The initial range-bound momentum driven by short-covering in view of August derivative expiry led to key indices ruling in the positive terrain till afternoon.
Mid-afternoon trade saw the market wobbled as jittery investors bridled by caution ahead of US Federal Reserve Chair Yellen's speech tomorrow, while lower European opening and lack of direction led the index succumb to selling pressure.
This was the biggest single-day fall for the benchmark index since August 10 when it had fallen by 310 points.
The broader NSE Nifty dipped below the 8,600-mark.
In the August series, the Sensex plunged by 372.71 points, or 1.32 per cent and NSE Nifty by 74.10 points, or 0.85 per cent.
teck, IT, consumer durables, auto and realty stocks falling up to 1.43 per cent.
The index had gained 77.99 points in the previous two sessions.
The broader Nifty also declined by 58.10 points, or 0.67 per cent, to close at 8,592.20, after hovering between 8,683.05 and 8,583.65.
Market heavyweights like Adani Ports plunged 3.02 per cent, Wipro 2.84 per cent, Tata Steel 2.04 per cent, Infosys 1.99 per cent, HDFC 1.93 per cent, Bharti Airtel 1.83 per cent, SBI 1.81 per cent, NTPC 1.58 per cent and M&M 1.46 per cent.
Meanwhile, foreign portfolio investors (FPIs) sold shares worth a net Rs 39.28 crore yesterday.
In the 30-share Sensex constituents, 25 ended lower and 5 higher.
The BSE metal index suffered the most by losing 1.43 per cent, followed by teck (1.36 per cent), IT (1.28 per cent), consumer durables (0.83 per cent), auto (0.60 per cent), realty (0.58 per cent), capital goods (0.54 per cent), power (0.43 per cent), PSU (0.41 per cent and Bank (0.33 pc).
Profit-booking by retail investors dragged down mid-cap and small-cap indices by 0.35 per cent and 0.11 per cent, respectively.
Other indices in China and Japan fell by up to 0.57 per cent while Hong Kong's Hang Seng moved up by 0.03 per cent.
European markets were also trading lower as key indices in France, Germany and the UK fell up to 0.79 per cent.
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