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Anti-staphylococcal activity of C-methyl flavanones from propolis of Australian stingless bees (Tetragonula carbonaria) and fruit resins of Corymbia torelliana (Myrtaceae).
Fitoterapia. 2014 Jun; 95:247-57.F

Abstract

Propolis of Australian stingless bees (Tetragonula carbonaria, Meliponini) originating from Corymbia torelliana (Myrtaceae) fruit resins was tested for its antimicrobial activities as well as its flavonoid contents. This study aimed at the isolation, structural elucidation and antibacterial testing of flavanones of C. torelliana fruit resins that are incorporated into stingless bee propolis. Flavanones of this study were elucidated by spectroscopic and spectrometric methods including UV, 1D and 2D NMR, EI-MS, ESI-MS and HR-MS. The results indicated known C-methylated flavanones namely, 1 (2S)-cryptostrobin, its regioisomer 2 (2S)- stroboponin, 3 (2S)- cryptostrobin 7-methyl ether, and 6 (2S)- desmethoxymatteucinol, and known flavanones 4 (2S)- pinostrobin and 5 (2S)- pinocembrin as markers for C. torelliana fruit resins and one propolis type. Ethanolic preparations of propolis were shown to be active against Staphylococcus aureus (ATCC 25923) and to a lesser extent against Pseudomonas aeruginosa (ATCC 27853). C. torelliana flavanones inhibited the growth of S. aureus therefore contributing to the antibacterial effects observed for Australian stingless bee propolis extracts.

Authors+Show Affiliations

Genecology Research Centre, Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore DC, Australia. Electronic address: cfmassaro@gmail.com.Genecology Research Centre, Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore DC, Australia.Eskitis Institute for Drug Discovery, Griffith University, Nathan, Australia.Eskitis Institute for Drug Discovery, Griffith University, Nathan, Australia.Eskitis Institute for Drug Discovery, Griffith University, Nathan, Australia.CSIRO Brisbane, Ecosystem Sciences, Brisbane, Australia.Queensland University of Technology, Queensland, Brisbane, Australia.Chemistry Department, University of Waikato, Hamilton, New Zealand.Genecology Research Centre, Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore DC, Australia.Genecology Research Centre, Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore DC, Australia.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

24704551

Citation

Massaro, C F., et al. "Anti-staphylococcal Activity of C-methyl Flavanones From Propolis of Australian Stingless Bees (Tetragonula Carbonaria) and Fruit Resins of Corymbia Torelliana (Myrtaceae)." Fitoterapia, vol. 95, 2014, pp. 247-57.
Massaro CF, Katouli M, Grkovic T, et al. Anti-staphylococcal activity of C-methyl flavanones from propolis of Australian stingless bees (Tetragonula carbonaria) and fruit resins of Corymbia torelliana (Myrtaceae). Fitoterapia. 2014;95:247-57.
Massaro, C. F., Katouli, M., Grkovic, T., Vu, H., Quinn, R. J., Heard, T. A., Carvalho, C., Manley-Harris, M., Wallace, H. M., & Brooks, P. (2014). Anti-staphylococcal activity of C-methyl flavanones from propolis of Australian stingless bees (Tetragonula carbonaria) and fruit resins of Corymbia torelliana (Myrtaceae). Fitoterapia, 95, 247-57. https://doi.org/10.1016/j.fitote.2014.03.024
Massaro CF, et al. Anti-staphylococcal Activity of C-methyl Flavanones From Propolis of Australian Stingless Bees (Tetragonula Carbonaria) and Fruit Resins of Corymbia Torelliana (Myrtaceae). Fitoterapia. 2014;95:247-57. PubMed PMID: 24704551.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Anti-staphylococcal activity of C-methyl flavanones from propolis of Australian stingless bees (Tetragonula carbonaria) and fruit resins of Corymbia torelliana (Myrtaceae). AU - Massaro,C F, AU - Katouli,M, AU - Grkovic,T, AU - Vu,H, AU - Quinn,R J, AU - Heard,T A, AU - Carvalho,C, AU - Manley-Harris,M, AU - Wallace,H M, AU - Brooks,P, Y1 - 2014/04/04/ PY - 2014/01/03/received PY - 2014/03/24/revised PY - 2014/03/26/accepted PY - 2014/4/8/entrez PY - 2014/4/8/pubmed PY - 2015/1/8/medline KW - 1 (2S)-cryptostrobin (PubChem CID 15953986, CAS 55743-21-0) KW - 2 (2S)- strobopinin (PubChem CID 442520, CAS 11023-71-5) KW - 3 (2S)- cryptostrobin 7-methyl ether (CAS 55869-77-7) KW - 4 (2S)- pinostrobin (PubChem CID 73201, CAS 480-37-5) KW - 5 (2S)- pinocembrin (PubChem CID 25200438, CAS 480-39-7) KW - 6 (2S)- desmethoxymatteucinol (CID 180550, CAS 56297-79-1) KW - Antibacterial KW - Eucalyptus KW - NMR spectroscopy KW - Natural products KW - Staphylococcus aureus SP - 247 EP - 57 JF - Fitoterapia JO - Fitoterapia VL - 95 N2 - Propolis of Australian stingless bees (Tetragonula carbonaria, Meliponini) originating from Corymbia torelliana (Myrtaceae) fruit resins was tested for its antimicrobial activities as well as its flavonoid contents. This study aimed at the isolation, structural elucidation and antibacterial testing of flavanones of C. torelliana fruit resins that are incorporated into stingless bee propolis. Flavanones of this study were elucidated by spectroscopic and spectrometric methods including UV, 1D and 2D NMR, EI-MS, ESI-MS and HR-MS. The results indicated known C-methylated flavanones namely, 1 (2S)-cryptostrobin, its regioisomer 2 (2S)- stroboponin, 3 (2S)- cryptostrobin 7-methyl ether, and 6 (2S)- desmethoxymatteucinol, and known flavanones 4 (2S)- pinostrobin and 5 (2S)- pinocembrin as markers for C. torelliana fruit resins and one propolis type. Ethanolic preparations of propolis were shown to be active against Staphylococcus aureus (ATCC 25923) and to a lesser extent against Pseudomonas aeruginosa (ATCC 27853). C. torelliana flavanones inhibited the growth of S. aureus therefore contributing to the antibacterial effects observed for Australian stingless bee propolis extracts. SN - 1873-6971 UR - https://www.unboundmedicine.com/medline/citation/24704551/Anti_staphylococcal_activity_of_C_methyl_flavanones_from_propolis_of_Australian_stingless_bees__Tetragonula_carbonaria__and_fruit_resins_of_Corymbia_torelliana__Myrtaceae__ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0367-326X(14)00098-7 DB - PRIME DP - Unbound Medicine ER -