Enzymatic biotransformation of terpenes as bioactive agents

Abstract

The plant-derived terpenoids are considered to be the most potent anticancer, anti-inflammatory and anticarcinogenic compounds known. Enzymatic biotransformation is a very useful approach to expand the chemical diversity of natural products. Recent enzymatic biotransformation studies on terpenoids have resulted in the isolation of novel compounds. 14-hydroxy methyl caryophyllene oxide produced from caryophyllene oxide showed a potent inhibitory activity against the butyryl cholinesterase enzyme, and was found to be more potent than parent caryophyllene oxide. The metabolites 3β,7β-dihydroxy-11-oxo-olean-12-en-30-oic acid, betulin, betulonic acid, argentatin A, incanilin, 18β glycyrrhetinic acid, 3,11-dioxo-olean-12-en-30-oic acid produced from 18β glycyrrhetinic acid were screened against the enzyme lipoxygenase. 3,11-Dioxo-olean-12-en-30-oic acid, was found to be more active than the parent compound. The metabolites 3β-hydroxy sclareol 18α-hydroxy sclareol, 6α,18α-dihydroxy sclareol, 11S,18α-dihydroxy sclareol, and 1β-hydroxy sclareol and 11S,18α-dihydroxy sclareol produced from sclareol were screened for antibacterial activity. 1β-Hydroxy sclareol was found to be more active than parent sclareol. There are several reports on natural product enzymatic biotransformation, but few have been conducted on terpenes. This review summarizes the classification, advantages and agents of enzymatic transformation and examines the potential role of new enzymatically transformed terpenoids and their derivatives in the chemoprevention and treatment of other diseases.

Naturally Occurring and Synthetic Agents as Potential Anti-Inflammatory and Immunomodulants

“…In the context of our previous communications on bioactivities of oleanolic acid and ursolic acid related to derivatives as medicinally important compounds, enzymatic transformation of bioactive cyclic terpenoid compounds [1][2][3][4][5], now we report the naturally occurring terpenes and synthetic agents as potential analgesic, anti-inflammatory and immunomodulants.…”

Biotransformation of Ergostane Triterpenoid Antcin K from Antrodia cinnamomea by Soil-Isolated Psychrobacillus sp. AK 1817

“…From the results, it is clear that antcin K was catalyzed by the strain to compound (1) and compound (2). Moreover, compound (1) and compound (2) were potentially biotransformed from 25S-antcin K and 25R-antcin K, respectively.…”

“…Terpenoids, which are composed of isoprenoid subunits, are the largest group of phytochemicals in the world, and are widely distributed in almost all living organisms [1]. Based on the number of isoprenoid units, terpenoids are subdivided into monoterpenoids (C10), sesquiterpenoids (C15), diterpenoids (C20), sesterterpenoids (C25), triterpenoids (C30), and tetraterpenoids (C40).…”

Biotransformation of Ganoderic Acid A to 3-O-Acetyl Ganoderic Acid A by Soil-isolated Streptomyces sp.

“…Precursor compounds were biotransformed by microorganisms or enzymes to form new compounds. Additionally, some microbial transformations can modify the functional groups of precursors to improve the bioactivities of the precursor compounds [11][12][13][14]. For example, soy isoflavone daidzein was hydroxylated by Aspergillus oryzae to form 6-hyroxydaidzein or 8-hydroxydaidzein.…”