The benchmark indices closed lower for the first time in last seven consecutive trading sessions, weighed down by banking, auto, power, PSU, capital goods, technology and metal stocks.
The NSE Nifty also cracked below the 8,900-mark.
The selling came in the face of start of March futures and options series in the derivatives segment, dealers said.
Despite opening higher, the 30-share Sensex stayed in the negative zone for the most part and touched a low of 28,791.19 as investors booked profits in recent gainers. The gauge settled down 80.09 points, or 0.28 per cent, at 28,812.88.
The 50-share NSE Nifty ended lower by 42.80 points, or 0.48 per cent, at 8,896.70, after touching a high of 8,951.80 and a low of 8,888.65.
The index was dragged down by losses, mainly in banking, auto, power, PSU, capital goods, falling by up to 1.39 per cent.
Axis Bank was the biggest loser, which plunged 3.56 per cent followed by PowerGrid 3.14 per cent and Bharti Airtel 2.83 per cent.
Other losers were ICICI Bank 1.97 per cent, Maruti Suzuki 1.38 per cent, L&T 1.20 per cent, Dr Reddy's 1.12 per cent and Tata Motors 1.02 per cent.
Intra-day, RIL rose over 6 per cent to a more than 7-1/2 year high, with its market valuation getting past the Rs 4 lakh crore mark.
Other gainers were HUL, Wipro, Lupin, Coal India, Infosys and TCS.
In the 30-share Sensex constituents, 23 ended lower and 7 higher.
However, broader markets showed the upward trend as small-cap rose 0.16 per cent and mid-cap indices edged up 0.01 per cent.
Globally, European stocks witnessed a mixed trend, taking a weak lead from Asian losses as investors waited for a speech to the Congress by Trump this week, traders said.
Asian markets mostly ended lower. Europe was trading mixed.
Disclaimer: No Business Standard Journalist was involved in creation of this content
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