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Eicosanoid


DATA No : XPR8019 INFORMANT : Yasuji Yamada

NAME : methyl (5S,6R,7E)-7-[(2S)-4-chloro-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate

COMMON NAME: punaglandin 3
SYMBOL: PUG 3
FORMULA: C25H33ClO8 MOL.WT (average) : 496.977


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BIOLOGICAL ACTIVITY
Punaglandin 3 inhibits L 1210 leukemia cell proliferation with ac IC50 value of 0.02 mg/ml.(Ref. 8029)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D+66.8deg(c 0.54, MeOH) (Ref. 8029/8036/8037)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (MeOH)238 nm(e8600) (Ref. 8029/8036/8037)

IR SPECTRA:nmax(CHCl3) 3100-3600(br), 2960, 2940, 1725, 1680(sh), 1378, 1235, 1110-990(br) cm-1 (Ref. 8029/8036/8037)

NMR SPECTRA:1H-NMR(300MHz, CDCl3)dppm 0.94(3H, t, J=7.5Hz), 1.6(4H, m), 2.05(2H, m), 2.05(3H, s), 2.09(3H, s), 2.3(2H, m), 2.68(1H, dd, J=7.0, 14.3Hz), 2.74(2H, br dd, J=7.1, 7.1Hz), 3.01(1H, dd, J=8.1, 14.3Hz), 3.50(1H, s), 3.65(3H, s), 5.2(1H, m), 5.2(1H, m), 5.25(1H, m), 5.41(1H, m), 5.53(1H, m), 6.02(1H, dd, J=4.3, 9.1Hz), 6.35(1H, d, J=9.1Hz), 7.27(1H, s). (Ref. 8029/8036/8037)13C-NMR(75MHz, CDCl3)dppm 14.2(q), 20.2(t), 20.5(t), 20.8(q), 20.8(q), 25.6(t), 29.6(t), 33.2(t), 35.6(t), 51.7(q), 69.8(d), 73.7(d), 77.2(s), 122.0(d), 126.1(d), 130.5(d), 132.5(d), 133.1(d), 137.2(s), 140.5(s), 155.7(d), 169.9(s), 171.1(s), 173.8(s), 186.6(s). (Ref. 8029/8036/8037)

MASS SPECTRA:EIMS(25 eV)m/z 478(1), 418(14), 387(50), 376(14), 358(26), 327(100), 275(30), 267(38), 253(30), 235(35). (Ref. 8029/8036/8037)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)
CHEMICAL SYNTHESIS
Punaglandin 3 was synthesized from D-(-)-diethyl tartrate and 2-deoxy-D-ribose.(Ref. 8030)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[8029]
AUTHOR:Baker,B.J., Okuda,R.K., Yu,P.T.K., and Scheuer, P.J.
TITLE:Punaglandins: Halogenated Antitumor Eicosanoids from the Octocoral Telesto riisei.
JOURNAL:J. Am. Chem. Soc.
VOL:107 PAGE : 2976 -2977 (1985)
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[8030]
AUTHOR:Nagaoka,H.,Miyaoka,H.,Miyakoshi,T., and Yamada,Y.
TITLE:Synthesis of Punaglandin 3 and 4. Revision of the Structures.
JOURNAL:J. Am. Chem. Soc.
VOL:108 PAGE : 5019 -5021 (1986)
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[8036]
AUTHOR:Baker, B. J., and Scheuer, P. J.
TITLE:The punaglandins: 10-chloroprostanoids from the octocoral Telesto riisei PubMed ID:7857405
JOURNAL:J Nat Prod.
VOL:57 PAGE : 1346-1353 (1994)
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[8037]
AUTHOR:Scheuer.P.J.
TITLE:Marine Natural Products Research: A Look into the Dive Bag.
JOURNAL:J. Nat.Prod.
VOL:58 PAGE : 335 -343 (1995)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.