S1 Supporting Information Contents Page

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1 S1 Supporting Information Contents Page Title: Bioactive Dihydro-β-agarofuran Sesquiterpenoids from the Australian Rainforest Plant Maytenus bilocularis Authors: Mario Wibowo, Claire Levrier,, Martin C. Sadowski, Colleen C. Nelson, Qian Wang,, Jeff Holst,, Peter C. Healy, Andreas Hofmann,,ǁ and Rohan A. Davis*, Eskitis Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia Australian Prostate Cancer Research Centre - Queensland, Institute of Health and Biomedical Innovation, Queensland University of Technology, Princess Alexandra Hospital, Translational Research Institute, Brisbane, QLD 4102, Australia Origins of Cancer Program, Centenary Institute, University of Sydney, Camperdown, NSW 2050, Australia Sydney Medical School, University of Sydney, NSW 2006, Australia ǁ Faculty of Veterinary and Agricultural Sciences, The University of Melbourne, Parkville, Victoria 3010, Australia School of Natural Sciences, Griffith University, Brisbane, QLD, 4111, Australia Corresponding Author Contact Details: Tel.: Fax: r.davis@griffith.edu.au Contents: S1 1 H NMR (500 MHz) Spectrum of Bilocularin A (1) in CDCl 3 S2 13 C NMR Spectrum (125 MHz) of Bilocularin A (1) in CDCl 3 S3 HSQC Spectrum of Bilocularin A (1) in CDCl 3 S4 COSY Spectrum of Bilocularin A (1) in CDCl 3 S5 HMBC Spectrum of Bilocularin A (1) in CDCl 3

2 S6 ROESY Spectrum of Bilocularin A (1) in CDCl 3 S7 1 H NMR (500 MHz) Spectrum of Bilocularin B (2) in CDCl 3 S8 13 C NMR (125 MHz) Spectrum of Bilocularin B (2) in CDCl 3 S9 HSQC Spectrum of Bilocularin B (2) in CDCl 3 S10 COSY Spectrum of Bilocularin B (2) in CDCl 3 S11 HMBC Spectrum of Bilocularin B (2) in CDCl 3 S12 ROESY Spectrum of Bilocularin B (2) in CDCl 3 S13 1 H NMR (500 MHz) Spectrum of Bilocularin C (3) in CDCl 3 S14 13 C NMR (125 MHz) Spectrum of Bilocularin C (3) in CDCl 3 S15 HSQC Spectrum of Bilocularin C (3) in CDCl 3 S16 COSY Spectrum of Bilocularin C (3) in CDCl 3 S17 HMBC Spectrum of Bilocularin C (3) in CDCl 3 S18 ROESY Spectrum of Bilocularin C (3) in CDCl 3 S19 1 H NMR (500 MHz) Spectrum of Compound 7 in CDCl 3 S20 13 C NMR (125 MHz) Spectrum of Compound 7 in CDCl 3 S21 1 H NMR (500 MHz) Spectrum of Compound 8 in CDCl 3 S22 13 C NMR (125 MHz) Spectrum of Compound 8 in CDCl 3 S23 1 H NMR (500 MHz) Spectrum of Compound 10 in CDCl 3 S24 13 C NMR (125 MHz) Spectrum of Compound 10 in CDCl 3 S25 1 H NMR (500 MHz) Spectrum of Compound 11 in CDCl 3 S26 13 C NMR (125 MHz) Spectrum of Compound 11 in CDCl 3 S27 1 H NMR (500 MHz) Spectrum of Compound 13 in CDCl 3 S28 13 C NMR (125 MHz) Spectrum of Compound 13 in CDCl 3 S29 COSY and Selected HMBC Correlations of Compounds 2 and 3 S30 Key ROESY Correlations of Compounds 2 and 3 S31 Inhibitory Effect of Compounds 1 13 against the LNCaP Cell Line

3 S1 1H NMR (500 MHz) Spectrum of Bilocularin A (1) in CDCl3

4 S2 13 C NMR Spectrum (125 MHz) of Bilocularin A (1) in CDCl3

5 S3 HSQC Spectrum of Bilocularin A (1) in CDCl3

6 S4 COSY Spectrum of Bilocularin A (1) in CDCl3

7 S5 HMBC Spectrum of Bilocularin A (1) in CDCl3

8 S6 ROESY Spectrum of Bilocularin A (1) in CDCl3

9 S7 1H NMR (500 MHz) Spectrum of Bilocularin B (2) in CDCl3

10 S8 13C NMR (125 MHz) Spectrum of Bilocularin B (2) in CDCl3

11 S9 HSQC Spectrum of Bilocularin B (2) in CDCl3

12 S10 COSY Spectrum of Bilocularin B (2) in CDCl3

13 S11 HMBC Spectrum of Bilocularin B (2) in CDCl3

14 S12 ROESY Spectrum of Bilocularin B (2) in CDCl3

15 S13 1H NMR (500 MHz) Spectrum of Bilocularin C (3) in CDCl3

16 S14 13C NMR (125 MHz) Spectrum of Bilocularin C (3) in CDCl3

17 S15 HSQC Spectrum of Bilocularin C (3) in CDCl3

18 S16 COSY Spectrum of Bilocularin C (3) in CDCl3

19 S17 HMBC Spectrum of Bilocularin C (3) in CDCl3

20 S18 ROESY Spectrum of Bilocularin C (3) in CDCl3

21 S19 1H NMR (500 MHz) Spectrum of Compound 7 in CDCl3

22 S20 13C NMR (125 MHz) Spectrum of Compound 7 in CDCl3

23 S21 1H NMR (500 MHz) Spectrum of Compound 8 in CDCl3

24 S22 13C NMR (125 MHz) Spectrum of Compound 8 in CDCl3

25 S23 1H NMR (500 MHz) Spectrum of Compound 10 in CDCl3

26 S24 13C NMR (125 MHz) Spectrum of Compound 10 in CDCl3

27 S25 1H NMR (500 MHz) Spectrum of Compound 11 in CDCl3

28 S26 13C NMR (125 MHz) Spectrum of Compound 11 in CDCl3

29 S27 1H NMR (500 MHz) Spectrum of Compound 13 in CDCl3

30 S28 13C NMR (125 MHz) Spectrum of Compound 13 in CDCl3

31 S29 COSY and Selected HMBC Correlations of Compounds 2 and 3 S30 Key ROESY Correlations of Compounds 2 and 3

32 S31 Inhibitory Effect of Compounds 1 13 against the LNCaP Cell Line a Compound Inhibition at 10µM (%) ± ± ± ± ± ± ± ± ± ± ± ± ± 3.6 a Cell viability was measured using the alamarblue reagent after 72 h of treatment (n=4, mean ± SD). Vinblastine was used as positive control (IC 50 = 3.2 ± 0.1 nm)