The Anticancer, Antioxidant and Antimicrobial Properties of the Sesquiterpene β-Caryophyllene from the Essential Oil of Aquilaria crassna
The present study reports a bioassay-guided isolation of β-caryophyllene from the essential oil of Aquilaria crassna. The structure of β-caryophyllene was confirmed using FT-IR, NMR and MS. The antimicrobial effect of β-caryophyllene was examined using human pathogenic bacterial and fungal strains....
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MDPI AG
2015-06-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/7/11808 |
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| author | Saad S. Dahham Yasser M. Tabana Muhammad A. Iqbal Mohamed B. K. Ahamed Mohammed O. Ezzat Aman S. A. Majid Amin M. S. A. Majid |
| author_facet | Saad S. Dahham Yasser M. Tabana Muhammad A. Iqbal Mohamed B. K. Ahamed Mohammed O. Ezzat Aman S. A. Majid Amin M. S. A. Majid |
| author_sort | Saad S. Dahham |
| collection | DOAJ |
| description | The present study reports a bioassay-guided isolation of β-caryophyllene from the essential oil of Aquilaria crassna. The structure of β-caryophyllene was confirmed using FT-IR, NMR and MS. The antimicrobial effect of β-caryophyllene was examined using human pathogenic bacterial and fungal strains. Its anti-oxidant properties were evaluated by DPPH and FRAP scavenging assays. The cytotoxicity of β-caryophyllene was tested against seven human cancer cell lines. The corresponding selectivity index was determined by testing its cytotoxicity on normal cells. The effects of β-caryophyllene were studied on a series of in vitro antitumor-promoting assays using colon cancer cells. Results showed that β-caryophyllene demonstrated selective antibacterial activity against S. aureus (MIC 3 ± 1.0 µM) and more pronounced anti-fungal activity than kanamycin. β-Caryophyllene also displayed strong antioxidant effects. Additionally, β-caryophyllene exhibited selective anti-proliferative effects against colorectal cancer cells (IC50 19 µM). The results also showed that β-caryophyllene induces apoptosis via nuclear condensation and fragmentation pathways including disruption of mitochondrial membrane potential. Further, β-caryophyllene demonstrated potent inhibition against clonogenicity, migration, invasion and spheroid formation in colon cancer cells. These results prompt us to state that β-caryophyllene is the active principle responsible for the selective anticancer and antimicrobial activities of A. crassnia. β-Caryophyllene has great potential to be further developed as a promising chemotherapeutic agent against colorectal malignancies. |
| first_indexed | 2024-04-13T05:02:37Z |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T05:02:37Z |
| publishDate | 2015-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-723ede5dcca0485f83ffa6fc6e52f9c22022-12-22T03:01:16ZengMDPI AGMolecules1420-30492015-06-01207118081182910.3390/molecules200711808molecules200711808The Anticancer, Antioxidant and Antimicrobial Properties of the Sesquiterpene β-Caryophyllene from the Essential Oil of Aquilaria crassnaSaad S. Dahham0Yasser M. Tabana1Muhammad A. Iqbal2Mohamed B. K. Ahamed3Mohammed O. Ezzat4Aman S. A. Majid5Amin M. S. A. Majid6EMAN Research and Testing Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, MalaysiaEMAN Research and Testing Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, MalaysiaSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, MalaysiaEMAN Biodiscoveries Sdn. Bhd. EUREKA Complex, Universiti Sains Malaysia (USM) Campus, 11800 Minden, Pulau Pinang, MalaysiaCentre for Drug Research, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, MalaysiaAdvanced Medical and Dental Institute (IPPT), Universiti Sains Malaysia, Bertam, 13200 Kepala Batas, Penang, MalaysiaEMAN Research and Testing Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, MalaysiaThe present study reports a bioassay-guided isolation of β-caryophyllene from the essential oil of Aquilaria crassna. The structure of β-caryophyllene was confirmed using FT-IR, NMR and MS. The antimicrobial effect of β-caryophyllene was examined using human pathogenic bacterial and fungal strains. Its anti-oxidant properties were evaluated by DPPH and FRAP scavenging assays. The cytotoxicity of β-caryophyllene was tested against seven human cancer cell lines. The corresponding selectivity index was determined by testing its cytotoxicity on normal cells. The effects of β-caryophyllene were studied on a series of in vitro antitumor-promoting assays using colon cancer cells. Results showed that β-caryophyllene demonstrated selective antibacterial activity against S. aureus (MIC 3 ± 1.0 µM) and more pronounced anti-fungal activity than kanamycin. β-Caryophyllene also displayed strong antioxidant effects. Additionally, β-caryophyllene exhibited selective anti-proliferative effects against colorectal cancer cells (IC50 19 µM). The results also showed that β-caryophyllene induces apoptosis via nuclear condensation and fragmentation pathways including disruption of mitochondrial membrane potential. Further, β-caryophyllene demonstrated potent inhibition against clonogenicity, migration, invasion and spheroid formation in colon cancer cells. These results prompt us to state that β-caryophyllene is the active principle responsible for the selective anticancer and antimicrobial activities of A. crassnia. β-Caryophyllene has great potential to be further developed as a promising chemotherapeutic agent against colorectal malignancies.http://www.mdpi.com/1420-3049/20/7/11808β-caryophylleneanti-cancerapoptosisanti-clonogenicnuclear fragmentationcolorectal cancer |
| spellingShingle | Saad S. Dahham Yasser M. Tabana Muhammad A. Iqbal Mohamed B. K. Ahamed Mohammed O. Ezzat Aman S. A. Majid Amin M. S. A. Majid The Anticancer, Antioxidant and Antimicrobial Properties of the Sesquiterpene β-Caryophyllene from the Essential Oil of Aquilaria crassna Molecules β-caryophyllene anti-cancer apoptosis anti-clonogenic nuclear fragmentation colorectal cancer |
| title | The Anticancer, Antioxidant and Antimicrobial Properties of the Sesquiterpene β-Caryophyllene from the Essential Oil of Aquilaria crassna |
| title_full | The Anticancer, Antioxidant and Antimicrobial Properties of the Sesquiterpene β-Caryophyllene from the Essential Oil of Aquilaria crassna |
| title_fullStr | The Anticancer, Antioxidant and Antimicrobial Properties of the Sesquiterpene β-Caryophyllene from the Essential Oil of Aquilaria crassna |
| title_full_unstemmed | The Anticancer, Antioxidant and Antimicrobial Properties of the Sesquiterpene β-Caryophyllene from the Essential Oil of Aquilaria crassna |
| title_short | The Anticancer, Antioxidant and Antimicrobial Properties of the Sesquiterpene β-Caryophyllene from the Essential Oil of Aquilaria crassna |
| title_sort | anticancer antioxidant and antimicrobial properties of the sesquiterpene β caryophyllene from the essential oil of aquilaria crassna |
| topic | β-caryophyllene anti-cancer apoptosis anti-clonogenic nuclear fragmentation colorectal cancer |
| url | http://www.mdpi.com/1420-3049/20/7/11808 |
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