Isomeric kielcorins and dihydroxyxanthones: Synthesis, structure elucidation, and inhibitory activities of growth of human cancer cell lines and on the proliferation of human lymphocytes in vitro

• Type: Article in International Scientific Journal
• Date: 2002

Authors

Sousa, EP (Author) Other; Silva, AMS (Author) Other; Pinto, MMM (Author) FFUP; Pedro, MM (Author) Other; Cerqueira, FAM (Author) Other; Nascimento, MSJ (Author) FFUP

Journal

Title: Helvetica Chimica Acta

Vol. 85

Pages: 2862-2876

ISSN: 0018-019X

Publisher: Wiley-Blackwell

Indexing

ISI Proceedings

ISI Web of Knowledge - 43 Citations

Scopus - 43 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-000-R86

DOI: 10.1002/1522-2675(200209)85:9

Abstract (EN): The synthesis, structure elucidation, and biological activities of five isomeric xanthonolignoids. (+/-)-trans-kielcorin C, (+/-)-cis-kielcorin C, (+/-)-trans-kielcorin D, (+/-)-trans-isokielcorin D. and (+/-)-trans-kielcorin E, are reported. The synthetic approach is based on the oxidative coupling of coniferyl alcohol with an appropriate xanthone. The influence of different oxidizing agents was studied, and the best results were obtained with potassium hexacyanoferrate(III). The structure elucidation was achieved by 2D-NMR techniques such as COSY, HETCOR, HSQC, and HMBC. Long-range C,H connectivities were used to establish the orientation of the substituents on the 1,4-dioxine rings, while NOE experiments were used to determine the confil-urations of these rings. These xanthonolignoids. as well as (+/-)-trans-kielcorin, (+/-)-trans-kielcorin B, (+/-)-trans-isokielcorin B. and the xanthonic building blocks 3,4-. 1,2-, and 2.3-dihydroxy-9H-xanthen-9-ones. and 2,3-dihydroxy-4-methoxy-9H-xanthen-9-one. were evaluated for their in vitro effect on the growth of three human cancer cell lines, MCF-7 (breast), TK-10 (renal), and UACC-62 (melanoma), and on the proliferation of human lymphocytes.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 15