Chemical Constituents of Kino Extract from Corymbia torelliana

Nobakht, M.; Grkovic, Tanja; Trueman, Stephen J.; Wallace, Helen M.; Katouli, Mohammad; Quinn, Ronald J.; Brooks, Peter

doi:10.3390/molecules191117862

Cited by 19 publications

(20 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…torelliana resin can easily be distinguished from resins of other tree species. It consists of a variety of terpenoids, phloroglucinols and flavonoids, with minor differences between trunk resin and fruit resin [ 34 , 35 ]. Stingless bees accurately learn its volatile profile as minor changes to the profile strongly reduce the attraction of bees [ 22 ].…”

Section: Discussionmentioning

confidence: 99%

Do Hybrid Trees Inherit Invasive Characteristics? Fruits of Corymbia torelliana X C. citriodora Hybrids and Potential for Seed Dispersal by Bees

Wallace¹,

Leonhardt²

2015

PLoS ONE

View full text Add to dashboard Cite

Tree invasions have substantial impacts on biodiversity and ecosystem functioning, and trees that are dispersed by animals are more likely to become invasive. In addition, hybridisation between plants is well documented as a source of new weeds, as hybrids gain new characteristics that allow them to become invasive. Corymbia torelliana is an invasive tree with an unusual animal dispersal mechanism: seed dispersal by stingless bees, that hybridizes readily with other species. We examined hybrids between C. torelliana and C. citriodora subsp. citriodora to determine whether hybrids have inherited the seed dispersal characteristics of C. torelliana that allow bee dispersal. Some hybrid fruits displayed the characteristic hollowness, resin production and resin chemistry associated with seed dispersal by bees. However, we did not observe bees foraging on any hybrid fruits until they had been damaged. We conclude that C. torelliana and C. citriodora subsp. citriodora hybrids can inherit some fruit characters that are associated with dispersal by bees, but we did not find a hybrid with the complete set of characters that would enable bee dispersal. However, around 20,000 hybrids have been planted in Australia, and ongoing monitoring is necessary to identify any hybrids that may become invasive.

show abstract

Section: Discussionmentioning

confidence: 99%

Do Hybrid Trees Inherit Invasive Characteristics? Fruits of Corymbia torelliana X C. citriodora Hybrids and Potential for Seed Dispersal by Bees

Wallace¹,

Leonhardt²

2015

PLoS ONE

View full text Add to dashboard Cite

show abstract

“…HR ESI-MS m / z calculated for C 16 H 14 O 5 [M + H] + 287.0914, found [M + H] + 287.0917, lit. HR ESI-MS m / z calculated for C 16 H 13 O 5 [M − H] − 285.0763, found [M − H] − 285.0771 [ 8 ].…”

Section: Methodsmentioning

confidence: 99%

“…Currently, there are known O -alkyl derivatives of naringenin containing methyl and ethyl groups attached to ring A and B. Naringenin and ether derivatives of naringenin were observed in plant extracts of the Boraginaceae family. In particular, 5- O -methylnaringenin, 7,4′-di- O -methylnaringenin and sakuranetin (7- O -methylnaringenin) ( Figure 1 ) were isolated from Cordia globosa , Echiochilon fruticosum , Heliotropium indicum , Heliotropium stenophyllum and Corymbia torelliana [ 7 , 8 ]. Sakuranetin, which is present in rice plants, is a natural phytoalexin and provides effective protection against damage caused by microorganisms [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Biological Activity of Novel O-Alkyl Derivatives of Naringenin and Their Oximes

et al. 2017

View full text Add to dashboard Cite

O-Alkyl derivatives of naringenin (1a–10a) were prepared from naringenin using the corresponding alkyl iodides and anhydrous potassium carbonate. The resulting products were used to obtain oximes (1b–10b). All compounds were tested for antimicrobial activity against Escherichia coli ATCC10536, Staphylococcus aureus DSM799, Candida albicans DSM1386, Alternaria alternata CBS1526, Fusarium linii KB-F1, and Aspergillus niger DSM1957. The resulting biological activity was expressed as the increase in optical density (ΔOD). The highest inhibitory effect against E. coli ATCC10536 was observed for 7,4′-di-O-pentylnaringenin (8a), 7-O-dodecylnaringenin (9a), naringenin oxime (NG-OX), 7,4′-di-O-pentylnaringenin oxime (8b), and 7-O-dodecylnaringenin oxime (9b) (ΔOD = 0). 7-O-dodecylnaringenin oxime (9b) also inhibited the growth of S. aureus DSM799 (ΔOD = 0.35) and C. albicans DSM1386 (ΔOD = 0.22). The growth of A. alternata CBS1526 was inhibited as a result of the action of 7,4′-di-O-methylnaringenin (2a), 7-O-ethylnaringenin (4a), 7,4′-di-O-ethylnaringenin (5a), 5,7,4′-tri-O-ethylnaringenin (6a), 7,4′-di-O-pentylnaringenin (8a), and 7-O-dodecylnaringenin (9a) (ΔOD in the range of 0.49–0.42) in comparison to that of the control culture (ΔOD = 1.87). In the case of F. linii KB-F1, naringenin (NG), 7,4′-di-O-dodecylnaringenin (10a), 7-O-dodecylnaringenin oxime (9b), and 7,4′-di-O-dodecylnaringenin oxime (10b) showed the strongest effect (ΔOD = 0). 7,4′-Di-O-pentylnaringenin (8a) and naringenin oxime (NG-OX) hindered the growth of A. niger DSM1957 (ΔOD = 0).

show abstract

“…We examined their activity against three Gram-negative bacteria, P. aeruginosa , E. coli , and Salmonella typhimurium , two Gram-positive bacteria, S. aureus and B. cereus , and one fungus, Candida albicans . Furthermore, we investigated the antibacterial activity against P. aeruginosa and S. aureus of seven individual flavonoids ( Figure 1 ) isolated from the kino of C. torelliana [ 30 ]. We also assessed whether the kino extracts and one of the most-abundant and active flavonoids in C. torelliana kino had cytotoxic effects.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial Properties of Flavonoids from Kino of the Eucalypt Tree, Corymbia torelliana

Nobakht¹,

Trueman²,

Wallace³

et al. 2017

Plants

Self Cite

View full text Add to dashboard Cite

Traditional medicine and ecological cues can both help to reveal bioactive natural compounds. Indigenous Australians have long used kino from trunks of the eucalypt tree, Corymbia citriodora, in traditional medicine. A closely related eucalypt, C. torelliana, produces a fruit resin with antimicrobial properties that is highly attractive to stingless bees. We tested the antimicrobial activity of extracts from kino of C. citriodora, C. torelliana × C. citriodora, and C. torelliana against three Gram-negative and two Gram-positive bacteria and the unicellular fungus, Candida albicans. All extracts were active against all microbes, with the highest activity observed against P. aeruginosa. We tested the activity of seven flavonoids from the kino of C. torelliana against P. aeruginosa and S. aureus. All flavonoids were active against P. aeruginosa, and one compound, (+)-(2S)-4′,5,7-trihydroxy-6-methylflavanone, was active against S. aureus. Another compound, 4′,5,7-trihydroxy-6,8-dimethylflavanone, greatly increased biofilm formation by both P. aeruginosa and S. aureus. The presence or absence of methyl groups at positions 6 and 8 in the flavonoid A ring determined their anti-Staphylococcus and biofilm-stimulating activity. One of the most abundant and active compounds, 3,4′,5,7-tetrahydroxyflavanone, was tested further against P. aeruginosa and was found to be bacteriostatic at its minimum inhibitory concentration of 200 µg/mL. This flavanonol reduced adhesion of P. aeruginosa cells while inducing no cytotoxic effects in Vero cells. This study demonstrated the antimicrobial properties of flavonoids in eucalypt kino and highlighted that traditional medicinal knowledge and ecological cues can reveal valuable natural compounds.

show abstract

Chemical Constituents of Kino Extract from Corymbia torelliana

Cited by 19 publications

References 18 publications

Do Hybrid Trees Inherit Invasive Characteristics? Fruits of Corymbia torelliana X C. citriodora Hybrids and Potential for Seed Dispersal by Bees

Do Hybrid Trees Inherit Invasive Characteristics? Fruits of Corymbia torelliana X C. citriodora Hybrids and Potential for Seed Dispersal by Bees

Synthesis and Biological Activity of Novel O-Alkyl Derivatives of Naringenin and Their Oximes

Antibacterial Properties of Flavonoids from Kino of the Eucalypt Tree, Corymbia torelliana

Contact Info

Product

Resources

About