Supporting Information (SI) Isolation and Confirmation of the Proposed Cleistanthol Biogenic Link from Croton Insularis
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1 SI1 Supporting Information (SI) Isolation and Confirmation of the Proposed Cleistanthol Biogenic Link from Croton Insularis Lidia A. Maslovskaya, Andrei I. Savchenko, Victoria A. Gordon, Paul W. Reddell, Carly J. Pierce, Peter G. Parsons and Craig M. Williams*, School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 72, Queensland, Australia Queensland Institute of Medical Research, P Royal Brisbane Hospital, Brisbane, 29, Queensland, Australia EcoBiotics Limited, P Box 1, Yungaburra, 4884, Queensland, Australia Table of Contents: SI2 General Experimental Procedures. SI2 Plant material. SI3 Extraction and isolation. SI3 xidation of compound 5. SI4 Material and methods for growing cells and cell screening. SI5 1 H NMR spectrum for compound 5 recorded in CDCl 3 at 500 MHz. SI5 13 C NMR spectrum for compound 5 recorded in CDCl 3 at 125 MHz. SI6 HSQC spectrum for compound 5 recorded in CDCl 3 at 500 MHz. SI6 CSY spectrum for compound 5 recorded in CDCl 3 at 500 MHz. SI7 HMBC spectrum for compound 5 recorded in CDCl 3 at 500 MHz, SI7 HMBC spectrum for compound 5 recorded in CDCl 3 at 500 MHz, SI8 NESY spectrum for compound 5 recorded in CDCl 3 at 500 MHz, SI8NESY spectrum for compound 5 recorded in CDCl 3 at 500 MHz, SI9 Table 3. NMR data for compound 7 recorded in CDCl 3 at 500 MHz. SI9 1 H NMR spectrum for compound 7 recorded in CDCl 3 at 500 MHz. SI10 13 C NMR spectrum for compound 7 recorded in CDCl 3 at 125 MHz. SI10 HSQC spectrum for compound 7 recorded in CDCl 3 at 500 MHz. SI11 HSQC spectrum for compound 7 recorded in CDCl 3 at 500 MHz, methyl group range. SI11 HSQC spectrum for compound 7 recorded in CDCl 3 at 500 MHz, olefinic range. SI12 CSY spectrum for compound 7 recorded in CDCl 3 at 500 MHz. SI12 HMBC spectrum for compound 7 recorded in CDCl 3 at 500 MHz. SI13 NE difference spectra for compound 7 recorded in CDCl 3 at 500 MHz. SI13 Table 4. NMR data for the mixture of compounds 8 and 9 recorded in CDCl 3. SI14 1 H NMR spectrum for the mixture of compounds 8 and 9 recorded in CDCl 3 at 500 MHz. SI14 13 C NMR spectrum for the mixture of compounds 8 and 9 recorded in CDCl 3 at 125 MHz. SI15 13 C NMR spectrum for the mixture of compounds 8 and 9 recorded in CDCl 3 at 125 MHz, expansion SI15 HSQC spectrum for the mixture of compounds 8 and 9 recorded in CDCl 3 at 500 MHz. SI16 CSY spectrum for the mixture of compounds 8 and 9 recorded in CDCl 3 at 500 MHz. SI16 HMBC spectrum for the mixture of compounds 8 and 9 recorded in CDCl 3 at 500 MHz. SI17 1 H NMR superposition of Spruceanol (3) spectrum (upper trace) with 1 H NMR of material isolated after decomposition of 5. SI17 Table 5. NMR data for compound 11 recorded in CDCl 3 at 500 MHz SI18 1 H NMR spectrum for compound 11 recorded in CDCl 3 at 500 MHz.
2 SI2 SI18 13 C NMR spectrum for compound 11 recorded in CDCl 3 at 125 MHz. SI19 HSQC spectrum for compound 11 recorded in CDCl 3 at 500 MHz. SI19 CSY spectrum for compound 11 recorded in CDCl 3 at 500 MHz. SI HMBC spectrum for compound 11 recorded in CDCl 3 at 500 MHz. SI Fragment of NESY spectrum for compound 11 recorded in CDCl 3 at 500 MHz. SI21 Table 6. NMR data for compound 12 recorded in CDCl 3 at 500 MHz. SI21 1 H NMR spectrum for compound 12 recorded in CDCl 3 at 500 MHz. SI22 13 C NMR spectrum for compound 12 recorded in CDCl 3 at 125 MHz. SI22 HSQC spectrum for compound 12 recorded in CDCl 3 at 500 MHz. SI23 CSY spectrum for compound 12 recorded in CDCl 3 at 500 MHz. SI23 HMBC spectrum for compound 12 recorded in CDCl 3 at 500 MHz. SI24 NESY spectrum for compound 12 recorded in CDCl 3 at 500 MHz. SI24 Table 7. NMR data for compound 13 recorded in CDCl 3 at 500 MHz SI25 1 H NMR spectrum for compound 13 recorded in CDCl 3 at 500 MHz. SI25 13 C NMR spectrum for compound 13 recorded in CDCl 3 at 125 MHz. SI26 HSQC spectrum for compound 13 recorded in CDCl 3 at 500 MHz. SI26 CSY spectrum for compound 13 recorded in CDCl 3 at 500 MHz. SI27 HMBC spectrum for compound 13 recorded in CDCl 3 at 500 MHz. SI27 Fragments of NESY spectrum for compound 13 recorded in CDCl 3 at 500 MHz. General Experimental Procedures ptical rotations were measured using a Jasco P-00 spectrophotometer. IR spectra were obtained by ATR FT-IR spectrometer Perkin Elmer SPECTRUM 00. 1D and 2D NMR spectra were recorded on a DRX500 ( MHz; MHz) in CDCl 3 : δ in, J in Hz. Low resolution electrospray ionisation mass spectrometry measurements (LRESIMS) were recorded in positive or negative ionization mode on a Bruker Esquire HCT (High Capacity 3D ion trap) instrument with a Bruker ESI source. High resolution electrospray ionisation (HRESIMS) accurate mass measurements were recorded in positive mode on a Bruker MicrTF-Q (quadrupole Time of Flight) instrument with a Bruker ESI source. Accurate mass measurements were carried out with external calibration using sodium formate as reference calibrant. HPLC instruments include HPLC Agilent 1190 and Gilson Fraction collector FC4. Column chromatography (CC): Silica gel 60 (0-300mesch, 15-µ, Merck, Germany). Semipreparative HPLC was carried out on a Phenomenex Luna 5u C18 (2), mm, 5u micron column. Plant material. Stems (less than 2cm in diameter) and leaves of Croton insularis Baill. (family Euphorbiaceae) were sampled from trees growing in an arboretum in the grounds of the Ecobiotics Limited research laboratories at Yungaburra in north Queensland. The arboretum specimens had been established from vegetatively propagated Croton insularis that were originally collected (EcoBiotics herbarium voucher specimen Reddell 1714) from a natural population of the species growing in a semi-deciduous vine forest at Iron Range ( S, E), Queensland.
3 SI3 Extraction and isolation. The stem of Croton insularis (3.6kg) collected from Yangabura in March 09, was mulched and extracted three times (3 24h) with ethanol (3 8L) at ambient temperature. The ethanol extracts were evaporated under reduced pressure to yield a dark brown residue (450ml). The residue was suspended with water and consequently partitioned between water and hexane, chloroform and ethyl acetate layers. The hexane layer was concentrated to give a green viscous residue (25g). The hexane extract was applied to silica gel (0-300mesh, 250g) column chromatography (7 14 cm) and eluted with petroleum ether-etac gradient system (8:1, 4:1, 2:1, 1:1, 1:2, 1:4, EtAc, each 2 270ml). Fraction 7 (0.987g), containing compound 6 and 7 was eluted with 1:1 solvent mixture, and fraction 9 (1.189g) containing compounds 3 and 5 was eluted with 1:2. A portion (2mg) of fraction 9 was subjected to HPLC (MeH H 2, 80% 25min, gradient to 100% of MeH 10min) to give compound 5 (4.1 mg, R t 16.0 min) and spruceanol (3) (2.9 mg, R t 23.0min). Fraction 7 (260mg) was separated on HPLC (MeH H 2, 80% min, gradient to 100% of MeH 45min) to provide compound 7 (28.9 mg, R t 12.5 min) and sonderianol (6) (4.7 mg, R t 14.1min). Compound 5: Isolated as a colourless oil; [α] 25 D 57.2 (c 0.044, CDCl 3 ); 1 H NMR and 13 C NMR, see Table 1; IR cm 1 : 3430, 2933, 2870, 1735,1655, 1651, 1636,1624, 1555, 1456, 1375, 1175, 1087, 1031, 994, 917, 866, 729, 645; positive ion HRESIMS [M+Na]+m/z (calcd for C H 28 2 Na). Compound 7: Isolated as a colourless oil; [α] 25 D 89.5 (c 0.053, CDCl 3 ); 1 H NMR and 13 C NMR, see Table 3; IR cm 1 : 3085, 2971, 2935, 2870, 1705, 1658, 1626, 1553, 1455, 1381, 1363, 1173, 1112, 992, 9, 865, 728, 641, 580; positive ion HRESIMS [M+Na]+m/z (calcd for C H 26 2 Na). xidation of 5 to compounds 8 and 9: Compound 5 (4.25 mg) in CDCl 3 (0.45 ml) solution was left to stand for 25 days. The solvent was then slowly evaporated to give a dark yellow oil. The residue was dissolved in CDCl 3 and NMR spectra were recorded. According to 1 H NMR pure 2:1 mixture of oxidation products 8 and 9 respectively was formed. Isolation of spruceanol (3) after decomposition of 5: The NMR sample of compound 5 (4.05 mg) was evaporated and stored at ambient temperature for 16 months. 1 H NMR of the material was recorded to show a mixture of several products. The material was subjected to the HPLC method used for isolation of 3 and 5 to give a fraction with the R t range min. According to 1 H NMR the obtained fraction (1.02 mg) contained spruceanol (3) (see 1 H NMR). Compounds 8 and 9 were isolated as a yellow oil. 1 H NMR and 13 C NMR, see Table 4; negative ion HRESIMS [M H] m/z (calcd for C H 27 4 ). Isolation of after decomposition of 7: 28.9 mg of compound 7 was stored for 60 days at ambient temperature and repurified by HPLC using 75% MeH to isolate compound 11 (0.83 mg, R t 23.8 min), 12 (0.79 mg, R t 24.7 min) and 13 (0.54 mg, R t 17.2 min). Compound 11 was isolated as a colourless solid. [α] 25 D (c 0.079, CDCl 3 ); 1 H NMR and 13 C NMR, see Table 5; IR cm 1 : 2927, 2857, 1760, 1702, 1457, 1382, 1186, 1114, 1024, 952, 869, 817; HRESIMS [M+Na]+m/z (calcd for C H 26 2 Na).
4 SI4 Compound 12 was isolated as a colourless solid. [α] 25 D+30.5 (c 0.083, CDCl 3 ); 1 H NMR and 13 C NMR, see Table 6; IR cm 1 : 2953, 2926, 2868, 2858, 1765, 1704, 1647, 1458, 1432, 1379, 1184, 1159, 1114, 1050, 1026, 950, 817; HRESIMS [M+Na]+m/z (calcd for C H 26 2 Na). Compound 13 was isolated as a colourless. [α] 25 D (c 0.02, CDCl 3 ); 1 H NMR and 13 C NMR, see Table 7; IR cm 1 : 2927, 2857, 1729, 1696, 1594, 1456, 1380, 1194, 1112, 1024, 947; HRESIMS [M+Na]+m/z (calcd for C H 26 2 Na). Materials and methods for growing cells and cell screening: Cells ( /well) seeded in triplicate in 96-well plates in Roswell Park Memorial Institute 16 medium containing 10% fetal calf serum were treated with the compounds. After 6 days in culture at 37 degrees, the growth of treated K562 cells was compared with untreated controls by addition of MTS, and the colour change read at 5 nm in an ELISA reader. The other cell lines were fixed with ethanol in situ, stained with sulforhodamine B and absorbance at 564 nm determined in the ELISA reader. Cell seeded at the following densities: HeLa: 3000/well, HT29: 3000/well, MCF7: 00/well, MM96L: 3000/well, NFF: 5000/well, K562: 3500/well.
5 SI5 1 H NMR spectrum for compound 5 recorded in CDCl 3 at 500 MHz H C NMR spectrum for compound 5 recorded in CDCl 3 at 125 MHz H
6 SI6 HSQC spectrum for compound 5 recorded in CDCl 3 at 500 MHz H CSY spectrum for compound 5 recorded in CDCl 3 at 500 MHz H
7 SI7 HMBC spectrum for compound 5 recorded in CDCl 3 at 500 MHz, H HMBC spectrum for compound 5 recorded in CDCl 3 at 500 MHz, H
8 SI8 NESY spectrum for compound 5 recorded in CDCl 3 at 500 MHz, H NESY spectrum for compound 5 recorded in CDCl 3 at 500 MHz, H
9 SI9 Table 3. NMR data for compound 7 recorded in CDCl 3 at 500 MHz atom # 1 H δ, multiplicity, J 13 C δ 1a 1.89, 1H td, 13.08, b 2.25, 1H ddd, 13.45, 6.11, a 2.45, 1H ddd, 15.16, 5.62, b , 1H m , 1H dd, 11.25, , 2H m.1 7a , 1H m b , 1H m , 1H s , 1H t, , 1H dd, 17.61, a 5.02, 1H dd, 10.27, b 5.04, 1H dd, 17.12, , 3H s , 3H s , 3H s , 3H s H NMR spectrum for compound 7 recorded in CDCl 3 at 500 MHz
10 SI10 13 C NMR spectrum for compound 7 recorded in CDCl 3 at 125 MHz HSQC spectrum for compound 7 recorded in CDCl 3 at 500 MHz
11 SI11 HSQC spectrum for compound 7 recorded in CDCl 3 at 500 MHz, methyl groups range HSQC spectrum for compound 7 recorded in CDCl 3 at 500 MHz, olefinic range
12 SI12 CSY spectrum for compound 7 recorded in CDCl 3 at 500 MHz HMBC spectrum for compound 7 recorded in CDCl 3 at 500 MHz
13 SI13 NE difference spectra for compound 7 recorded in CDCl 3 at 500 MHz Table 4. NMR data for compounds 8 and 9 recorded in CDCl 3 at 500 MHz 8 9 atom # 1 H δ, multiplicity, J 13 C δ 1 H δ, multiplicity, J 13 C δ 1a 1.48, 1H m , 1H m b 1.78, 1H m , 1H m - 2a 1.77, 2H m , 1H m b , 1H m , 1H dd, 11.7, , 1H dd, 11.3, dd, 12.5, , 1H m a 1.49, 1H m , 1H m b 1.82, 1H m , 1H m - 7a 2.16, 1H m , 1H m b 2.42, 1H m , 1H dd, 18.3, , 1H s , 1H s , 1H s , 1H s , 1H dd, 17.6, dd, 17.6, a 5.12, 1H d, , 1H d, b 5.16, 1H d, , 1H d, , 3H s , 3H s , 3H s , 3H s , 3H s , 3H s , 3H s , 3H s.3
14 SI14 1 H NMR spectrum for the mixture of compounds 8 and 9 recorded in CDCl 3 at 500 MHz H H C NMR spectrum for the mixture of compounds 8 and 9 recorded in CDCl 3 at 125 MHz H H
15 SI15 13 C NMR spectrum for the mixture of compounds 8 and 9 recorded in CDCl 3 at 125 MHz, expansion H H HSQC spectrum for the mixture of compounds 8 and 9 recorded in CDCl 3 at 500 MHz H H
16 SI16 CSY spectrum for the mixture of compounds 8 and 9 recorded in CDCl 3 at 500 MHz 1 H H HMBC spectrum for the mixture of compounds 8 and 9 recorded in CDCl 3 at 500 MHz H H
17 SI17 1 H NMR superposition of Spruceanol (3) spectrum (upper trace) with 1 H NMR of material isolated after decomposition of H H Table 5. NMR data for compound 11 recorded in CDCl 3 at 500 MHz atom # 1 H σ, multiplicity, J 13 C σ 1a , 2H, m b 2.47, 1H, dd, 5.9, , 1H, m , 1H, d, a , 1H, m b 1.70, 1H, dddd, 13.3, 6.5, 2.0, 1.7 7a , 1H, m b , 1H, m , 1H, dm, a , 1H, m b , 1H, m , 1H, m , 1H, s , 3H, dd, 4.2, , 3H, s , 3H, s , 3H, s 18.1
18 SI18 1 H NMR spectrum for compound 11 recorded in CDCl 3 at 500 MHz C NMR spectrum for compound 11 recorded in CDCl 3 at 125 MHz
19 SI19 HSQC spectrum for compound 11 recorded in CDCl 3 at 500 MHz CSY spectrum for compound 11 recorded in CDCl 3 at 500 MHz
20 SI HMBC spectrum for compound 11 recorded in CDCl 3 at 500 MHz Fragment of NESY spectrum for compound 11 recorded in CDCl 3 at 500 MHz
21 SI21 Table 6. NMR data for compound 12 recorded in CDCl 3 at 500 MHz atom # 1 H σ, multiplicity, J 13 C σ 1a , 1H, m b 1.91, 1H, dd, 7.3, , 2H, m , 1H, m a , 1H, m.3 6b , 1H, m - 7a , 1H, m b 2., 1H, dd, 17.9, , 1H, brs a 2.46, 1H, brs b , 1H, m , 1H, brs , 1H, s , 3H, brs , 3H, s , 3H, s , 3H, s H NMR spectrum for compound 12 recorded in CDCl 3 at 500 MHz
22 SI22 13 C NMR spectrum for compound 12 recorded in CDCl 3 at 125 MHz HSQC spectrum for compound 12 recorded in CDCl 3 at 500 MHz
23 SI23 CSY spectrum for compound 12 recorded in CDCl 3 at 500 MHz HMBC spectrum for compound 12 recorded in CDCl 3 at 500 MHz
24 SI24 Fragment of NESY spectrum for compound 12 recorded in CDCl 3 at 500 MHz Table 7. NMR data for compound 13 recorded in CDCl 3 at 500 MHz atom # 1 H σ, multiplicity, J 13 C σ 1a 1.94 td, 1 H, 13.38, b 2.11 ddd, 1 H, 13.32, 6.57, a 2.47 ddd, 1 H, 15.79, 5.60, b 2.72 ddd, 1 H, 15.84, 13.24, d, 1 H, m, 2 H a 1.82 td, 1 H, 13.09, b 2. ddd, 1H, 14.05, 3.23, dd, 1 H, 1.05, d, 1 H, dd, 1 H, 17.24, a 5.16 dd, 1 H, 17.24, b 5.21 dd, 1 H, 10.78, s, 3 H s, 3 H s, 3 H d, 3 H,
25 SI25 1 H NMR spectrum for compound 13 recorded in CDCl 3 at 500 MHz C NMR spectrum for compound 13 recorded in CDCl 3 at 125 MHz CH 3 H H 3 C H CH 3 H 3 C CH
26 SI26 HSQC spectrum for compound 13 recorded in CDCl 3 at 500 MHz CSY spectrum for compound 13 recorded in CDCl 3 at 500 MHz
27 SI27 HMBC spectrum for compound 13 recorded in CDCl 3 at 500 MHz Fragments of NESY spectrum for compound 13 recorded in CDCl 3 at 500 MHz CH 3 H 2.6 H 3 C H CH 3 H 3 C CH
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