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Hiromu Kameoka - One of the best experts on this subject based on the ideXlab platform.
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Biotransformations of acyclic terpenoids, (±)-trans-Nerolidol and geranylacetone, by Glomerella cingulata
Journal of Agricultural and Food Chemistry, 1996Co-Authors: Mitsuo Miyazawa, Hirokazu Nankai, Hiromu KameokaAbstract:Microbial transformations of (±)-trans-Nerolidol and geranylacetone were carried out with a plant pathogenic fungus, Glomerella cingulata. (±)-trans-Nerolidol and geranylacetone were hydrated at a remote double bond as the main metabolic pathway. A large amount of (E)-3,7,11-trimethyl-1,6-dodecadiene-3,11-diol and small amount of (E)-3,7,11-trimethyl-1,6-dodecadiene-3,10,11-triol were obtained from (±)-trans-Nerolidol. Geranylacetone was transformed to (E)-10-hydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. (E)-9,10-Dihydroxy-6,10-dimethyl-5-undecen-2-one, (E)-6,10-dimethyl-5,9-undecadien-2-ol, (E)-6,10-dimethyl-5-undecene-2,9,10-triol, and (E)-6,10-dimethyl-5-undecene-2,10-diol were also obtained from geranylacetone. The structures of metabolic products were determined by spectroscopic data. Keywords: Biotransformation; microbial transformation; Glomerella cingulata; plant pathogenic fungus; (±)-trans-Nerolidol; geranylacetone
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biotransformations of acyclic terpenoids trans Nerolidol and geranylacetone by glomerella cingulata
Journal of Agricultural and Food Chemistry, 1996Co-Authors: Mitsuo Miyazawa, Hirokazu Nankai, Hiromu KameokaAbstract:Microbial transformations of (±)-trans-Nerolidol and geranylacetone were carried out with a plant pathogenic fungus, Glomerella cingulata. (±)-trans-Nerolidol and geranylacetone were hydrated at a remote double bond as the main metabolic pathway. A large amount of (E)-3,7,11-trimethyl-1,6-dodecadiene-3,11-diol and small amount of (E)-3,7,11-trimethyl-1,6-dodecadiene-3,10,11-triol were obtained from (±)-trans-Nerolidol. Geranylacetone was transformed to (E)-10-hydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. (E)-9,10-Dihydroxy-6,10-dimethyl-5-undecen-2-one, (E)-6,10-dimethyl-5,9-undecadien-2-ol, (E)-6,10-dimethyl-5-undecene-2,9,10-triol, and (E)-6,10-dimethyl-5-undecene-2,10-diol were also obtained from geranylacetone. The structures of metabolic products were determined by spectroscopic data. Keywords: Biotransformation; microbial transformation; Glomerella cingulata; plant pathogenic fungus; (±)-trans-Nerolidol; geranylacetone
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biotransformations of acyclic terpenoids cis Nerolidol and nerylacetone by plant pathogenic fungus glomerella cingulata
Phytochemistry, 1995Co-Authors: Mitsuo Miyazawa, Hirokazu Nankai, Hiromu KameokaAbstract:Microbial transformations of (±)-cis-Nerolidol and nerylacetone were investigated using the plant pathogenic fungus, Glomerella cingulata. Both (±)-cis-Nerolidol and nerylacetone were mainly oxidized at the remote double bond. (±)-cis-Nerolidol was transformed into (Z)-3,7,11-trimethyl-1,6-dodecadien-3,10,11-triol while nerylacetone was transformed into (Z)-9,10-dihydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. In addition, the biotransformation of nerylacetone resulted in hydration at the remote double bond and reduction of the carbonyl group and produced (Z)-6,10-dimethyl-5,9-undecadien-2-ol, (Z)-10-hydroxy-6,10-dimethyl-5-undecen-2-one and (Z)-6,10-dimethyl-5-undecen-2,9,10-triol. The structures of the metabolic products were determined by spectroscopic data.
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Biotransformations of acyclic terpenoids, (±)-cis-Nerolidol and nerylacetone, by plant pathogenic fungus, Glomerella cingulata
Phytochemistry, 1995Co-Authors: Mitsuo Miyazawa, Hirokazu Nankai, Hiromu KameokaAbstract:Microbial transformations of (±)-cis-Nerolidol and nerylacetone were investigated using the plant pathogenic fungus, Glomerella cingulata. Both (±)-cis-Nerolidol and nerylacetone were mainly oxidized at the remote double bond. (±)-cis-Nerolidol was transformed into (Z)-3,7,11-trimethyl-1,6-dodecadien-3,10,11-triol while nerylacetone was transformed into (Z)-9,10-dihydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. In addition, the biotransformation of nerylacetone resulted in hydration at the remote double bond and reduction of the carbonyl group and produced (Z)-6,10-dimethyl-5,9-undecadien-2-ol, (Z)-10-hydroxy-6,10-dimethyl-5-undecen-2-one and (Z)-6,10-dimethyl-5-undecen-2,9,10-triol. The structures of the metabolic products were determined by spectroscopic data.
Mitsuo Miyazawa - One of the best experts on this subject based on the ideXlab platform.
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Biotransformations of acyclic terpenoids, (±)-trans-Nerolidol and geranylacetone, by Glomerella cingulata
Journal of Agricultural and Food Chemistry, 1996Co-Authors: Mitsuo Miyazawa, Hirokazu Nankai, Hiromu KameokaAbstract:Microbial transformations of (±)-trans-Nerolidol and geranylacetone were carried out with a plant pathogenic fungus, Glomerella cingulata. (±)-trans-Nerolidol and geranylacetone were hydrated at a remote double bond as the main metabolic pathway. A large amount of (E)-3,7,11-trimethyl-1,6-dodecadiene-3,11-diol and small amount of (E)-3,7,11-trimethyl-1,6-dodecadiene-3,10,11-triol were obtained from (±)-trans-Nerolidol. Geranylacetone was transformed to (E)-10-hydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. (E)-9,10-Dihydroxy-6,10-dimethyl-5-undecen-2-one, (E)-6,10-dimethyl-5,9-undecadien-2-ol, (E)-6,10-dimethyl-5-undecene-2,9,10-triol, and (E)-6,10-dimethyl-5-undecene-2,10-diol were also obtained from geranylacetone. The structures of metabolic products were determined by spectroscopic data. Keywords: Biotransformation; microbial transformation; Glomerella cingulata; plant pathogenic fungus; (±)-trans-Nerolidol; geranylacetone
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biotransformations of acyclic terpenoids trans Nerolidol and geranylacetone by glomerella cingulata
Journal of Agricultural and Food Chemistry, 1996Co-Authors: Mitsuo Miyazawa, Hirokazu Nankai, Hiromu KameokaAbstract:Microbial transformations of (±)-trans-Nerolidol and geranylacetone were carried out with a plant pathogenic fungus, Glomerella cingulata. (±)-trans-Nerolidol and geranylacetone were hydrated at a remote double bond as the main metabolic pathway. A large amount of (E)-3,7,11-trimethyl-1,6-dodecadiene-3,11-diol and small amount of (E)-3,7,11-trimethyl-1,6-dodecadiene-3,10,11-triol were obtained from (±)-trans-Nerolidol. Geranylacetone was transformed to (E)-10-hydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. (E)-9,10-Dihydroxy-6,10-dimethyl-5-undecen-2-one, (E)-6,10-dimethyl-5,9-undecadien-2-ol, (E)-6,10-dimethyl-5-undecene-2,9,10-triol, and (E)-6,10-dimethyl-5-undecene-2,10-diol were also obtained from geranylacetone. The structures of metabolic products were determined by spectroscopic data. Keywords: Biotransformation; microbial transformation; Glomerella cingulata; plant pathogenic fungus; (±)-trans-Nerolidol; geranylacetone
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biotransformations of acyclic terpenoids cis Nerolidol and nerylacetone by plant pathogenic fungus glomerella cingulata
Phytochemistry, 1995Co-Authors: Mitsuo Miyazawa, Hirokazu Nankai, Hiromu KameokaAbstract:Microbial transformations of (±)-cis-Nerolidol and nerylacetone were investigated using the plant pathogenic fungus, Glomerella cingulata. Both (±)-cis-Nerolidol and nerylacetone were mainly oxidized at the remote double bond. (±)-cis-Nerolidol was transformed into (Z)-3,7,11-trimethyl-1,6-dodecadien-3,10,11-triol while nerylacetone was transformed into (Z)-9,10-dihydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. In addition, the biotransformation of nerylacetone resulted in hydration at the remote double bond and reduction of the carbonyl group and produced (Z)-6,10-dimethyl-5,9-undecadien-2-ol, (Z)-10-hydroxy-6,10-dimethyl-5-undecen-2-one and (Z)-6,10-dimethyl-5-undecen-2,9,10-triol. The structures of the metabolic products were determined by spectroscopic data.
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Biotransformations of acyclic terpenoids, (±)-cis-Nerolidol and nerylacetone, by plant pathogenic fungus, Glomerella cingulata
Phytochemistry, 1995Co-Authors: Mitsuo Miyazawa, Hirokazu Nankai, Hiromu KameokaAbstract:Microbial transformations of (±)-cis-Nerolidol and nerylacetone were investigated using the plant pathogenic fungus, Glomerella cingulata. Both (±)-cis-Nerolidol and nerylacetone were mainly oxidized at the remote double bond. (±)-cis-Nerolidol was transformed into (Z)-3,7,11-trimethyl-1,6-dodecadien-3,10,11-triol while nerylacetone was transformed into (Z)-9,10-dihydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. In addition, the biotransformation of nerylacetone resulted in hydration at the remote double bond and reduction of the carbonyl group and produced (Z)-6,10-dimethyl-5,9-undecadien-2-ol, (Z)-10-hydroxy-6,10-dimethyl-5-undecen-2-one and (Z)-6,10-dimethyl-5-undecen-2,9,10-triol. The structures of the metabolic products were determined by spectroscopic data.
Jianjun Qiao - One of the best experts on this subject based on the ideXlab platform.
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Characterization of trans-Nerolidol Synthase from Celastrus angulatus Maxim and Production of trans-Nerolidol in Engineered Saccharomyces cerevisiae.
Journal of agricultural and food chemistry, 2021Co-Authors: Li Weiguo, Xiaoguang Yan, Zhang Yuting, Dongmei Liang, Qinggele Caiyin, Jianjun QiaoAbstract:Volatile terpenoids are a large group of important secondary metabolites and possess many biological activities. The acyclic sesquiterpene trans-Nerolidol is one of the typical representatives and widely used in cosmetics and agriculture. Here, the accumulation of volatile terpenes in different tissues of Celastrus angulatus was investigated, and two trans-Nerolidol synthases, CaNES1 and CaNES2, were identified and characterized by in vitro enzymatic assays. Both genes are differentially transcribed in different tissues of C. angulatus. Next, we constructed a Saccharomyces cerevisiae cell factory to enable high-level production of trans-Nerolidol. Glucose was the sole carbon source to sequentially control gene expression between the competitive squalene and trans-Nerolidol pathways. Finally, the trans-Nerolidol production of recombinant strain LWG003-CaNES2 was 7.01 g/L by fed-batch fermentation in a 5 L bioreactor. The results clarify volatile terpenoid biosynthesis in C. angulatus and provide a promising potential for industrial production of trans-Nerolidol in S. cerevisiae.
Chih Yang Huang - One of the best experts on this subject based on the ideXlab platform.
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Small Molecule Compound Nerolidol attenuates Hypertension induced hypertrophy in spontaneously hypertensive rats through modulation of Mel-18-IGF-IIR signalling.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 2021Co-Authors: Yueh-min Lin, Khan Farheen Badrealam, Chia-hua Kuo, Jayasimharayalu Daddam, Marthandam Asokan Shibu, Kuan Ho Lin, Vijaya Padma Viswanadha, Wei Wen Kuo, Chih Yang HuangAbstract:Abstract Background : Cardiovascular diseases are caused by multitudes of stress factors like hypertension and their outcomes are associated with high mortality and morbidity worldwide. Nerolidol, a naturally occurring sesquiterpene found in several plant species, embodies various pharmacological benefits against numerous health disorders. However, their effects on hypertension induced cardiac complications are not completely understood. Purpose : The present study is to elucidate the efficacy of Nerolidol against hypertension related cardiac hypertrophy in spontaneously hypertensive rats (SHRs). Study Design : For preliminary in vitro studies, H9c2 cardiomyoblasts cells were challenged with 200 nM Angiotensin-II (AngII) for 12 h and were then treated with Nerolidol for 24 h. The hypertrophic effect in H9c2 cells were analyzed by actin staining and the modulations in hypertrophic protein markers and mediators were determined by Western blotting analysis. For in vivo experiments, sixteen week-old male Wistar Kyoto (WKY) and SHRs were segregated into five groups (n=9): Control WKY, hypertensive SHRs, SHRs with low dose (75 mg/kg b.w/day) Nerolidol, SHRs with high dose (150 mg/kg b.w/day) Nerolidol and SHR rats treated with an anti-hypertensive drug captopril (50 mg/kg b.w/day). Nerolidol treatment was given orally for 8 weeks and were analysed through Echocardiography. After euthanasia, hematoxylin and eosin staining, Immunohistochemical analysis and Western blotting was performed on left ventricle tissue. Results : Western blotting analysis revealed that Nerolidol significantly attenuates AngII induced expression of hypertrophic markers ANP and BNP in H9c2 cardiomyoblasts. In addition, actin staining further ascertained the potential of Nerolidol to ameliorate AngII induced cardiac hypertrophy. Moreover, Nerolidol administration suppressed the hypertrophic signalling mediators like calcineurin, GATA4, Mel-18, HSF-2 and IGFIIR in a dose-dependent fashion. In silico studies also ascertained the role of Mel-18 in the ameliorative effects of Nerolidol. Further, these intriguing in vitro results were further confirmed in in vivo SHR model. Oral neraolidol in SHRs efficiently reduced blood pressure and ameliorated hypertension induced cardiac hypertrophic effects by effectively reducing the levels of proteins involved in cardiac MeL-18-HSF2-IGF-IIR signalling. Conclusion : Collectively, the data reveals that the cardioprotective effect of Nerolidol against hypertension induced hypertrophy involves reduction in blood pressure and regulation of the cardiac Mel-18-IGFIIR signalling cascade.
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Nerolidol improves cardiac function in spontaneously hypertensive rats by inhibiting cardiac inflammation and remodelling associated tlr4 nf κb signalling cascade
Food and Chemical Toxicology, 2021Co-Authors: Yueh-min Lin, Khan Farheen Badrealam, Marthandam Asokan Shibu, Vijaya Padma Viswanadha, Wei Wen Kuo, Pei Fang Lai, William Shaotsu Chen, Cecilia Hsuan Day, Chih Yang HuangAbstract:Abstract Toll-like receptor 4 (TLR4) is an important mediator of hypertension and AngII induced cardiac inflammation and remodelling. In this study, the potential of Nerolidol to ameliorate hypertension induced cardiac injuries and the underlying mechanism of action was explored by using in vitro and in vivo models. The in vitro analysis was performed on AngII challenged H9c2 cells and their ability to overcome cardiac inflammation and cardiac remodelling effects was determined by evaluating TLR4/NF-κB signalling cascade using Western blot analysis and immunofluorescence. The results were further ascertained using in vivo experiments. Eighteen week old male rats were randomly allocated into different groups i.e. Wistar Kyoto (WKY) rats, hypertensive SHRs, SHRs treated with a low-dose (75 mg/kg b.w) and high-dose of Nerolidol (150 mg/kg b.w) and SHRs treated with captopril (50 mg/kg b.w) through oral gauge and finally analysed through echocardiography, histopathological techniques and molecular analysis. The results show that nerilodol target TLR4/NF-κB signalling and thereby attenuate hypertension associated inflammation and oxidative stress thereby provides effective cardioprotection. Echocardiography analysis showed that Nerolidol improved cardiac functional characteristics including Ejection Fraction and Fractional Shortening in the SHRs. Collectively, the data of the study demonstrates Nerolidol as a cardio-protective agent against hypertension induced cardiac remodelling.
Hirokazu Nankai - One of the best experts on this subject based on the ideXlab platform.
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Biotransformations of acyclic terpenoids, (±)-trans-Nerolidol and geranylacetone, by Glomerella cingulata
Journal of Agricultural and Food Chemistry, 1996Co-Authors: Mitsuo Miyazawa, Hirokazu Nankai, Hiromu KameokaAbstract:Microbial transformations of (±)-trans-Nerolidol and geranylacetone were carried out with a plant pathogenic fungus, Glomerella cingulata. (±)-trans-Nerolidol and geranylacetone were hydrated at a remote double bond as the main metabolic pathway. A large amount of (E)-3,7,11-trimethyl-1,6-dodecadiene-3,11-diol and small amount of (E)-3,7,11-trimethyl-1,6-dodecadiene-3,10,11-triol were obtained from (±)-trans-Nerolidol. Geranylacetone was transformed to (E)-10-hydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. (E)-9,10-Dihydroxy-6,10-dimethyl-5-undecen-2-one, (E)-6,10-dimethyl-5,9-undecadien-2-ol, (E)-6,10-dimethyl-5-undecene-2,9,10-triol, and (E)-6,10-dimethyl-5-undecene-2,10-diol were also obtained from geranylacetone. The structures of metabolic products were determined by spectroscopic data. Keywords: Biotransformation; microbial transformation; Glomerella cingulata; plant pathogenic fungus; (±)-trans-Nerolidol; geranylacetone
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biotransformations of acyclic terpenoids trans Nerolidol and geranylacetone by glomerella cingulata
Journal of Agricultural and Food Chemistry, 1996Co-Authors: Mitsuo Miyazawa, Hirokazu Nankai, Hiromu KameokaAbstract:Microbial transformations of (±)-trans-Nerolidol and geranylacetone were carried out with a plant pathogenic fungus, Glomerella cingulata. (±)-trans-Nerolidol and geranylacetone were hydrated at a remote double bond as the main metabolic pathway. A large amount of (E)-3,7,11-trimethyl-1,6-dodecadiene-3,11-diol and small amount of (E)-3,7,11-trimethyl-1,6-dodecadiene-3,10,11-triol were obtained from (±)-trans-Nerolidol. Geranylacetone was transformed to (E)-10-hydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. (E)-9,10-Dihydroxy-6,10-dimethyl-5-undecen-2-one, (E)-6,10-dimethyl-5,9-undecadien-2-ol, (E)-6,10-dimethyl-5-undecene-2,9,10-triol, and (E)-6,10-dimethyl-5-undecene-2,10-diol were also obtained from geranylacetone. The structures of metabolic products were determined by spectroscopic data. Keywords: Biotransformation; microbial transformation; Glomerella cingulata; plant pathogenic fungus; (±)-trans-Nerolidol; geranylacetone
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biotransformations of acyclic terpenoids cis Nerolidol and nerylacetone by plant pathogenic fungus glomerella cingulata
Phytochemistry, 1995Co-Authors: Mitsuo Miyazawa, Hirokazu Nankai, Hiromu KameokaAbstract:Microbial transformations of (±)-cis-Nerolidol and nerylacetone were investigated using the plant pathogenic fungus, Glomerella cingulata. Both (±)-cis-Nerolidol and nerylacetone were mainly oxidized at the remote double bond. (±)-cis-Nerolidol was transformed into (Z)-3,7,11-trimethyl-1,6-dodecadien-3,10,11-triol while nerylacetone was transformed into (Z)-9,10-dihydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. In addition, the biotransformation of nerylacetone resulted in hydration at the remote double bond and reduction of the carbonyl group and produced (Z)-6,10-dimethyl-5,9-undecadien-2-ol, (Z)-10-hydroxy-6,10-dimethyl-5-undecen-2-one and (Z)-6,10-dimethyl-5-undecen-2,9,10-triol. The structures of the metabolic products were determined by spectroscopic data.
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Biotransformations of acyclic terpenoids, (±)-cis-Nerolidol and nerylacetone, by plant pathogenic fungus, Glomerella cingulata
Phytochemistry, 1995Co-Authors: Mitsuo Miyazawa, Hirokazu Nankai, Hiromu KameokaAbstract:Microbial transformations of (±)-cis-Nerolidol and nerylacetone were investigated using the plant pathogenic fungus, Glomerella cingulata. Both (±)-cis-Nerolidol and nerylacetone were mainly oxidized at the remote double bond. (±)-cis-Nerolidol was transformed into (Z)-3,7,11-trimethyl-1,6-dodecadien-3,10,11-triol while nerylacetone was transformed into (Z)-9,10-dihydroxy-6,10-dimethyl-5-undecen-2-one as the major metabolite. In addition, the biotransformation of nerylacetone resulted in hydration at the remote double bond and reduction of the carbonyl group and produced (Z)-6,10-dimethyl-5,9-undecadien-2-ol, (Z)-10-hydroxy-6,10-dimethyl-5-undecen-2-one and (Z)-6,10-dimethyl-5-undecen-2,9,10-triol. The structures of the metabolic products were determined by spectroscopic data.
