The emergence of selling pressure towards the fag-end washed out early gains, with participants offloading stocks in mainly oil & gas, realty and information technology sectors.
However, buying interest was witnessed in select sectors such as telecommunication and fast-moving consumer goods.
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Besides, investors were keenly awaiting the outcome of the two-day Goods and Services Tax (GST) Council meet starting Thursday to finalise a four-tier tax structure.
Anand James, chief market strategist, Geojit BNP Paribas Financial Services, said: "Markets were not entirely bereft of domestic cues, with textile, pharma and services getting brief fillips. But with global markets still on uncertain footing ahead of US elections, Indian stocks fluctuated. Little respite is expected until at least next week... while consensus on GST rates, could also give a distraction for domestic markets."
After opening lower at 27,518.06, the Sensex recovered to the day's high of 27,600.7 on bargain-buying by participants, including domestic financial institutions. However, it again slipped into negative terrain to hit a low of 27,399.3 before settling 96.9 points, or 0.35 per cent, lower at 27,430.3 - its weakest closing since July 8, when it ended at 27,126.9.
The gauge had lost 414.3 points in the previous three days, tracking negative global cues.
The Nifty after shuttling between 8,476.15 and 8,537.65, concluded 29.05 points, or 0.34 per cent, down at 8,484.95.
Meanwhile, services sector activity in the country gathered pace in October. The Nikkei India Services Purchasing Managers' Index (PMI), which tracks services sector companies on a monthly basis, stood at 54.5 in October as against 52.0 in September.
Investor sentiment remained downbeat in anticipation of a possible win for Trump in US presidential poll, with markets globally could not cheer the US Fed decision to keep interest rate unchanged.
In the foreign markets, Asian stocks ended largely mixed with Hong Kong's Hang Seng falling 0.56 per cent, while Shanghai Composite Index moved up 0.84 per cent. Japanese financial markets were closed on Thursday for a public holiday.
Europe too was mixed in early deals with Frankfurt down 0.06 per cent, while London's FTSE and Paris rose 0.22 per cent each.