Foreign investors' concerns over retrospective taxation continued to weigh on sentiments, traders said.
FIIs had sold shares worth Rs 1,506.86 crore yesterday, as per provisional data.
Sun Pharma was the top loser on 30-share Sensex by tumbling 8.86 per cent to Rs 961.60 after Japan's Daiichi Sankyo announced sale of its holding in the Indian firm.
Other pharma stocks, Cipla and Dr Reddy's fell by 0.94 per cent and 2.81 per cent, respectively, on the Sensex.
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A round of late selling in select bluechip stocks dragged Sensex down to touch low of 27,598.21 before closing at 27,676.04 points -- its weakest level since March 27 -- down 210.17 points or 0.75 per cent.
The gauge has now lost over 1,370 points in five sessions.
The NSE Nifty slipped below the 8,400-mark by falling 70.35 points or 0.83 per cent at 8,377.75. It shuttled between 8,469.35 and 8,352.70, intraday.
Moreover, the rupee which breached the crucial 63-mark to touch a low of 63.15 at the outset, rebounded by 16 paise to trade higher at 62.75 against the dollar (intra-session).
Sectorwise, the BSE healthcare index suffered the most by falling 3.24 per cent, followed by Auto at 1.31 per cent, FMCG by 1.17 per cent, Oil & Gas 1.08 per cent, Power 0.73 per cent, capital goods 0.48 per cent and realty by 0.37 per cent.
Globally, other Asian markets ended in positive zone, while European markets were trading higher in their opening trade.