University of Otago, Department of Chemistry
Plant and Food Research Dunedin
Discovery of unique bibenzyl cannabinoids in the taonga liverwort Radula marginata: parallels with Cannabis chemistry
Plant & Food Research natural chemists Catherine Sansom and Nigel Perry, working with Māori partners Manu Caddie and Waikato hapu and PFR biologists, have just published their discovery of “new” cannabinoids in an endemic liverwort Unique bibenzyl cannabinoids in the liverwort Radula marginata: parallels with Cannabis chemistry - Andre - New Phytologist - Wiley Online Library
Perrottetinene diol (trans-PTD), analogous to cannabidiol (trans-CBD) in medicinal cannabis, and its acid precursor (PTDA), were identified and fully characterised from nature for the first time. Bibenzyl-4-geranyl (BB4G), analogous to cannabigerol (CBG), and its corresponding acid (BB4GA), were also isolated. Radula marginata showed chemotypes dominated by PET, PTD, or BB4G, in striking analogy to the main Cannabis chemotypes. They add a new dimension to liverwort cannabinoids and suggest convergent evolution of biosynthesis in two distant plant lineages.
We are very pleased with this collaboration with kaitiaki (guardians) of this taonga (treasured native plant) – see video at Journal website, plus a couple of media items.
This tiny native plant has cannabis-like properties – here’s why that’s exciting - NZ Herald
Native species of liverwort mimics medicinal cannabis effect | RNZ
Gordon Group
Second year PhD student Jervee Punzalan has made promising contributions to food science with two recent publications. In Food Chemistry, Jervee introduced a rapid method for evaluating protein content in semi-refined flaxseed protein extracts using MicroNIR spectroscopy and chemometric analysis. This technique focuses on extracts produced through pulsed electric field (PEF)-assisted extraction.
Following this, her study in the Journal of Raman Spectroscopy (recently accepted) explored the fingerprinting of semi-refined flaxseed protein using Raman spectroscopy and multivariate analysis. This research revealed how PEF-assisted alkali and aqueous extraction methods affect the composition and protein conformation of flaxseed extracts. These consecutive publications not only showcase Jervee's work in plant-based proteins but also set the tone for her future contributions to food science and spectroscopy.
The 11th International Conference on Advanced Materials and Nanotechnology (AMN11) was recently held in Christchurch, and ElKhansa ElBashier, Keith Gordon and Sam Harris all gave talks at it. Khansa talked about here recent work on donor-acceptor systems which she published in January (https://pubs.acs.org/doi/full/10.1021/acs.jpca.4c07364). Keith talked about new strategies to extend excited state lifetimes and how that might help develop hydrogen generation photocatalysts.
The session of talks also included presentations from Stephan Kupfer and Georgina Shillito (from Jena) about their work on excited state calculations and was a great focus for the hydrogen generation photocatalyst project funded by Marsden; Stephan and Georgina were in Dunedin for a Marsden catch up meeting after the conference.
There was also a nice catch up with our Korean research colleagues including Han Young Woo (Korea University), Tae-Hyuk Kwon (Ulsan) and Jin Young Kim (Ulsan). Our ongoing work with them includes using resonance Raman to investigate degradation in polymer solar cells, correlation of GIWAXS signatures to low frequency Raman spectra and donor-acceptor systems.
Anam Zulfiqar, a PhD research scholar who commenced her studies in October 2024 under the supervision of Prof. Keith C. Gordon. Anam is funded by Te Whai Ao the Dodd-Walls Centre Originally from Pakistan, she completed her master's degree at the University of Agriculture, Faisalabad, Pakistan.
Wu Group
Dr Yanfang Wu joined the chemistry department at Otago as a lecturer in November 2024. His research focuses on measurement science and disease diagnostics. His primary interests are developing and applying new biosensors and sensing technologies to address fundamental and applied problems in chemistry and biochemistry.
We also welcomed new PhD student, Andrew Wilson, to the group in early February 2025.
Students’ conference reports
Simon Su attended the CRS Annual Meeting at Bologna (8-12 July 2024, Bologna, Italy) and gave his poster presentation on, “Overcoming efflux-mediated multidrug resistance in Pseudomonas aeruginosa”.
“The CRS annual meeting in Bologna was held from the 7th July to 13th July 2024 at the Bologna Congress Center. The theme of the conference this year was: “Integrating delivery science across disciplines” and the organisers were true to their word, offering an impressive 17 session categories ranging from nanomedicines to artificial intelligence & predictive models in pharmaceuticals technologies.
The judges appeared as a pair to critique my poster. Both judges were very intrigued by the idea of using a bacteria’s own machinery to overcome antimicrobial resistance. Personally, I believe that my short poster presentation was well received by the judges. This was hinted via multiple factors. Despite the time crunch and the numerous posters they had to mark, they showed genuine interest in my work and they took the time to stay much longer at my booth and spent a majority of the questioning asking “what if” questions to determine the future prospects of the project. They ended off their remarks with, “I hope it works” and I remember feeling quite accomplished and proud of the project.
I also had the opportunity to talk to many of the companies sponsoring the event and we are currently in talks discussing what we could try to improve the delivery of my prodrugs for in vivo studies. An example of this communication is with InsideTx, which has an innovative system called the “TAMARA” to aid the development of lipid nanoparticles. I am excited to see if this ends up as a collaboration!
Ultimately, going overseas to attend an international conference has been eye-opening for both my personal and professional development. I am very grateful to the NZIC for the financial aid to support my attendance.”
Selena Gilmer attended the RACI Organic24 conference in Adelaide, Australia.
“I had the pleasure of attending the RACI Organic 24 conference in November 2024 in Adelaide, Australia. The conference was located at the National Wine Centre of Australia in the botanical gardens which made for an amazing venue for a great 4 days of talks and discussion.
Talks ranged from total synthesis to methodology and med chem, all of which were interesting and thought provoking. I thoroughly enjoyed the plenary talks by Professor Tehshik Yoon from the University of Wisconsin-Madison which explored the use of photochemistry in total synthesis and a plenary talk by Daniel Werz from the University of Freiberg which explored novel BODIPY fluorophore chemistry.
The Organic 24 conference was a great chance to meet academics from NZ, Australia and beyond but also a great opportunity to meet other PhD students and postdoctoral researchers. The poster session of the conference was also a highlight, as it was a good way to casually meet fellow PhD students and chat with academics. I was grateful to have been awarded one of the five poster prizes for the work I presented on, “Development of photocleavable, fluorogenic dihydrotetrazines for a triggered tetrazine ligation”.
I am also very thankful to NZIC for helping to sponsor my travel!”
Jackson Henneveld also attended the RACI Organic24 conference in Adelaide, Australia and won the best oral presentation award from his talk about his PhD work. Well done!
“In November 2024, I was fortunate enough to attend the RACI Organic24 conference in Adelaide, Australia. As well as being my first conference experience, this was also my first time out of New Zealand, which was really exciting. The conference was held at the National Wine Centre of Australia in the botanic gardens, and Australian native plants and animals could be readily encountered on the walk to the venue.
The keynote and plenary talks were all super interesting – I particularly liked the presentations given by Lara Malins, Richmond Sarpong and Jonathan George. My brain was completely full of chemistry by the last day, and I even came away with some fresh ideas for my own research. The parallel talks and poster sessions were an excellent way to meet students and researchers, all while partaking in the great food and wine.
I presented the latter half of my PhD work during the parallel talk sessions on the first day, and was pleased to be awarded one of the best talk prizes. I also won a CAS Australia random giveaway bag, including a Bluetooth speaker, a keep cup, a moleskin journal and lots of other goodies.
A big thank you to the NZIC for helping sponsor this trip!”
