Investors were cautious ahead of October series expiry in the derivatives segment on Thursday, brokers said.
The 30-share barometer, which had lost 108.85 points yesterday, fell further by 106.83 points or 0.39 per cent to 27,255.13.
All the sectoral indices led by healthcare, realty and banking were trading in the negative zone with losses up to 0.39 per cent.
Also, the NSE Nifty declined by 27.40 points or 0.33 per cent to 8,233.15.
Housing finance major HDFC was down over 2 per cent after it posted moderate growth in profit for the second quarter of 2015-16 fiscal.
ITC, Coal India and Tata Steel were also down up to 1 per cent, dragging the broader index into negative zone.
On the other hand, auto stocks Maruti Suzuki, Bajaj Auto and Mahindra and Mahindra posted gains of up to 1 per cent.
Brokers said offloading of positions by participants, tracking a weak trend at the other Asian markets as investors await the start of a US Federal Reserve meeting later in the day influenced sentiments.
The Dow Jones Industrial Average ended 0.13 per cent lower in yesterday's trade.
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