Isolation and Characterization of Cyclic C33 Botryococcenes and a Trimethylsqualene Isomer from Botryococcus braunii Race B.

Three cyclic C33 botryococcenes and one new trimethylsqualene isomer were isolated from the B race, Showa (Berkeley) strain of Botryococcus braunii, which is known to produce large amounts of isoprenoid hydrocarbons ranging in carbon number from 30 to 34. Their purity was determined by GC-MS, and structures were characterized by 1D and 2D NMR. One of these molecules, cyclic C33-1 botryococcene (5), has an unusual connection of a methylenecyclohexane ring to the molecule backbone not seen before in botryococcenes. This report further adds to our knowledge of the wide range of isoprenoid hydrocarbon structures produced by B. braunii.