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Natural Colours of Australia University of Wollongong Research Online University of Wollongong Thesis Collection 2017+ University of Wollongong Thesis Collections 2017 Natural colours of Australia Rudi Hendra University of Wollongong Follow this and additional works at: https://ro.uow.edu.au/theses1 University of Wollongong Copyright Warning You may print or download ONE copy of this document for the purpose of your own research or study. The University does not authorise you to copy, communicate or otherwise make available electronically to any other person any copyright material contained on this site. You are reminded of the following: This work is copyright. Apart from any use permitted under the Copyright Act 1968, no part of this work may be reproduced by any process, nor may any other exclusive right be exercised, without the permission of the author. Copyright owners are entitled to take legal action against persons who infringe their copyright. A reproduction of material that is protected by copyright may be a copyright infringement. A court may impose penalties and award damages in relation to offences and infringements relating to copyright material. Higher penalties may apply, and higher damages may be awarded, for offences and infringements involving the conversion of material into digital or electronic form. Unless otherwise indicated, the views expressed in this thesis are those of the author and do not necessarily represent the views of the University of Wollongong. Recommended Citation Hendra, Rudi, Natural colours of Australia, Doctor of Philosophy thesis, School of Chemistry, University of Wollongong, 2017. https://ro.uow.edu.au/theses1/23 Research Online is the open access institutional repository for the University of Wollongong. For further information contact the UOW Library: [email protected] NATURAL COLOURS OF AUSTRALIA A thesis submitted in fulfillment of the requirements for the award of the degree of DOCTOR OF PHILOSOPHY UNIVERSITY OF WOLLONGONG by Rudi Hendra S.Si., Apt., University of Padjadjaran (Indonesia) M.Sc, University of Putra Malaysia (Malaysia) Supervisor: Prof. Paul A. Keller SCHOOL OF CHEMISTRY 2017 Declaration I, Rudi Hendra hereby declare that this thesis, submitted in fulfilment of the requeirements for the award of the degree of Doctor of Phylosophy, in the School of Chemistry, University of Wollongong, is fully my own work unless otherwise referenced or acknowledged. The document has not been submitted for qualifications at any other academic institutions. i Abstract The environment of Australia is rich with colourful plants and animals, which have been used for different purposes. This thesis describes the identification of fifty secondary metabolites from eight separate species Australian, including from flowers, parrot feathers, and moss. Phytochemical studies on the flowers from four native Australian species (Brachychiton acerifolius, Anigozanthos rufus, Anigozanthos pulcherrimus, and Acacia pycnantha) and additionally, two introduced species (Tibouchina lepidota and Jacaranda mimosafolia) that are commonly grow in Australia, revealed a total of 36 secondary metabolites including five examples which may be responsible for the colouration of the flowers: These were pelargonidin-3-(6-coumaryl-β-glucoside)-5-(6-acetyl-β-glucoside) 47, malvidin 3-(p-coumarylglucoside)-5-acetylxyloside 58, cyanidin-3-rutinoside 62, cyanidin-3-O-(6-O-p-coumaryl)glucoside 65, and isosalipurposide 84) and four new secondary metabolites (2S)-4',5-dihydroxylavanone 7-O-β-D-glucuronide methyl ester 50, 2-amino-6-O-p-coumarylheptanedioic acid 64, chalcone-5'-O-(4-O-p-coumaryl)- glucoside 70, and phenylethanoid glucoside 73. All secondary metabolites isolated in these studies were the first reported from the flowers of the species. Furthermore, the polar extracts from B. acerifolius and T. lepidota, and compounds 46, 49, and 58 showed inhibition of growth of Staphylococcus aureus (ATCC 43300) and Acinetobacter baumannii (ATCC 19606) at concentration value of 32 µg/mL. The second part of this thesis used natural product techniques to fully characterize the chemical components from the feathers of Australian parrots. Australian king parrot (Alisterus scapularis) feathers were initially investigated since this species was the most ii abundant deceased specimen available during the sample collection period. Standard extraction protocols were successfully developed and involved a soxhlet apparatus and methanol in contrast to published methods of acidic pyridine extraction in which our studies showed the generation of unwanted non-natural products. The GC-MS analysis of the hexane fraction indicated four common fatty acid identified as methyl palmitate (104), linoleic acid (105), methyl oleate (106), and methyl stearate (107). Furthermore, the methanol extract of green feathers of A. scapularis provided five major chemical components, identified as (3,4-dihdroxybenzoic acid (108), butanoic acid (109), 4- hydroxymethyl benzoate (110), p-hydroxybenzaldehyde (111), and genistein (112). During the isolation of chemical constituents from the green feathers, we were not able to isolate and identifiy any psittacofulvins-typed compounds which have been previously reported to be responsible for the colouration in parrots feathers. In addition, these laboratory protocols can be applied to investigate the chemical constituents from different coloured feathers e.g. red feathers from this species and other species in order to accumulated data from a wide range of Australian parrots. Our last natural product study was a re-evaluation the NMR spectroscopy data of biflavone compounds (113 and 114) from Australian populations of Ceratodon purpureus by following the same reported method of extraction and separation, then comparing the outcomes with Antarctic populations of this species. This resulted in the isolation and structural reassignment to 120 and 121, and an additional 3 different biflavanones-like compounds (119, 122 and 123). Compounds 120 and 121 were found to have similar spectroscopy data (MS and NMR) to 113 and 114, both were reassigned 5',3''''-dihydroxyamentoflavone and 2,3-dihydro-5',3''''-dihydroxyamentoflavone, respectively. All isolates absorbed in the ultraviolet spectrum and the two biflavones iii (120 and 121) showed relatively high antioxidant activities in comparison to the rutin positive control. These properties of 120 and 121 suggest that they are potentially involved in dual photoprotection mechanisms via both direct (UV-screening) and indirect (radical-scavenging) capacities in the moss and contributes to it survival mechanism in the harsh Antarctic environment. iv Acknowledments First, I would like to give my big sincere thanks my supervisor, Prof. Paul A. Keller, for giving me such a great opportunity to study of Australian natural products, guidance and support during the whole of my study in the School of Chemistry University of Wollongong. I have learnt so many things under your supervison, for helped me in developing scientific writing, and for being there every time I had a question. I would like also to thank to Dr Ari Nugraha for being such a good friend, mentor, and helping me during my early study specialy in elucidation structure. Another special thanks to Prof. Sharon A. Robinson and Dr Mellinda Waterman who with my supervisor allowed me to involve in the Antarctic moss (Ceratodon purpureus) project. I am also greatly indebted to to the following people who provided their help in completing this study: Dr Wilford Lie and Dr. Graham E. Ball for the NMR discussion and guideline, Dr Celine Kelso, Dr Alan Maccarone, Karin Maxwell for the Mass spectroscopic support, Mr Joe Daunt for the HPLC support, Dr. Anthony Willis for the crystallography, Australian National Wildlife Collection, CSIRO, Canberra and Cannon & Ball veterinary surgeons, Wollongong, Australia for supplying the parrots samples, Mr. Nathan Butterworth for GCMS support, Chemistry society UOW and Monica Birrento for giving me an experience as one of executive former and current KRG member: Alex, Alireza, Andrew, Aaron, Akash, Ashraf, Adel, Hendris, Yueting, Sreenu, Phuong, Matt, Stephen Bailey, Stephen Tibben, Steve, Harry, Patrick, Jayden, Mohammed, you are chemistry rockers. Special thanks to dynamic duo (Mr Jamie Smyth and Mr Nicholas Butler) for being great friend and time in the lab and office, you v are real marvel chaps and chemists. I would also like to thank the rest of school of chemistry members for showing me a great time during my study. Special appreciation to Dr. Glennys O’Brien for giving me an opportunity in the first- year teaching lab which were a valuable experience for my future academi career. I would like to thank to the Indonesian Directorate General Higher Education (DGHE) for providing scholarship and University of Wollongong for International Postgraduate Tuition Award (IPTA). Extended thanks go to Prof. Adel Zamri, Dr Hilwan Y. Teruna, Dr Christine Jose, Dr Yum Eryanti, Dr Yuana Nurulita, Yuharmen, Nurbalatif, Yuli Haryani, Ganis Fia Kartika at the Department of chemistry University of Riau for giving me support and being not only as colleague but also mentor, friend, and family. Finally thank to my family for infinite love and support, my parents, Rosni and the late Syamsuddin MY, Afrizal, Meri, Yoel, Budi, Lisa, Dewi, and all my nephews and nieces, I never thank you enough. I would also like to thanks to my extended family: om Aka, om Elan, om Rizky, om Widi, nenek Homsah, tante Tami, tante Unink, Haning, Laura,
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