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Phloroglucinol derivatives of Dryopteris sieboldii
Phytochemstry,
1973, Vol
12. p 2055
Pergamon
Press
Prmted
m England
PHYTOCHEMICAL
PHLOROGLUCINOL
OF DR YOPTERIS
DERIVATIVES
SUEO HISADA, 0
REPORTS
INOUE
SZEBOLDZI
and ISAO INAGAKI
Faculty of Pharmaceutical Sciences, Nagoya City Umverslty, Mizuho. Nagoya, Japan (Recerved Key Word Index-Byopterrs
srebo’drl,
11 Aprd
1973
Accepted
24 Aprd
1973)
Asprdlaceae, fern, acylphloroglucmol,
fillxlc acid-ABB
In previous paper,’ we reported the Isolations of fihx~c acid-PBP, flavaspldlc actd-AB and -PB from the rhizomes of Dryoptens sreboldrr From the same material we have also Isolated another acylphloroglucmol, fihx~c acid-A BB The Et20 solution of crude fihcm after removal of flavaspldlc acid-AB was chromatographed on slhca and the elutlon of cyclohexane-CHCI, (I I) gave fihx~c acid-ABB FIIIXIC acid-ABB C30H400,2, m p 175-177” (needle tryst from acetone) IR v:iX cm-’ 3150 (OH), 2950 (methylene), 1640-1610 (enohc 1,3-dtketo system or 2_hydroxarylketone), 1430, I 193 uv x:2: nm (log c) 224 (4 43), 299 (4 28), 345 (4 28) UV ii$z’+NsoH nm (log c) 241 (4 37), 314 (4 33) R, 0 62 on TLC m CHCI,-MeOH-H,O (7 3 I, lower) spot color gave orange yellow with dlazotlzed benzldme The NMR spectrum (100 MHz, J 7 5 Hz), I I7 (3H, t -COCH,CDCI,) gave bands at (6) I 00 (3H, t -COCH,CH,CH,, CH,CH,, J 7 5 Hz), I 43, I 54 (l2H, each s two gem-dlmethylgroups), ca I 76 (4H, m two -COCH,CH,CH,), 2 72 (3H, s -COCH,), 3 20 (4H. ovellapplng t two -COCI-_I,CH,CH,), 4 02, 4 06 (4H, each s two 3 C-CH,-C < group?) The signals at IO I6 (4H, br), 13 05 (I H, br) and 16 24 (2H, br) are all due to hydrogen bonded OH-groups, and quenched by addltron of D20 The MS shows the parent peak at m/c 640 Other Important peaks at m/e 432,404, 236, 193, 181, I65 1 HISADA, S , IYOLJE,0 and
JNAGAKI,
J (1973)
Ph~tnchemrstry
12.1493
Ackt?ow/edpements-The authors thank Professor H Jtokawa, Tokyo College of Pharmacy for measurement of NMR and MS We are also Indebted to AnalytIcal Center of our Unlverslty for elemental analysis
2055
1973, Vol
12. p 2055
Pergamon
Press
Prmted
m England
PHYTOCHEMICAL
PHLOROGLUCINOL
OF DR YOPTERIS
DERIVATIVES
SUEO HISADA, 0
REPORTS
INOUE
SZEBOLDZI
and ISAO INAGAKI
Faculty of Pharmaceutical Sciences, Nagoya City Umverslty, Mizuho. Nagoya, Japan (Recerved Key Word Index-Byopterrs
srebo’drl,
11 Aprd
1973
Accepted
24 Aprd
1973)
Asprdlaceae, fern, acylphloroglucmol,
fillxlc acid-ABB
In previous paper,’ we reported the Isolations of fihx~c acid-PBP, flavaspldlc actd-AB and -PB from the rhizomes of Dryoptens sreboldrr From the same material we have also Isolated another acylphloroglucmol, fihx~c acid-A BB The Et20 solution of crude fihcm after removal of flavaspldlc acid-AB was chromatographed on slhca and the elutlon of cyclohexane-CHCI, (I I) gave fihx~c acid-ABB FIIIXIC acid-ABB C30H400,2, m p 175-177” (needle tryst from acetone) IR v:iX cm-’ 3150 (OH), 2950 (methylene), 1640-1610 (enohc 1,3-dtketo system or 2_hydroxarylketone), 1430, I 193 uv x:2: nm (log c) 224 (4 43), 299 (4 28), 345 (4 28) UV ii$z’+NsoH nm (log c) 241 (4 37), 314 (4 33) R, 0 62 on TLC m CHCI,-MeOH-H,O (7 3 I, lower) spot color gave orange yellow with dlazotlzed benzldme The NMR spectrum (100 MHz, J 7 5 Hz), I I7 (3H, t -COCH,CDCI,) gave bands at (6) I 00 (3H, t -COCH,CH,CH,, CH,CH,, J 7 5 Hz), I 43, I 54 (l2H, each s two gem-dlmethylgroups), ca I 76 (4H, m two -COCH,CH,CH,), 2 72 (3H, s -COCH,), 3 20 (4H. ovellapplng t two -COCI-_I,CH,CH,), 4 02, 4 06 (4H, each s two 3 C-CH,-C < group?) The signals at IO I6 (4H, br), 13 05 (I H, br) and 16 24 (2H, br) are all due to hydrogen bonded OH-groups, and quenched by addltron of D20 The MS shows the parent peak at m/c 640 Other Important peaks at m/e 432,404, 236, 193, 181, I65 1 HISADA, S , IYOLJE,0 and
JNAGAKI,
J (1973)
Ph~tnchemrstry
12.1493
Ackt?ow/edpements-The authors thank Professor H Jtokawa, Tokyo College of Pharmacy for measurement of NMR and MS We are also Indebted to AnalytIcal Center of our Unlverslty for elemental analysis
2055