ABSTRACT
Herein we describe a concise assembly of the central 1,6-dioxaspiro[4.4]nonane core of cephalosporolides E/F by employing a Pd-mediated alkynediol cycloisomerization and their total synthesis. On the basis of spectroscopic data and optical rotation values, the absolute configurations of cephalosporolides E/F were proposed.
Subject(s)
Alkenes/chemistry , Palladium/chemistry , Spiro Compounds/chemical synthesis , Molecular Structure , Spiro Compounds/chemistryABSTRACT
ETHNOPHARMACOLOGICAL RELEVANCE: Eulophia nuda L. (Orchidaceae) is a medicinally important terrestrial orchid used for the treatment of tumours and various health problems by the local healers throughout the Western Ghats region in Maharashtra (India). AIM OF THE STUDY: To isolate the active molecule from Eulophia nuda and to study its cytotoxic potential against human cancer cells. MATERIALS AND METHODS: The crude methanolic extract of Eulophia nuda tubers was fractionated by stepwise gradient of the solvents-chloroform-methanol to isolate the pure compound. Isolated pure compound was assessed for its cytotoxic potential against human breast cancer cell lines, MCF-7 and MDA-MB-231 using MTT assay. Structure elucidation of the isolated active compound was carried out by extensive spectroscopic analysis including (1)H NMR, (13)C NMR, NOESY, COSY, LC-MS and IR. RESULTS: The isolated active molecule was identified as phenanthrene derivative 9,10-dihydro-2,5-dimethoxyphenanthrene-1,7-diol. This compound showed good antiproliferative activity against human breast cancer cell lines MCF-7 (91%) and MDA-MB-231 (85%) at 1000 microg/ml concentration. CONCLUSION: 9,10-Dihydro-2,5-dimethoxyphenanthrene-1,7-diol from Eulophia nuda tubers showed good growth suppressive effect against human cancer cell lines MCF-7 and MDA-MB-231 making it a potential biomolecule against human cancer.