Bilobalide

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Structural formula
Structural formula of bilobalide
General
Surname Bilobalide
other names

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

Molecular formula C 15 H 18 O 8
Brief description

colorless and odorless crystals

External identifiers / databases
CAS number 33570-04-6
EC number 608-892-9
ECHA InfoCard 100.125.716
PubChem 73581
Wikidata Q418459
properties
Molar mass 326.31 g mol −1
Physical state

firmly

Melting point

> 300 ° C

solubility

soluble in organic solvents

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bilobalid is a tetracycline sesquiterpene with three γ- lactone rings and a tert. -Butyl group. The tert- butyl group has not yet been detected in other natural products . Its constitution is closely related to the ginkgolids .

biosynthesis

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

Occurrence

For the first time, Major isolated a hydroxylactone of unknown constitution from Ginkgo biloba extracts. Weinges et al. In 1969 they also isolated this hydroxylactone, called bilobalide, from fresh leaves of the ginkgo tree. Major, Nakanishi and Weinges together clarified its structure. Bilobalid is contained in the leaves in amounts of 0.02 to 0.06%, and in smaller amounts in the wooden parts of the tree.

use

Bilobalid is an ingredient in the ginkgo preparation tebonin , which - in terms of sales - is the world's best-selling herbal medicine.

Individual evidence

  1. a b c data sheet (-) - Bilobalid from Sigma-Aldrich , accessed on February 7, 2019 ( PDF ).
  2. Shmuel Yannai: Dictionary of Food Compounds with CD-ROM Additives, Flavors, and Ingredients . CRC Press, 2003, ISBN 978-1-4200-6845-0 , pp. 112 ( limited preview in Google Book search).
  3. Burkhard Fugmann: RÖMPP Lexikon Naturstoffe, 1st edition, 1997 . Georg Thieme Verlag, 2014, ISBN 3-13-179541-7 , p. 36 ( limited preview in Google Book search).
  4. K. Nakanishi et al .: J. Am. Chem. Soc. , 1971 , 93; P. 3546.
  5. ^ RT Major: The Ginkgo, the most ancient living tree . In: Science , 1967 ; 127; P. 1270. PMID 5341600 .
  6. Klaus Weinges, Wolfgang Bähr: Liebigs Ann. Chem. , 1969 ; Vol. 724, pp. 214-216.
  7. K. Nakanishi et al., RT Major et al., K. Weinges et al .: J. Am. Chem. Soc. , 1971 , 93; P. 3544.
  8. Klaus Weinges, Wolfgang Bähr: Liebigs Ann. Chem. , 1972 ; Vol. 759, pp. 158-172.
  9. Weinges, K., Hepp, M., Huber-Patz, U., Irngartinger, H .: Liebigs Ann. Chem. , 1987 , pp. 1079-1085.