His family had lost a son and a daughter now.
( ( His family ) ( ( had ( ( lost ( ( ( a son ) and ) ( a daughter ) ) ) now ) ) . ) )
(ROOT (S (NP (PRP$ His) (NN family)) (VP (VBD had) (VP (VBN lost) (NP (NP (DT a) (NN son)) (CC and) (NP (DT a) (NN daughter))) (ADVP (RB now)))) (. .)))
The son and daughter had lost their father.
( ( The ( ( son and ) daughter ) ) ( ( had ( lost ( their father ) ) ) . ) )
(ROOT (S (NP (DT The) (NN son) (CC and) (NN daughter)) (VP (VBD had) (VP (VBN lost) (NP (PRP$ their) (NN father)))) (. .)))