1433 N. Phillip Serm. in A. G. Little Franciscan Papers, Lists, & Documents (1943) 251 (MED) Prima littera est A, que denotat his [sc. Jesus's] angussynge and his noye.

1521 St. Werburge Prol. O cruell deth..Thou causest wo, languor, and anguissyng.

a1617 S. Hieron Penance for Sinne in Wks. (1620) II. 204 This renting of the heart, and anguishing of the bones.

1646 J. Goodwin Twelve Cautions 6 Gratifying, inriching the strong, and those that think they know all things, to the grieving, anguishing, afflicting of those that are weak.

1730 Dr. Allen's Synopsis Medicinæ I. vi. 275 They have also cold Sweats, Anxieties about the Heart, Faintings, Anguishings, Despair, and the like.

1776 A. Bayly Apocrypha Wisd. v. 3 They repenting, and groaning for anguishing of spirit.

1867 C. Elder My Gift 26 I lost the weary anguishing Of the long Winter's pains.

1914 Outlook 16 Sept. 151 Will history still repeat the sanguine past, With all its trail of ruthless anguishings?

1983 Univ. Coll. London Bull. May 1/1 After much anguishing, it has been decided that the main entrance to the College in Gower Street should be closed.

2003 J. Weeks in J. Weeks et al. Sexualities & Society x. 124 Such anguishings have characterized the sexual politics of the past thirty years.

?1566 J. Phillip Commodye Pacient & Meeke Grissill sig. Hiii Hast thou suffred for mee, such anguishing tribulacion, God graunt I may requite the, with condinge venerasion.

1595 T. W. tr. P. Leroy et al. Pleasant Satyre 175 Ye will cause me to dye quickly, rather then to let me languish a long while in these anguishing and grieuous miseries.

1648 J. Sparrow tr. J. Böhme Descr. Three Princ. iii. 12 An anguishing dark vale..where there could be no mobility, nor any light or life.

1665 G. Harvey Disc. Plague 3 A perpetual restlesness, with anguishing jactitations, or throwing ones self from one part of the bed to the other.

1742 W. Law Appeal to All that Doubt iii. 194 The anguishing Terrors of thy Soul.

1760 R. Clarke Second Warning to World 12 The compressing, drawing, and anguishing Operation of God, which is the Way through Tribulation..into the Kingdom of Heaven.

1810 T. Campbell Poems I. 128 Heaven's mercy relieving Each anguishing wound.

1864 W. W. Brown Clotelle xiv. 43 Deep in her heart's ambrosial cells was the most anguishing distress.

1968 U. Molinaro tr. H. Hesse Narcissus & Goldmund v. 58 He did feel strongly, often with anguishing clarity, that his destiny was shaping itself.

1997 High Country News 17 Feb. 9/2 For me, it is terribly anguishing.

a1642 W. Crompton Wilderness of Trouble (1679) 161 The anguishing Spirits of a poor Penitent..are much moved and affrighted.

1770 H. Brooke Fool of Quality (Dublin ed.) V. 205 The Marchioness, with an anguishing Heart, but amazing Resolution, issued her Orders with a Presence of Mind that seemed serene in the Midst of Tempest.

1896 C. F. Johnson Angling Lakes Northern Illinois x. 78 The surprised look he wore when the pie struck him was followed by..horribly anguishing howls.

1965 E. Dahlberg Reasons of Heart 98 The bloody, anguishing feet of the Christs in the Spanish cathedrals.

2010 P. J. Curtis Searcher of Hearts 234 She dropped to the floor with a wailing, anguishing plea.