John Fredriksen has put $100m of his own money into a private placement carried out by Flex LNG, but has seen his holding reduced.
The Oslo-listed company's billionaire backer bought 57.64m shares at NOK 14.25 each for a NOK 821m ($100m) outlay.
Fredriksen's private Geveran Trading now has 44.6% of Flex, down from 49.91%.
Geveran is also party to total return swap agreements with underlying exposure to 8.25m shares.
The $300m placement was part of a deal that saw Flex agree to buy five LNG carrier newbuildings from Fredriksen.
It is paying $180m for each of the five vessels at DSME and Hyundai Samho Heavy Industries.
An extra $6m will be paid on each of the three DSME ships for the addition of full reliquifaction systems.
The deal means Flex will have more than doubled its fleet in around six months and will take its market capitalisation close to the critical $1bn level.
