Naphthalene Quinones

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.

Menadione is a naphthoquinone that is converted into active vitamin K2 in the body. Menadione is a potential anticancer agent and radiosensitizer.

Tanshinone IIA (Tan IIA) is one of the main compositions in the root of Salvia miltiorrhiza Bunge. Tanshinone IIA may suppress angiogenesis by targeting the protein kinase domains of VEGF/VEGFR2.

Vitamin K1 a naturally occurring vitamin required for blood coagulation and bone and vascular metabolism.

Menaquinone-4 is a vitamin K, used as a hemostatic agent, and also a adjunctive therapy for the pain of osteoporosis.

Vitamin K2 (5) (Compound 1) is a prenylogue of the Vitamin K2 (HY-109569) series that can be found in the heartwood of Tabebuia avellanedae.

Eleuthoside B is a naphthyl gentiobioside identified from the bulbs of Eleutherine americana. Eleuthoside B has an IC₅₀ >1.00 mM against α-glucosidase, and it is not the main contributor to the antidiabetic (hypoglycemic) activity exhibited by the plant extract.

(-)-3--2-hydroxy-8-methoxy-1,4-naphthoquinone (Compound 1) is a naphthoquinone compound. (-)-3--2-hydroxy-8-methoxy-1,4-naphthoquinone is isolated from the bulbs of Eleutherine americana. (-)-3--2-hydroxy-8-methoxy-1,4-naphthoquinone shows no activity against lipopolysaccharide-induced nitric oxide production.

Cryptotanshinone is a natural compound extracted from the root of Salvia miltiorrhiza Bunge that shows antitumor activities. Cryptotanshinone inhibits STAT3 with an IC₅₀ of 4.6 μM.

β-Lapachone (ARQ-501;NSC-26326) is a naturally occurring O-naphthoquinone, acts as a topoisomerase I inhibitor, and induces apoptosis by inhibiting cell cycle progression.

Juglone (5-hydroxy-1,4-naphthalenedione) is a yellow dye that can be extracted from Juglans regia. Juglone induces apoptosis through the mitochondrial pathway. Juglone has antibacterial and antitumor activity .

Lawsone is an orally active naphthoquinone dye that can be isolated from the leaves of Lawsonia inermis. Lawsone can induce apoptosis. Lawsone has antibacterial, antitumor and antioxidant activities. Lawsone can be used in anti-tumor drug research.

Plumbagin (2-Methyljuglone) is a naphthoquinone isolated from Plumbago zeylanica, exhibits anticancer and antiproliferative activities.

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).

Trilobatin, a natural sweetener derived from Lithocarpus polystachyus Rehd, Trilobatin is an HIV-1 entry inhibitor targeting the HIV-1 Gp41 envelope. Neuroprotective effects. Trilobatin is also a SGLT1/2 inhibitor that selectively induces the proliferation of human hepatoblastoma cells.

Lawsone methyl ether (2-Methoxy-1,4-naphthoquinone), isolated from Impatiens balsamina L. and Swertia calycina, exhibits potent antifungal and antibacterial activities.

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.

β,β-Dimethylacrylalkannin (Arnebin 1) is an orally active FGFR1 inhibitor (IC₅₀=2.5 μM) and the main active component of Lithospermum erythrorhizon. β,β-Dimethylacrylalkannin blocks downstream signaling by binding to the ATP pocket of FGFR1, and regulates the CDK1/Cdc25C pathway and ROS-JNK axis, thereby inducing G2/M phase arrest, necrosis and apoptosis in cancer cells, and inhibiting tumor proliferation. β,β-Dimethylacrylalkannin also acts as a colistin adjuvant to disrupt the cell membrane of Gram-negative bacteria. β,β-Dimethylacrylalkannin exhibits significant tumor-inhibitory effects with no obvious toxicity in PDX models, but chronic exposure to high doses may alter the relative lung/liver weights of rats, while acute exposure to high doses causes responses such as reduced motor activity. β,β-Dimethylacrylalkannin finds wide application in studies related to hepatocellular carcinoma, colorectal cancer, colistin-resistant bacterial infections, hepatitis and psoriasis.

Lapachol, a natural naphthoquinone, is an orally active, potent DHODH inhibitor. Lapachol has immunosuppressive activity on lymphocytes through its direct ability to block DHODH activity and inhibit pyrimidine synthesis. Lapachol is a vitamin K antagonist with antitumor activity and can inhibit DNA and RNA synthesis in neoplastic cells. Lapachol has anti-Leishmania activity.