Supporting Information. Antiproliferative Cardenolides from the Aerial Parts of Pergularia tomentosa

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Lucrezia Torre
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1 Supporting Information Antiproliferative Cardenolides from the Aerial Parts of Pergularia tomentosa Seyed Hamzeh Hosseini,, # Milena Masullo,, # Antonietta Cerulli, Stefania Martucciello, Mahdi Ayyari, Cosimo Pizza, Sonia Piacente * Department of Plant Biology, University of Jiroft, Jiroft, Iran Dipartimento di Farmacia, Università degli Studi di Salerno, Via Giovanni Paolo II 132, Fisciano, Salerno, Italy Dipartimento di Chimica e Biologia, Università degli Studi di Salerno, Via Giovanni Paolo II 132, Fisciano, Salerno, Italy Department of Horticultural Science, Faculty of Agriculture, Tarbiat Modares University, Tehran, Iran

2 Figure S1. A: LC-HRESIMS profile (negative-ion mode) of the methanol extract of P. tomentosa aerial parts. B: LC-HRESIMS profile (negative-ion mode) of the methanol extract of P. tomentosa roots. Figure S2. 1 H NMR Spectrum (600 MHz, CD 3 OD) of compound 4. Figure S3. HSQC Spectrum (CD 3 OD) of compound 4. Figure S4. HMBC Spectrum (CD 3 OD) of compound 4. Figure S5. COSY Spectrum (CD 3 OD) of compound 4. Figure S6. ROESY Spectrum (CD 3 OD) of compound 4. Figure S7. 1 H NMR Spectrum (600 MHz, CD 3 OD) of compound 13. Figure S8. HSQC Spectrum (CD 3 OD) of compound 13. Figure S9. HMBC Spectrum (CD 3 OD) of compound 13. Figure S10. COSY Spectrum (CD 3 OD) of compound 13. Figure S11. ROESY Spectrum (CD 3 OD) of compound 13. Figure S12. 1 H NMR Spectrum (600 MHz, CD 3 OD) of compound 14. Figure S13. HSQC Spectrum (CD 3 OD) of compound 14. Figure S14. HMBC Spectrum (CD 3 OD) of compound 14. Figure S15. COSY Spectrum (CD 3 OD) of compound 14. Figure S16. ROESY Spectrum (CD 3 OD) of compound 14. Table S1. Retention Times (R t ), Δ ppm, Molecular Formula, [M-H] -, [(M+HCOOH)-H] - and MS/MS values of compounds 1-25 of the MeOH Extract of P. tomentosa aerial parts and roots by LC-HRESIMS.

3 A B Figure S1. A: LC-HRESIMS profile (negative-ion mode) of the methanol extract of P. tomentosa aerial parts. B: LC-HRESIMS profile (negative-ion mode) of the methanol extract of P. tomentosa roots.

4 Figure S2. 1 H NMR Spectrum (600 MHz, CD 3 OD) of compound 4. Figure S3. HSQC Spectrum (CD 3 OD) of compound 4.

5 Figure S4. HMBC Spectrum (CD 3 OD) of compound 4. Figure S5. COSY Spectrum (CD 3 OD) of compound 4.

6 Figure S6. ROESY Spectrum (CD 3 OD) of compound 4. Figure S7. 1 H NMR Spectrum (600 MHz, CD 3 OD) of compound 13.

7 Figure S8. HSQC Spectrum (CD 3 OD) of compound 13. Figure S9. HMBC Spectrum (CD 3 OD) of compound 13.

8 Figure S10. COSY Spectrum (CD 3 OD) of compound 13. Figure S11. ROESY Spectrum (CD 3 OD) of compound 13.

9 Figure S12. 1 H NMR Spectrum (600 MHz, CD 3 OD) of compound 14. Figure S13. HSQC Spectrum (CD 3 OD) of compound 14.

10 Figure S14. HMBC Spectrum (CD 3 OD) of compound 14. Figure S15. COSY Spectrum (CD 3 OD) of compound 14.

11 Figure S16. ROESY Spectrum (CD 3 OD) of compound 14.

12 Table S1. Retention Times (R t ), Δ ppm, Molecular Formula, [M-H] -, [(M+HCOOH)-H] - and MS/MS Values of Compounds 1-25 of the MeOH Extract of P. tomentosa Aerial Parts and Roots by LC-HRESIMS. code t R a molecular formula Δ ppm [(M+HCOOH)-H] - [M-H] - MS/MS compound aerial parts roots (min) C 30 H 44 O , 467, 421 ghalakinoside X X C 30 H 42 O '-hydroxycalactin X X C 24 H 36 O β-hydroxycoroglaucigenin X X C 29 H 39 O , β,6'-dihydroxycalotropin. X X C 30 H 44 O , '-dehydroxyghalakinoside X X C 21 H 20 O quercetin 3-O-β-D-galactopyranoside X C 30 H 42 O α-hydroxycalotropin X X C 30 H 46 O , 373 glucocoroglaucigenin X X C 21 H 20 O , 255, 227 kaempferol-3-o-β-d-galactopyranoside X C 21 H 20 O , 255, 227 kaempferol-3-o-β-d-glucopyranoside X C 21 H 20 O quercetin-3-o-β-d-glucopyranoside X C 22 H 22 O , 315 isorhamnetin-3-o-β-d-glucopyranoside X C 30 H 42 O , 419, 401 6'β-hydroxycalotropin X X C 30 H 42 O β-hydroxycalactin X X C 30 H 44 O '-dehydroxyghalakinoside X X C 35 H 50 O O-β-glucopyranosiylcalactin X X C 30 H 46 O , 391,373 desglucouzarin X X C 24 H 36 O coroglaucigenin X X C 32 H 44 O α-acetoxycalotropin X X C 30 H 42 O , 403, 373, 271 calotropin X X C 30 H 42 O , 403, 373, 271 calactin X X C 39 H 52 O , 571, 373 6'-O-feruloyl-desglucouzarin X X C 24 H 36 O uzarigenin X X C 32 H 44 O hydroxy-16α-acetoxycalactin X C 29 H 40 O α-hydroxycalactin X a Calculated from the LC-MS analysis of MeOH extract of P. tomentosa aerial parts.

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