The barometer index hit a low below the psychological 28,000 mark at onset of trading session.
The market breadth indicating the overall health of the market was also weak.
The Sensex resumed lower at 27,857.20 and hovered in a range of 27,946.68 and 27,774.80 before quoting at 27,800.40 at 1105 hrs a loss of 292.39 points or 1.04 per cent.
The 50-share Nifty fell by 77.40 points or 0.91 per cent to 8,407.50 at 1105 hrs.
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Foreign portfolio investors (FPIs) bought shares worth a net Rs 356.29 crore last Friday, as per provisional data. While, Domestic institutional investors (DIIs) sold shares worth a net Rs 220.61 crore.
Asian stocks edged lower early today, as Greece voted against accepting further austerity, increasing the risk of the country's exit from the euro zone.
Greeks overwhelmingly voted against their international creditors' conditions for further bailout aid, in a result that could deepen the rift between Greece and the rest of Europe and push the country out of the Eurozone.