Bilobalide

( 3aS, 5aR, 8aS, 9R, 10aR )-9- tert-Butyl- 8, 9 - dihydroxydihydro -9H- furo [2,3 -b] furo [3 ', 2': 2,3] cyclopenta [ 1, 2-c ] furan -2, 4,7 (3H, 8H ) -trione

Colorless and odorless crystals

Fixed

280-285 ° C

Insoluble in water

Template: Infobox chemical / molecular formula search available

Bilobalide is a tetracylisches sesquiterpene with three γ -lactone rings and a tert -butyl group. The tert- butyl group, has not been detected in other natural products. It is in its constitution closely related to the ginkgolides.

Biosynthesis

Nakanishi was able to show that the ginkgo tree incorporating radioactive 14C from the labeled compounds sodium acetate, mevalonic acid and methionine in ginkgolides. This completes the proof of terpenoid origin of polycyclic hydroxy lactones from Ginkgo biloba was provided. The exact biosynthesis has not been elucidated in detail.

Occurrence

For the first time isolated from Major Ginkgo biloba extracts a hydroxylactone unknown constitution. Weinges et al. isolated in 1969 also this hydroxylactone called bilobalide, from fresh leaves of the ginkgo tree. Major, Nakanishi and Weinges clarified together on its structure. Bilobalide is present in amounts of 0.02-0.06 % in the leaves, contained in small quantities in the wood parts of the tree.

Use

Bilobalide is an ingredient of Ginkgo preparation Tebonin. Tebonin 's terms of sales, the world's best selling herbal medicines.