1. Comanthus parvicirrus ( 小卷海齒花 ) 動物界 (Animalia) 棘皮動物門 (Echinodermata) 海百合綱 (Crinoidea) 關節亞鋼 (Articulata) 海羊齒目 (Comatulida) 櫛羽星科 (Comasteridae) 為一種始見於石炭紀的棘皮動物，生活於海裡， 具多條腕足，身體呈花狀，錶面有石灰質的殼。 常棲息於岩縫、石、軟珊瑚的基部。

2. 抽取與分離

3. General Experimental Procedures. UV spectra were measured in MeOH on a Perkin-Elmer Lambda 15 UV/vis spectrometer. IR spectra were recorded on an ATI Mattson Genesis FTIR, using KBr discs. 1 H, 13 C, and all other NMR 2D experiments were recorded in CDCl 3, either on a Varian Unity INOVA 400 MHz spectrometer or on a Bruker Avance 600 MHz spectrometer with a cryoprobe. TMS was used as an internal reference for the 1H NMR spectra, and the CDCl3 signal at 77.0 ppm was used as a reference for 13 C NMR spectra. ESIMS was carried out on a Perseptive Biosystem Mariner LC-MS. HRESIMS analysis was carried out at the EPSRC National Mass Spectrometry Service Centre in Swansea (UK). HPLC separations were carried out using a Phenomenex reversed- phase (C18, 10 × 250 mm, 5 μm) HPLC column and an HP1100 HPLC system (Agilent Technologies) with a diode array detector (DAD).

4. MeOH extract of C. parvicirrus (1.1g dry weight) Partitioned by H 2 O-CH 2 Cl 2 fractionation H 2 O-solubleCH 2 Cl 2 -soluble 50% MeOH-soluble Compound 1 (61 mg) Compound 2 (34 mg) Reversed-phase HPLC 抽取與分離 Hexanes/10%MeOH Partitione Extracted with CH 2 Cl 2 CH 2 Cl 2 -soluble

5. naphthopyrones 6-methoxycomaparvin (1)6-methoxycomaparvin 5-methyl ether (2)

6. 結構解析

7. naphthopyrones 6-methoxycomaparvin (1) brown needle-shaped crystals UV (MeOH) λ max (logε) 245 (4.57), 290 (4.37), 380 (3.77) nm IR (KBr) ν max 3341, 2950, 1667, 1615, 1571, 1537, 1448 cm -1 LRESIMS m/z 331 [M + H]+ (C 18 H 18 O 6 ) HRESIMS m/z 331.1176 [M + H]+, (calc for C 18 H 19 O 6 ) 1 H NMR (400 MHz, CDCl 3 ) δ : 6.23 (1H, s, H-3) 7.01 (1H, d, J=1.6 Hz, H-7) 6.43 (1H, d, J=1.6 Hz, H-9) 6.23 (2H, t J=7.7 Hz, H-11) 1.8 (2H, m, H-12) Methine (CH) Methylene (CH 2 ) 1.01 (3H, t, H-13) 3.94 (3H, s, H-16) 3.95 (3H, s, H-15) Methyl (CH 3 ) 12.90 (s, OH-5)

8. 13 C NMR : 170.1 (C-2) 183.4 (C-4) 147.1 (C-4a) 109.3 (C-5) 134.7 (C-6) 158.3 (C-6a) 104.9 (C-8) 160.2 (C-10) 136.1 (C-10a) 152.4 (C-10b) 109.5 (C-3) 96.3 (C-7) 96.7 (C-9) 36.5 (C-11) 20.0 (C-12) 13.7 (C-13) 60.4 (C-15) 56.2 (C-16)

9. HMBC

10. COSY

11. single-crystal X-ray diffraction analysis

12. 6-methoxycomaparvin 5-methyl ether (2) brown needle-shaped crystals UV (MeOH) λ max (logε) 240 (4.58), 280 (4.51), 365 (4.05) nm IR (KBr) ν max 3229, 2960, 1642, 1584, 1415 cm-1 LRESIMS m/z 345 [M + H]+ (C 19 H 20 O 6 ) HRESIMS m/z 345.1337 [M + H]+, (calc for C 19 H 21 O 6 ) 1 H NMR (400 MHz, CDCl3) δ : naphthopyrones 6-methoxycomaparvin (1)6-methoxycomaparvin 5-methyl ether (2) 12.90 (s, OH-5) 3.93 (s, H-14)

13. naphthopyrones 6-methoxycomaparvin (1)6-methoxycomaparvin 5-methyl ether (2) 13 C NMR : 62.0 (C-14)

14. HMBC