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Aurantio-obtusin

$198

  • Brand : BIOFRON

  • Catalogue Number : BF-A1012

  • Specification : 98%

  • CAS number : 67979-25-3

  • Formula : C17H14O7

  • Molecular Weight : 330.291

  • PUBCHEM ID : 155011

  • Volume : 20mg

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Catalogue Number

BF-A1012

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

330.291

Appearance

Orange crystalline powder

Botanical Source

Senna tora

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

CC1=CC2=C(C(=C1O)OC)C(=O)C3=C(C(=C(C=C3C2=O)O)OC)O

Synonyms

9,10-Anthracenedione, 1,3,7-trihydroxy-2,8-dimethoxy-6-methyl-/aurantio-obtusin/1,3,7-trihydroxy-2,8-dimethoxy-6-methylanthracene-9,10-dione/1,3,7-Trihydroxy-2,8-dimethoxy-6-methyl-9,10-anthraquinone

IUPAC Name

1,3,7-trihydroxy-2,8-dimethoxy-6-methylanthracene-9,10-dione

Density

1.5±0.1 g/cm3

Solubility

Methanol; Absolute ethyl alcohol

Flash Point

222.4±23.6 °C

Boiling Point

594.6±50.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2932990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:67979-25-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30486383

Abstract

Aurantio-obtusin, an anthraquinone compound, isolated from dried seeds of Cassia obtusifolia L. (syn. Senna obtusifolia; Fabaceae) and Cassia tora L. (syn. Senna tora). Although the biological activities of Semen Cassiae have been reported, the anti-inflammatory mechanism of aurantio-obtusin, its main compound, on RAW264.7 cells, remained unknown. We investigated the anti-inflammatory effect of aurantio-obtusin on lipopolysaccharide- (LPS)-induced RAW264.7 cells in vitro and elucidated the possible underlying molecular mechanisms. Nitric oxide production (NO) and prostaglandin E₂ (PGE₂) were measured by the Griess colorimetric method and enzyme-linked immunosorbent assay (ELISA), respectively. Protein expression levels of cyclooxygenase 2 (COX-2) were monitored by cell-based ELISA. Interleukin 6 (IL-6) and tumor necrosis factor-alpha (TNF-α) synthesis were analyzed using ELISA. The mRNA expression of nitric oxide synthase (iNOS), COX-2, and the critical pro-inflammatory cytokines (IL-6 and TNF-α) were detected by quantitative real-time PCR. Aurantio-obtusin significantly decreased the production of NO, PGE₂, and inhibited the protein expression of COX-2, TNF-α and IL-6, which were similar to those gene expression of iNOS, COX-2, TNF-α and IL-6 (p < 0.01). Consistent with the pro-inflammatory gene expression, the Aurantio-obtusin efficiently reduced the LPS-induced activation of nuclear factor-κB in RAW264.7 cells. These results suggested that aurantio-obtusin may function as a therapeutic agent and can be considered in the further development of treatments for a variety of inflammatory diseases. Further studies may provide scientific evidence for the use of aurantio-obstusin as a new therapeutic agent for inflammation-related diseases.

KEYWORDS

NF-κB; Semen Cassiae; anthraquinone; inflammation

Title

Anti-Inflammatory Effects of Aurantio-Obtusin from Seed of Cassia obtusifolia L. through Modulation of the NF-κB Pathway.

Author

Hou J1,2, Gu Y3,4, Zhao S5,6, Huo M7,8, Wang S9,10, Zhang Y11,12, Qiao Y13,14, Li X15,16.

Publish date

2018 Nov 27

PMID

29675883

Abstract

The purpose of the present study is to find the natural compound(s) having a therapeutic potential to treat lung inflammatory disorders. In our screening procedure, the methanol extract of the seeds of Cassia obtusifolia (cassiae semen) inhibited inducible nitric oxide synthase-catalyzed nitric oxide production in alveolar macrophages (MH-S). From the extract, 8 major anthraquinone derivatives were successfully isolated. They are chrysophanol, physcion, 2-hydroxy-emodin 1-methyl ether, obtusifolin, obtusin, aurantio-obtusin, chryso-obtusin, and gluco-obtusifolin, among which aurantio-obtusin (IC50 = 71.7 μM) showed significant inhibitory action on nitric oxide production from lipopolysaccharide-treated MH-S cells, mainly by downregulation of inducible nitric oxide synthase expression. This down-regulatory action of aurantio-obtusin was mediated at least in part via interrupting c-Jun N-terminal kinase/IκB kinase/nuclear transcription factor-κB pathways. Aurantio-obtusin also inhibited IL-6 production in IL-1β-treated lung epithelial cells, A549. Importantly, this compound (10 and 100 mg/kg) by oral administration attenuated lung inflammatory responses in a mouse model of lipopolysaccharide-induced acute lung injury. Therefore, it is for the first time found that aurantio-obtusin may have a therapeutic potential for treating lung inflammatory diseases.

Copyright © 2018 John Wiley & Sons, Ltd.

KEYWORDS

Cassia obtusifolia; anthraquinone; aurantio-obtusin; lung inflammation

Title

Aurantio-obtusin, an anthraquinone from cassiae semen, ameliorates lung inflammatory responses.

Author

Kwon KS1, Lee JH1, So KS1, Park BK1, Lim H1, Choi JS2, Kim HP1.

Publish date

2018 Aug

PMID

28745001

Abstract

The interaction between human serum albumin (HSA) and aurantio-obtusin was investigated by spectroscopic techniques combined with molecular docking. The Stern-Volmer quenching constants (KSV ) decreased from 8.56 × 105 M-1 to 5.13 × 105 M-1 with a rise in temperatures from 289 to 310 K, indicating that aurantio-obtusin produced a static quenching of the intrinsic fluorescence of HSA. Time-resolved fluorescence studies proved again that the static quenching mechanism was involved in the interaction. The sign and magnitude of the enthalpy change as well as the entropy change suggested involvement of hydrogen bonding and hydrophobic interaction in aurantio-obtusin-HSA complex formation. Aurantio-obtusin binding to HSA produced significant alterations in secondary structures of HSA, as revealed from the time-resolved fluorescence, Fourier transform infrared (FT-IR) spectroscopy, three-dimensional (3D) fluorescence and circular dichroism (CD) spectral results. Molecular docking study and site marker competitive experiment confirmed aurantio-obtusin bound to HSA at site I (subdomain IIA).

Copyright © 2017 John Wiley & Sons, Ltd.

KEYWORDS

aurantio-obtusin; binding thermodynamics; fluorescence; human serum albumin; molecular docking

Title

Investigation of the interaction of aurantio-obtusin with human serum albumin by spectroscopic and molecular docking methods.

Author

Liu J1,2, Yan X1, Yue Y1,2, Zhao S1.

Publish date

2018 Feb


Description :

Aurantio-obtusin is an anthraquinone isolated from Semen Cassiae, with anti-Inflammatory, anti-oxidative, anti-coagulating and anti-hypertension activities[1][2][3]. Aurantio-obtusin relaxes systemic arteries through endothelial PI3K/AKT/eNOS-dependent signaling pathway in rats, thus acts as a new potential vasodilator[2]. Aurantio-obtusin inhibits allergic responses in IgE-mediated mast cells and anaphylactic models and is potential for treatment for allergy-related diseases[3].