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Based on its HREIMS, compound 3 possessed the same molecular formula

C21H28O3 as compound 2. Its spectroscopic properties were very similar to


those of compound 1, with the same enediyne UV absorption spectrum, and IR
absorptions bands of a hydroxyl (3422 cm1) and a lactone carbonyl function
(1729 cm1). The 1H NMR spectrum of 3 (Table 1) showed a vinylic protons at
dH 5.77 (ddt, J = 17.0, 10.2, 6.5 Hz, H-150), 4.99 (brd, J = 10.2 Hz, H-160a) and
5.04 (m, H-160b), and a transdisubstituted double bond at dH 6.27 (dt, J =
15.8, 6.9 Hz, H-120) and 5.51 (brd, J = 15.8 Hz, H-110). The oxymethine protons
of the g- lactone, appeared at dH 4.46 (dq, J = 3.2, 6.4 Hz, H-5) and dH 4.32 (dd,
J = 4.8, 3.2 Hz, H-4), and the methyl signal at 1.44 (d, J = 6.4 Hz). The 1H1H
COSY and HMBC spectra were used to determine the planar structure of
compound 3. The 1H1H COSY (Fig. 2) spectrum displayed two spin systems
showing connectivi- ties from the methyl group to the CH2-60, and from the
vinylic H- 110 to the terminal exo-methylene. In addition, H-110 showed a long
range correlation (7JHH) with the CH2-60 at dH 2.32 (J = 6.9 Hz), which is
clearly coupled to CH2-50 at dH 1.55. In the HMBC spectrum, CH2-140
correlated with C-120, C-130, C-150 and C-160, and CH2-130 correlated with C110, C-120, C-140and C-150, while H- 110 showed correlations to all the
acetylenic carbons at dC 83.6 (C- 70), 65.3 (C-80), 73.1 (C-90), 73.9 (C-100),
and C-60 (5JCH). The geometry of the C-110 double bond was determined to
be in the E conguration on the basis of the vicinal coupling constant (J =
15.8 Hz). The all-cis stereochemistry of the lactone ring substituents was
suggested by the coupling constants of 4.8 and 3.2 Hz (JH3H4 and JH4H5,
respectively), and was supported by NOE correlations observed between H-3 and
H-4/H-5 in the NOESY spectrum, indicating that they are on the same face. The
chemical shifts of the CH3-6, CH2-10, CH-4 and CH-5 at dC 13.7, 23.3, 71.3 and
78.7, respectively, conrmed an all-cis relationship of the lactone ring
substituents (Werner and Hadacek, 1995; Lorenzo et al., 2006). The sign of the
optical rotation of compound 3, named sapranthin C, is opposite to the
30R,40S,50S-g-lactone derivatives isolated from the fruits of Trichilia claussenii
(Pupo et al., 1998) indicating that 3 is the (3S,4R,5R)-3-(11(E),15hexadecadiene
-7.9- diinyl)-4,5dihydro-4-hydroxy-5-methyl-2(3H)-furanone.

Berdasarkan HREIMS nya, 3 senyawa memiliki rumus molekul yang sama C21H28O3
sebagai senyawa 2. Sifat spektroskopi yang sangat mirip dengan 1 senyawa, dengan spektrum
penyerapan sama enediyne UV dan IR absorptions band dari hidroksil (3422 cm-1) dan
laktone karbonil fungsi (1729 cm-1). Spektrum NMR 1H 3 (Tabel 1) menunjukkan proton
vinylic di dH 5.77 (ddt, J = 17,0, 10.2, 6.5 Hz, H-150), 4,99 (brd, J = 10.2 Hz, H-160a) dan
5,04 (m, H-160b), dan ikatan ganda transdisubstituted di dH 6,27 (dt, J = 15,8, 6.9 Hz, H120) dan 5,51 (brd, J = 15.8 Hz, H-110). Proton oxymethine dari g-laktone, muncul di dH
4.46 (dq, J = 3.2, 6.4 Hz, H-5) dan dH 4,32 (dd, J = 4.8, 3.2 Hz, H-4), dan sinyal metil di 1.44
(d, J = 6.4 Hz). Spektrum 1H-1H nyaman dan HMBC digunakan untuk menentukan struktur
planar 3 senyawa. 1H-1H COSY (Fig. 2) spektrum ditampilkan dua sistem spin yang
menampilkan connectivi-ikatan dari gugus metil CH2-60, dan dari vinylic H - 110 ke
terminal exo-metilena. Selain itu, H-110 menunjukkan korelasi jangka panjang (7JHH)
dengan CH2-60 di dH 2.32 (J = 6.9 Hz), yang jelas digabungkan ke CH2-50 di dH 1,55.

Dalam spektrum HMBC, CH2-140 berkorelasi dengan C-120, C-130, C-150 dan C-160, dan
CH2-130 berkorelasi dengan C-110, C-120, C-140and C-150, sementara H - 110
menunjukkan korelasi untuk semua karbon acetylenic di dC 83.6 (C - 70), 65.3 (C-80), 73,1
(C-90), 73.9 (C-100) dan C-60 (5JCH). Geometri ikatan ganda C-110 bertekad untuk menjadi
di konfigurasi E berdasarkan konstan vicinal kopling (J = 15.8 Hz). Semua-cis Stereokimia
laktone cincin substituen disarankan oleh konstanta coupling 4.8 dan 3.2 Hz (JH3-H4 dan
JH4 H5, masing-masing), dan didukung oleh NOE korelasi diamati antara H-3 dan H-4/H-5
dalam spektrum NOESY, menunjukkan bahwa mereka adalah pada wajah yang sama. Kimia
bergeser CH3-6, CH2-10, CH-4 dan CH-5 di dC 13,7, 23,3, 71,3 dan 78,7, masing-masing,
conrmed semua-cis hubungan laktone cincin substituen (Werner dan Hadacek, 1995;
Lorenzo et al., 2006). Tanda rotasi optik senyawa 3, bernama sapranthin C, adalah
berlawanan 30R, 40-an, 50S-g-laktone derivatif terisolasi dari buah-buahan Trichilia
claussenii (Pupo et al. 1998) menunjukkan bahwa 3 (3S, 4R, 5R) -3-(11 (E),
15hexadecadiene-7.9-diinyl)-4,5dihydro-4-hydroxy-5-methyl-2(3H)-furanone.

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