Adriana R. Dutra‐Nobre

University of Tasmania

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Nathan L. Kilah

University of Tasmania

Alex C. Bissember

University of Tasmania

Jason A. Smith

University of Tasmania

Wesley J. Olivier

University of Tasmania

Fernando Maya

University of Tasmania

Bianca J. Deans

University of Tasmania

Thinley Gyeltshen

University of Tasmania

Cooperative Institutions

University of Tasmania

Australian National University

University of Oxford

Hobart Private Hospital

Green Chemistry

California Institute of Technology

Massachusetts Institute of Technology

Universitat de les Illes Balears

Clinica Rotger

Sapporo Science Center

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Intraspecific Variation in the Terpene Profiles of Dodonaea viscosa

Asian Journal of Organic Chemistry (2023)

Adriana R. Dutra‐Nobre Wesley J. Olivier Bianca J. Deans Nathan L. Kilah Fernando Maya

Abstract Natural products isolation studies were performed on Dodonaea viscosa plant individuals sampled across seven different populations, which revealed considerable intraspecific variation in the terpene profiles across D. viscosa . In total, 14 ent‐ labdane diterpenoids (seven of which are previously unreported), four ent‐ kauranes (one which is previously unreported), one rare norhopene, and two previously unreported monoterpenoid wax esters were isolated. Exceedingly few terpene wax esters have been reported in Nature and the isolation of these unusual secondary metabolites is particularly notable for this reason. In each case, the proposed structures were elucidated employing various standard one‐ and two‐dimensional NMR ( 1 H, 13 C, NOESY, COSY, HSQC, HMBC) spectroscopic techniques and complemented by IR spectroscopy, mass spectrometry, and polarimetry, where appropriate. Synthetic derivatization and X‐ray crystallographic analysis were also employed to further support or secure structural assignments.

Terpene

Labdane

10.1002/ajoc.202300039

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Terpenoids and Unusual Flavonoids Bearing Prenylated Malonic Acids in Dodonaea Species

Asian Journal of Organic Chemistry (2023)

Thinley Gyeltshen Wesley J. Olivier Adriana R. Dutra‐Nobre Nathan L. Kilah Jason A. Smith

Abstract Natural products isolation studies were performed on two Dodonaea species. This led to the discovery of one previously unreported prenylated flavonoid bearing a malonic acid moiety and six known compounds from the aerial parts of Dodonaea filiformis . In addition, three previously unreported natural products (another malonic‐acid‐containing prenylated flavonoid, a prenylated flavonoid and an ent ‐labdane diterpenoid) and seven known compounds were found from the flowers of D. viscosa . Furthermore, as a result of this work, a revised structure is proposed for a prenylated flavonoid previously isolated from D. viscosa .

Labdane

Malonic acid

10.1002/ajoc.202300259

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