Boraginaceae

Shikonin is a major component of a Chinese herbal medicine named zicao. Shikonin is a potent TMEM16A chloride channel inhibitor with an IC₅₀ of 6.5 μM. Shikonin is a specific pyruvate kinase M2 (PKM2) inhibitor and can also inhibit TNF-α and NF-κB pathway. Shikonin decreases exosome secretion through the inhibition of glycolysis. Shikonin inhibits AIM2 inflammasome activation.

Acetylshikonin is an oral active anti-cancer, anti-inflammatory, antioxidant, anti-fertility, antibacterial, and neuroprotective agent. Acetylshikonin is a inhibitor of acetylcholinase (AChE) (IC₅₀=34.6 μM) and nonselective cytochrome P450. Acetylshikonin can induce Apoptosis and Autophagy in cancer cells. Acetylshikonin regulates blood glucose, liver fat metabolism, and renal fibrosis, and is used in the study of diabetes, diabetic nephropathy (DN), obesity, and nonalcoholic fatty liver disease (NAFLD).

Deoxyshikonin increases the expression of VEGF-C and VEGF-A mRNA in HMVEC-dLy, promotes HIF-1α and HIF-1β subunit interaction and binds to specific DNA sequences targeted by HIF. Deoxyshikonin inhibited colorectal cancer (CRC) through the PI3K/Akt/mTOR pathway. Deoxyshikonin has proangiogenesis effect and antitumor activity. Deoxyshikonin is an antibacterial agent against methicillin-resistant S. aureus (MRSA) and S. pneumonia (MIC=17 μg/mL).

(-)-Alkannin, found in Alkanna tinctoria, is used as a food coloring. (-)-Alkannin shows anticancer activity, arrests cell cycle, and induces apoptosis. (-)-Alkannin improves hepatic inflammation in a Rho-kinase pathway.

(Rac)-Arnebin 1 ((Rac)-β,β-Dimethylacrylalkannin) is the racemate of β,β-Dimethylacrylalkannin and/or β,β-Dimethylacrylshikonin. β,β-Dimethylacrylalkannin and β,β-Dimethylacrylshikonin are napthoquinones isolated from Arnebia nobilis. β,β-Dimethylacrylshikonin has anti-tumor activity.

β,β-Dimethylacrylshikonin (Isoarnebin I) is a naphthoquinone derivative that can be isolated from Lithospermum erythrorhizon Sieb. et Zucc. β,β-Dimethylacrylshikonin promotes angiogenesis by inducing eNOS, VEGF and HIF-1α expression through the PI3K-dependent pathway. β,β-Dimethylacrylshikonin inhibits Notch-1 activation. β,β-Dimethylacrylshikonin inhibtis tumor cell proliferation, induces tumor cell apoptosis, and inhibits tumor growth.

Shikonin (Standard) is the analytical standard of Shikonin. This product is intended for research and analytical applications. Shikonin is a major component of a Chinese herbal medicine named zicao. Shikonin is a potent TMEM16A chloride channel inhibitor with an IC₅₀ of 6.5 μM. Shikonin is a specific pyruvate kinase M2 (PKM2) inhibitor and can also inhibit TNF-α and NF-κB pathway. Shikonin decreases exosome secretion through the inhibition of glycolysis. Shikonin inhibits AIM2 inflammasome activation.

Europine N-oxide is a heliotridine-type alkaloid. Europine N-oxide exists as a contaminant in oregano samples.

Europine is a pyrrolizidine alkaloid present in the whole plant of Heliotropium crassifolium. Europine dose-dependently increases the micronucleus rate of metabolically active HepaRG cells, while reducing the relative cell viability.

Acetylalkannin (Alkannin acetate) is an isohexenylnaphthazarin pigment isolated from Arnebia euchroma with antimicrobial and cytotoxic activities.

Isobutylshikonin is a kind of shikonin pigments found in hairy root culture of Lithospermum canescens. Isobutylshikonin decreases cell viability induces marked changes in JA-4 cells with nuclear condensation and swelling in the presence of LPS (HY-D1056).

Beta-hydroxyisovalerylshikonin is a natural product isolated from Lithospermum erythrorhizon, acts as a potent inhibitor of protein tyrosine kinases (PTK), with IC₅₀s of 0.7μM and 1μM for EGFR and v-Src receptor, respectively. Beta-hydroxyisovalerylshikonin is effective against a wide variety of tumor cell lines, and most efficiently induces cell-death in NCI-H522 and DMS114 cells.

Beta-Acetoxyisovalerylshikonin is a naturally occurring naphthoquinone-type shikonin derivative that is widely distributed in the roots and cell suspension cultures of *Arnebia euchroma*, *Arnebia guttata*, *Onosma hispidum* and *Lithospermum erythrorhizon*. Beta-Acetoxyisovalerylshikonin exhibits favorable antibacterial, anti-inflammatory, wound-healing promoting and antioxidant activities, and also possesses potential anti-tumor and anti-HIV properties.

4-(β-D-glucopyranosyloxy)benzoic acid is a phenolic glucoside can be isolated from fennel seeds.

(+)-Intermedine, a pyrrolizidine alkaloid (PA), exhibits significant cytotoxicity in neural progenitor cells (NPCs).

(-)-Rabdosiin is a novel phenolic marker, found from Symphytum officinale L. (-)-Rabdosiin shows antioxidant, neuroprotective or anti-HIV activities.

Thesinine-4'-O-β-D-glucoside is a glycosylated plant pyrrolizidine alkaloid isolated from the seeds of Borago officinalis. Thesinine-4'-O-β-D-glucoside is present in dried seeds at an approximate content of 0.5%.

Thesinine is a saturated pyrrolizidine alkaloid and the primary alkaloid found in the seeds and flowers of Borago officinalis. Thesinine binds to AKT1, MAPK3, MMP9, and MAPK14 proteins as predicted by in silico analysis. Thesinine is applicable to research related to skin aging

Heliotridine ((+)-Heliotridine) is a monoesters-type necine base of pyrrolizidine alkaloid with genotoxic and antibacterial properties. Heliotridine can be isolated from the aerial parts of Heliotropium ellipticum, Heliotropium circinatum and other Heliotropium species (Boraginaceae). Heliotridine shows high tolerance in normal human hepatocytes (EC₅₀ > 400 μM). Mediated by the organic cation transporter OCT1, Heliotridine exhibits in vitro growth inhibition and weak antibacterial activity against Drechslera tetramera. Heliotridine can be used in infection-related studies of specific pathogenic bacteria.

Acetylechimidine is a dehydropyrrolizidine alkaloid, and it is a minor component in honey and mead derived from Echium plantagineum.