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Three types of cytotoxic natural caged-scaffolds: pure enantiomers or partial racemates.
J Nat Prod. 2014 Jul 25; 77(7):1562-71.JN

Abstract

Two rare new natural products, the neocaged-xanthone pruniflorone T (1) and the rearranged caged-xanthone pruniflorone U (3), and the known caged-xanthone cochinchinone C (2) were isolated from the roots of Cratoxylum formosum ssp. pruniflorum. The unique structures of 1-3 were determined by analysis of NMR and X-ray diffraction data. The X-ray data of 1-3 revealed that they all exist with both enantiomers in their crystal packing. Separation of 1-3 by chiral HPLC led to the isolation of three pairs of enantiomers, (-)-1/(+)-1, (-)-2/(+)-2, and (-)-3/(+)-3, and their absolute configurations were determined by analysis of single-crystal X-ray diffraction and ECD spectroscopic data. A 1:1 mixture of 1 and 3 showed potent in vitro cytotoxicity against an MCF-7 human breast cancer cell line with an IC50 value of 0.11 μg/mL.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Boonnak N
Faculty of Traditional Thai Medicine, Prince of Songkla University , Hat-Yai, Songkhla 90112, Thailand.
Chantrapromma S
No affiliation info available
Fun HK
No affiliation info available
Yuenyongsawad S
No affiliation info available
Patrick BO
No affiliation info available
Maneerat W
No affiliation info available
Williams DE
No affiliation info available
Andersen RJ
No affiliation info available

MeSH

Antineoplastic Agents, PhytogenicCamptothecinChromatography, High Pressure LiquidClusiaceaeCrystallography, X-RayDrug Screening Assays, AntitumorFemaleHumansInhibitory Concentration 50Molecular ConformationMolecular StructureNuclear Magnetic Resonance, BiomolecularPlant RootsStereoisomerismThailandXanthones

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24940955

Citation

Boonnak, Nawong, et al. "Three Types of Cytotoxic Natural Caged-scaffolds: Pure Enantiomers or Partial Racemates." Journal of Natural Products, vol. 77, no. 7, 2014, pp. 1562-71.
Boonnak N, Chantrapromma S, Fun HK, et al. Three types of cytotoxic natural caged-scaffolds: pure enantiomers or partial racemates. J Nat Prod. 2014;77(7):1562-71.
Boonnak, N., Chantrapromma, S., Fun, H. K., Yuenyongsawad, S., Patrick, B. O., Maneerat, W., Williams, D. E., & Andersen, R. J. (2014). Three types of cytotoxic natural caged-scaffolds: pure enantiomers or partial racemates. Journal of Natural Products, 77(7), 1562-71. https://doi.org/10.1021/np400996k
Boonnak N, et al. Three Types of Cytotoxic Natural Caged-scaffolds: Pure Enantiomers or Partial Racemates. J Nat Prod. 2014 Jul 25;77(7):1562-71. PubMed PMID: 24940955.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Three types of cytotoxic natural caged-scaffolds: pure enantiomers or partial racemates. AU - Boonnak,Nawong, AU - Chantrapromma,Suchada, AU - Fun,Hoong-Kun, AU - Yuenyongsawad,Supreeya, AU - Patrick,Brian O, AU - Maneerat,Wisanu, AU - Williams,David E, AU - Andersen,Raymond J, Y1 - 2014/06/18/ PY - 2014/6/19/entrez PY - 2014/6/19/pubmed PY - 2014/9/23/medline SP - 1562 EP - 71 JF - Journal of natural products JO - J Nat Prod VL - 77 IS - 7 N2 - Two rare new natural products, the neocaged-xanthone pruniflorone T (1) and the rearranged caged-xanthone pruniflorone U (3), and the known caged-xanthone cochinchinone C (2) were isolated from the roots of Cratoxylum formosum ssp. pruniflorum. The unique structures of 1-3 were determined by analysis of NMR and X-ray diffraction data. The X-ray data of 1-3 revealed that they all exist with both enantiomers in their crystal packing. Separation of 1-3 by chiral HPLC led to the isolation of three pairs of enantiomers, (-)-1/(+)-1, (-)-2/(+)-2, and (-)-3/(+)-3, and their absolute configurations were determined by analysis of single-crystal X-ray diffraction and ECD spectroscopic data. A 1:1 mixture of 1 and 3 showed potent in vitro cytotoxicity against an MCF-7 human breast cancer cell line with an IC50 value of 0.11 μg/mL. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/24940955/Three_types_of_cytotoxic_natural_caged_scaffolds:_pure_enantiomers_or_partial_racemates_ DB - PRIME DP - Unbound Medicine ER -