Rugulosin ((+) form)
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| Category | Antibiotics |
| Catalog number | BBF-02639 |
| CAS | 23537-16-8 |
| Molecular Weight | 542.49 |
| Molecular Formula | C30H22O10 |
| Purity | >98% by HPLC |
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Description
An intense yellow pigment produced by some species of penicillium, aspergillus and the fungal symbiotants of some lichens; shows antibacterial and insecticidal activity; an inhibitor of RNA Polymerase and Rnase.
Specification
| Related CAS | 21884-45-7 |
| Synonyms | (+)-Rugulosin; Radicalisin; NSC 160880; 5H,13a,5a,14-[1,2,3,4]Butanetetraylcycloocta[1,2-b:5,6-b']dinaphthalene-5,8,13,16(14H)-tetrone, 1,7,9,15,17,20-hexahydroxy-3,11-dimethyl- |
| Storage | Store at -20°C |
| IUPAC Name | 8,10,14,23,25,28-hexahydroxy-6,21-dimethyloctacyclo[14.11.1.02,11.02,15.04,9.013,17.017,26.019,24]octacosa-4(9),5,7,10,19(24),20,22,25-octaene-3,12,18,27-tetrone |
| Canonical SMILES | CC1=CC2=C(C(=C1)O)C(=C3C(=O)C4C(C5C3(C2=O)C6C(C5C47C(=C(C8=C(C7=O)C=C(C=C8O)C)O)C6=O)O)O)O |
| InChI | InChI=1S/C30H22O10/c1-7-3-9-13(11(31)5-7)21(33)17-25(37)20-23(35)15-16-24(36)19(29(15,17)27(9)39)26(38)18-22(34)14-10(28(40)30(16,18)20)4-8(2)6-12(14)32/h3-6,15-16,19-20,23-24,31-36H,1-2H3 |
| InChI Key | QFDPVUTXKUGISP-UHFFFAOYSA-N |
| Source | Penicillium sp. |
Properties
| Appearance | Yellow Brown Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Boiling Point | 980.03°C at 760 mmHg |
| Melting Point | 290°C |
| Density | 1.88 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
Reference Reading
1. A metabolomic study of vegetative incompatibility in Cryphonectria parasitica
Thomas E Witte, Graham W Heberlig, Anatoly Belov, Myron L Smith, Amanda Sproule, Christopher N Boddy, Mike G Darnowski, David P Overy, Sam Shields Fungal Genet Biol . 2021 Dec;157:103633. doi: 10.1016/j.fgb.2021.103633.
Vegetative incompatibility (VI) is a form of non-self allorecognition in filamentous fungi that restricts conspecific hyphal fusion and the formation of heterokaryons. In the chestnut pathogenic fungus, Cryphonectria parasitica, VI is controlled by six vic loci and has been of particular interest because it impedes the spread of hypoviruses and thus biocontrol strategies. We use nuclear magnetic resonance and high-resolution mass spectrometry to characterize alterations in the metabolome of C. parasitica over an eight-day time course of vic3 incompatibility. Our findings support transcriptomic data that indicated remodeling of secondary metabolite profiles occurs during vic3 -associated VI. VI-associated secondary metabolites include novel forms of calbistrin, decumbenone B, a sulfoxygenated farnesyl S-cysteine analog, lysophosphatidylcholines, and an as-yet unidentified group of lipid disaccharides. The farnesyl S-cysteine analog is structurally similar to pheromones predicted to be produced during VI and is here named 'crypheromonin'. Mass features associated with C. parasitica secondary metabolites skyrin, rugulosin and cryphonectric acid were also detected but were not VI specific. Partitioning of VI-associated secondary metabolites was observed, with crypheromonins and most calbistrins accumulating in the growth medium over time, whereas lysophosphatidylcholines, lipid disaccharide-associated mass features and other calbistrin-associated mass features peaked at distinct time points in the mycelium. Secondary metabolite biosynthetic gene clusters and potential biological roles associated with the detected secondary metabolites are discussed.
2. Intertwined Biosynthesis of Skyrin and Rugulosin A Underlies the Formation of Cage-Structured Bisanthraquinones
Jie Liang, Chun Xia Ding, Yun Bin Han, Wei Bai, Shao-Hua Wu, Ren Xiang Tan J Am Chem Soc . 2021 Sep 8;143(35):14218-14226. doi: 10.1021/jacs.1c05421.
Skyrin and rugulosin A are bioactive bisanthraquinones found in many fungi, with the former suggested as a precursor of hypericin (a diversely bioactive phytochemical) and the latter characterized by its distinct cage-like structure. However, their biosynthetic pathways remain mysterious, although they have been characterized for over six decades. Here, we present theruggene cluster that governs simultaneously the biosynthesis of skyrin and rugulosin A inTalaromycessp. YE3016, a fungal endophyte residing inAconitum carmichaeli. A combination of genome sequencing, gene inactivation, heterologous expression, and biotransformation tests allowed the identification of the gene function, biosynthetic precursor, and enzymatic sets involved in their molecular architecture constructions. In particular, skyrin was demonstrated to form from the 5,5'-dimerization of emodin radicals catalyzed by RugG, a cytochrome P450 monooxygenase evidenced to be potentially applicable for the (chemo)enzymatic synthesis of dimeric polyphenols. The fungal aldo-keto reductase RugH was shown to be capable of hijacking the closest skyrin precursor (CSP) immediately after the emodin radical coupling, catalyzing the ketone reduction of CSP to inactivate its tautomerization into skyrin and thus allowing for the spontaneous intramolecular Michael addition to cyclize the ketone-reduced form of CSP into rugulosin A, a representative of diverse cage-structured bisanthraquinones. Collectively, the work updates our understanding of bisanthraquinone biosynthesis and paves the way for synthetic biology accesses to skyrin, rugulosin A, and their siblings.
3. Chemoenzymatic reduction of citreorosein and its implications on aloe-emodin and rugulosin C (bio)synthesis
Syed Masood Husain, Anshul Rajput, Brindaban Roy, Shailesh Kumar Singh, Amit Mondal, Nirmal Saha Org Biomol Chem . 2019 Oct 14;17(38):8711-8715. doi: 10.1039/c9ob01690b.
A chemoenzymatic reduction of citreorosein by the NADPH-dependent polyhydroxyanthracene reductase from Cochliobolus lunatus or MdpC from Aspergillus nidulans in the presence of Na2S2O4gave access to putative biosynthetic intermediates, (R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracene-1(2H)-one and its oxidized form, (R)-3,4-dihydrocitreorosein. Herein, we discuss the implications of these results towards the (bio)synthesis of aloe-emodin and (+)-rugulosin C in fungi.
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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 ╳
