Kibdelone A
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| Category | Bioactive by-products |
| Catalog number | BBF-04261 |
| CAS | 934464-77-4 |
| Molecular Weight | 581.96 |
| Molecular Formula | C29H24ClNO10 |
| Purity | >95% by HPLC |
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Description
It is a potent antitumour metabolite isolated from kibdelosporangium sp. MST-108465. It is structurally related to lysolipin and albofungin. It's cytotoxic.
Specification
| Synonyms | (10S,12S,13R)-4-Chloro-10,11,12,13-tetrahydro-10,12,13,15-tetrahydroxy-8-methoxy-2-methyl-3-propyl-2H-[1]benzopyrano[2',3':6,7]naphth[2,1-g]isoquinoline-1,5,14,16-tetrone |
| Storage | Store at -20°C |
| IUPAC Name | (19S,21S,22R)-8-chloro-19,21,22,26-tetrahydroxy-15-methoxy-6-methyl-7-propyl-17-oxa-6-azahexacyclo[12.12.0.02,11.04,9.016,25.018,23]hexacosa-1(14),2(11),4(9),7,12,15,18(23),25-octaene-3,5,10,24-tetrone |
| Canonical SMILES | CCCC1=C(C2=C(C(=O)C3=C(C2=O)C=CC4=C3C(=C5C(=C4OC)OC6=C(C5=O)C(C(CC6O)O)O)O)C(=O)N1C)Cl |
| InChI | InChI=1S/C29H24ClNO10/c1-4-5-11-20(30)16-17(29(39)31(11)2)23(36)14-9(21(16)34)6-7-10-15(14)24(37)19-25(38)18-22(35)12(32)8-13(33)27(18)41-28(19)26(10)40-3/h6-7,12-13,22,32-33,35,37H,4-5,8H2,1-3H3/t12-,13-,22-/m0/s1 |
| InChI Key | VXXQRIDYOXHDCN-MZFXBISCSA-N |
| Source | Kibdelosporangium sp. |
Properties
| Appearance | Orange Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 844.2±65.0°C at 760 mmHg |
| Density | 1.69±0.1 g/cm3 at 20°C 760 mmHg |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Kibdelones: novel anticancer polyketides from a rare Australian actinomycete
Ranjala Ratnayake, Jennifer H Gill, Robert J Capon, Ernest Lacey, Shaun Tennant Chemistry . 2007;13(5):1610-9. doi: 10.1002/chem.200601236.
The kibdelones are a novel family of bioactive heterocyclic polyketides produced by a rare soil actinomycete, Kibdelosporangium sp. (MST-108465). Complete relative stereostructures were assigned to kibdelones A-C (1-3), kibdelone B rhamnoside (5), 13-oxokibdelone A (7), and 25-methoxy-24-oxokibdelone C (8) on the basis of detailed spectroscopic analysis and chemical interconversion, as well as mechanistic and biosynthetic considerations. Under mild conditions, kibdelones B (2) and C (3) undergo a facile equilibration to kibdelones A-C (1-3), while kibdelone B rhamnoside (5) equilibrates to a mixture of kibdelone A-C rhamnosides (4-6). A plausible mechanism for this equilibration is proposed and involves air oxidation, quinone/hydroquinone redox transformations, and a choreographed sequence of keto/enol tautomerizations that aromatize ring C via a quinone methide intermediate. Kibdelones exhibit potent and selective cytotoxicity against a panel of human tumor cell lines and display significant antibacterial and nematocidal activity.
2. Enantioselective total synthesis and biological evaluation of (+)-kibdelone A and a tetrahydroxanthone analogue
John A Porco Jr, Dana K Winter, Tomas Hudlicky, Mary Ann Endoma-Arias, John A Beutler J Org Chem . 2013 Aug 2;78(15):7617-26. doi: 10.1021/jo401169z.
The total synthesis of kibdelone A has been accomplished via In(III)-catalyzed arylation of a heterocyclic quinone monoketal and iodine-mediated oxidative photochemical electrocyclization for construction of the ABCD ring moiety. Enzymatic dihydroxylation of methyl 2-halobenzoate substrates was employed for synthesis of activated 2-halo-cyclohexene F-ring fragments. A one pot oxa-Michael/Friedel-Crafts process allowed access to the first simplified DEF ring analogues of the kibdelones.
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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 ╳
