Parallel ZIP drives specifically required an ECP parallel port in order to operate. In its heyday, the feature that distinguished ECP from EPP and SPP parallel ports was its use of DMA to do data transfers.
USB does not support DMA, so most USB parallel adapters don't either. You must find a parallel adapter that specifically cites ECP support in its specs. Emulating DMA over USB is hard (i.e. more expensive to implement), and this one is the only adapter I found from a cursory Google search that specifically states it supports ECP in the specs.
Additionally, Macs never supported parallel ports at all. Before Macs had USB, they used a proprietary serial port to do printing. So who knows if this thing will work on a Mac even with pass-thru to a VM. You may need an actual PC for this.
What kind of Mac do you have? Some 2008-2011 MacBook Pros had an ExpressCard slot. ExpressCard does support DMA natively, and there are tons of EC to Parallel adapters out there that are likely fully compliant with the ECP spec.