Our data demonstrate that basil EGS1 and petunia IGS1, which catalyze the formation of eugenol and isoeugenol, respectively, are related to PLRs, IFRs, and PCBERs and are thus members of the PIP family of NADPH-dependent reductases () (–). PLRs and PCBERs are involved in the biosynthesis of lignans throughout the plant kingdom, and IFRs are involved in the modification of some isoflavonoids (isoflavonoids occur mostly in legumes). Although the majority of compounds produced by PIP reductases are believed to function in plant defense (), a subset of these compounds may have acquired additional roles. For example, both eugenol and isoeugenol are components of the floral scent of Clarkia breweri flowers (, ).
The coding regions of IGS1 and EGS1 were each separately inserted into the Escherichia coli expression vectors pCRT7/CT-TOPO TA (without a His tag), and E. coli cells were transformed with these expression constructs. Cells were grown in LB medium supplemented with coniferyl alcohol at a concentration of 100 μg/ml. After induction with isopropylthio-β-galactoside, cells were allowed to grow for an additional 15-h period, after which the cells were isolated by centrifugation and the remaining culture medium (5 ml) was extracted one time with an equal volume of hexane. The spent medium of E. coli cells expressing basil EGS1 contained eugenol (A) at a concentration of 7.1 μg/ml. Similarly, the spent medium of E. coli cells expressing petunia IGS1 contained isoeugenol (B) at a concentration of 6.5 μg/ml. Control E. coli cells expressing an unrelated gene (MKS1) () and cultured under identical conditions as those expressing EGS1 and IGS1 did not produce either eugenol or isoeugenol (data not shown). Expression of IGS1 and EGS1 in E. coli using a pHIS-9 vector (a pET-based vector; see Materials and Methods) with an N-terminal His-tag extension gave similar results.
Keyword Eugenol | Collection of Czechoslovak ...
The major groups of angiosperms synthesize various phenylpropenes, which include molecules such as the allylphenols chavicol and eugenol and the propenylphenols t-anol and isoeugenol () and their derivatives (, ). Some monomeric phenylpropenes, including methyleugenol and methylchavicol, have also been reported from gymnosperms (–). These monomeric compounds are easily volatilized, and some are toxic to insects and microbes. Eugenol, for example, is a general acting antimicrobial and antianimal toxin with analgesic properties for humans (–). Plants often produce and store phenylpropenes in their vegetative parts as a defense against herbivores and parasitic bacteria and fungi. Moreover, phenylpropenes are sometimes emitted from flowers to attract insect pollinators, which detect the highly diluted airborne volatiles through their antennae ().
Converting acetyleugenol to eugenol
The limitations apply to Methyleugenol (ME) originating from all sources. Contributions from essential oils can be significant. Names of essential oils, which should also be considered in the application of the Standard, are given below. Maximum percentage of the reference material is included for use when no analytical data is available.
Eugenol CAS 97-53-0 | 818455 - Merck | Life Science
It has a pleasant, spicy, clove-like odor.; Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic.
Eugenol and isoeugenol, characteristic aromatic constituents of ..
It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from petrochemicals or from by-products of paper manufacture (Wikipedia).; Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anesthetic.
pathways for the synthesis of eugenol, ..
It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from phenol or from lignin.; It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.