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Maslovskaya L.A.,University of Queensland | Savchenko A.I.,Po Royal Brisbane Hospital | Gordon V.A.,EcoBiotics Ltd | Reddell P.W.,EcoBiotics Ltd | And 3 more authors.
Organic Letters | Year: 2011

The proposed cleistanthol biosynthetic intermediate en route to spruceanol, and other related family members, was isolated for the first time from Croton insularis, confirming the Jacobs-Reynolds hypothesis. Anticancer evaluation of the new isolates and their aerial oxidation products is also reported.(Figure Presented) © 2011 American Chemical Society.


Lamont R.W.,University of The Sunshine Coast | Conroy G.C.,University of The Sunshine Coast | Reddell P.,EcoBiotics Ltd. | Ogbourne S.M.,University of The Sunshine Coast
BMC Plant Biology | Year: 2016

Background: Fontainea picrosperma, a subcanopy tree endemic to the rainforests of northeastern Australia, is of medicinal significance following the discovery of the novel anti-cancer natural product, EBC-46. Laboratory synthesis of EBC-46 is unlikely to be commercially feasible and consequently production of the molecule is via isolation from F. picrosperma grown in plantations. Successful domestication and plantation production requires an intimate knowledge of a taxon's life-history attributes and genetic architecture, not only to ensure the maximum capture of genetic diversity from wild source populations, but also to minimise the risk of a detrimental loss in genetic diversity via founder effects during subsequent breeding programs designed to enhance commercially significant agronomic traits. Results: Here we report the use of eleven microsatellite loci (PIC = 0.429; P ID = 1.72 × 10-6) to investigate the partitioning of genetic diversity within and among seven natural populations of F. picrosperma. Genetic variation among individuals and within populations was found to be relatively low (A = 2.831; H E = 0.407), although there was marked differentiation among populations (PhiPT = 0.248). Bayesian, UPGMA and principal coordinates analyses detected three main genotypic clusters (K = 3), which were present at all seven populations. Despite low levels of historical gene flow (N m = 1.382), inbreeding was negligible (F = -0.003); presumably due to the taxon's dioecious breeding system. Conclusion: The data suggests that F. picrosperma was previously more continuously distributed, but that rainforest contraction and expansion in response to glacial-interglacial cycles, together with significant anthropogenic effects have resulted in significant fragmentation. This research provides important tools to support plantation establishment, selection and genetic improvement of this medicinally significant Australian rainforest species. © 2016 Lamont et al.


Maslovskaya L.A.,QIMR Berghofer Medical Research Institute | Savchenko A.I.,University of Queensland | Krenske E.H.,University of Queensland | Gordon V.A.,EcoBiotics Ltd | And 4 more authors.
Chemical Communications | Year: 2014

Investigation of Croton insularis afforded the first in class seco-casbane diterpene, EBC-329. A highly oxidised casbane, EBC-324, was also isolated. The structural motif within EBC-324, which consists of an epoxidised hemi-acetal endoperoxide, is new to the casbane family. This journal is © the Partner Organisations 2014.


Maslovskaya L.A.,QIMR Berghofer Medical Research Institute | Savchenko A.I.,University of Queensland | Pierce C.J.,QIMR Berghofer Medical Research Institute | Gordon V.A.,EcoBiotics Ltd | And 3 more authors.
Chemistry - A European Journal | Year: 2014

EBC-162 isolated from Croton insularis, obtained from the northern rainforest of Australia, was structurally affirmed as crotofolin C (4). Novel oxidative degradation products, EBC-233 and EBC-300, which are the first crotofolane endoperoxides, were also isolated. Both endoperoxides were found to be stable intermediates, which are proposed to undergo an unprecedented homo-Baeyer-Villiger biosynthetic rearrangement to give a new class of 1,14-seco-crotofolane diterpenes. Prolonged storage of all isolates assisted in authenticating their natural product status. Anticancer activities of reported compounds are presented. © 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.


Maslovskaya L.A.,Queensland Institute of Medical Research | Savchenko A.I.,University of Queensland | Krenske E.H.,University of Queensland | Pierce C.J.,Queensland Institute of Medical Research | And 4 more authors.
Angewandte Chemie - International Edition | Year: 2014

EBC-219 (4), isolated from Croton insularis (Baill), was established by spectroscopic and DFT methods as the first member of a new diterpene skeletal class, uniquely defined by the presence of a bicyclo[10.2.1] bridgehead olefin. The proposed biogenetic pathway to 4 from the co-isolated natural products EBC-131 (1), EBC-180 (2) and EBC-181 (3) is highly likely. EBC-180 (2) and EBC-181 (3) showed moderate to strong cytotoxic activity against various cancer cell lines. Julius Bredt and Australia have a common history in the search for naturally occurring gems. The work on monoterpenes leading to Bredt's rule continues to develop over a hundred years later in that the search for bioactive natural products has delivered EBC-219, a bicyclo[10.2.1] bridgehead olefin with an unprecedented diterpene carbon skeleton. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Patent
Ecobiotics Ltd | Date: 2013-05-17

The present invention relates to spiroketal compounds that are useful in methods of treating or preventing protozoal infections, parasitic infections, bacterial infections, cell proliferative disorders and anti inflammatory disorders. The spiroketal compounds are also useful as immunosuppressive agents, and also in methods of controlling pests.


Patent
Ecobiotics Ltd | Date: 2011-08-11

The present invention relates to spiroketal compounds that are useful in methods of treating or preventing protozoal infections, parasitic infections, bacterial infections, cell proliferative disorders and anti inflammatory disorders. The spiroketal compounds are also useful as immunosuppressive agents, and also in methods of controlling pests.


PubMed | Ecobiotics Ltd and University of Western Sydney
Type: Journal Article | Journal: Molecules (Basel, Switzerland) | Year: 2016

Chronic inflammation is an important pathological condition in many human diseases, and due to the side effects of the currently used non-steroidal anti-inflammatory drugs, discovery of novel anti-inflammatory drugs is of general interest. Anti-inflammatory activity guided compound isolation from the plant


Patent
EcoBiotics Ltd | Date: 2014-03-21

The present invention relates to spiroketal compounds that are useful in methods of treating or preventing protozoal infections, parasitic infections, bacterial infections, cell proliferative disorders and anti inflammatory disorders. The spiroketal compounds are also useful as immunosuppressive agents, and also in methods of controlling pests.


PubMed | QIMR Berghofer Medical Research Institute, University of Queensland and EcoBiotics Ltd
Type: | Journal: Chemistry (Weinheim an der Bergstrasse, Germany) | Year: 2016

Investigation of the Australian rainforest plant Croton insularis led to isolation of the first casbane hydroperoxide diterpenes EBC-304 and EBC-320. Extensive DFT and electronic circular dichroism (ECD) calculations in combination with 2D NMR spectroscopy determined the absolute configurations. EBC-304 and EBC-320 both display significant cytotoxicity.

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