drimane and drimenol

drimane has been researched along with drimenol* in 2 studies

Other Studies

2 other study(ies) available for drimane and drimenol

Article	Year
Identification of a drimenol synthase and drimenol oxidase from Persicaria hydropiper, involved in the biosynthesis of insect deterrent drimanes. The Plant journal : for cell and molecular biology, 2017, Volume: 90, Issue:6 The sesquiterpenoid polygodial, which belongs to the drimane family, has been shown to be an antifeedant for a number of herbivorous insects. It is presumed to be synthesized from farnesyl diphosphate via drimenol, subsequent C-12 hydroxylation and further oxidations at both C-11 and C-12 to form a dialdehyde. Here, we have identified a drimenol synthase (PhDS) and a cytochrome P450 drimenol oxidase (PhDOX1) from Persicaria hydropiper. Expression of PhDS in yeast and plants resulted in production of drimenol alone. Co-expression of PhDS with PhDOX1 in yeast yielded drimendiol, the 12-hydroxylation product of drimenol, as a major product, and cinnamolide. When PhDS and PhDOX1 were transiently expressed by agro-infiltration in Nicotiana benthamiana leaves, drimenol was almost completely converted into cinnamolide and several additional drimenol derivatives were observed. In vitro assays showed that PhDOX1 only catalyses the conversion from drimenol to drimendiol, and not the further oxidation into an aldehyde. In yeast and heterologous plant hosts, the C-12 position of drimendiol is therefore likely to be further oxidized by endogenous enzymes into an aldehyde and subsequently converted to cinnamolide, presumably by spontaneous hemiacetal formation with the C-11 hydroxyl group followed by oxidation. Purified cinnamolide was confirmed by NMR and shown to be deterrent with an effective deterrent dose (ED Topics: Animals; Aphids; Hemiptera; Nicotiana; Plant Extracts; Plant Leaves; Plants, Genetically Modified; Polycyclic Sesquiterpenes; Polygonaceae; Sesquiterpenes; Terpenes	2017
Study on the cytotoxic activity of drimane sesquiterpenes and nordrimane compounds against cancer cell lines. Molecules (Basel, Switzerland), 2014, Nov-18, Volume: 19, Issue:11 Twelve drimanes, including polygodial (1), isopolygodial (2), drimenol (3), confertifolin (4), and isodrimenin (5), were obtained from natural sources. Semi-synthetic derivatives 6-12 were obtained from 1 and 2, and cytotoxic activity was evaluated in vitro against cancer cell lines (HT-29, MDA-MB231, DHF, MCF-7, PC-3, DU-145, and CoN). IC50 values were determined at concentrations of 12.5-100 µM of each compound for 72 h. In addition, it was found that polygodial (1), 8, and 12 induced changes in mitochondrial membrane permeability in CoN, MCF-7, and PC-3 cells. Topics: Cell Line, Tumor; Cell Membrane Permeability; Furans; HT29 Cells; Humans; Inhibitory Concentration 50; MCF-7 Cells; Mitochondrial Membranes; Neoplasms; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Tetrahydronaphthalenes	2014

Article

Year

Identification of a drimenol synthase and drimenol oxidase from Persicaria hydropiper, involved in the biosynthesis of insect deterrent drimanes.

The Plant journal : for cell and molecular biology, 2017, Volume: 90, Issue:6

The sesquiterpenoid polygodial, which belongs to the drimane family, has been shown to be an antifeedant for a number of herbivorous insects. It is presumed to be synthesized from farnesyl diphosphate via drimenol, subsequent C-12 hydroxylation and further oxidations at both C-11 and C-12 to form a dialdehyde. Here, we have identified a drimenol synthase (PhDS) and a cytochrome P450 drimenol oxidase (PhDOX1) from Persicaria hydropiper. Expression of PhDS in yeast and plants resulted in production of drimenol alone. Co-expression of PhDS with PhDOX1 in yeast yielded drimendiol, the 12-hydroxylation product of drimenol, as a major product, and cinnamolide. When PhDS and PhDOX1 were transiently expressed by agro-infiltration in Nicotiana benthamiana leaves, drimenol was almost completely converted into cinnamolide and several additional drimenol derivatives were observed. In vitro assays showed that PhDOX1 only catalyses the conversion from drimenol to drimendiol, and not the further oxidation into an aldehyde. In yeast and heterologous plant hosts, the C-12 position of drimendiol is therefore likely to be further oxidized by endogenous enzymes into an aldehyde and subsequently converted to cinnamolide, presumably by spontaneous hemiacetal formation with the C-11 hydroxyl group followed by oxidation. Purified cinnamolide was confirmed by NMR and shown to be deterrent with an effective deterrent dose (ED

Topics: Animals; Aphids; Hemiptera; Nicotiana; Plant Extracts; Plant Leaves; Plants, Genetically Modified; Polycyclic Sesquiterpenes; Polygonaceae; Sesquiterpenes; Terpenes

2017

Study on the cytotoxic activity of drimane sesquiterpenes and nordrimane compounds against cancer cell lines.

Molecules (Basel, Switzerland), 2014, Nov-18, Volume: 19, Issue:11

Twelve drimanes, including polygodial (1), isopolygodial (2), drimenol (3), confertifolin (4), and isodrimenin (5), were obtained from natural sources. Semi-synthetic derivatives 6-12 were obtained from 1 and 2, and cytotoxic activity was evaluated in vitro against cancer cell lines (HT-29, MDA-MB231, DHF, MCF-7, PC-3, DU-145, and CoN). IC50 values were determined at concentrations of 12.5-100 µM of each compound for 72 h. In addition, it was found that polygodial (1), 8, and 12 induced changes in mitochondrial membrane permeability in CoN, MCF-7, and PC-3 cells.

Topics: Cell Line, Tumor; Cell Membrane Permeability; Furans; HT29 Cells; Humans; Inhibitory Concentration 50; MCF-7 Cells; Mitochondrial Membranes; Neoplasms; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Tetrahydronaphthalenes

2014