Concerns about muted September earnings, profit-booking by participants after recent gains and sustained capital outflows by foreign funds dampened stocks, brokers said.
Weighed down by heavy selling in blue-chips, the BSE Sensex stayed in the negative zone for the most part of the session and closed down 381.95 points, or 1.48 per cent, at 25,482.52 -- a level last seen on September 8.
"A weakening rupee against the American currency also negatively impacted market sentiment," said Manoj Choraria, a Delhi-based NSE stock broker.
At the forex market, the rupee was trading 25 paise lower at 66.28 a dollar (intra-day).
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Hindalco suffered the most by plunging 5.07 per cent.
Technology stocks continued to remain under pressure for yet another session, with the worst hit BSE IT index down 2.29 per cent.
Bucking the trend, Coal India surged 0.83 per cent after the Cabinet approved sale of 10 per cent in the company.
The broader markets too displayed a weak trend as investors trimmed their positions. The BSE small-cap index edged lower by 0.71 per cent while mid-cap shed 0.68 per cent.
There were heightened fears of selling as foreign investors net sold shares worth Rs 492.45 crore yesterday, provisional data showed.
On the global front, Asian markets ended lower, with Shanghai shares falling by 1.01 per cent. Europe was also trading down in early trade as investors stayed cautious before the release of Fed minutes.