Anti-staphylococcal activity of C-methyl flavanones from propolis of Australian stingless bees (Tetragonula carbonaria) and fruit resins of Corymbia torelliana (Myrtaceae).
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.
Genecology Research Centre, Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore DC, Australia. Electronic address: cfmassaro@gmail.com.
C F
CF
Massaro
Genecology Research Centre, Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore DC, Australia.
M
M
Katouli
Eskitis Institute for Drug Discovery, Griffith University, Nathan, Australia.
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T
Grkovic
Eskitis Institute for Drug Discovery, Griffith University, Nathan, Australia.
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H
Vu
Eskitis Institute for Drug Discovery, Griffith University, Nathan, Australia.
R J
RJ
Quinn
CSIRO Brisbane, Ecosystem Sciences, Brisbane, Australia.
T A
TA
Heard
Queensland University of Technology, Queensland, Brisbane, Australia.
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C
Carvalho
Chemistry Department, University of Waikato, Hamilton, New Zealand.
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M
Manley-Harris
Genecology Research Centre, Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore DC, Australia.
H M
HM
Wallace
Genecology Research Centre, Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore DC, Australia.
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P
Brooks
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001516:Bees / Q000737:chemistry*; D001688:Biological Products; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005638:Fruit / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D027822:Myrtaceae / Q000737:chemistry*; D011429:Propolis / Q000737:chemistry*; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D012116:Resins, Plant / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects
D000900:Anti-Bacterial Agents; D001688:Biological Products; D005419:Flavonoids; D012116:Resins, Plant; D011429:Propolis
1 (2S)-cryptostrobin (PubChem CID 15953986, CAS 55743-21-0); 2 (2S)- strobopinin (PubChem CID 442520, CAS 11023-71-5); 3 (2S)- cryptostrobin 7-methyl ether (CAS 55869-77-7); 4 (2S)- pinostrobin (PubChem CID 73201, CAS 480-37-5); 5 (2S)- pinocembrin (PubChem CID 25200438, CAS 480-39-7); 6 (2S)- desmethoxymatteucinol (CID 180550, CAS 56297-79-1); Antibacterial; Eucalyptus; NMR spectroscopy; Natural products; Staphylococcus aureus