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Kirenol

$78

  • Brand : BIOFRON

  • Catalogue Number : BF-K1003

  • Specification : 98%

  • CAS number : 52659-56-0

  • Formula : C20H34O4

  • Molecular Weight : 338.48

  • PUBCHEM ID : 15736732

  • Volume : 20mg

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Catalogue Number

BF-K1003

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

338.48

Appearance

Yellow crystalline powder

Botanical Source

Siegesbeckia orientalis

Structure Type

Terpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1(CCC2C(=C1)CCC3C2(CC(CC3(C)CO)O)C)C(CO)O

Synonyms

1,7-Phenanthrenedimethanol, 1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-3-hydroxy-α-(hydroxymethyl)-1,4a,7-trimethyl-, (αR,1R,3S,4aS,4bR,7S,10aS)-/Kirel/(2β,5β,9β,10α,13α,15R)-Pimar-8(14)-ene-2,15,16,18-tetrol

IUPAC Name

(1R)-1-[(2S,4aR,4bS,6S,8R,8aS)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-2-yl]ethane-1,2-diol

Density

1.2±0.1 g/cm3

Solubility

Methanol; Ethanol

Flash Point

233.6±20.5 °C

Boiling Point

516.9±35.0 °C at 760 mmHg

Melting Point

197.0 to 201.0 °C

InChl

InChI=1S/C20H34O4/c1-18(17(24)11-21)7-6-15-13(8-18)4-5-16-19(2,12-22)9-14(23)10-20(15,16)3/h8,14-17,21-24H,4-7,9-12H2,1-3H3/t14-,15-,16-,17+,18+,19+,20+/m1/s1

InChl Key

NRYNTARIOIRWAB-JPDRSCFKSA-N

WGK Germany

RID/ADR

HS Code Reference

2906190000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:52659-56-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31907162

Abstract

OBJECTIVE:
To investigate whether kirenol, the major pharmacologically active compound of the Chinese medicinal herb Herba Siegesbeckiae, can protect mice from dextran sulfate sodium (DSS)-induced ulcerative colitis (UC).

METHODS:
C57BL/6 mice with or without kirenol pretreatment were treated with DSS in drinking water for 7 days to induce UC. The symptoms of UC including weight loss, diarrhea and bloody stool were observed daily and graded using the disease activity index (DAI). Colon injury of the mice was assessed by measuring the length of the colon and HE staining of the colon tissue. The levels of inflammatory cytokines produced by the mesenteric lymph nodes (MLNs) lymphocytes were measured using enzyme-linked immunosorbent assay; the apoptosis of the lymphocytes and CD4+ T cells was analyzed using flow cytometry.

RESULTS:
The mice receiving pretreatment with kirenol showed obviously ameliorated symptoms of UC and milder pathological changes in the colon as compared with the control mice. Kirenol treatment significantly down-regulated the secretion of IFN-γ, IL-17A, IL-6 and TNF-α by the MLNs lymphocytes and increased the apoptosis of lymphocytes, especially CD4+ T cells in the DSS-treated mice.

CONCLUSIONS:
Kirenol can protect against T cell-mediated colon injury in DSS-treated mice possibly by suppressing the secretion of inflammatory mediators and inducing apoptosis of the inflammatory lymphocytes.

KEYWORDS

apoptosis; kirenol; lymphocytes; ulcerative colitis

Title

[Kirenol relieves dextran sulfate sodium-induced ulcerative colitis in mice by inhibiting inflammatory cytokines and inducing CD4+ T lymphocyte apoptosis].

Author

Xiuhong L1,2, Yajun DU1,2, Guoxing L1,2, Guomei D1,2, Xin T2, Juan X2.

Publish date

2019 Dec 30

PMID

25762107

Abstract

Experimental autoimmune encephalomyelitis (EAE), a model of multiple sclerosis (MS), is characterized by CNS demyelination mediated by autoreactive T cells. Kirenol, a biologically active substance isolated from Herba Siegesbeckiae, has potent anti-inflammatory activities. Here we investigated effects of kirenol on EAE. Kirenol treatment markedly delayed onset of disease and reduced clinical scores in EAE mice. Kirenol treatment reduced expression of IFN-γ and IL-17A in the serum and proportion of Th1 and Th17 cells in draining lymph nodes. Priming of lymphocytes was reduced and apoptosis of MOG-activated CD4+ T cells was increased in kirenol treated EAE mice. Kirenol treatment of healthy animals did not affect the lymphocytes in these non-immunized mice. Further in vitro studies showed that kirenol inhibited viability of MOG-specific lymphocytes and induced apoptosis of MOG-specific CD4+ T cells in a dose- and time-dependent manner. Kirenol treatment upregulated Bax,downregulated Bcl-2,and increased activation of caspase-3 and release of cytochrome c, indicating that a mitochondrial pathway was involved in kirenol induced apoptosis. Moreover, pretreatment with either a pan-caspase inhibitor z-VAD-fmk or a more specific caspase 3 inhibitor Ac-DEVD-CHO in lymphocytes reduced kirenol induced apoptosis. Our findings implicate kirenol as a useful agent for the treatment of MS.

Title

Kirenol attenuates experimental autoimmune encephalomyelitis by inhibiting differentiation of Th1 and th17 cells and inducing apoptosis of effector T cells.

Author

Xiao J1, Yang R2, Yang L3, Fan X3, Liu W3, Deng W4.

Publish date

2015 Mar 12

PMID

31244849

Abstract

Kirenol is a diterpenoid extracted from the Chinese herbal medicine Siegesbeckiae. Siegesbeckiae has been used to treat Rheumatoid arthritis (RA) in China for several centuries. RA is characterized by the proliferation of synoviocytes in inflamed synovia, as well as by their expression of inflammatory cytokines. In the present study, we found that Kirenol inhibited the migration, invasion, and proinflammatory of IL-6 secretion of RA-associated synovial fibroblasts (FLS) at a concentration of 100-200 μg/ml in vitro. Proinflammatory cytokines production and synovium hyperplasia and cartilage erosion were also inhibited in a collagen-induced arthritis (CIA) mouse model upon Kirenol treatment. Together, our results thus confirm that Kirenol has potent therapeutic efficacy in RA owing to its ability to suppress negative FLS activities.

KEYWORDS

IL-6; Rheumatoid arthritis; fibroblast-like synoviocytes; invasion; kirenol; migration

Title

Kirenol Inhibits the Function and Inflammation of Fibroblast-like Synoviocytes in Rheumatoid Arthritis in vitro and in vivo.

Author

Wu J1, Li Q1, Jin L1, Qu Y1, Liang BB1, Zhu XT1, Du HY2, Jie LG1, Yu QH1.

Publish date

2019 Jun 6


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