Back to HOME

Eicosanoid


DATA No : XPR8030 INFORMANT : Yasuji Yamada

NAME : methyl (5S,6R)-7-[(1R,2S)-4-chloro-2-hydroxy-2-[(2Z,5Z)-2,5-octadienyl]-5-oxo-3-cyclopentenyl]-5,6-diacetoxyheptanoate

COMMON NAME: punaglandin 5 acetate
SYMBOL:
FORMULA: C27H37ClO9 MOL.WT (average) : 541.030


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D+8deg(c 1.2, MeOH) (Ref. 8036/8037)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax(CHCl3) 240 nm(e4500) (Ref. 8036/8037)

IR SPECTRA:

NMR SPECTRA:1H-NMR(300MHz, CDCl3)dppm 0.95(3H, t, J=7Hz), 1.6(4H, m), 1.9(2H, m), 2.0(2H, m), 2.1(3H, s), 2.2(3H, s), 2.2(3H, s), 2.3(2H, m), 2.3(2H, m), 2.6(2H, t), 3.0(1H,dd), 3.2(1H, t), 3.6(3H, s), 5.0(1H, m), 5.2(1H, dt, J=10.5Hz), 5.2(1H, dd, J=8, 10Hz), 5.3(1H, m), 5.4(1H, m), 5.5(1H, ddd, J=1, 7, 10.8Hz), 7.5(1H, s). (Ref. 8036/8037)13C-NMR(75MHz, CDCl3)dppm 14.2, 20.6, 20.9, 21.0, 21.5, 25.7, 26.4, 30.0, 33.4, 35, 36, 52, 52.2, 72.3, 72.8, 85.5, 121.0, 123.0, 125.7, 132.8, 133.4, 155.6, 169.9, 170.3, 170.5, 173.0, 197. (Ref. 8036/8037)

MASS SPECTRA:EIMS(70 eV)m/z 480(4.9), 420(27.4), 407(13.6), 378(12.4), 360(25.6), 329(33.4), 269(29.2), 43(100). (Ref. 8036/8037)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)
CHEMICAL SYNTHESIS

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)
[TOP]

[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)
[TOP]

[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)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.