The benchmark BSE Sensex found itself on a sticky wicket on Monday, which fell a huge 551 points to 27,561.38, an over 5-week low, amid fears over stricter norms on participatory notes (PNs) and a Chinese stock rout.
Nifty met with the same fate, down 161 points.
PNs are a popular offshore derivative instrument used by overseas investors to invest in Indian stocks.
Other Asian markets did no better, which ended in the red due to worries that China is headed for a sharp slowdown despite the government's efforts to revive it. The Shanghai Composite plunged as much as over 8 per cent.
Further weakness in the rupee against the dollar made things worse.
Starting lower, the 30-share gauge broke below the crucial 28,000-level before ending at 27,561.38, down 550.93 points, or 1.96 per cent, its biggest single-day fall since June 2.
The NSE Nifty slipped below the 8,400-mark to settle at 8,361, down 160.55 points, or 1.88 per cent. Intra-day, it shuttled between 8,351.55 and 8,492.20.
Tata Steel lost most (5.17 per cent), followed by Hero MotoCorp.
Of the 30-share Sensex pack, 29 ended lower. Only Bajaj Auto gained.
Sectorally, shares of metal, capital goods, banking, power, realty, auto, oil and gas and IT all suffered losses.
Broader markets mid-cap and small-cap indices didn't escape the selling pressure, which closed lower 1.38 per cent and 1.07 per cent, respectively.
Globally, Hong Kong's Hang Seng closed 3.09 per cent lower while Japan's Nikkei slumped 0.95 per cent. European markets slid for the fifth day.