Rubiginone D2
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| Category | Antibiotics |
| Catalog number | BBF-02213 |
| CAS | 274913-71-2 |
| Molecular Weight | 352.34 |
| Molecular Formula | C20H16O6 |
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Description
Rubiginone D2 is an antibiotic originally isolated from Streptomyces sp. Go N1/5. It has the activity of inhibiting tumor cells.
Specification
| Storage | Store at -20°C |
| IUPAC Name | (2S,3S,4R)-2,4-dihydroxy-8-methoxy-3-methyl-3,4-dihydro-2H-benzo[a]anthracene-1,7,12-trione |
| Canonical SMILES | CC1C(C2=C(C(=O)C1O)C3=C(C=C2)C(=O)C4=C(C3=O)C=CC=C4OC)O |
| InChI | InChI=1S/C20H16O6/c1-8-16(21)10-6-7-11-14(15(10)20(25)17(8)22)19(24)9-4-3-5-12(26-2)13(9)18(11)23/h3-8,16-17,21-22H,1-2H3/t8-,16+,17-/m0/s1 |
| InChI Key | DWIWLEGGRHIXAH-KDLNQGCSSA-N |
Properties
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 639.5±55.0°C at 760 mmHg |
| Density | 1.465±0.06 g/cm3 |
| Solubility | Soluble in DMSO or acetone; slightly soluble in methanol. |
Reference Reading
1. New biologically active rubiginones from Streptomyces sp
C Puder, A Zeeck, W Beil J Antibiot (Tokyo). 2000 Apr;53(4):329-36. doi: 10.7164/antibiotics.53.329.
Four new polyketides, named rubiginone D2 (2), 4-O-acetyl-rubiginone D2 (3), rubiginone H (6) and rubiginone I (7) were isolated from the cultures of Streptomyces sp. (strain Gö N1/5). Their structures were established by a detailed spectroscopic analysis. The absolute configuration of 3 was determined by derivatization with chiral acids (Helmchen's method). The rubiginones inhibit the growth of some Gram-positive bacteria and are cytostatically active against different tumor cell lines.
2. Herbicidal characteristics and structural identification of a potential active compound produced by Streptomyces sp. KRA18-249
Mirjalol Umurzokov, Youn-Me Lee, Hye Jin Kim, Kwang Min Cho, Young Sook Kim, Jung Sup Choi, Kee Woong Park Pestic Biochem Physiol. 2022 Oct;187:105213. doi: 10.1016/j.pestbp.2022.105213. Epub 2022 Aug 18.
The KRA18-249 strain, isolated from a natural recreational forest near Jeongseon, Gangwon-do, when applied to plants induced signs of wilting within 24 h, leading to plant death. The isolated actinomycete was identified as Streptomyces gardneri based on 16S rRNA gene homogeneity analysis. The culture filtrate was solvent fractionated to obtain the active substance, and the active compound 249-Y1 was isolated from the purified fractions via a herbicide activity test using Digitaria ciliaris. NMR and ESI-MS analyses revealed that the molecular formula of 249-Y1 is C20H16O6 [MW = 352.0947] and is an anthraquinone (rubiginone D2) produce by polyketide synthetase system. The active compound 249-Y1 showed strong (100%) herbicidal activity against several weeds at 500 μg mL-1 concentration. Twisting symptoms began to appear within 24 h of treatment and intensified over time. The KRA18-249 strain produced the herbicidal compound under specific culture conditions, that is, at 200 rpm, 35 °C, for eight days at an initial pH of 10. We also found that 249-Y1 inhibited chlorophyll, but was not a radical generator. Overall, the secondary metabolite 249-Y1, produced by KRA18-249, can be used as a new biological agent for weed control.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
