1)

(a)In the opinion of Rav Papa, Resh Lakish's query on Rebbi Akiva was from 'Lugin'. In the case where someone purchases a hundred Lugin of wine from Kutim on Friday afternoon, Rebbi Meir in a Beraisa, permits the purchaser to - rely on the Ma'asros that he declares before Shabbos, and to then drink the wine (leaving over sufficient to remove from it Terumah Gedolah and Ma'aser Rishon) after Shabbos).

(b)After declaring two Lugin Terumah Gedolah, ten, Ma'aser Rishon - he must declare nine, Ma'aser Sheini.

(c)Before drinking from the wine - he still needs to redeem the Ma'aser-Sheini on to a coin.

2)

(a)Rebbi Yehudah, Rebbi Yossi and Rebbi Shimon - forbid separating Ma'asros in this manner.

(b)The basis of their Machlokes is - whether we say Yesh B'reirah (Rebbi Meir [meaning that when the owner eventually separates T'rumos and Ma'asros, it works retroactively]) or not (Rebbi Yehudah, Rebbi Yossi and Rebbi Shimon).

(c)The Kashya on Rebbi Akiva in our Mishnah is that - assuming that Rebbi Akiva holds like the latter (majority) opinion, then he ought to have forbidden all the coins in the purse in the Seifa too (due to Ein B'reirah) see also Tosfos DH 'di'Tenan'.

(d)And we answer - by establishing the Seifa where the owner specifically declared 'Lo Yiftor Kis Zeh min ha'Hekdesh' (like Rebbi Yochanan answered earlier).