A new ent-kaurane diterpene from Euphorbia stracheyi Boiss

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1 SUPPLEMENTARY MATERIAL A new ent-kaurane diterpene from Euphorbia stracheyi Boiss Tie Liu a, Qian Liang a,b, Na-Na Xiong a, Lin-Feng Dai a, Jun-Ming Wang a,b, Xiao-Hui Ji c, Wen-Hui Xu a, * a Key Laboratory for Forest Resources Conservation and Utilization in the Southwest Mountains of China, Ministry of Education, Southwest Forestry University, Kunming 65224, PR China b Department of Medicinal Plant, School of Forestry, Southwest Forestry University, Kunming 65224, PR China c Department of Applied Chemistry, School of Chemistry and Environment Science, Shaanxi University of Technology, Hanzhong 723, PR China Corresponding author: To whom correspondence should be addressed: Tel: ;Fax: ; address: Wenhuix@ hotmail.com Abstract: The chemical investigation of whole plants Euphorbia stracheyi Boiss from China led to the isolation of one new ent-kaurane diterpene, ent-kaurane-6β,7,9-triol-3-one (), along with three known ent-kaurane diterpenoids (2 4) as ent-kaurane-3α,6β,7-triol (2), ent-6s,7-dihydroxy-kaurane-3-one (3), and ent-3s,6s,7-trihydroxy-kaurane-2-one (4). Their structures were elucidated by extensive spectroscopic analyses including D, 2D NMR, HR-ESI-MS, and by comparison with the literature. Compound 2 was a new natural product and firstly isolated from nature, while compounds (3 4) were isolated from E. stracheyi for the first time. All isolated compounds ( 4) were evaluated for their cytotoxic activities against five human cancer cell lines (including A-549, SMMC-772, HL-6, MCF-7, and SW-48).

2 Contents of supplementary data Figure S. H -NMR spectrum of compound (5MHz, Pyridine-d 5 ) Figure S2. 3 C-NMR spectrum of compound (25MHz, Pyridine-d 5 ) Figure S3. DEPT-9,35 NMR spectrum of compound (Pyridine-d 5 ) Figure S4. H - H COSY spectrum of compound (Pyridine-d 5 ) Figure S5. HMQC NMR spectrum of compound (Pyridine-d 5 ) Figure S6. HMBC NMR spectrum of compound (Pyridine-d 5 ) Figure S7. ROESY NMR spectrum of compound (Pyridine-d 5 ) Figure S8. ESI-MS spectrum of compound Figure S9. ESI-HR-MS spectrum of compound Figure S. H -NMR spectrum of compound 2 (5MHz, Pyridine-d 5 ) Figure S. 3 C-NMR spectrum of compound 2 (25MHz, Pyridine-d 5 ) Figure S2. H -NMR spectrum of compound 3 (5MHz, Methanol-d4) Figure S3. 3 C-NMR spectrum of compound 3 (25MHz, Methanol-d4) Figure S4. H -NMR spectrum of compound 4 (5MHz, Pyridine-d 5 ) Figure S5. 3 C-NMR spectrum of compound 4 (25MHz, Pyridine-d 5 ) Figure S6. Key HMBC and COSY correlations of compound Table S. 3 C NMR data for compounds -4

3 gs64a.2..r gs64a H Figure S. H -NMR spectrum of compound (5MHz, Pyridine-d 5 ) 3 2

4 gs64a.22..r gs64a c

5 gs64a.23..r gs64a c3 6E+6 4E+6 2E+6 E gs64a.24..r gs64a c gs64a.22..r gs64a c Figure S3. DEPT-9,35 NMR spectrum of compound (Pyridine-d5) 4 3 2

6 gs64a.26..2rr gs64a cosy (ppm) of compound (Pyridine-d ) Figure S4. H -H COSYf2 spectrum

7 gs64a.27..2rr gs64a hsqc f2 compound (ppm) Figure S5. HMQC NMR spectrum of (Pyridine-d5) 3 2 9

8 gs64a.28..2rr gs64a hmbc f2 (ppm) Figure S6. HMBC NMR spectrum of compound (Pyridine-d5)

9 gs64a.29..2rr gs64a roesy f2 (ppm) Figure S7. ROESY NMR spectrum of compound (Pyridine-d5)

10 Sample Name GS-64A Position P-C3 Instrument Name Instrument User Name Inj Vol. InjPosition SampleType Sample IRM Calibration Status Success Data Filename GS-64A.d ACQ Method SIBU.m Comment Acquired Time 2/29/25 :8:5 AM

11 Qualitative Analysis Report Data Filename GS-64A.d Sample Name GS-64A Sample Type Sample Position P-C3 Instrument Name Instrument User Name Acq Method SIBU.m Acquired Time IRM Calibration Status Success DA Method ESI+.m Comment Column3 Sample Group Acquisition SW Version Column4 62 series TOF/65 series Q-TOF B.5. (B525.2) Column3 Info. 2/29/25 :8:5 AM User Spectra Fragmentor Voltage 35 Collision Energy Ionization Mode ESI Peak List m/z z 2 Abund Formula C2 H32 O4 C2 H32 O4 Ion (M+Na)+ (M+Na)+ Formula Calculator Element Limits Element Min Max C 3 6 H 2 O 3 N Formula Calculator Results Formula CalculatedMass CalculatedMz Mz Diff. (mda) C2 H32 O Diff. (ppm) -.2 DBE End Of Report ---

12 pdata/

13 gs54f.2..r gs54f c

14 Figure S2. 7. H NMR spectrum of compound 3 (5MHz, Methanol-d4) E+8 3.5E+8 3.E+8 2.5E+8 2.E+8.5E+8.E+8 5.E+7.E+

15 E+8 5.E+8 4.5E+8 4.E+8 3.5E+8 3.E+8 2.5E+8 2.E+8.5E+8.E+8 5.E+7.E+ -5.E Figure S C-NMR spectrum of compound 3 (25MHz, Methanol-d4)

16 gs64c.2..r gs64c H

17 gs64c.22..r gs64c c

18 OH OH H O H OH Cosy Key HMBC Figure S6. Key HMBC and COSY correlations of compound Table S. 3 C-NMR (25 MHz) Data of Compounds 4 Position a 2 a 3 b 4 a 4.6 t 39.5 t 4.6 t 54.3 t t 28.6 s 35. t 2.5 s s 78.6 d 22.2 s d s 39.8 s 48.4 s 45.8 s d 55.8 d 55.6 d 54.8 d t 2.7 t 22.4 t 2.7 t t 42.7 t 42.2 t 4.9 t s 44. s 44.7 s 44.2 s d 57.9 d 57.3 d 56.8 d 39.4 s 39.8 s 39.9 s 45.8 s 2. t 9.7 t 2.4 t 9.6 t t 28. t 27.9 t 27.6 t d 42.2 d 42.3 d 42. d t 39. t 39. t 38.4 t t 53.8 t 52.9 t 53.4 t 6 8. s 8. s 8.6 s 79.9 s t 7.9 t 7.5 t 7.8 t q 29.3 q 27.9 q 3. q t 6.8 q 2.5 q 7.5 q q 8.3 q 8.4 q 9. q a) Measured in Pyridine-d 5. b) Measured in Methanol-d 4.