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, Key Laboratory of Biotechnology of Chinese Traditional Medicine, School of Life Science, Hubei University, 430062, Hubei Province, P. R. ; 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)

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1 Figure S2. H NMR spectrum of hyperjaponol H (1, in CDCl3)

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13 Figure S3. C NMR and DEPT135 spectra of hyperjaponol H (1, in CDCl3)

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Figure S4. HSQC spectrum of hyperjaponol H (1, in CDCl3)

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Figure S5. HMBC spectrum of hyperjaponol H (1, in CDCl3)

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1 1 Figure S6. H– H COSY spectrum of hyperjaponol H (1, in CDCl3)

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Figure S7. NOESY spectrum of hyperjaponol H (1, in CDCl3)

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Figure S8. UV spectrum of hyperjaponol H (1, in methanol)

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E:\20171130\20171130HULINZ\1.0 14:19:02 2017-11-30 95.0 94.5 619.55 501.85 676.82 821.45 579.85 457.07 94.0 881.82 1919.37 752.01 989.16 93.5 1720.64 3875.63 3921.83 2224.30 3757.82 3673.41 2307.27 2381.44 2528.70 3111.42 1259.33 938.55 93.0 3826.53 3720.07 3455.00 Transmittance [%] Transmittance 1313.52 1140.69 92.5 1063.58 2874.83 1378.07 92.0 1189.42 1654.55 2966.81 91.5 1612.99 1523.39 2932.80 1464.58

4000 3500 3000 2500 2000 1500 1000 500

Wavenumber cm-1 Figure S9. IR spectrum of hyperjaponol H (1, KBr disc)

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