Quadrone

Quadrone

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Quadrone
Category Bioactive by-products
Catalog number BBF-04284
CAS 66550-08-1
Molecular Weight 248.32
Molecular Formula C15H20O3
Purity >98% by HPLC

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Description

It is an unusual sesquiterpene metabolite isolated from aspergillus terreus. It exhibits antitumor activity.

Specification

Related CAS 87480-01-1 ((+)-isomer)
Synonyms (-)-Quadrone; [3aS-(3aα,5aβ,6α,8aα,8bα)]-Octahydro-10,10-dimethyl-6,8b-ethano-8bH-cyclopenta[de]-2-benzopyran-1,4-dione; (3aS,5aR,6R,8aR,8bR)-octahydro-10,10-dimethyl-6,8b-ethano-8bH-cyclopenta[de]-2-benzopyran-1,4-dione
Storage Store at -20°C
IUPAC Name (1R,2R,5S,9R,12R)-13,13-dimethyl-7-oxatetracyclo[7.5.0.01,5.02,12]tetradecane-4,8-dione
Canonical SMILES CC1(CC23C4CCC1C2CC(=O)C3COC4=O)C
InChI InChI=1S/C15H20O3/c1-14(2)7-15-9-4-3-8(14)10(15)5-12(16)11(15)6-18-13(9)17/h8-11H,3-7H2,1-2H3/t8-,9+,10-,11+,15-/m1/s1
InChI Key BBIDMUQZCCGABN-DWJWARBKSA-N
Source Unidentified fungus

Properties

Appearance Colorless to Light Tan Residue
Antibiotic Activity Spectrum Neoplastics (Tumor)
Boiling Point 418.8±38.0°C (Predicted)
Melting Point 183-184°C
Density 1.21±0.1 g/cm3 (Predicted)
Solubility Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water

Reference Reading

1. Cytotoxic constituents of Aspergillus terreus from the rhizosphere of Opuntia versicolor of the Sonoran Desert
Zhongge Zhang, Hans D VanEtten, Louise M Canfield, A A Leslie Gunatilaka, Leland S Pierson 3rd, Donna Bigelow, Luke Whitesell, Thomas J Turbyville, E M Kithsiri Wijeratne J Nat Prod . 2003 Dec;66(12):1567-73. doi: 10.1021/np030266u.
A novel cyclopentenedione, asterredione (1), two new terrecyclic acid A derivatives, (+)-5(6)-dihydro-6-methoxyterrecyclic acid A (2) and (+)-5(6)-dihydro-6-hydroxyterrecyclic acid A (3), and five known compounds, (+)-terrecyclic acid A (4), (-)-quadrone (5), betulinan A (6), asterriquinone D (7), and asterriquinone C-1 (8), were isolated from Aspergillus terreus occurring in the rhizosphere of Opuntia versicolor, using bioassay-guided fractionation. Acid-catalyzed reaction of 2 under mild conditions afforded 4, whereas under harsh conditions 2 yielded 5 and (-)-isoquadrone (9). Catalytic hydrogenation and methylation of 4 afforded 5(6)-dihydro-terrecyclic acid A (10) and (+)-terrecyclic acid A methyl ester (11), respectively. The structures of 1-11 were elucidated by spectroscopic methods. All compounds were evaluated for cytotoxicity in a panel of three sentinel cancer cell lines, NCI-H460 (non-small cell lung cancer), MCF-7 (breast cancer), and SF-268 (CNS glioma), and were found to be moderately active. Cell cycle analysis of 2, 4, and 5 using the NCI-H460 cell line indicated that 4 is capable of disrupting the cell cycle through an apparent arrest to progression at the G(1) and G(2)/M phases in this p53 competent cell line. A pathway for the biosynthetic origin of asterredione (1) from asterriquinone D (7) is proposed.
2. Quadrone, a new antitumor substance produced by Aspergillus terreus. Production, isolation and properties
M A Espenshade, R L Ranieri, G J Calton J Antibiot (Tokyo) . 1978 Jan;31(1):38-42. doi: 10.7164/antibiotics.31.38.
A new antitumor compound named quadrone was isolated from the culture broth of Aspergillus terreus NRRL 11,156. Quadrone was active against KB cells in vitro, but died not possess antimicrobial activity.
3. Determination of the absolute configurations of natural products via density functional theory calculations of optical rotation, electronic circular dichroism, and vibrational circular dichroism: the cytotoxic sesquiterpene natural products quadrone, suberosenone, suberosanone, and suberosenol A acetate
P J Stephens, F J Devlin, A B Smith 3rd, D M McCann J Nat Prod . 2006 Jul;69(7):1055-64. doi: 10.1021/np060112p.
The determination of the absolute configurations (ACs) of chiral molecules using the chiroptical techniques of optical rotation (OR), electronic circular dichroism (ECD), and vibrational circular dichroism (VCD) has been revolutionized by the development of density functional theory (DFT) methods for the prediction of these properties. Here, we demonstrate the significance of these advances for the stereochemical characterization of natural products. Time-dependent DFT (TDDFT) calculations of the specific rotations, [alpha](D), of four cytotoxic natural products, quadrone (1), suberosenone (2), suberosanone (3), and suberosenol A acetate (4), are used to assign their ACs. TDDFT calculations of the ECD of 1 are used to assign its AC. The VCD spectrum of 1 is reported and also used, together with DFT calculations, to assign its AC. The ACs of 1 derived from its [alpha](D), ECD, and VCD are identical and in agreement with the AC previously determined via total synthesis. The previously undetermined ACs of 2-4, derived from their [alpha](D) values, have absolute configurations of their tricyclic cores identical to that of 1. Further studies of the ACs of these molecules using ECD and, especially, VCD are recommended to establish more definitively this finding. Our studies of the OR, ECD, and VCD of quadrone are the first to utilize DFT calculations of all three properties for the determination of the AC of a chiral natural product molecule.

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