Granaticinic acid

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Category Antibiotics
Catalog number BBF-01279
CAS 71203-17-3
Molecular Weight 462.40
Molecular Formula C22H22O11

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Description

It is produced by the strain of Streptomyces sp. XT-11989. It's a quinone antibiotic. It has anti-gram-positive bacterial activity.

Specification

Synonyms (1R,13R)-1,3,4,6,7,9,10,11-Octahydro-4α,5,10β,12,13-pentahydroxy-3α,7α-dimethyl-6,11-dioxo-1β,4-ethanonaphtho[2,3-c:6,7-c']dipyran-9β-acetic acid; 10-Hydroxygranatomycin D; Granatomycin E
IUPAC Name 2-[(1S,7S,9S,10S,16R,18R,19R)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.02,15.04,13.06,11]icosa-2(15),3,6(11),13-tetraen-9-yl]acetic acid
Canonical SMILES CC1C2=C(C(C(O1)CC(=O)O)O)C(=O)C3=C(C4=C(C(=C3C2=O)O)C5(C(OC4CC5O)C)O)O
InChI InChI=1S/C22H22O11/c1-5-11-13(17(26)8(32-5)4-10(24)25)20(29)14-15(18(11)27)21(30)16-12(19(14)28)7-3-9(23)22(16,31)6(2)33-7/h5-9,17,23,26,28,30-31H,3-4H2,1-2H3,(H,24,25)/t5-,6+,7+,8-,9+,17+,22+/m0/s1
InChI Key WCEOQCLZGCMUEV-MJDCBFFMSA-N

Properties

Appearance Red Powder
Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 858.8±65.0 °C (Predicted)
Density 1.79±0.1 g/cm3 (Predicted)

Reference Reading

1. Multi-Response Optimization of Granaticinic Acid Production by Endophytic Streptomyces thermoviolaceus NT1, Using Response Surface Methodology
Sudipta Roy, Suman Kumar Halder, Debdulal Banerjee Bioengineering (Basel). 2016 Jul 27;3(3):19. doi: 10.3390/bioengineering3030019.
Streptomyces thermoviolaceus NT1, an endophytic isolate, was studied for optimization of granaticinic acid production. It is an antimicrobial metabolite active against even drug resistant bacteria. Different media, optimum glucose concentration, initial media pH, incubation temperature, incubation period, and inoculum size were among the selected parameters optimized in the one-variable-at-a-time (OVAT) approach, where glucose concentration, pH, and temperature were found to play a critical role in antibiotic production by this strain. Finally, the Box-Behnken experimental design (BBD) was employed with three key factors (selected after OVAT studies) for response surface methodological (RSM) analysis of this optimization study.RSM analysis revealed a multifactorial combination; glucose 0.38%, pH 7.02, and temperature 36.53 °C as the optimum conditions for maximum antimicrobial yield. Experimental verification of model analysis led to 3.30-fold (61.35 mg/L as compared to 18.64 mg/L produced in un-optimized condition) enhanced granaticinic acid production in ISP2 medium with 5% inoculum and a suitable incubation period of 10 days. So, the conjugated optimization study for maximum antibiotic production from Streptomyces thermoviolaceus NT1 was found to result in significantly higher yield, which might be exploited in industrial applications.

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