The gauge after opening a tad higher quickly slipped into negative terrain following profit-booking in recent gainers and touched a low of 27,216.40.
However, it staged a comeback temporarily to hit a high of 27,432.07 during mid-session.
Soon, profit-booking resurfaced which ate into the gains and took the benchmark back to the negative zone, which closed down 58.09 points, or 0.21 per cent, at 27,306.83. The index had risen over 585 points in the past three sessions.
In the previous three sessions, the markets rose on the back of continued foreign fund inflows and a mixed bag of earnings by blue-chips so far.
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Of the 30-pack Sensex, 23 ended with losses and 7 finished higher.
Investors after remaining buyers in the past three sessions opted to book profit in heavy-weight stocks, brokers said.
The rupee depreciated 16 paise to 64.96 against the American currency (intra-day), which too weighed, they said, adding that a mixed closing at other Asian markets and a lower opening in Europe influenced sentiment.
Metal company stocks bore the brunt during the session with Vedanta Ltd, Tata Steel and Hindalco falling up to 6.42 per cent.
Other losers which also contributed to the fall include ONGC, Cipla, M&M, RIL, Bajaj Auto and Sun Pharma.
TCS, Maruti Suzuki, Tata Motors, Infosys and NTPC bucked the trend, thus cushioning the impact.
Sector-wise, the BSE Metal index suffered the most by losing 1.80 per cent, followed by oil & gas, realty, healthcare, PSU and FMCG.
Meanwhile, foreign portfolio investors (FPIs) bought shares worth a net Rs 898.23 crore yesterday, as per provisional data released by stock exchanges.