Phyto – Monoterpene linalool as precursor to synthesis epoxides and hydroperoxides as anti carcinogenic agents via thermal and photo chemical oxidation reactions
Linalool (I) was extracted from Zingiber officinale. The oxidation of linalool using m-chloroperbenzoic acid at room temperature gave the mixture of 2,2,6-trimethyl-6-vinyl-tetrahydro-pyran-3-ol (IIa) & 2-(5-methyl-5-vinyl- tetrahydro-furan-2-yl)-propan-2-ol (IIa′), which cannot be separated. Wh...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2019-11-01
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| Series: | Arabian Journal of Chemistry |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535218302016 |
| _version_ | 1828815771694792704 |
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| author | Eman M. Elgendy Manal Y. Semeih |
| author_facet | Eman M. Elgendy Manal Y. Semeih |
| author_sort | Eman M. Elgendy |
| collection | DOAJ |
| description | Linalool (I) was extracted from Zingiber officinale. The oxidation of linalool using m-chloroperbenzoic acid at room temperature gave the mixture of 2,2,6-trimethyl-6-vinyl-tetrahydro-pyran-3-ol (IIa) & 2-(5-methyl-5-vinyl- tetrahydro-furan-2-yl)-propan-2-ol (IIa′), which cannot be separated. Whereas, the photo-epoxidation of it using hydrogen peroxide gave the above mixture IIa/IIa′, beside 2,2,8-trimethyl-6-oxianyl-tetrahydro-pyran-3-ol (IIb). It was evaluated for anti-oxidant, using erythrocyte hemolysis and ABTS methods. It showed inhibitory effect in case of erythrocyte hemolysis and low inhibitory effect in case of ABTS method. Photosensitization reactions of linalool with tetraphenyl porphyrin or chlorophyll produced a mixture of two isomeric hydroperoxides, 7-hydroperoxy-3,7-dimethylocta-1,5-dien-3-ol (IIIa) & 6-hydroperoxy-3,7-dimethyl octa-1,7-dien-3-ol (IIIb), which can be successfully separated. On the other hand, the cytotoxic activity of linalool (I) was tested against epdermoid carcinoma (HEP2), it has medium effect. Whereas, in case of human prostate cancer (PC-3), it has weak effect. From this study concludes that ginger has good antioxidant potential and this spice can be used to produce novel natural antioxidants and flavoring agent like linalool which recommends it as an active therapy for humans. Monoterpene linalool abstract singlet oxygen (1O2) by photosensitization reactions to produce these hydroperoxides, which are caused relatively little oxidative DNA damage. Keywords: Linalool, Epoxidation, Photosensitization, Hydroperoxides, Anticancer, Antioxidant |
| first_indexed | 2024-12-12T10:51:04Z |
| format | Article |
| id | doaj.art-acbd4d35529945e797bc3cad396b8123 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-12T10:51:04Z |
| publishDate | 2019-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-acbd4d35529945e797bc3cad396b81232022-12-22T00:26:46ZengElsevierArabian Journal of Chemistry1878-53522019-11-01127966973Phyto – Monoterpene linalool as precursor to synthesis epoxides and hydroperoxides as anti carcinogenic agents via thermal and photo chemical oxidation reactionsEman M. Elgendy0Manal Y. Semeih1Faculty of Specific Education, Mansoura University, Mansoura, Egypt; Corresponding author.Al Leith College, Umm Al-Qura University, Al Leith, Saudi ArabiaLinalool (I) was extracted from Zingiber officinale. The oxidation of linalool using m-chloroperbenzoic acid at room temperature gave the mixture of 2,2,6-trimethyl-6-vinyl-tetrahydro-pyran-3-ol (IIa) & 2-(5-methyl-5-vinyl- tetrahydro-furan-2-yl)-propan-2-ol (IIa′), which cannot be separated. Whereas, the photo-epoxidation of it using hydrogen peroxide gave the above mixture IIa/IIa′, beside 2,2,8-trimethyl-6-oxianyl-tetrahydro-pyran-3-ol (IIb). It was evaluated for anti-oxidant, using erythrocyte hemolysis and ABTS methods. It showed inhibitory effect in case of erythrocyte hemolysis and low inhibitory effect in case of ABTS method. Photosensitization reactions of linalool with tetraphenyl porphyrin or chlorophyll produced a mixture of two isomeric hydroperoxides, 7-hydroperoxy-3,7-dimethylocta-1,5-dien-3-ol (IIIa) & 6-hydroperoxy-3,7-dimethyl octa-1,7-dien-3-ol (IIIb), which can be successfully separated. On the other hand, the cytotoxic activity of linalool (I) was tested against epdermoid carcinoma (HEP2), it has medium effect. Whereas, in case of human prostate cancer (PC-3), it has weak effect. From this study concludes that ginger has good antioxidant potential and this spice can be used to produce novel natural antioxidants and flavoring agent like linalool which recommends it as an active therapy for humans. Monoterpene linalool abstract singlet oxygen (1O2) by photosensitization reactions to produce these hydroperoxides, which are caused relatively little oxidative DNA damage. Keywords: Linalool, Epoxidation, Photosensitization, Hydroperoxides, Anticancer, Antioxidanthttp://www.sciencedirect.com/science/article/pii/S1878535218302016 |
| spellingShingle | Eman M. Elgendy Manal Y. Semeih Phyto – Monoterpene linalool as precursor to synthesis epoxides and hydroperoxides as anti carcinogenic agents via thermal and photo chemical oxidation reactions Arabian Journal of Chemistry |
| title | Phyto – Monoterpene linalool as precursor to synthesis epoxides and hydroperoxides as anti carcinogenic agents via thermal and photo chemical oxidation reactions |
| title_full | Phyto – Monoterpene linalool as precursor to synthesis epoxides and hydroperoxides as anti carcinogenic agents via thermal and photo chemical oxidation reactions |
| title_fullStr | Phyto – Monoterpene linalool as precursor to synthesis epoxides and hydroperoxides as anti carcinogenic agents via thermal and photo chemical oxidation reactions |
| title_full_unstemmed | Phyto – Monoterpene linalool as precursor to synthesis epoxides and hydroperoxides as anti carcinogenic agents via thermal and photo chemical oxidation reactions |
| title_short | Phyto – Monoterpene linalool as precursor to synthesis epoxides and hydroperoxides as anti carcinogenic agents via thermal and photo chemical oxidation reactions |
| title_sort | phyto monoterpene linalool as precursor to synthesis epoxides and hydroperoxides as anti carcinogenic agents via thermal and photo chemical oxidation reactions |
| url | http://www.sciencedirect.com/science/article/pii/S1878535218302016 |
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