extensively studied. It can effectively inhibit the proliferation and induce apoptosis of various CRC cells. Its anti-tumor effect has multi-channel characteristics and does not rely on a single signaling node.
Pro angiogenic activity It is worth noting that deoxyriboflavin is present in Human microvascular endothelial cells dermal lymphatic vessels (HMVEC dLy) It can significantly upregulate the mRNA expression of VEGF-C and VEGF-A. VEGF-C is a key factor in lymphangiogenesis, while VEGF-A is a core factor in angiogenesis. This effect is closely related to its promotion of the binding of hypoxia inducible factor-1 alpha (HIF-1 alpha) to the HIF-1 β subunit, and the enhancement of the ability of HIF to bind to downstream gene hypoxia response elements (HRE). This characteristic may have positive implications in the treatment of chronic ischemic diseases or the promotion of tissue engineering angiogenesis, but it also suggests that attention should be paid to its potential impact on tumor angiogenesis/lymphangiogenesis in tumor applications, reflecting its "double-edged sword" nature.
The multiple pharmacological effects of deoxyriboflavin stem from its precise regulation of multiple key signaling pathways and molecular targets.
The functional network in wound healing and inflammation regulation Its function involves a complex target network. By raising TGFB1(Transforming Growth Factor - β 1) and FGF2 Promote fibroblast proliferation and differentiation. regulation MMP9/TIMP1 Balance to ensure orderly remodeling of extracellular matrix. By influencing NOS2(pro-inflammatory) and ARG1 Balance of (promoting repair) and induction IL10 Polarization of macrophage phenotype from M1 type (pro-inflammatory) to M2 type (pro reparative) creates a microenvironment conducive to healing.
Pathways of action in anti-tumor therapy：PI3K/Akt/mTOR pathway It is one of the core mechanisms by which it inhibits colorectal cancer. Deoxystrobin can effectively inhibit the excessive activation of this pathway, thereby downregulating the expression of downstream proteins related to cell proliferation, survival, and metabolism, ultimately leading to tumor cell cycle arrest and apoptosis. In addition, it may also exert synergistic anti-tumor effects by regulating other pathways such as MAPK and NF - κ B.
Transcriptional regulation in promoting angiogenesis/lymphangiogenesis The core of its role in promoting VEGF expression lies in stabilizing and activating it Hypoxia inducible factor 1 (HIF-1)Deoxystrobin can promote the heterodimerization of HIF-1 α and HIF-1 β subunits, and enhance the binding ability of this complex to the HRE sequence of the target gene promoter region, thereby transcribing and activating genes such as VEGFA and VEGFC, driving endothelial cell migration, proliferation, and luminal formation.
Possible targets for antibacterial activity As a naphthoquinone molecule, its antibacterial effect may be related to its redox properties, by producing reactive oxygen species (ROS) to disrupt bacterial membrane structure, or as an electron transfer chain inhibitor to interfere with bacterial energy metabolism.
Despite the significant in vitro activity of deoxyriboflavin, its pharmacological development still faces challenges, and related pharmacokinetic studies are still in their early stages.
Absorption, distribution, metabolism, excretion (ADME)Its high LogP value and low water solubility may affect its oral bioavailability, and its absorption in the gastrointestinal tract may be limited and irregular. Predict low blood-brain barrier permeability, mainly distributed in peripheral tissues. As naphthoquinone compounds, they are likely to undergo extensive phase I and phase II metabolism in vivo, such as hydroxylation, glucuronidation, and sulfation. The excretion pathways (kidney or bile) of prototype drugs and their metabolites need to be clarified. Developing appropriate drug delivery systems (such as nanoliposomes, micelles, cyclodextrin inclusion complexes) is key to improving their solubility, stability, and bioavailability.
Preliminary evaluation of safety The existing data suggests some positive signals. The negative inhibition of hERG reduces the risk of cardiac toxicity associated with its induction of apical torsion ventricular tachycardia. The Ames test did not show strong mutagenicity. However, naphthoquinone compounds usually have certain cytotoxicity, and their therapeutic window, long-term toxicity, reproductive toxicity, etc. still need to be comprehensively evaluated through systematic preclinical safety evaluations (GLP toxicology studies).
Pharmaceutical Science Challenge: Due to its light instability and chemical instability, it needs to be protected from light and antioxidant treatment during the preparation process, and select appropriate excipients and dosage forms (such as ointment, gel for local trauma; liposome for injection for tumor targeting).
The multi-target activity of deoxypurpurin has brought its application prospects in multiple therapeutic fields, but its challenges also need to be viewed rationally.
Topical preparations for local use This is the direction closest to clinical translation. Based on its excellent antibacterial, anti-inflammatory, and healing promoting abilities, developed for treatment Chronic difficult to heal wounds External gel, creams or dressings (such as diabetes foot ulcers and pressure ulcers), burns, surgical incision infections (especially MRSA infections) have huge market potential. Its multi-target repair mechanism is superior to drugs with a single mechanism.
Development of anti-tumor drugs As a potential therapeutic drug for solid tumors such as colorectal cancer, its ability to inhibit multiple pathways such as PI3K/Akt/mTOR may help overcome tumor drug resistance. Future research directions include: a) combining with existing chemotherapy drugs to enhance efficacy; b) Perform structural modifications to enhance selectivity and reduce toxicity; c) Utilizing nano delivery systems to achieve targeted drug delivery to tumors, while exerting anti-tumor effects, minimizing the potential risk of promoting angiogenesis.
Diseases related to angiogenesis Its ability to promote angiogenesis in normal endothelial cells can be used for treatment Lower limb ischemic disease Angiogenesis after myocardial ischemia, etc. But it is necessary to strictly distinguish the differences in its effects on blood vessels in different pathological and physiological environments, and precisely control the dosage and timing of administration.
Challenges and Future Directions Faced：
Deoxypurpurin, as a natural naphthoquinone compound derived from traditional Chinese medicine, has revealed a multifaceted and active molecular image beyond traditional understanding through modern pharmacological research. It not only demonstrates a solid foundation in antibacterial, anti-inflammatory, and tissue repair promotion, but also demonstrates unique value in modern medical frontiers such as anti-tumor and vascular regulation. The multi-target and multi pathway characteristics of its action are not only its therapeutic advantages, but also bring about complexity of action and challenges in drug development. Future research should focus on further elucidating the mechanism of its cellular environment dependence, overcoming its drug development bottleneck through medicinal chemistry and pharmacology, and actively promoting high-quality clinical translational research. With the advancement of these works, deoxyriboflavin is expected to transform from an ancient plant active ingredient into a modern innovative drug or lead compound for treating various diseases such as infections, trauma, and tumors, fully demonstrating the sustained vitality of natural products in drug discovery.
