Complex sentence: Under the context of the Habsburg Philippine Dynasty which ruled all of its empire then, the first occupiers, an expedition sent by the Dutch merchant Balthazar de Moucheron, occupied the island from August to October 1598 and again in a second expedition in 1600.
Split into simpler sentences: Under the context of the Habsburg Philippine Dynasty which ruled all of its empire. The first occupiers of the Island were the Dutch, an expedition sent by the Dutch merchant Balthazar de Moucheron, occupied the island from August to October 1598 and again a second Dutch expedition was sent in 1600.