This was the fourth consecutive session of downtrend in the 30-share index, which has now lost around 1,160 points since crossing 29,000-levels last Monday.
Concerns by foreign investors over retrospective taxation weighed on trading sentiments, traders said.
Moreover, lower closing in other Asian markets combined with India's exports falling 21 per cent in March to a six-year low also bogged markets.
The 50-share NSE Nifty end below 8,500-mark by losing 157.90 points or 1.83 per cent to close at 8,448.10, while moving between 8,619.95 and 8,422.75 intraday.
More From This Section
In a report, global brokerage firm UBS also cut its Nifty target for December this year to 9,200 from 9,600 amid slower-than-expected recovery in growth.
The bullish trend in Indian markets over the last one year was mainly driven by "positive surprise on rate cycle, lower oil prices and reforms news-flow" but hereon, actual earnings and macro data points would matter increasingly, UBS said
The 30-share Sensex opened up more than than 95 points, but on emergence of profit-booking in realty, FMCG and IT it dipped to the session's low of 27,802.37. The barometer finally settled the day lower by 555.89 points or 1.95 per cent at 27,886.21.
RIL was the worst performer on Sensex and Nifty with 4.46 per cent plunge in its share price. It posted 8.5 per cent fourth quarter profit growth after market hours last Friday.
Out of 30 Sensex stocks, 28 ended in negative zone, while only Sun pharma and ICICI Bank managed to gain.
Sectorwise, the BSE realty index suffered the most by losing 2.78 per cent, followed by FMCG 2.71 per cent, capital goods down 2.17 per cent, IT 2.08 per cent, power 2.04 per cent and oil and gas 1.91 per cent.
The BSE smallcap index fell 2.17 per cent while the midcap index ended 2.02 per cent lower.