Journal of Environmental Protection, 2010, 1, 70-72
doi:10.4236/jep.2010.11009 Published Online March 2010 (http://www.SciRP.org/journal/jep)
Polyprenol from the Whole Plants of Leucaena leucocephala
Chung-Yi Chen*, Yau-Der Wang
School of Medical and Heath Science, The Fooyin University, Ta-Liao, Kaohuing, Taiwan, China.
Received January 14th, 2010; revised February 24th, 2010; accepted February 25th, 2010.
ABSTRACT
Ficaprenol-11 (polyprenol) (1), squalene (2), lupeol (3),  -sitostenone (4), trans-coumaric acid (5), cis-coumaric acid
(6) pheophytin-a (7), pheophorbide a methyl ester (8), methyl-132-hydroxy-(132-S)- pheophorbide-b (9) and aristo-
phyll-C (10) were isolated from the whole plants of Leucaena leucocephala (Leguminosae). Among them, 1 and 2 was
found for the first time from this species. The structure of these compounds were characterized and identified by spectra
analyses.
Keywords: Polyprenol, Leucaena leucocephala, Leguminosae
Leucaena leucocephala (Leguminosae) is a small, legu-
minous and native to tropical America, now widely dis-
tributed in southern Asia and neighboring islands [1].
This plant’s reproductive capacity is extremely strong. If
can henceforth the plant separate the effective component,
applies, will be able to reduce it to the environment threat.
Previous studies have show that the extract of L. leuco-
cephala was found to exhibit various pharmacological
effects [2–8], L. leucocephala was chosen for further
phytochemical investigation. The MeOH extract of its
plants were subjected to solvent partitioning and chro-
matographic separation to afford 10 pure substances. The
chemical constituents in the plants of L. leucocephala
were separated with column chromatography.
Investigation on the MeOH extract of the plants has
led to the isolation of 10 compounds, one polyprenol:
ficaprenol-11 (1) (Figure 1) [9]; two terpenoids:
squalene (2) (Figure 2) [10] and lupeol (3) [11]; one
steroid: β-sitostenone (4) [12]; two benzenoids: trans-
coumaric acid (5) and cis-coumaric acid (6) [13]; and
four chlorophylls: pheophytin-a (7) [14], pheophorbide a
methyl ester (8) [15], methyl-132-hydroxy-(132-S)-
pheophorbide-b (9) [16] and aristophyll-C (10) [17].
These compounds were obtained and characterized by
the comparison of their physical and spectral data (UV,
IR, NMR and MS) with values obtained in the literature.
Among them, 1 (Figure 1) and 2 (Figure 2) was found
for the first time from this species.
The specimen of L. leucocephala was collected from
Kenting National Park, Pingtung County, Taiwan in May,
2009. A voucher specimen was characterized by Dr.
Jin-Cheng Huang of Department of Forest Products Sci-
ence and Furniture Engine ering, National Chiayi Univer-
sity, Chiayi, Taiwan and deposited in the School of
Medical and Health Sciences, Fooyin University, Kaoh-
siung County, Taiwan. The air-dried green beans of L.
leucocephala (5.0 kg) were extracted with MeOH (80 L
x 6) at room temperature and the MeOH extract (132.5 g)
was obtained upon concentration und er reduced pressure.
The MeOH extract was chromatographed over silica gel
using n-hexane/acetone as eluent to produce 10 fractions.
Part of fraction 1 (8.24 g) was subjected to Si gel chro-
matography by eluting with n-hexane/acetone (50:1),
then enriched with acetone to furnish 7 fractions (1-1~
1-7). Fraction 1-4 (2.17 g) was re-subjected to Si gel
chromatography, eluting with n-hexane/Acetone (40:1)
to obtain -sitostenone (4) (9 mg, 0.0068%). Part of frac-
tion 2 (2.67 g) was subjected to Si gel chromatography
by eluting with n-hexane/acetone (50:1) to obtain fi-
caprenol-11 (1) (Figure 1) (21 mg, 0.0158%). Part of
fraction 3 (6.77 g) was subjected to Si gel chromatogra-
phy by eluting with n-hexane/acetone (8:1), then en-
riched with acetone to furnish 5 fractions (3-1~3-5).
Fraction 3-3 (1.33 g) was further purified by another sil-
ica gel column using n-hexane/acetone to obtain squalene
(2) (Figure 2) (5 mg, 0.0038%) and lupeol (3) (24 mg,
0.0181%). Part of fraction 5 (7.42 g) was subjected to Si
gel chromatography by eluting with n-hexane/acetone
(8:1) to obtain pheophorbide a methyl ester (8) (12 mg,
0.0091%). Part of fraction 6 (5.31 g) was subjected to Si
gel chromatography by eluting with n-hexane/acetone
(8:1) to obtain methyl-132-hydroxy-(132-S)-pheopho r-
bide-b (9) (6 mg, 0.0045%). Part of fraction 8 (4.91 g)
was subjected to Si gel chromatography by eluting with
n-hexane/acetone (5:1) to obtain pheophytin-a (7) (8 mg,
0.0060%).

Polyprenol from the Whole Plants of Leucaena leucocephala 71
CH2OH
n = 5
1
Figure 1. Chemical structure of Ficaprenol-11 (1)
2
Figure 2. Chemical struct ur e of Squale ne (2)
The air-dried leaves of L. leucocephala (5.8 kg) were
extracted with MeOH (80 L × 6) at room tempera ture and
the MeOH extract (143.5 g) was obtained upon concen-
tration under reduced pressure. The MeOH extract was
chromatographed over silica gel using n-hexane/acetone
as eluent to produce 8 fractions. Part of fraction 5 (9.22 g)
was subjected to Si gel chromatography by eluting with
n-hexane/acetone (8:1) to obtain aristophyll-C (10) (13
mg, 0.0091%). Part of fraction 8 (7.16 g) was subjected
to Si gel chromatography by eluting with n-hexane/ace-
tone (5:1) to obtain trans-coumaric acid (5) and cis-
coumaric acid (6) mixture (5 mg, 0.0035%) .
Acknowledgment
This investigation was supported by a grant from the
National Science Council of Republic of China (NSC
97-2320-B-242-002-MY3).
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