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Santamarine

$1,120

  • Brand : BIOFRON

  • Catalogue Number : BN-O1454

  • Specification : 98%(HPLC)

  • CAS number : 4290-13-5

  • Formula : C15H20O3

  • Molecular Weight : 248.3

  • PUBCHEM ID : 188297

  • Volume : 5mg

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Catalogue Number

BN-O1454

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

-20℃

Molecular Weight

248.3

Appearance

Powder

Botanical Source

This product is isolated and purified from the root of Dolomiaea souliei (Franch.) Shih

Structure Type

Sesquiterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC1=CCC(C2(C1C3C(CC2)C(=C)C(=O)O3)C)O

Synonyms

(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-b]furan-2(3H)-one/Naphtho(1,2-b)furan-2(3H)-one, 3a,4,5,5a,6,7,9a,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene-, (3aS,5aR,6R,9aS,9bS)-/Naphtho[1,2-b]furan-2(3H)-one, 3a,4,5,5a,6,7,9a,9b-octahydro-6-hydroxy-5a,9-dimethyl-3-methylene-, (3aS,5aR,6R,9aS,9bS)-/Santamarin/(3aS,5aR,6R,9aS,9bS)-6-Hydroxy-5a,9-dimethyl-3-methylene-3a,4,5,5a,6,7,9a,9b-octahydronaphtho[1,2-b]furan-2(3H)-one/Balchanin/(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one

IUPAC Name

(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one

Density

1.2±0.1 g/cm3

Solubility

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

Flash Point

176.5±21.5 °C

Boiling Point

415.6±45.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h4,10-13,16H,2,5-7H2,1,3H3/t10-,11+,12+,13-,15-/m0/s1

InChl Key

PLSSEPIRACGCBO-PFFFPCNUSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:4290-13-5) 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

29119107

Abstract

Santamarine (STM), a sesquiterpene lactone component of Magnolia grandiflora and Ambrosia confertiflora, has been shown to possess antimicrobial, antifungal, antibacterial, anti-inflammatory, and anticancer activities. However, no study has yet been conducted to investigate the molecular mechanism of STM-mediated anticancer activity. In the present study, we found that STM inhibits growth and induces apoptosis in A549 lung adenocarcinoma cells through induction of oxidative stress. STM induces oxidative stress by promoting reactive oxygen species (ROS) generation, depleting intracellular glutathione (GSH), and inhibiting thioredoxin reductase (TrxR) activity in a dose-dependent manner. Further mechanistic study demonstrated that STM induces apoptosis by modulation of Bax/Bcl-2 expressions, disruption of mitochondrial membrane potential, activation of caspase-3, and cleavage of PARP in a dose-dependent manner. Moreover, STM inhibited the constitutive and inducible translocation of NF-κBp65 into the nucleus. IKK-16 (I-κB kinase inhibitor) augmented the STM-induced apoptosis, indicating that STM induces apoptosis in A549 cells at least in part through NF-κB inhibition. Finally, STM-induced apoptosis and expressions of apoptosis regulators were effectively inhibited by thiol antioxidant N-acetyl-L-cysteine (NAC), indicating that STM exerts its anticancer effects mainly through oxidative stress. To the best of our knowledge, this is the first report providing evidence of anticancer activity and molecular mechanism of STM.

Title

Santamarine Inhibits NF-κB Activation and Induces Mitochondrial Apoptosis in A549 Lung Adenocarcinoma Cells via Oxidative Stress.

Author

Wu X1, Zhu H1, Yan J2, Khan M3, Yu X1.

Publish date

2017;

PMID

27180996

Abstract

CONTEXT:
Tuberculosis is primarily caused by Mycobacterium tuberculosis (Mtb). Previous studies have shown that the dichloromethanic extract of Ambrosia confertiflora DC (Asteraceae) inhibited Mtb.

OBJECTIVE:
To isolate the compounds responsible for the mycobactericidal activity against clinical Mtb strains.

MATERIALS AND METHODS:
The dichloromethanic extract of aerial parts of A. confertiflora was separated using chromatography columns. Mycobactericidal activity of the isolated compounds was evaluated using the Alamar Blue bioassay (128-16 μg/mL, 7 days). Cytotoxicity was tested against normal cell line L929 using the MTT ([3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium]) assay (100-3.125 μg/mL, 48 h). Compound structures were elucidated by 1H and 13C uni- and bidimensional NMR.

RESULTS:
Two sesquiterpene lactones (SQLs) with mycobactericidal activity were identified: santamarine and reynosin. Reynosin was the most active compound, with a minimal bactericidal concentration (MBC) of 128 μg/mL against the H37Rv, 366-2009 and 104-2010 Mtb strains and a minimal inhibitory concentration (MIC) of 64, 64, 128, 128 and 128 μg/mL against the H37Rv, 104-2010, 63-2009, 366-2009 and 430-2010 Mtb strains, respectively. Santamarine had MBCs of 128 μg/mL against the H3Rv and 104-2010 Mtb strains and MICs of 128 μg/mL against the H37Rv, 366-2009 and 104-2010 Mtb strains. We also isolated 1,10-epoxyparthenolide but only showed mycobacteriostatic activity (MIC 128 μg/mL) against the Mtb strain. Compounds were tested against the L929 cell line and the calculated selectivity index was <1. DISCUSSION AND CONCLUSIONS: This is the first report of the mycobactericidal activity of these compounds against clinical Mtb strains. It is also the first report of the isolation of 1,10-epoxyparthenolide from A. confertiflora. The anti-mycobacterial activity of A. confertiflora was attributed to the SQLs identified.

KEYWORDS

1,10-Epoxyparthenolide; mycobactericidal; sesquiterpenlactones

Title

Reynosin and santamarine: two sesquiterpene lactones from Ambrosia confertiflora with bactericidal activity against clinical strains of Mycobacterium tuberculosis.

Author

Coronado-Aceves EW1, Velazquez C1, Robles-Zepeda RE1, Jimenez-Estrada M2, Hernandez-Martinez J3, Galvez-Ruiz JC1, Garibay-Escobar A1.

Publish date

2016 Nov;

PMID

22803370

Abstract

OBJECTIVE:
To study the chemical constituents of Dolomiaea souliei.

METHOD:
Various chromatographic techniques were adopted to separate the constituents, and the spectrum analysis was made to identify their structures.

RESULT:
Seventeen compounds were isolated and identified as: dehydrocostus lactone (1), costunolide (2), mokko lactone (3), santamarine(4), reynosin (5), 4alpha-hydroxy-4beta-methyldihydrocostol (6), sulfocostunolide A (7), beta-costic acid (8), beta-cyclocostunolide (9), vladinol A (10), ursolic acid (11), betulinic acid (12), betulin (13), dibutyl terephthalate (14), dibutyl phthalate (15), uridine (16), and emodin (17).

CONCLUSION:
Compounds 6-9 and 12-17 were obtained from this genus for the first time, and compound 11 was obtained from this plant for the first time.

Title

[Chemical constituents of Dolomiaea souliei].

Author

Wei H1, He C, Peng Y, Ma G, Xiao P.

Publish date

2012 May


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