1397-77-9

Basic information

• Product Name: actinorhodin
• Synonyms: actinorhodin;3,3',4,4',5,5',10,10'-Octahydro-6,6',9,9'-tetrahydroxy-1β,1'β-dimethyl-5,5',10,10'-tetraoxo-8,8'-bi[1H-naphtho[2,3-c]pyran]-3α,3'α-diacetic acid;Mederrhodin;Actinorhodine;C06691
• CAS NO: 1397-77-9
• Molecular Formula: C₃₂H₂₆O₁₄
• Molecular Weight: 634.54044
• Mol File: 1397-77-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 918.5°Cat760mmHg
• Flash Point: 299.9°C
• Appearance: /
• Density: 1.632g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.699
• PKA: 3.84±0.10(Predicted)
• CAS DataBase Reference: actinorhodin(CAS DataBase Reference)
• NIST Chemistry Reference: actinorhodin(1397-77-9)
• EPA Substance Registry System: actinorhodin(1397-77-9)

Safety Data

• Hazardous Substances Data: 1397-77-9(Hazardous Substances Data)

Usage

Description

Actinorhodin is a benzoisochromanequinone polyketide antibiotic produced from Streptomyces coelicolor (Magnolo et al. 1991). It belongs to a class of aromatic polyketides synthesized by type II PKSs (Manikprabhu and Lingappa 2013). It can be used as a pH indicator, turning red below pH 8.5 and blue above.

Definition

ChEBI: Actinorhodin is a member of the class of benzoisochromanequinone that is produced by Streptomyces coelicolor A3(2) and exhibits antibiotic activity. It has a role as a bacterial metabolite and an antimicrobial agent. It is a benzoisochromanequinone, a polyketide, a dicarboxylic acid, a polyphenol, a ring assembly and a member of p-quinones. It is a conjugate acid of an actinorhodin(3-).

InChI:InChI=1/C32H26O14/c1-9-21-15(3-11(45-9)5-19(35)36)29(41)23-17(33)7-13(27(39)25(23)31(21)43)14-8-18(34)24-26(28(14)40)32(44)22-10(2)46-12(6-20(37)38)4-16(22)30(24)42/h7-12,41-44H,3-6H2,1-2H3,(H,35,36)(H,37,38)/t9-,10-,11+,12+/m1/s1

Upstream product

• 958730-34-2 6-deoxykalafungin 

Related news

Response surface methodological approach for inclusion of perfluorocarbon in actinorhodin (cas 1397-77-9) fermentation medium09/10/2019

The combined effects of perfluorocarbon and glucose concentrations on actinorhodin production by Streptomyces coelicolor A3(2) were studied in a 2-l bioreactor using response surface methodology. A 22 full-factorial central composite design was employed for experimental design and analysis of th...detailed

ArticleBiosynthetic Conclusions from the Functional Dissection of Oxygenases for Biosynthesis of actinorhodin (cas 1397-77-9) and Related Streptomyces Antibiotics09/09/2019

SummaryActinorhodin (ACT) produced by Streptomyces coelicolor A3(2) belongs to the benzoisochromanequinone (BIQ) class of antibiotics. ActVA-ORF5, a flavin-dependent monooxygenase (FMO) essential for ACT biosynthesis, forms a two-component enzyme system in combination with a flavin:NADH oxidored...detailed

Short communicationA putative secreted solute binding protein, SCO6569 is a possible AfsR2-dependent down-regulator of actinorhodin (cas 1397-77-9) biosynthesis in Streptomyces coelicolor09/08/2019

AfsR2 is a global regulatory protein involved in stimulating the biosynthesis of antibiotics in various Streptomyces species. Using 2-D gel electrophoresis and MALDI-TOF analyses, several putative AfsR2-target proteins were previously identified. In order to verify the biological significance of...detailed

Ligand Recognition by ActR, a TetR-Like Regulator of actinorhodin (cas 1397-77-9) Export09/07/2019

TetR-like transcriptional repressors interact with small-molecule ligands to control many facets of prokaryotic biology, including clinical antibiotic resistance. ActR is a TetR-like protein encoded in the biosynthetic gene cluster for the antibiotic actinorhodin and controls the expression of t...detailed

Crystal Structures of the Streptomyces coelicolor TetR-Like Protein ActR Alone and in Complex with actinorhodin (cas 1397-77-9) or the actinorhodin (cas 1397-77-9) Biosynthetic Precursor (S)-DNPA09/06/2019

Actinorhodin, an antibiotic produced by Streptomyces coelicolor, is exported from the cell by the ActA efflux pump. actA is divergently transcribed from actR, which encodes a TetR-like transcriptional repressor. We showed previously that ActR represses transcription by binding to an operator fro...detailed

Identification of the actinorhodin (cas 1397-77-9) monomer and its related compound from a deletion mutant of the actVA-ORF4 gene of Streptomyces coelicolor A3(2)09/05/2019

An oxygenated derivative of dihydrokalafungin (DHK) was isolated from a deletion mutant of the actVA-ORF4 gene involved in the biosynthesis of a dimeric benzoisochromanequinone (BIQ) antibiotic, actinorhodin (ACT), in Streptomyces coelicolor A3(2). Spectroscopic analysis elucidated its structure...detailed

Original articleγ actinorhodin (cas 1397-77-9) a natural and attorney source for synthetic dye to detect acid production of fungi09/04/2019

Colors from natural sources are gaining popularity because synthetic colors are carcinogenic. Natural colors are obtained from plants or microorganisms. Pigments produced by microorganisms have advantages over plant pigments, due to their ease of use and reliability. In the present study, a blue...detailed

Recovery of actinorhodin (cas 1397-77-9) from fermentation broth09/03/2019

In the present work, a new method of purification for actinorhodin was developed using an expanded bed chromatography technique in which antibiotic capture, feedstock clarification, centrifugation, dialysis and concentration are done in one step. The cation-exchanger (P-11) resulted in 26% adsor...detailed

Original Research ArticlePlasma modified PLA electrospun membranes for actinorhodin (cas 1397-77-9) production intensification in Streptomyces coelicolor immobilized-cell cultivations09/02/2019

Most of industrially relevant bioproducts are produced by submerged cultivations of actinomycetes. The immobilization of these Gram-positive filamentous bacteria on suitable porous supports may prevent mycelial cell-cell aggregation and pellet formation which usually negatively affect actinomyce...detailed

Effects of particle addition to Streptomyces cultivations to optimize the production of actinorhodin (cas 1397-77-9) and streptavidin09/01/2019

Streptomyces is a genus of Gram-positive bacteria that grow in various environments, and its shape resembles filamentous fungi. The most interesting property of Streptomyces is the ability to produce bioactive secondary metabolites, such as antifungals, antivirals, antitumorals, and especially a...detailed

Relevant articles and documents

Epoxyquinone formation catalyzed by a two-component flavin-dependent monooxygenase involved in biosynthesis of the antibiotic actinorhodin

The biosynthetic gene cluster of the aromatic polyketide antibiotic actinorhodin (ACT) in Streptomyces coelicolor A3(2) carries a pair of genes, actVA-ORF5 and actVB, that encode a two-component flavin-dependent monooxygenase (FMO). Our previous studies have demonstrated that the ActVA-ORF5/ActVB system functions as a quinone-forming C-6 oxygenase in ACT biosynthesis. Furthermore, we found that this enzyme system exhibits an additional oxygenation activity with dihydrokalafungin (DHK), a proposed intermediate in the ACT biosynthetic pathway, and generates two reaction products. These compounds were revealed to be monooxygenated derivatives of kalafungin, which is spontaneously formed through oxidative lactonization of DHK. Their absolute structures were elucidated from their NMR spectroscopic data and by computer modeling and X-ray crystallography as (5S,14R)-epoxykalafungin and (5R,14S)-epoxykalafungin, demonstrating an additional epoxyquinone-forming activity of the ActVA-ORF5/ActVB system in vitro.