Shikonin Powder CAS 517-89-5

Shikonin is a natural product with naphthoquinone structure extracted from the roots of purple grass, which has anti-inflammatory, antioxidant, anti-tumor, and wound healing promoting effects. Especially in terms of anti-tumor effects, purpurin and its derivatives have been widely studied. Many in vitro and in vivo studies have shown that shikonin and its derivatives can effectively inhibit the occurrence and development of gynecological malignancies such as breast cancer and cervical cancer.High purity Shikonin powder is a purple flake crystal or crystalline powder . Due to its excellent coloring function, this product is also a commonly used food coloring agent in the food industry. According to China's regulations, it can be used for juice (flavored) beverages, fruit wine, ice cream, and popsicles, with a maximum usage of 0.1g/kg. Used for coloring spicy canned meat and poultry, with a dosage of 0.35-0.56g/kg.

What are the structural modifications of purpurin?

Shikonin powder has attracted the interest of many researchers at home and abroad because of its remarkable and extensive anti-tumor activity. However, due to its multiple targeting, it has great toxic and side effects and poor water solubility, which seriously hinders its becoming an anti-tumor drug in clinical application. In order to overcome the above shortcomings of natural Shikonin powder, researchers at home and abroad have done a lot of structural modification work around Shikalkin 54952-43-1 (right-handed structure of shikonin) and Alkannin 517-88-4 (left-handed structure of shikonin).

Among them, the modification of Shikalkin compounds accounts for most of this kind of research, while the modification of Akkanen compounds is relatively less. Therefore, the following will mainly introduce the structural modification of Shikalkin compounds by researchers.

Shikalkin powder has a mother nucleus structure of 5,8- dihydroxy -1,4- naphthoquinone, and has an isohexenyl side chain structure. The naphthoquinone ring of the mother nucleus and the branched hydroxyl group are both modifiable sites. Therefore, most of the structural modification work is carried out around the mother nucleus and its branched hydroxyl groups.

1. modify the side chain of isohexenyl.
The modification of isohexenyl side chain focuses on the active hydroxyl group on the side chain. It is reported that a series of compounds synthesized by acylation or cyclization of hydroxyl groups, such as phenylacetylShikalkin analogues, Shikalkin furoate and Shikalkin analogues, have different anti-tumor targets, but all have good anti-tumor activities. It is worth mentioning that the indole acyl Shikalkin derivatives not only have significant anti-tumor activity, but also have good antiviral effect, and have significant inhibitory effects on human hand-foot-mouth disease virus EV71 and influenza virus H1N1.

2. modify the naphthoquinone ring
Compared with branched hydroxyl groups, the hydroxyl activity of naphthoquinone ring is not strong, so there are few studies on structural modification of naphthoquinone ring of Shikalkin alone. The representative achievement is that the naphthoquinone derivative (3a) synthesized by a research team can exert anti-tumor effect by targeting thioredoxin reductase (TrxR). The naphthoquinone derivatives (3b, 3c) synthesized by another research team can inhibit protein kinase B(Akt) to exert anti-tumor activity.

3. modify the side chain and naphthoquinone ring at the same time
In the aspect of simultaneous modification of Shikalkin side chain and naphthoquinone ring, it is mainly based on the original compound. From 2010 to 2014, researchers reported methylation modification of hydroxyl and carbonyl groups on naphthoquinone ring, and acylation modification of branched hydroxyl groups at the same time (2a, 2b, 2c) to improve the anti-tumor activity of natural shikonin. Since 2014, researchers have changed the structural modification strategy for naphthoquinone ring from simple methylation modification to hydroxamine structure modification, and the obtained shikonin oxime (2d) has significantly improved the tumor targeting of shikonin and reduced the toxic and side effects. By continuously optimizing the structure, the sulfur-containing shikonin oxime (2e) has stronger anti-tumor activity and lower toxic and side effects, but the specific molecular mechanism has not been reported.

In addition, a series of compounds obtained by glycosylation modification of shikonin by some research teams can also selectively kill tumor cells.

Why is it said that anti oral ulcer film containing purpurin has become a new direction for relieving pain?

Lithospermum naphthoquinones are the most important compounds in Lithospermum, including shikonin, acetyl shikonin, β, β-dimethyl acryloyl shikonin and so on. These Arnebia euchroma naphthoquinone compounds have been proved to have extensive biological activities, including: antibacterial, promoting burn wound healing and so on. We know that oral ulcer, also known as recurrent aphtha, is the most common oral mucosal disease with high incidence and easy recurrence. Clinically, it is mainly manifested as small round or oval rotten noodles scattered in the mouth, surrounded by congestion and edema, and patients often feel pain, which affects daily life behaviors such as eating and speaking. So far, there is no medicine or method in the world that can completely cure oral ulcer. People can only promote ulcer healing, shorten the course of disease, reduce the frequency of ulcer attack or extend the intermittent period of ulcer through different medicines. The film agent of the new drug dosage form can dissolve the drug and disperse it evenly in the film-forming material. It can be applied to the surface of skin and mucous membrane wound or ulcer to cover, which is beneficial to wound healing. If shikonin powder and film agent are combined together, the oral mucosa can provide the possibility for the direct and effective absorption and utilization of drugs; And the film agent has accurate drug content, good stability, light weight, small volume and convenient carrying. It is the main direction of future development that films with different drug release rates can be made as needed.

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