The anticancer, antioxidant and antimicrobial properties of the sesquiterpene β-Caryophyllene from the essential oil of Aquilaria crassna
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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.
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β-Caryophyllene has demonstrated antimicrobial, anticarcinogenic, anti-inflammatory, antioxidant, anxiolytic-like, and local anesthetic effects and anticancer properties, including against prostate, breast, pancreatic, skin, leukemia, lymphatic, and cervical cancer.
“It has demonstrated antimicrobial, anticarcinogenic, anti-inflammatory, antioxidant, anxiolytic-like, and local anesthetic effects and anticancer properties, including against prostate, breast, pancreatic, skin, leukemia, lymphatic, and cervical cancer [11,14,21,37,38,39,40,41].”
From Clove essential oil (Syzygium aromaticum L. Myrtaceae): Extraction, chemical composition, food applications, and essential bioactivity for human health (2021) · cites this paper as [41]
Split into 2 atoms — 0 confirmed, 2 partially supported, 0 disputed, 0 misattributed, 0 unverifiable. Expand the claim to see per-atom verdicts.
Experimental — accuracy not yet measuredCEO has shown scavenging activity on radicals and inhibition of lipid peroxidation.
“CEO has shown scavenging activity on radicals and inhibition of lipid peroxidation [41,93].”
From Clove essential oil (Syzygium aromaticum L. Myrtaceae): Extraction, chemical composition, food applications, and essential bioactivity for human health (2021) · cites this paper as [41]
Section 2.3 (page unavailable) reports radical-scavenging activity for β-caryophyllene isolated from an essential oil, supporting that part of the claim. It does not report an inhibition-of-lipid-peroxidation test, and its antioxidant results concern the isolated compound rather than CEO as an oil. (LLM, conf=0.86)
Experimental — accuracy not yet measuredCEO has been tested against different cancer types, such as colon, lung, breast, pancreatic, leukemia, cervical, and prostate.
“CEO has been tested against different cancer types, such as colon [41,93], lung [93,95], breast [41], pancreatic [41], leukemia [41,94], cervical [41], and prostate [41,93].”
From Clove essential oil (Syzygium aromaticum L. Myrtaceae): Extraction, chemical composition, food applications, and essential bioactivity for human health (2021) · cites this paper as [41]
Section 3.10.1 and Table 3 in Section 2.5 report tests involving A. crassna essential oil or its isolated β-caryophyllene against colorectal, pancreatic, breast, leukemia and prostate cancer cell lines. The paper identifies ME-180 only as an invasive squamous cell carcinoma line, without specifying cervical cancer. Lung is cited to other sources in the citing sentence, not to this paper. (LLM, conf=0.84)
Experimental — accuracy not yet measuredThe radical scavenging ability of β-caryophyllene was approximately 1.25 and 3.23 μM by the DPPH and FRAP scavenging methods, respectively.
“Dahham et al. [41] reported that the radical scavenging ability of β-caryophyllene was approximately 1.25 and 3.23 μM by the DPPH and FRAP scavenging methods, respectively.”
From Clove essential oil (Syzygium aromaticum L. Myrtaceae): Extraction, chemical composition, food applications, and essential bioactivity for human health (2021) · cites this paper as [41]
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Cites
Mosmann, T. (1983) · Journal of Immunological Methods · doi:10.1016/0022-1759(83)90303-4 · Cited by 56,104 · see citing works
Antimicrobial agents from plants: Antibacterial activity of plant volatile oils
Dorman, H. J. D., & Deans, S. G. (2000) · Journal of Applied Microbiology · doi:10.1046/j.1365-2672.2000.00969.x · Cited by 4,334 · see citing works
Vinson, J. A., Dabbagh, Y. A., Serry, M. M., & Jang, J. (1995) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf00059a005 · Cited by 736 · see citing works
Cytotoxic activity screening of some indigenous Thai plants
Prayong, P., Barusrux, S., & Weerapreeyakul, N. (2008) · Fitoterapia · doi:10.1016/j.fitote.2008.06.007 · Cited by 337 · see citing works
Park, K., Nam, D., Yun, H., Lee, S., Jang, H.-J., Sethi, G., Cho, S. K., & Ahn, K. S. (2011) · Cancer Letters · doi:10.1016/j.canlet.2011.08.001 · Cited by 331 · see citing works
Cell migration and invasion assays
Valster, A. H., Tran, N. L., Nakada, M., Berens, M. E., Chan, A. Y., & Symons, M. H. (2005) · Methods · doi:10.1016/j.ymeth.2005.08.001 · Cited by 321 · see citing works
Apoptosis, cancer and cancer therapy
Bold, R. J., Termuhlen, P. M., & McConkey, D. J. (1997) · Surgical Oncology · doi:10.1016/s0960-7404(97)00015-7 · Cited by 286 · see citing works
Potential medicinal plants for CNS disorders: an overview
Kumar, V. (2006) · Phytotherapy Research · doi:10.1002/ptr.1970 · Cited by 268 · see citing works
Calleja, M. Á., Vieites, J. M., Montero‐Melendez, T., et al. (2012) · British Journal Of Nutrition · doi:10.1017/s0007114512001298 · Cited by 219 · see citing works
Chemical Constituents of Agarwood Originating from the Endemic Genus Aquilaria Plants
Chen, H., Wei, J., Yang, J., et al. (2012) · Chemistry & Biodiversity · doi:10.1002/cbdv.201100077 · Cited by 185 · see citing works
Chen, H., Yang, Y., Xue, J., et al. (2011) · Molecules · doi:10.3390/molecules16064884 · Cited by 177 · see citing works
Kamonwannasit, S., Nantapong, N., Kumkrai, P., et al. (2013) · Annals of Clinical Microbiology and Antimicrobials · doi:10.1186/1476-0711-12-20 · Cited by 128 · see citing works
Amiel, E., Ofir, R., Dudai, N., et al. (2012) · Evidence-based Complementary and Alternative Medicine · doi:10.1155/2012/872394 · Cited by 123 · see citing works
Chemoprevention of cancer: Phenolic antioxidants (BHT, BHA)
Hocman, G. (1988) · International Journal of Biochemistry · doi:10.1016/0020-711x(88)90158-9 · Cited by 116 · see citing works
Larger than life: Mitochondria and the Bcl-2 family
Skommer, J., Włodkowic, D., & Deptała, A. (2006) · Leukemia Research · doi:10.1016/j.leukres.2006.06.027 · Cited by 92 · see citing works
Kakino, M., Izuta, H., Ito, T., et al. (2010) · Bioscience Biotechnology and Biochemistry · doi:10.1271/bbb.100122 · Cited by 81 · see citing works
Effects of Agarwood Extracts on the Central Nervous System in Mice
Okugawa, H., Ueda, R., Matsumoto, K., et al. (1993) · Planta Medica · doi:10.1055/s-2006-959599 · Cited by 80 · see citing works
Effect of Jinkoh-eremol and Agarospirol from Agarwood on the Central Nervous System in Mice
Okugawa, H., Ueda, R., Matsumoto, K., et al. (1996) · Planta Medica · doi:10.1055/s-2006-957784 · Cited by 77 · see citing works
Haque, R. A., Iqbal, M. A., Asekunowo, P. O., et al. (2013) · Medicinal Chemistry Research · doi:10.1007/s00044-012-0461-8 · Cited by 76 · see citing works
Self-citationLaxative Effect of Agarwood Leaves and Its Mechanism
Hara, H., Yasuaki, I. S. E., Morimoto, N., et al. (2008) · Bioscience Biotechnology and Biochemistry · doi:10.1271/bbb.70361 · Cited by 68 · see citing works
Ahamed, M. B. K., Aisha, A. F. A., Nassar, Z. D., Siddiqui, J., Ismail, Z., Omari, S. M. S., Parish, C. R., & Majid, A. M. S. A. (2011) · Nutrition and Cancer · doi:10.1080/01635581.2012.630160 · Cited by 62 · see citing works
Self-citationWetwitayaklung, P., Thavanapong, N., & Charoenteeraboon, J. (2009) · Science, Engineering and Health Studies · doi:10.14456/sustj.2009.3 · Cited by 61 · see citing works
Antibacterial Compounds from Rose Bengal‐Sensitized Photooxidation of β‐Caryophyllene
Kim, Y. S., Park, S. J., Lee, E. J., Cerbo, R. M., Lee, S. M., Ryu, C.-H., Kim, G. S., Kim, J. O., & Ha, Y. L. (2008) · Journal of Food Science · doi:10.1111/j.1750-3841.2008.00879.x · Cited by 47 · see citing works
Antipyretic, analgesic and anti-oxidative activities of Aquilaria crassna leaves extract in rodents
Sattayasai, J., Bantadkit, J., Aromdee, C., et al. (2012) · Journal of Ayurveda and Integrative Medicine · doi:10.4103/0975-9476.104427 · Cited by 45 · see citing works
Baharetha, H. M., Nassar, Z. D., Aisha, A. F. A., et al. (2013) · Journal of Medicinal Food · doi:10.1089/jmf.2012.2624 · Cited by 37 · see citing works
Al‐Suede, F. S. R., Ahamed, M. B. K., Majid, A. S. A., Baharetha, H. M., Hassan, L. E. A., Kadir, M. O. A., Nassar, Z. D., & Majid, A. M. S. A. (2014) · Evidence-based Complementary and Alternative Medicine · doi:10.1155/2014/396016 · Cited by 37 · see citing works
Self-citationAntimicrobial activity and cytotoxicity of Trapa bispinosa
Rahman, M. (2000) · Fitoterapia · doi:10.1016/s0367-326x(00)00226-4 · Cited by 36 · see citing works
Jafari, S. F., Ahamed, M. B. K., Iqbal, M. A., Al‐Suede, F. S. R., Khalid, S. H., Haque, R. A., Nassar, Z. D., Umar, M. I., & Majid, A. M. S. A. (2014) · Journal of Pharmacy and Pharmacology · doi:10.1111/jphp.12272 · Cited by 32 · see citing works
Self-citationHassan, L. E. A., Ahamed, M. B. K., Majid, A. S. A., et al. (2014) · PLoS ONE · doi:10.1371/journal.pone.0090806 · Cited by 32 · see citing works
Self-citationAhamed, M. B. K., Krishna, V., & Dandin, C. J. (2010) · European Journal of Pharmacology · doi:10.1016/j.ejphar.2009.12.034 · Cited by 32 · see citing works
Self-citationIto, T., Kakino, M., Tazawa, S., et al. (2012) · Food Science and Technology Research · doi:10.3136/fstr.18.259 · Cited by 32 · see citing works
Synthesis, characterization and antibacterial activity of a curcumin–silver(I) complex
Syed, H. K., Iqbal, M. A., Haque, R. A., et al. (2015) · Journal of Coordination Chemistry · doi:10.1080/00958972.2014.1003051 · Cited by 30 · see citing works
Self-citationKoetjapic acid, a natural triterpenoid, induces apoptosis in colon cancer cells
Majid, A. M. S. A. (2011) · Oncology Reports · doi:10.3892/or.2011.1569 · Cited by 27 · see citing works
Self-citationIsolation of Bactericidal Constituents from the Stem Bark Extract of Grewia tiliaefolia Vahl.
Ahamed, M. B. K., Krishna, V., ., H. B. G., et al. (2007) · Research Journal of Medicinal Plant · doi:10.3923/rjmp.2007.72.82 · Cited by 23 · see citing works
Self-citationKumphune, S., Prompunt, E., Phaebuaw, K., et al. (2011) · International Journal of Green Pharmacy · doi:10.4103/0973-8258.82099 · Cited by 21 · see citing works
Kumphune, S., Prompunt, E., Phaebuaw, K., et al. (2011) · International Journal of Green Pharmacy · doi:10.22377/ijgp.v5i1.173 · Cited by 20 · see citing works
Kakino, M., Sugiyama, T., Kunieda, H., et al. (2012) · Pharmaceutica Analytica Acta · doi:10.4172/2153-2435.1000152 · Cited by 20 · see citing works
Bioactive essential oils from Aquilaria crassna for cancer prevention and treatment
Dahham, S. S., Ahamed, M. B. K., Saghir, S. M., et al. (2014) · doi:10.13140/2.1.3315.7125 · Cited by 14 · see citing works
Self-citationEffects of Ya-hom on blood pressure in rats
Suvitayavat, W., Tunglert, S., Thirawarapan, S. S., et al. (2005) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2004.12.004 · Cited by 10 · see citing works
Novriyanti, E., & Santosa, E. (2011) · Indonesian Journal of Forestry Research · doi:10.20886/ijfr.2011.8.2.101-113 · Cited by 10 · see citing works
Crystal Structures and Cytotoxicity of Ortho-Xylene Linked Bis-benzimidazolium Salts
Iqbal, M. A., Haque, R. A., Ahamed, S. A., et al. (2015) · Medicinal Chemistry · doi:10.2174/1573406411666150101153115 · Cited by 5 · see citing works
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Yeshi, K., Crayn, D., Ritmejerytė, E., & Wangchuk, P. (2022) · Molecules · doi:10.3390/molecules27010313 · Cited by 488 · see citing works
Haro-González, J. N., Castillo-Herrera, G. A., Martínez-Velázquez, M., & Espinosa-Andrews, H. (2021) · Molecules · doi:10.3390/molecules26216387 · Cited by 463 · see citing works
Li, W., Chen, H.-Q., Wang, H., Mei, W.-L., & Dai, H.-F. (2021) · Natural Product Reports · doi:10.1039/d0np00042f · Cited by 190 · see citing works
Mostafa, H. S. (2021) · Journal of Food Science · doi:10.1111/1750-3841.15854 · Cited by 78 · see citing works
Najar, B., Shortrede, J. E., Pistelli, L., & Buhagiar, J. (2020) · Chemistry & Biodiversity · doi:10.1002/cbdv.201900478 · Cited by 76 · see citing works
Nguyen, L. T., Myslivečková, Z., Szotáková, B., Špičáková, A., Lněničková, K., Ambrož, M., Kubíček, V., Krasulová, K., Anzenbacher, P., & Skálová, L. (2017) · Chemico-Biological Interactions · doi:10.1016/j.cbi.2017.10.021 · Cited by 67 · see citing works
- Authors
- Dahham, S., Tabana, Y., Iqbal, M., Ahamed, M., Ezzat, M., Majid, A., & Majid, A.
- Affiliations
- Universiti Sains Malaysia (MY)
- Corresponding author
- Majid, Aman
- Majid, Amin
- Venue
- Molecules
- Publisher
- MDPI AG
- Published
- 2015-06-26
- Volume
- 20
- Issue
- 7
- Pages
- 11808-11829
- ISSN
- 1420-3049 (ISSN-L)
- PMC
- PMC6331975
- OpenAlex
- W1629950689
- Cited by
- 834
- References
- 41
- Citations by year
- 2026: 69 · 2025: 116 · 2024: 108 · 2023: 124 · 2022: 82 · 2021: 91 · 2020: 86 · 2019: 58 · 2018: 41 · 2017: 34 · 2016: 22 · 2015: 2
- FWCI
- 15.07
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Licence
- Locations
- Molecules (publishedVersion, cc-by)
- Europe PMC (PubMed Central) (publishedVersion, other-oa)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- Funders
- The authors gratefully acknowledge the financial support from Ministry of Agriculture, Malaysia (NRGS grant No: 304/PFARMASI/650583/K123)
- Universiti Sains Malaysia (USM) for the Research University Team (RUT Grant No.: 1001/PFARMASI/851001)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Wood and Agarwood Research
- Life Sciences › Agricultural and Biological Sciences › Food Science › Essential Oils and Antimicrobial Activity
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
- Keywords
- β-caryophyllene, Aquilaria crassna, essential oils, sesquiterpenes, antimicrobial activity, antibacterial activity, antifungal activity, antioxidant activity, cytotoxicity, colorectal cancer, apoptosis, mitochondrial membrane potential, cell migration and invasion, anticancer agents
- MeSH terms
- Polycyclic Sesquiterpenes, Anti-Infective Agents, Antineoplastic Agents, Antioxidants, Drug Screening Assays, Antitumor, Humans, Microbial Sensitivity Tests, Oils, Volatile, Sesquiterpenes, Molecular Structure, Thymelaeaceae, Cell Line, Tumor
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