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Molecules. 2015 Jun 26;20(7):11808-29. doi: 10.3390/molecules200711808.

The Anticancer, Antioxidant and Antimicrobial Properties of the Sesquiterpene β-Caryophyllene from the Essential Oil of Aquilaria crassna.

Author information

1
EMAN Research and Testing Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia. hawk_dijla@yahoo.com.
2
EMAN Research and Testing Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia. yasser.tabana@hotmail.com.
3
School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia. adnan_chem38@yahoo.com.
4
EMAN Biodiscoveries Sdn. Bhd. EUREKA Complex, Universiti Sains Malaysia (USM) Campus, 11800 Minden, Pulau Pinang, Malaysia. khadeer.nc@gmail.com.
5
Centre for Drug Research, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia. mohamed_oday@yahoo.com.
6
Advanced Medical and Dental Institute (IPPT), Universiti Sains Malaysia, Bertam, 13200 Kepala Batas, Penang, Malaysia. aminmalikshah@gmail.com.
7
EMAN Research and Testing Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 Minden, Pulau Pinang, Malaysia. aminmalikshah@gmail.com.

Abstract

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.

KEYWORDS:

anti-cancer; anti-clonogenic; apoptosis; colorectal cancer; nuclear fragmentation; β-caryophyllene

PMID:
26132906
PMCID:
PMC6331975
DOI:
10.3390/molecules200711808
[Indexed for MEDLINE]
Free PMC Article

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