Anna Anachoutlou (Greek: Ἄννα Ἀναχουτλοῦ), (died 1342) was Empress of Trebizond from July 17, 1341 to September 4, 1342. Anna was the elder daughter of Emperor Alexios II of Trebizond and his Georgian wife, Djiadjak Jaqeli.
Anna's only notable act, before becoming empress, was to endow a small monastery in Jerusalem dedicated to St. Euthymios. This monastery is documented in a single document, the Testament of a monk Gerasimos, dated 18 November 1344. When she first made this endowment is not known, but Anna had taken monastic vows during the reign of Irene Palaiologina.
Trapezuntine aristocrats persuaded her to abandon the cloister and seize the crown; she was proclaimed empress in Lazia and her supporters escorted her to Trebizond. Wherever she went, according to William Miller, the people joined the revolt and when Anna, reinforced by the troops sent by the Georgian king George V, arrived at the walls of Trebizond on July 17, 1341 she was admitted without resistance and acclaimed empress, while Irene was deposed.
Three weeks later three Byzantine galleys arrived at Trebizond with troops under the leaders of the Scholarioi faction, Niketas Scholares and Gregory Meitzomates. With them came Anna's uncle Michael, who was the husband chosen for the now deposed Irene by the regents of her half-brother John V Palaiologos. The Metropolitan Akakios and some of the nobility seemed to accept Michael as the legitimate ruler of Trebizond. Not wishing to be governed by a forceful man of mature years, they promptly imprisoned Michael in the palace, while Anna's Lazic troops dispersed the crowd supporting Michael and plundered his ships.
The next day Michael was sent off in exile to Oinaion where he was guarded by megas doux John the Eunuch, and Anna's predecessor Irene was sent to Constantinople on a western ship. Although Anna was now on the throne, William Miller points out that the aristocrats who put her there -- "the senatorial party"—had the ascendancy: "Two or three of the senators governed behind the scenes, while Anna Comnena sat on the throne, the people insulted the ruling clique and plotted another insurrection, and the Turkomans had seized the opportunity of these internal troubles to make another, providentially fruitless, raid."
Niketas and Gregory, the leaders of the Scholarioi, returned to Constantinople with Constantine Doranites and others, and convinced the government to give them Michael's young son, John, as a claimant to the throne of Trebizond. In September 1342, with the help of the Genoese, John's small fleet of five galleys made their way to Trebizond. Although Anna and her courtiers prepared to defend themselves, they were sabotaged by a popular revolt. John's supporters took control of the city on September 4, 1342 and crowned John III emperor. The Scholarioi executed many of their rivals, and Anna was strangled soon after her deposition.