The remarkable structural diversity achieved in ent-Kaurane Diterpenes by fungal biotransformations

• Published in: Molecules Vol. 19; no. 2; pp. 1856 - 1886
• Main Authors: Takahashi, Jacqueline A, Gomes, Dhionne C, Lyra, Fernanda H, Dos Santos, Gabriel F, Martins, Leonardo R
• Format: Journal Article Book Review
• Language: English
• Published: Switzerland MDPI AG 10.02.2014; MDPI
• Subjects: Biological Products - chemistry; biotransformation; Biotransformation - genetics; Carbon - chemistry; Diterpenes, Kaurane - chemistry; Diterpenes, Kaurane - therapeutic use; Fermentation; filamentous fungi; Fungi - metabolism; Humans; hydroxylation; kaurane diterpenes; Molecular Structure; Plants - chemistry; Review; structure diversification
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules19021856

The use of biotransformations in organic chemistry is widespread, with highlights of interesting applications in the functionalization of natural products containing unactivated carbons, like the kaurane diterpenes. A number of compounds with kaurane skeletons can be isolated in large amounts from several plant species and a myriad of biological activities has been related to these compounds. Studies on structure versus activity have showed that, in most cases, in kaurane diterpenes, activity increases with the increase of functionalization. Since naturally occurring kaurane diterpenes usually have limited functional groups to be used as targets for semi-synthetic modifications, production of more polar derivatives from kaurane diterpenes have been achieved mostly through the use of fungal biotransformations. In this review, selected examples the wonderful chemical diversity produced by fungi in kaurane diterpenes is presented. This diversity includes mainly hydroxylation of nearly all carbon atoms of the kaurane molecule, many of them carried out stereoselectively, as well as ring rearrangements, among other chemical modifications. Sources of starting materials, general biotransformation protocols employed, fungi with most consistent regioselectivity towards kaurane skeleton, as well as biological activities associated with starting materials and products are also described.