I think the difficulty with identifying 'the messiah' with the 'serpent' is paralleled by other difficulties equating the messiah (= 358) with other words that = 358. The winepress for instance. Jesus is the clearly likened to Dionysus the god of the grape and wine. But Christ is the winepress the one who initiates the 'crushing' or 'bleeding' of Jesus. Of course the distinction between 'Jesus' and 'Christ' was smoothed over in the third century. Jesus became the Christ. But as Irenaeus famously noted the Gospel of Mark was read in a manner in which Christ and Jesus were not only two different figures but - tellingly - the gospel was understood to conclude with Christ watching Jesus suffer 'impassably' - "Those, again, who separate Jesus from Christ, alleging that Christ remained impassible, but that it was Jesus who suffered, preferring the Gospel by Mark, if they read it with a love of truth, may have their errors rectified."
To this end it makes perfect sense to see Jesus as the wine but Christ (= 358) as the winepress (= 358) as we see in Tertullian:
In order, however, that you may discover how anciently wine is used as a figure for blood, turn to Isaiah, who asks, "Who is this that cometh from Edom, from Bosor with garments dyed in red, so glorious in His apparel, in the greatness of his might? Why are thy garments red, and thy raiment as his who cometh from the treading of the full winepress?" The prophetic Spirit contemplates the Lord as if He were already on His way to His passion, clad in His fleshly nature; and as He was to suffer therein, He represents the bleeding condition of His flesh under the metaphor of garments dyed in red, as if reddened in the treading and crushing process of the wine-press, from which the labourers descend reddened with the wine-juice, like men stained in blood. Much more clearly still does the book of Genesis foretell this, when (in the blessing of Judah, out of whose tribe Christ was to come according to the flesh) it even then delineated Christ in the person of that patriarch, saying, "He washed His garments in wine, and His clothes in the blood of grapes"--in His garments and clothes the prophecy pointed out his flesh, and His blood in the wine. Thus did He now consecrate His blood in wine, who then (by the patriarch) used the figure of wine to describe His blood.
By the time of Augustine, who wrote in Latin, the gematria was lost perhaps and the 'spiritual meaning' of the winepress was transferred to the 'church.' But I think we can still see the strangeness inherent in likening Christ to a winepress:
let us recall to mind what takes place in these visible winepresses, and see how this takes place spiritually in the Church. The grape hangs on the vines, and the olive on its trees. For it is for these two fruits that presses are usually made ready; and as long as they hang on their boughs, they seem to enjoy free air; and neither is the grape wine, nor the olive oil, before they are pressed. Thus it is with men whom God predestined before the world to be conformed to the image of His only-begotten Son, Romans 8:29 who has been first and especially pressed in His Passion, as the great Cluster. Men of this kind, therefore, before they draw near to the service of God, enjoy in the world a kind of delicious liberty, like hanging grapes or olives: but as it is said, My son, when you draw near to the service of God, stand in judgment and fear, and make your soul ready for temptation: Sirach 2:1 so each, as he draws near to the service of God, finds that he has come to the winepress; he shall undergo tribulation, shall be crushed, shall be pressed, not that he may perish in this world, but that he may flow down into the storehouses of God. He has the coverings of carnal desires stripped off from him, like grape-skins: for this has taken place in him in carnal desires, of which the Apostle speaks, Put ye off the old man, and put on the new man. All this is not done but by pressure: therefore the Churches of God of this time are called winepresses.
What I am suggesting is that in the same way as snake = 358 = messiah leads to strangeness (i.e. likening Christ to the snake) likening Christ to the winepress (against winepress = 358 = messiah) essentially puts Christ in the role of killing Jesus, trampling him into wine, and indeed all of the martyrs that followed him.
But clearly 'the winepress' and the serpent likely made Christ seem a 'hostile' figure in the sense that he caused torment for mankind. Note the art:
The symbolism of grapes-wine-blood is frequently found in early Christian and medieval art ; the Mystic Wine Press further develops the symbolism by depicting Christ treading on grapes or being crushed in a winepress out of which his blood flows. The image is often found in illustrated manuscripts of the *Apocalypse and became very popular in late medieval stained glass. Christ may be shown kneeling before the wine press or standing in it and treading on grapes (the machinery of the press may be shown as an upright *cross behind Christ), or Christ may be shown horizontally, actually squeezed in the press. Vats of his blood may be collected by kneeling and praying figures.
Note Christ is the winepress crushing the grapes which are - paradoxically Jesus or the martyrs that followed him. The paradox that not Jesus is both the Christ who treads and the Jesus who suffers was not there for the first readers of the Gospel of Mark (according to Irenaeus). Jesus suffers while Christ watches impassably and possibly approvingly.
Christ wants Jesus to suffer. Thus in a sense his role is perhaps likened to that of the serpent in the garden of Eden.