We Offer Worldwide Shipping
Login Wishlist

Rubiadin 1-methyl ether

$896

  • Brand : BIOFRON

  • Catalogue Number : BD-P1001

  • Specification : 98.0%(HPLC)

  • CAS number : 7460-43-7

  • Formula : C16H12O4

  • Molecular Weight : 268.26

  • PUBCHEM ID : 96191

  • Volume : 25mg

Available on backorder

Quantity
Checkout Bulk Order?

Catalogue Number

BD-P1001

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

268.26

Appearance

Yellow powder

Botanical Source

Structure Type

Anthraquinones

Category

Standards;Natural Pytochemical;API

SMILES

CC1=C(C=C2C(=C1OC)C(=O)C3=CC=CC=C3C2=O)O

Synonyms

9,10-Anthracenedione, 3-hydroxy-1-methoxy-2-methyl-/9,10-Anthracenedione,3-hydroxy-1-methoxy-2-methyl/3-Hydroxy-1-methoxy-2-methylanthraquinone/1,3-dimethoxy-2-methylanthraquinone/3-Hydroxy-1-methoxy-2-methyl-anthraquinone/3-Hydroxy-1-methoxy-2-methyl-9,10-anthraquinone/rubiadin-1-methyl ether/3-Hydroxy-1-methoxy-2-methyl-anthrachinon

IUPAC Name

3-hydroxy-1-methoxy-2-methylanthracene-9,10-dione

Applications

Anthraquinones from Morinda officinalis roots enhance adipocyte differentiation in 3T3-L1 cells. PUMID/DOI:DOI: 10.1080/14786419.2011.608676 Nat Prod Res. 2012;26(18):1750-4. To search for anti-diabetic and insulin-sensitising natural products, the effect on adipocyte differentiation was investigated by assessing fat accumulation in 3T3-L1 preadipocytes using Oil Red O staining. Fractionation and separation of n-hexane and CHCl? fractions of Morinda officinalis (Rubiaceae) using several chromatographic methods led to the isolation of three anthraquinones, 1,2-dimethoxyanthraquinone (1), alizarin-2-methyl ether (2) and rubiadin-1-methyl ether (3). Among them, alizarin-2-methyl ether (2) showed the strongest enhancing activity, followed by rubiadin-1-methyl ether (3) and 1,2-dimethoxyanthraquinone (1). At a concentration of 100??M, alizarin-2-methyl ether (2) enhanced adipocyte differentiation by up to 131% (compared to insulin-treated cells). Thus, these compounds could be beneficial in the treatment of diabetes. The anthraquinones rubiadin and its 1-methyl ether isolated from Heterophyllaea pustulata reduces Candida tropicalis biofilms formation. PUMID/DOI:DOI: 10.1016/j.phymed.2016.07.008 Phytomedicine. 2016 Nov 15;23(12):1321-1328. Background: Candida tropicalis is increasingly becoming among the most commonly isolated pathogens causing fungal infections with an important biofilm-forming capacity.Purpose: This study addresses the antifungal effect of rubiadin (AQ1) and rubiadin 1-methyl ether (AQ2), two photosensitizing anthraquinones (AQs) isolated from Heterophyllaea pustulata, against C tropicalis biofilms, by studying the cellular stress and antioxidant response in two experimental conditions: darkness and irradiation. The combination with Amphotericin B (AmB) was assayed to evaluate the synergic effect. Study design/Methods: Biofilms of clinical isolates and reference strain of Candida tropicalis were treated with AQs (AQ1 or AQ2) and/or AmB, and the biofilms depletion was studied by crystal violet and confocal scanning laser microscopy (CSLM). The oxidant metabolites production and the response of antioxidant defense system were also evaluated under dark and irradiation conditions, being the light a trigger for photo-activation of the AQs. The Reactive Oxygen Species (ROS) were detected by the reduction of Nitro Blue Tetrazolium test, and Reactive Nitrogen Intermediates (RNI) by the Griess assay. ROS accumulation was also detected inside biofilms by using 2',7'-dichlorodihydrofluorescein diacetate (DCFH-DA) probe, which was visualized by CSLM. Superoxide dismutase (SOD) activity and the total antioxidant capacity of biofilms were measured by spectrophotometric methods. The minimun inhibitory concentration for sessile cells (SMIC) was determined for each AQs and AmB. The fractional inhibitory concentration index (FICI) was calculated for the combinations of each AQ with AmB by the checkerboard microdilution method. Results: Biofilm reduction of both strains was more effective with AQ1 than with AQ2. The antifungal effect was mediated by an oxidative and nitrosative stress under irradiation, with a significant accumulation of endogenous ROS detected by CSLM and an increase in the SOD activity. Thus, the prooxidantantioxidant balance was altered especially by AQ1. The best synergic combination with AmB was also obtained with AQ1 (80.5%) (FICI = 0.74).Conclusion: Under irradiation, the oxidative stress was the predominant effect, altering the prooxidantantioxidant balance, which may be the cause of the irreversible cell injury in the biofilm. Our results showed synergism of these natural AQs with AmB. Therefore, the photosensitizing AQ1 could be an alternative for the Candida infections treatment, which deserves further investigation. (C) 2016 Elsevier GmbH. All rights reserved. Antiosteoporotic activity of anthraquinones from Morinda officinalis on osteoblasts and osteoclasts. PUMID/DOI:DOI: 10.3390/molecules14010573 Molecules. 2009 Jan 23;14(1):573-83. Bioactivity-guided fractionation led to the successful isolation of antiosteoporotic components, i.e. physicion (1), rubiadin-1-methyl ether (2), 2-hydroxy-1-methoxy- anthraquinone (3), 1,2-dihydroxy-3-methylanthraquinone (4), 1,3,8-trihydroxy-2-methoxy- anthraquinone (5), 2-hydroxymethyl-3-hydroxyanthraquinone (6), 2-methoxyanthraquinone (7) and scopoletin (8) from an ethanolic extract of the roots of Morinda officinalis. Compounds 4-8 are isolated for the first time from M. officinalis. Among them, compounds 2 and 3 promoted osteoblast proliferation, while compounds 4, 5 increased osteoblast ALP activity. All of the isolated compounds inhibited osteoclast TRAP activity and bone resorption, and the inhibitory effects on osteoclastic bone resorption of compounds 1 and 5 were stronger than that of other compounds. Taken together, antiosteoporotic activity of M. officinalis and its anthraquinones suggest therapeutic potential against osteoporosis. Effects of three compounds extracted from Morinda lucida on Plasmodium falciparum. PUMID/DOI:DOI: 10.1055/s-2006-961543 Planta Med. 1992 Dec;58(6):533-4. The effects of three compounds, digitolutein (1), rubiadin 1-methyl ether (2) and damnacanthal (3) extracted from the stem bark and the roots of Morinda lucida Benth. on the growth of Plasmodium falciparum in vitro were investigated. The number of parasites (schizonts) decreased significantly in a dose-dependent manner, and 100% of inhibition was obtained with 30 to 40 micrograms of each compound tested. The IC50 values were calculated.

Density

1.4±0.1 g/cm3

Solubility

Methanol

Flash Point

193.0±23.6 °C

Boiling Point

502.2±50.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C16H12O4/c1-8-12(17)7-11-13(16(8)20-2)15(19)10-6-4-3-5-9(10)14(11)18/h3-7,17H,1-2H3

InChl Key

NTBUBTCXACOEEC-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#:7460-43-7) 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

28723923

Abstract

The photoprocesses involved in the photo-induced Candida tropicalis biofilm reduction by two natural anthraquinones (AQs), rubiadin (1) and rubiadin-1-methyl ether (2), were examined. Production of singlet oxygen (1O2) and of superoxide radical anion (O2•-) was studied. Although it was not possible to detect the triplet state absorption of any AQs in biofilms, observation of 1O2 phosphorescence incubated with deuterated Phosphate Buffer Solution, indicated that this species is actually formed in biofilms. 2 was accumulated in the biofilm to a greater extent than 1 and produced measurable amounts of O2•- after 3h incubation in biofilms. The effect of reactive oxygen species scavengers on the photo-induced biofilm reduction showed that Tiron (a specific O2•- scavenger) is most effective than sodium azide (a specific 1O2 quencher). This suggests that O2•- formed by electron transfer quenching of the AQs excited states, is the main photosensitizing mechanism involved in the photo-induced antibiofilm activity, whereas 1O2 participation seems of lesser importance

Title

On the mechanism of Candida tropicalis biofilm reduction by the combined action of naturally-occurring anthraquinones and blue light.

Author

Marioni J1, Bresoli-Obach R2, Agut M2, Comini LR1, Cabrera JL1, Paraje MG3, Nonell S2, NúNez Montoya SC1.

Publish date

2017 Jul 19;

PMID

27765351

Abstract

BACKGROUND:
Candida tropicalis is increasingly becoming among the most commonly isolated pathogens causing fungal infections with an important biofilm-forming capacity.

PURPOSE:
This study addresses the antifungal effect of rubiadin (AQ1) and rubiadin 1-methyl ether (AQ2), two photosensitizing anthraquinones (AQs) isolated from Heterophyllaea pustulata, against C. tropicalis biofilms, by studying the cellular stress and antioxidant response in two experimental conditions: darkness and irradiation. The combination with Amphotericin B (AmB) was assayed to evaluate the synergic effect.

STUDY DESIGN/METHODS:
Biofilms of clinical isolates and reference strain of Candida tropicalis were treated with AQs (AQ1 or AQ2) and/or AmB, and the biofilms depletion was studied by crystal violet and confocal scanning laser microscopy (CSLM). The oxidant metabolites production and the response of antioxidant defense system were also evaluated under dark and irradiation conditions, being the light a trigger for photo-activation of the AQs. The Reactive Oxygen Species (ROS) were detected by the reduction of Nitro Blue Tetrazolium test, and Reactive Nitrogen Intermediates (RNI) by the Griess assay. ROS accumulation was also detected inside biofilms by using 2′,7′-dichlorodihydrofluorescein diacetate (DCFH-DA) probe, which was visualized by CSLM. Superoxide dismutase (SOD) activity and the total antioxidant capacity of biofilms were measured by spectrophotometric methods. The minimun inhibitory concentration for sessile cells (SMIC) was determined for each AQs and AmB. The fractional inhibitory concentration index (FICI) was calculated for the combinations of each AQ with AmB by the checkerboard microdilution method.

RESULTS:
Biofilm reduction of both strains was more effective with AQ1 than with AQ2. The antifungal effect was mediated by an oxidative and nitrosative stress under irradiation, with a significant accumulation of endogenous ROS detected by CSLM and an increase in the SOD activity. Thus, the prooxidant-antioxidant balance was altered especially by AQ1. The best synergic combination with AmB was also obtained with AQ1 (80.5%) (FICI=0.74).

CONCLUSION:
Under irradiation, the oxidative stress was the predominant effect, altering the prooxidant-antioxidant balance, which may be the cause of the irreversible cell injury in the biofilm. Our results showed synergism of these natural AQs with AmB. Therefore, the photosensitizing AQ1 could be an alternative for the Candida infections treatment, which deserves further investigation.

Copyright © 2016 Elsevier GmbH. All rights reserved.

KEYWORDS

Antifungal; Biofilms; Candida tropicalis; Heterophyllaea pustulata; Oxidative stress; Synergistic activity

Title

The anthraquinones rubiadin and its 1-methyl ether isolated from Heterophyllaea pustulata reduces Candida tropicalis biofilms formation.

Author

Marioni J1, da Silva MA2, Cabrera JL1, Montoya SC1, Paraje MG3.

Publish date

2016 Nov 15

PMID

26415396

Abstract

OBJECTIVE:
To establish a sensitive and specific high performance liquid chromatography (HPLC) method for simultaneous determination of alizarin anthraquinones (1-methoxy-2-hydroxy anthraquinone,1,2-dimethoxy-3-hydroxy anthraquinone, rubiadin-1- methylether, 1,3-dihydroxy-2-methoxy anthraquinone, rubiadin) in Morinda officinalis from different habitats.

METHODS:
The analysis was carried out on an Ecosil C18 column (250 mm x 4.6 mm, 5 µm) and detected with an UV detector at the wavelength of 277 nm. Gradient elution was carried out with acetonitrile-0.2% phosphoric acid at the flow rate of 0. 8 mL/min. The column temperature was set at 30 °C.

RESULTS:
The calibration curves were linear in the range of 0.2856-34.27 g/mL for 1-methoxy-2-hydroxy anthraquinone (r = 0.9999), 0.3268-39.22 g/mL for 1,2-dimethoxy-3-hydroxy anthraquinone (r = 0.9999), 0.3450-41.40 µg/mL for rubiadin-1- methylether (r = 0.9999), 0.1248-14. 98 µg/mL for 1,3-dihydroxy-2-methoxy anthraquinone (r = 0.9999) and 0.0508-6.096 µg/ mL for rubiadin (r = 0.9994), respectively. The average recoveries of the five components were 99.4%, 100.2%, 101.4%, 97.2%, 103.2%, respectively. The content of active components of samples from 10 different hatitats were in the range of 0.0025-0.0722 mg/ g, 0.0016-0.0658 mg/g, 0.0022-0.0684 mg/g, 0.0182-0.3965 mg/g and 0. 0014-0.0179 mg/g.

CONCLUSION:
The established method is accurate, reliable, and can be used for the simultaneous determination of the five components in Morinda officinalis, which provides a scientific basis for the quality evaluation of Morinda officinalis

Title

[Determination of Five Active Components in Morinda officinalis from Different Habitats by HPLC].

Author

Shi J, Liu ZH, Wang L, Jia TZ.

Publish date

2015 Feb 15