Usage: 5 forms in 5 verses
Form Translated As     In Verse(s)
λυπηρόσ a distressing LXX.Prov.15.1
λυπηρόν it was distressing LXX.Gen.34.7
λυπηρού a distressed LXX.Prov.17.22
λυπηράν a distressed LXX.Prov.26.23
λυπηρά distress LXX.Prov.14.10

Liddell-Scott-Jones

λυπηρός (lupēros) distressing G:A

λυπηρός-ηρός, , όν,

__I of things, painful, distressing, [Refs 5th c.BC+]; τί σοι τοῦτ᾽ ἐστὶ λ. κλύει; [Refs 5th c.BC+]; ἀζημίους μέν, λ. δὲ ἀχθηδόνας causing pain, [Refs 5th c.BC+]; opposed to τὸ ἡδύ, [Refs 5th c.BC+]
__II of persons,
__II.1 causing sorrow, λυπηρὸς ἡμῖν τούσδ᾽ ἂν ἐκλίποι δόμους [Refs 5th c.BC+]
__II.2 causing pain, troublesome, λ. κλύειν [Refs 5th c.BC+]; of those who are objects of jealousy and envy, [Refs]
__III of persons, sad, ={ἄθυμος}, [LXX+5th c.AD+]
__IV adverb -ρῶς painfully, so as to cause pain, [Refs 5th c.BC+]; λ. δ᾽ ἔχει, εἰ.. it is painful that.., [Refs 5th c.BC+]
__IV.2 with pain, so as to feel or show pain, λ. φέρειν τι [Refs 5th c.BC+]

LSJ Scripture Refs: LXX.Prov.17.22