Hyperjaponol H, A New Bioactive Filicinic Acid-based Meroterpenoid from Hypericum japonicum Thunb. ex Murray Rongrong Wu 1,†, Zijun Le 2,†, Zhenzhen Wang 3, Shuying Tian 1, Yongbo Xue 3, Yong Chen 1, Linzhen Hu 1, * and Yonghui Zhang 3 1 National & Local Joint Engineering Research Center of High-throughput Drug Screening Technology, Hubei Key Laboratory of Biotechnology of Chinese Traditional Medicine, School of Life Science, Hubei University, Wuhan 430062, Hubei Province, P. R. China; E-mails: [email protected] (R. R. W.); [email protected] (S. Y. T.); [email protected] (Y. C.) 2 Wuhan Rayson School, Wuhan 430040, Hubei Province, P. R. China; E-mail: [email protected] (Z. J. L.) 3 Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology; Wuhan 430030, Hubei, China; E-mails : [email protected] (Z. Z. W.); [email protected] (Y. B. X.); [email protected] (Y. H. Z.) † These authors contributed equally to this work. * Author to whom correspondence should be addressed; E-mail: [email protected] (L. Z. H.); Tel.: +86-27-88668023 (L. Z. H.) Content Figure S1. HRESIMS spectrum of hyperjaponol H (1) ..................................................................... 1 1 Figure S2. H NMR spectrum of hyperjaponol H (1, in CDCl3) ....................................................... 2 13 Figure S3. C NMR and DEPT135 spectra of hyperjaponol H (1, in CDCl3) .................................. 3 Figure S4. HSQC spectrum of hyperjaponol H (1, in CDCl3) ........................................................... 4 Figure S5. HMBC spectrum of hyperjaponol H (1, in CDCl3) .......................................................... 5 1 1 Figure S6. H– H COSY spectrum of hyperjaponol H (1, in CDCl3) ................................................ 6 Figure S7. NOESY spectrum of hyperjaponol H (1, in CDCl3) ........................................................ 7 Figure S8. UV spectrum of hyperjaponol H (1, in methanol) ........................................................... 8 Figure S9. IR spectrum of hyperjaponol H (1, KBr disc) ................................................................ 9 x10 4 +ESI Scan (0.106 min) Frag=70.0V 20180308-WRR.P.1.d 459.3119 2.4 2.2 2 1.8 1.6 1.4 1.2 1 0.8 460.3157 0.6 0.4 0.2 0 458.5 459 459.5 460 460.5 461 461.5 462 462.5 463 463.5 464 Counts vs. Mass-to-Charge (m/z) Figure S1. HRESIMS spectrum of hyperjaponol H (1) 1 1 Figure S2. H NMR spectrum of hyperjaponol H (1, in CDCl3) 2 13 Figure S3. C NMR and DEPT135 spectra of hyperjaponol H (1, in CDCl3) 3 Figure S4. HSQC spectrum of hyperjaponol H (1, in CDCl3) 4 Figure S5. HMBC spectrum of hyperjaponol H (1, in CDCl3) 5 1 1 Figure S6. H– H COSY spectrum of hyperjaponol H (1, in CDCl3) 6 Figure S7. NOESY spectrum of hyperjaponol H (1, in CDCl3) 7 Figure S8. UV spectrum of hyperjaponol H (1, in methanol) 8 E:\20171130\20171130HULINZ\1.0 Transmittance [%] 4000 91.5 92.0 92.5 93.0 93.5 94.0 94.5 95.0 3921.83 3875.63 3826.53 3757.82 3720.07 3673.41 3500 Figure S9. Figure 3455.00 3111.42 3000 IR spectrum of hyperjaponol H ( 2966.81 2932.80 2874.83 2500 2528.70 Wavenumber cm-1 Wavenumber 2381.44 9 2307.27 2224.30 2000 1919.37 1720.64 1 1654.55 , KBr disc) , KBrdisc) 1612.99 1500 1523.39 1464.58 1378.07 1313.52 1259.33 1189.42 1140.69 1000 1063.58 989.16 938.55 14:19:02 2017-11-30 881.82 821.45 752.01 676.82 619.55 500 579.85 501.85 457.07 .