SUPPLEMENTARY MATERIAL Lasibidoupins A and B, two new compounds from the stems of Lasianthus bidoupensis V.S. Dang & Naiki Nguyen Kim Tuyen Phama, Thi Diem Huong Nguyena, Thi Mong Cam Nguyena, Gia Dinh Nguyena, Cong Doan Huynhb, Thi Nga Voc, Thi Quynh Trang Nguyena, Thuc Huy Duongd, Van Son Dange, Bui Linh Chi Huynhf, Thi Ngoc Mai Trang*, Tan Phat Nguyenh,i* a Faculty of Environmental Science, Sai Gon University, 273 An Duong Vuong, Ho Chi Minh City, Vietnam b Ca Mau Medical College, Ca Mau Province, Vietnam c Department of Chemical Technology, Ho Chi Minh University of Technology and Education, Ho Chi Minh City, Vietnam d Faculty of Chemistry, University of Education, Ho Chi Minh City, Vietnam e Institute of Tropical Biology, Vietnam Academy of Science and Technology, Ho Chi Minh City, Vietnam f Department of Science, Dong Nai University, Bien Hoa City, Dong Nai Province, Vietnam gInstitute of Applied Sciences Ho Chi Minh City University of Technology (HUTECH), 475 A Dien Bien Phu Street, Ward 25, Binh Thanh District, Ho Chi Minh City, Vietnam h Faculty of Chemistry, Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam i Bioactive Compounds Laboratory, Institute of Chemical Technology, Vietnam Academy of Science and Technology, 01A Thanh Loc 29, Thanh Loc, District 12, Ho Chi Minh City, Vietnam *Corresponding author. Email: ntphat@ict.vast.vn or ttn.mai79@hutech.edu.vn ORCID ID: https://orcid.org/0000-0001-9672-2785 Abstract From the Lasianthus bidoupensis stems, two new compounds, including one new 9,10anthraquinone, lasibidoupin A (1), and one new 6,7-benzocoumarin, lasibidoupin B (2), together with one known compound, 11-O-methyldamnacanthol (3) were isolated using chromatographic method. Their structures were determined by extensive HRMS, and NMR assignments. Compound 3 was reported for the first time from this species. New compounds (1 & 2) were tested for the cytotoxicity against three human cancer cell lines (MCF-7, HeLa, and NCI-H460) by SRB assay. As results, 1 & 2 exhibited significant cytotoxic activity against all cancer cell lines (IC50 ranged from 0.058 ± 0.003 to 0.177 ± 0.014 μM). Keywords: Lasianthus bidoupensis; 9,10-anthraquinone; 6,7-benzocoumarin; lasibidoupin A; lasibidoupin B; cytotoxic activity. List of supporting information Table S1. NMR spectral data for compounds 1 and 2 in CDCl3. Table S2. The cytotoxic activity of compounds 1 and 2. Figure S1. Chemical structures of 1-3. Figure S2. Selected HMBC and NOESY correlations of 1 and 2. Figure S3. 1H-NMR spectrum (500 MHz) of compound 1 in CDCl3. Figure S4. 13C-NMR spectrum (125 MHz) of compound 1 in CDCl3. Figure S5. HSQC spectrum of compound 1 in CDCl3. Figure S6. HMBC spectrum of compound 1 in CDCl3. Figure S7. NOESY spectrum of compound 1 in CDCl3. Figure S8. HR-ESI-MS spectrum (positive) of compound 1. Figure S9. IR spectrum of compound 1. Figure S10. 1H-NMR spectrum (500 MHz) of compound 2 in CDCl3. Figure S11. 13C-NMR spectrum (125 MHz) of compound 2 in CDCl3. Figure S12. HSQC spectrum of compound 2 in CDCl3. Figure S13. HMBC spectrum of compound 2 in CDCl3. Figure S14. NOESY spectrum of compound 2 in CDCl3. Figure S15. HR-ESI-MS spectrum (positive) of compound 2. Figure S16. IR spectrum of compound 2. Figure S17. 1H-NMR spectrum (500 MHz) of compound 3 in CDCl3. Figure S18. 13C-NMR spectrum (125 MHz) of compound 3 in CDCl3. Figure S19. HR-ESI-MS spectrum (positive) of compound 3. Table S1. NMR spectral data for compounds 1 and 2 in CDCl3. 1 No. 1 2 3 4 4a 5 5a 6 7 8 8a 9 9a 10 10a 11 12 13 14 OH-2 OH-8 dH 7.72 (1H, s) 8.04 (1H, s) 8.28 (2H, m) 7.78 (1H, m) 7.50 (1H, m) 8.28 (2H, m) 4.83 (2H, s) 3.53 (3H, s) - 2 dC 114.6 161.7 128.3 128.0 126.3 127.2 134.1 133.7 127.1 133.7 182.9 135.4 182.1 134.1 73.6 58.9 8.60 (1H, s) - dH 6.51 (1H, d, 9.5) 7.97 (1H, d, 9.5) 7.31 (1H, s) 2.55 (3H, s) 3.85 (3H, s) 10.55 (1H, s) 4.20 (3H, s) - 11.42 (1H, s) Table S2. The cytotoxic activity of compounds 1 and 2. Compound IC50 (µM) 1 2 Camptothecin MCF-7 0.177 ± 0.014 0.071 ± 0.004 0.007 ± 0.002 HeLa 0.229 ± 0.014 0.058 ± 0.003 0.890 ± 0.088 NCI-H460 0.072 ± 0.030 0.063 ± 0.002 0.003 ± 0.000 dC 159.9 114.5 141.1 113.6 126.8 137.2 148.9 103.6 160.1 115.9 111.4 165.3 149.6 12.0 61.4 195.3 66.1 Figure S1. Chemical structures of 1-3. Figure S2. Selected HMBC and NOESY correlations of 1 and 2. Figure S3. 1H-NMR spectrum (500 MHz) of compound 1 in CDCl3. Figure S4. 13C-NMR spectrum (125 MHz) of compound 1 in CDCl3. Figure S5. HSQC spectrum of compound 1 in CDCl3. Figure S6. HMBC spectrum of compound 1 in CDCl3. Figure S7. NOESY spectrum of compound 1 in CDCl3. Figure S8. HR-ESI-MS spectrum (positive) of compound 1. 104 104 102 100 1218.92 98 813.51 96 %T 1673.83cm -1 1197.30 3674.24cm-1 497.30 1124.32 943.84cm-1 431.90cm-1 1103.92cm-1 1583.50cm -1 90 1296.36cm-1 1469.83cm-1 88 600.00 913.51 624.32 94 92 991.30cm-1 1418.92 3312.14cm-1 1346.63cm-1 719.45cm-1 1047.13cm-1 1180.11cm-1 1391.89 1278.38 86 84 2850.62cm -1 82 1730.90cm-1 80 78 4000 2918.03cm-1 3500 3000 2500 2000 1750 1500 1250 1000 750 cm-1 Figure S9. IR spectrum of compound 1. Figure S10. 1H-NMR spectrum (500 MHz) of compound 2 in CDCl3. 500 400 Figure S11. 13C-NMR spectrum (125 MHz) of compound 2 in CDCl3. Figure S12. HSQC spectrum of compound 2 in CDCl3. Figure S13. HMBC spectrum of compound 2 in CDCl3. Figure S14. NOESY spectrum of compound 2 in CDCl3 Figure S15. HR-ESI-MS spectrum (positive) of compound 2. 98 95 90 890.52 826.04 1669.78cm-1 85 1024.09 80 651.02 614.17 968.82 715.53cm-1 1067.85 %T 1226.75 75 1735.70cm-1 3300.97cm-1 1378.74 1117.45cm-1 1277.53cm-1 1185.94cm-1 1416.31cm-1 1562.55cm-1 70 1463.56cm-1 1331.27cm-1 65 2955.25cm-1 2851.15cm-1 60 55 50 4000 2919.64cm-1 3500 3000 2500 2000 1750 1500 1250 1000 750 cm-1 Figure S16. IR spectrum of compound 2. Figure S17. 1H-NMR spectrum (500 MHz) of compound 3 in CDCl3. 500 400 Figure S18. 13C-NMR spectrum (125 MHz) of compound 3 in CDCl3. Figure S19. HR-ESI-MS spectrum (positive) of compound 3.