Shipping to Germany We Offer Worldwide Shipping
Login Wishlist

Lapachol

$96

  • Brand : BIOFRON

  • Catalogue Number : BD-P0620

  • Specification : 98.0%(HPLC)

  • CAS number : 84-79-7

  • Formula : C15H14O3

  • Molecular Weight : 242.27

  • Volume : 20mg

Available on backorder

Quantity
Checkout Bulk Order?

Catalogue Number

BD-P0620

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

242.27

Appearance

powder

Botanical Source

Widespread occurrence in the plant world, particularly in heartwood, bark and roots, e.g. the Bignoniaceae and various Tabebuia, Tecomella and Tectona spp.

Structure Type

Quinones

Category

SMILES

CC(=CCC1=C(C2=CC=CC=C2C(=O)C1=O)O)C

Synonyms

IUPAC Name

Applications

Density

1.2±0.1 g/cm3

Solubility

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

Flash Point

203.9±24.4 °C

Boiling Point

390.1±42.0 °C at 760 mmHg

Melting Point

141-143ºC(lit.)

InChl

InChI=1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,16H,8H2,1-2H3

InChl Key

CWPGNVFCJOPXFB-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2914690000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:84-79-7) 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

31225674

Abstract

Lapachol is a 1,4-naphthoquinone that is isolated from the Bignoniaceae family. It has been reported to exert anti-inflammatory, antibacterial, and anticancer activities. However, the anticancer activity of lapachol and its molecular mechanisms against esophageal squamous cell carcinoma (ESCC) cells have not been fully investigated. Herein, we report that lapachol is a novel ribosomal protein S6 kinase 2 (RSK2) inhibitor that suppresses growth and induces intrinsic apoptosis in ESCC cells. We found that lapachol strongly attenuates downstream signaling molecules of RSK2 in ESCC cells and also directly inhibits RSK2 activity in vitro. The RSK protein is highly activated in ESCC cells and knockdown of RSK2 significantly suppresses anchorage-dependent and anchorage-independent growth of ESCC cells. Additionally, lapachol inhibits anchorage-dependent and anchorage-independent growth of ESCC cells, and the inhibition of cell growth by lapachol is dependent on the expression of RSK2. We also found that lapachol induces mitochondria-mediated cellular apoptosis by activating caspases-3, -7, and PARP, inducing the expression of cytochrome c and BAX by inhibiting downstream molecules of RSK2. Overall, lapachol is a potent RSK2 inhibitor that might be used for chemotherapy against ESCC.

KEYWORDS

RSK2; apoptosis; esophageal squamous cell carcinoma; lapachol.

Title

Lapachol is a novel ribosomal protein S6 kinase 2 inhibitor that suppresses growth and induces intrinsic apoptosis in esophageal squamous cell carcinoma cells

Author

Xueyin Zu 1 2, Xiaomeng Xie 1 2, Yuanyuan Zhang 1 2, Kangdong Liu 1 2 3 4, Ann M Bode 5, Zigang Dong 1 2 4 5 6, Dong Joon Kim 1 2 4

Publish date

2019 Sep;

PMID

30896339

Abstract

Lapachol is a natural naphthoquinone with a range of biological effects, including anticancer activity. Microbial transformations of lapachol can lead to the formation of new biologically active compounds. In addition, fungi can produce secondary metabolites that are also important for drug discovery. The goal of this study was to evaluate the ability of filamentous fungi to biotransform lapachol into biologically active compounds and identify secondary metabolites produced in the presence of lapachol. Seven out of nine strains of filamentous fungi tested exhibited the ability to biotransform or biodegrade lapachol. The bioactive derivatives norlapachol and isolapachol were identified among biotransformation products. Moreover, lapachol stimulated the production of pyrrolo-[1,2-a] pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl) and phenol-2,4-bis-(1,1-dimethylethyl), secondary metabolites already known to have antimicrobial and antioxidant activities. These results open the perspective of using these strains of filamentous fungi for lapachol biotransformation and efficient production of several biologically active compounds.

KEYWORDS

Biocatalysts; fungi; gas chromatography; lapachol; mass spectrometry.

Title

Lapachol biotransformation by filamentous fungi yields bioactive quinone derivatives and lapachol-stimulated secondary metabolites

Author

Luciana Barbosa Coitinho 1, Fernando Fumagalli 1, Nathalia Gonsales da Rosa-Garzon 1, Flavio da Silva Emery 1, Hamilton Cabral 1

Publish date

2019;

PMID

30797783

Abstract

Leishmaniasis is one of the most important neglected diseases worldwide. It is a life-threatening disease and causes significant morbidity, long-term disability, and early death. Treatment involves disease control or use of intervention measures, although the currently used drugs require long-lasting therapy, and display toxicity and reduced efficacy. The use of natural products isolated from plants, such as lapachol, an abundant naphthoquinone naturally occurring in South American Handroanthus species (Tabebuia, Bignoniaceae), is a promising option for the treatment of leishmaniasis. In this study, we investigated the leishmanicidal activity of lapachol in vitro and in vivo against Leishmania infantum and L. amazonensis, causative agents of visceral and cutaneous leishmaniasis, respectively. Low cytotoxicity in HepG2 cells (3405.8 ± 261.33 μM), good anti-Leishmania activity, and favorable selectivity indexes (SI) against promastigotes of both L. amazonensis (IC50 = 79.84 ± 9.10 μM, SI = 42.65) and L. infantum (IC50 = 135.79 ± 33.04 μM, SI = 25.08) were observed. Furthermore, anti-Leishmania activity assays performed on intracellular amastigotes showed good activity for lapachol (IC50 = 191.95 μM for L. amazonensis and 171.26 μM for L. infantum). Flow cytometric analysis demonstrated that the cytotoxic effect of lapachol in Leishmania promastigotes was caused by apoptosis-like death. Interestingly, the in vitro leishmanicidal effect of lapachol was confirmed in vivo in murine models of visceral and cutaneous leishmaniasis, as lapachol (25 mg/kg oral route for 24 h over 10 days) was able to significantly reduce the parasitic load in skin lesions, liver, and spleen, similar to amphotericin B, the reference drug. These results reinforce the therapeutic potential of lapachol, which warrants further investigations as an anti-leishmaniasis therapeutic.

KEYWORDS

L. amazonensis; Lapachol; Leishmania infantum; Leishmaniasis; Naphthoquinones; Natural products.

Title

Efficacy of lapachol on treatment of cutaneous and visceral leishmaniasis

Author

Iasmin Aparecida Cunha Araújo 1, Renata Cristina de Paula 1, Ceres Luciana Alves 2, Karen Ferraz Faria 1, Marco Miguel de Oliveira 1, Gabriela Goncalves Mendes 1, Eliane Martins Ferreira Abdias Dias 1, Raul Rio Ribeiro 3, Alaide Braga de Oliveira 2, Sydnei Magno da Silva 4

Publish date

2019 Apr;