The support, however, came in from software firm Infosys, which surged 11 per cent on better-than-expected Q1 earning.
Brokers said sentiments turned somewhat weak on investors concerns over the fate of land and GST bills to be presented in Parliament.
The 30-share BSE barometer fell by 237.98 points or 0.84 per cent to 28,182.14, with all the sectoral indices, except IT and teck, ending in negative zone.
On similar lines, the NSE Nifty failed to maintain the 8,600-mark and ended 74.00 points or 0.86 per cent down at 8,529.45.
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Stocks of Sun Pharma and Infosys remained at the centre of brisk activity during the session.
Shares of the pharma firm suffered the most among Sensex stocks by plunging 14.95 per cent -- its biggest single-day fall -- to Rs 805.30 after the drug major said it expects to take a hit on profit for the fiscal due to charges related to the integration with Ranbaxy Laboratories.
Infosys' bullish guidance propped up other IT stocks including Wipro (1.69 per cent), HCL Technologies (2.91 per cent)) and Tech Mahindra (1.69 per cent).
Sectorwise, healthcare index suffered the most by losing 5.93 per cent, followed by realty 2.16 per cent, oil&gas 1.74 per cent, FMCG 1.67 per cent and banking 1.66 per cent.
Bucking the trend, IT index rose 4.57 per cent, while Teck index gained 3.82 per cent.
Globally, other Asian markets ended higher, while European markets were mixed in their early trade.