Actinoplanones A

Actinoplanones A

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Category Antibiotics
Catalog number BBF-00030
CAS
Molecular Weight 584.96
Molecular Formula C28H25N2O10Cl

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Description

Actinoplanones were isolated from the Actinoplanes sp. R-304. Actinoplanone A was extremely cytotoxic against HeLa cells and also has antifungal and bacterial activity.

Specification

Synonyms (1R)-13-Amino-11-chloro-1alpha,4beta-dimethoxy-12-methyl-3beta,15,16-trihydroxy-3,4,8abeta,13-tetrahydro-1H-xantheno[4',3',2':4,5][1,3]benzodioxino[7,6-g]isoquinoline-14,17(2H,9H)-dione
IUPAC Name (13R,21R,22R,24R)-6-amino-8-chloro-3,22,28-trihydroxy-21,24-dimethoxy-7-methyl-14,16,19-trioxa-6-azaheptacyclo[15.11.1.02,11.04,9.013,29.018,27.020,25]nonacosa-1(29),2,4(9),7,10,17,20(25),27-octaene-5,26-dione
Canonical SMILES CC1=C(C2=C(C(=C3C(=C2)CC4C5=C3C(=C6C(=C5OCO4)OC7=C(C6=O)C(CC(C7OC)O)OC)O)O)C(=O)N1N)Cl
InChI InChI=1S/C28H25ClN2O10/c1-8-20(29)10-4-9-5-13-16-18(14(9)21(33)15(10)28(36)31(8)30)23(35)19-22(34)17-12(37-2)6-11(32)24(38-3)26(17)41-27(19)25(16)40-7-39-13/h4,11-13,24,32-33,35H,5-7,30H2,1-3H3/t11-,12-,13-,24-/m1/s1
InChI Key RMBAWLJPGJDEJW-RBHLGUSVSA-N

Properties

Antibiotic Activity Spectrum fungi; Gram-positive bacteria; Gram-negative bacteria
Melting Point 276-278°C

Reference Reading

1. Actinoplanones C, D, E, F and G, new cytotoxic polycyclic xanthones from Actinoplanes sp
K Kobayashi, C Nishino, J Ohya, S Sato, T Mikawa, Y Shiobara, M Kodama J Antibiot (Tokyo). 1988 Jun;41(6):741-50. doi: 10.7164/antibiotics.41.741.
Our previous finding of strong cytotoxic polycyclic xanthones, actinoplanones A (1) and B (2), in the culture broth of Actinoplanes sp. R-304 stimulated us to isolate further five new cytotoxic polycyclic xanthones which were named actinoplanones C (3), D (4), E (5), F (6) and G (7) from the broth. Actinoplanones C (3) and G (7) showed very strong cytotoxicity against HeLa cells at less than 0.00004 microgram/ml dosage (IC50). The structures of 3-7 were varieties of 1 for the N-2 and C-4 substituents. All or several actinoplanones showed strong antimicrobial activities against bacteria and the rice blast fungus. Actinoplanone A (1) was tested for cytotoxicity against various tumor cells and for inhibitory effect on HeLa cell macromolecular synthesis, and 1 exhibited strong cytotoxicity against the cells and inhibitory action on DNA synthesis.
2. Actinoplanones A and B, new cytotoxic polycyclic xanthones from Actinoplanes sp
K Kobayashi, C Nishino, J Ohya, S Sato, T Mikawa, Y Shiobara, M Kodama J Antibiot (Tokyo). 1988 Apr;41(4):502-11. doi: 10.7164/antibiotics.41.502.
Two new cytotoxic polycyclic xanthones, actinoplanones A (1) and B (2) were isolated from the culture broth of Actinoplanes sp. R-304 by monitoring their bioactivity against HeLa cells. Compound 1 was extremely cytotoxic (IC50 0.00004 micrograms/ml) against HeLa cells. The structures of 1 and 2 were established mainly by analyses of 2D heteronuclear correlation NMR experiments. The absolute configurations of the asymmetric carbons of the compounds have been assigned to be 9R, 24S, 25R and 27S by circular dichroism spectra and NMR analysis using chiral derivatives (esters of alpha-methoxy-alpha-(trifluoromethyl)acetic acid).

Bio Calculators

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L

* 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
g/mol
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