Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Flowers in Australia: Phytochemical Studies on the Illawarra Flame Tree and Alstonville

Rudi Hendra A and Paul A. Keller A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry, University of Wollongong, NSW 2522, Australia.

B Corresponding author. Email: keller@uow.edu.au

Australian Journal of Chemistry 69(8) 925-927 https://doi.org/10.1071/CH16058
Submitted: 1 February 2016  Accepted: 28 April 2016   Published: 3 June 2016

Abstract

The first reported phytochemical studies on two species of flowers in Australia enabled the identification of six secondary metabolites from Illawarra flame tree flower (Brachychiton acerifolius) and seven secondary metabolites from the flowers of the Alstonville (Tibouchina lepidota). Pelargonidin 3-(6-coumarylglucoside)-5-(6-acetylglucoside) was found to be responsible for the red colour of B. acerifolius, whereas malvidin 3-(coumarylglucoside)-5-(acetylxyloside) was responsible for the purple colour of (T. lepidota) flowers. (2S)-4,5-Dihydroxyflavanone 7-O-β-d-glucuronide methyl ester was isolated for the first time from B. acerifolius, and its absolute configuration was determined by circular dichroism spectroscopy. Some of the traditional uses of B. acerifolius could also be correlated with the known activity of the isolated metabolites.


References

[1]  Aboriginal Communities of the Northern Territory of Australia, (Australia ACotNTo), Traditional Bush Medicines: An Aboriginal Pharmacopoeia 1988 (Greenhouse Publication Pty Ltd: Australia).

[2]  E. V. Lassak, T. McCarthy, Australian Medicinal Plants 2011 (Reed New Holland).

[3]  UNSW, Flora of New South Wales 2002 (UNSW, Australia).

[4]  P. G. Vital, W. L. Rivera, Asian Pac. J. Trop. Med. 2011, 4, 824.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsFSqu7nO&md5=14fef11cbcf341b3d690c4e17b2616d5CAS | 22014741PubMed |

[5]  K. Desoky, S. A. Youssef, Bull. Fac. Pharm. 1997, 35, 257.
         | 1:CAS:528:DyaK1cXktVSqtLY%3D&md5=732ecb21ee8e8afdf3948370e02dbaafCAS |

[6]  I. Cock, Internet J. Microbiol. 2007, 4, 1.

[7]  M. A. Farag, A. H. Abou Zeid, M. A. Hamed, Z. Kandeel, H. M. El-Rafie, R. H. El-Akad, Nat. Prod. Res. 2015, 29, 116.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhslCit7%2FL&md5=7b0d090b19ef6965710d4528634367ddCAS | 25296242PubMed |

[8]  F. M. dos Santos, M. G. de Souza, A. E. M. Crotti, C. H. Martins, S. R. Ambrósio, R. Veneziani, M. L. Silva, W. R. Cunha, Braz. J. Microbiol. 2012, 43, 793.
         | Crossref | GoogleScholarGoogle Scholar | 24031892PubMed |

[9]  D. Bass, V. Delpech, J. Beard, P. Bass, R. Walls, Aerobiologia 2000, 16, 107.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  R. M. Kuster, N. Arnold, L. Wessjohann, Biochem. Syst. Ecol. 2009, 37, 63.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXivVektr0%3D&md5=c426cda1507c6d00351fbfef1017e779CAS |

[11]  O. M. Mosquera, Y. M. Correra, J. Niño, Rev. Bras. Farmacogn. 2009, 19, 382.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  H. M. Sirat, M. F. Rezali, Z. Ujang, J. Agric. Food Chem. 2010, 58, 10404.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtFSjur3I&md5=d4fc3c0b1f19f341c3e86b5712d430bdCAS | 20809630PubMed |

[13]  W. R. Cunha, F. M. dos Santos, J. d. A. Peixoto, R. C. Veneziani, A. E. Crotti, M. L. Silva, A. A. d. S. Filho, S. Albuquerque, I. C. Turatti, J. K. Bastos, Pharm. Biol. 2009, 47, 744.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  K. Kazuma, N. Noda, M. Suzuki, Phytochemistry 2003, 62, 229.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XptlCkt7Y%3D&md5=0f117da9aefeafee8f3aba87921aa497CAS | 12482461PubMed |

[15]  K. Hosokawa, Y. Fukunaga, E. Fukushi, J. Kawabata, Phytochemistry 1995, 40, 567.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXot1GitLs%3D&md5=ed7cb7d8d0ab59a63886b59c06dabb31CAS |

[16]  S. Klaiklay, Y. Sukpondma, V. Rukachaisirikul, N. Hutadilok-Towatana, K. Chareonrat, Can. J. Chem. 2011, 89, 461.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjvFemsbs%3D&md5=51dc278c0dea527018e281dc516a78a4CAS |

[17]  D. Tarbeeva, S. Fedoreev, M. Veselova, A. Kalinovskii, P. Gorovoi, O. Vishchuk, S. Ermakova, P. Zadorozhnyi, Chem. Nat. Compd. 2015, 51, 451.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXptlOrsLw%3D&md5=c9c5b3eec5d71c2784a32b9fa1be7554CAS |

[18]  K.-J. Wang, C.-R. Yang, Y.-J. Zhang, Food Chem. 2007, 101, 365.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XotVehtrc%3D&md5=295ddcc223da6f64ace7932ce7fb4bf6CAS |

[19]  I. O. Vvedenskaya, R. T. Rosen, J. E. Guido, D. J. Russell, K. A. Mills, N. Vorsa, J. Agric. Food Chem. 2004, 52, 188.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhtVWitL3N&md5=2ce916b9bbd0a99f3ce71eaadd6eeb4fCAS | 14733493PubMed |

[20]  N. Terahara, H. Suzuki, K. Toki, H. Kuwano, N. Saito, T. Honda, J. Nat. Prod. 1993, 56, 335.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXktV2jt74%3D&md5=c55acad35a836e8d97eabcd4aa35ed0fCAS |

[21]  K. S. Rao, G. P. Jones, D. E. Rivett, D. J. Tucker, J. Agric. Food Chem. 1989, 37, 916.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXksFKjurY%3D&md5=d707711b35a814ac012f1f9e3eae5d25CAS |

[22]  T. P. T. Cushnie, A. J. Lamb, Int. J. Antimicrob. Agents 2005, 26, 343.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtFeitbfP&md5=02a1ec8ab9f5ebb209a3729358bc33f6CAS |

[23]  J. M. Calderon-Montano, E. Burgos-Morón, C. Pérez-Guerrero, M. López-Lázaro, Mini-Rev. Med. Chem. 2011, 11, 298.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXltlKgtL8%3D&md5=a9987bc764eff0f37fc1d90f515be1c6CAS | 21428901PubMed |

[24]  M. I. Tracanna, A. M. Fortuna, A. V. Contreras Cárdenas, A. K. Marr, W. R. McMaster, A. Gómez-Velasco, E. Sánchez-Arreola, L. R. Hernández, H. Bach, Phytother. Res. 2015, 29, 393.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXjvFyltbk%3D&md5=f09fad4562d3f3bc43654ccc53c0d43dCAS | 25417600PubMed |

[25]  A. Faried, D. Kurnia, L. Faried, N. Usman, T. Miyazaki, H. Kato, H. Kuwano, Int. J. Oncol. 2007, 30, 605.
         | 1:CAS:528:DC%2BD2sXjtFGgt7Y%3D&md5=2016b91335df238e2d48e73e298fe9edCAS | 17273761PubMed |

[26]  I. P. Süntar, E. K. Akkol, F. N. Yalçın, U. Koca, H. Keleş, E. Yesilada, J. Ethnopharmacol. 2010, 129, 106.
         | Crossref | GoogleScholarGoogle Scholar | 20132876PubMed |

[27]  A. Castañeda-Ovando, M. D. L. Pacheco-Hernández, M. E. Páez-Hernández, J. A. Rodríguez, C. A. Galán-Vidal, Food Chem. 2009, 113, 859.
         | Crossref | GoogleScholarGoogle Scholar |