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Terpenoids and sterols from endemic and endangered Philippine trees, Ficus pseudopalma and Ficus ulmifolia

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Abstract

The dichloromethane extract of the air-dried leaves of the endemic and endangered Philippine trees, Ficus pseudopalma and Ficus ulmifolia afforded squalene, polyprenol, β-amyrin fatty acid ester, α-amyrin acetate and β-amyrin acetate. F. pseudopalma also yielded lupeol fatty acid ester, lupenone, oleanone, and ursenone, while F. ulmifolia also afforded lutein, lupeol acetate, β-carotene, phytol, α-amyrin fatty acid ester, sitosterol, and stigmasterol. Their structures were identified by NMR spectroscopy.
Philippine Journal of Science
138 (2): 205-209, December 2009
ISSN 0031 - 7683
Key Words: Carotenoids, Ficus pseudopalma, Ficus ulmifolia, Moreaceae, phytol, polyprenol,
sterols, triterpenes
*Corresponding author: ragasa@dlsu.edu.ph
205
Terpenoids and Sterols from the Endemic and Endangered
Philippine Trees, Ficus pseudopalma and Ficus ulmifolia
Consolacion Y. Ragasa,1,* Po-wei Tsai,1 and Chien-Chang Shen2
1Chemistry Department, De La Salle University, 2401 Taft Avenue, Manila 1004, Philippines and
Center for Natural Sciences and Ecological Research, De La Salle University
2401 Taft Avenue, 1004 Manila
2National Research Institute of Chinese Medicine, 155-1, Li-Nong St., Sec 2, Taipei 112, Taiwan
The dichloromethane extract of the air-dried leaves of the endemic and endangered Philippine
trees, Ficus pseudopalma and Ficus ulmifolia afforded squalene, polyprenol,
β
-amyrin fatty acid
ester,
α
-amyrin acetate and
β
-amyrin acetate. F. pseudopalma also yielded lupeol fatty acid
ester, lupenone, oleanone, and ursenone, while F. ulmifolia also afforded lutein, lupeol acetate,
β
-carotene, phytol,
α
-amyrin fatty acid ester, sitosterol, and stigmasterol. Their structures were
identified by NMR spectroscopy.
INTRODUCTION
The diversity of Philippine plants is exceptional,
however, many have yet to be studied for their chemical
constituents. Ficus pseudopalma and Ficus ulmifolia are
endemic and endangered Philippine trees with no reported
chemical studies. Thus, this research was conducted to
isolate and identify the dichloromethane soluble secondary
metabolites in both trees. F. pseudopalma is a medicinal
and ornamental tree found throughout the Philippines.
A decoction of the leaves is used for the treatment of
kidney stones and diabetes, while the young shoots are
eaten as vegetables (Stuart 2008). On the other hand, F.
ulmifolia has no reported medicinal properties. The hard
and rough leaves are used to clean cooking utensils and
to scour wood. The fruits are edible, but has little flavor
(Jansen et al. 1991).
We report here the isolation and identification of
the dichloromethane soluble constituents of Ficus
pseudopalma and Ficus ulmifolia. F. pseudopalma
afforded the triterpenes: ursenone (1c), β-amyrin fatty acid
ester (2a), α-amyrin acetate (1b), β-amyrin acetate (2b),
oleanone (2c), lupeol fatty acid ester (3a), lupenone (3c),
and squalene (4); and polyprenol (5), while F. ulmifolia
yielded the triterpenes: α-amyrin fatty acid ester (1a),
α-amyrin acetate (1b), -amyrin fatty acid ester (2a),
β-amyrin acetate (2b), lupeol acetate (3b), and squalene
(4); polyprenol (5), phytol (6), β-carotene (7), lutein (8),
stigmasterol (9), and sitosterol (10) (Figure 1). This is
the first report on the isolation of the aforementioned
compounds from Ficus pseudopalma and Ficus ulmifolia.
MATERIALS AND METHODS
General Experimental Procedures: NMR spectra were
recorded on a Varian Unity Inova spectrometer in CDCl3
at 500 MHz for 1H NMR and 125 MHz for 13C NMR
spectra. Column chromatography was performed with
silica gel 60 (70-230 mesh), while the TLC was performed
with plastic backed plates coated with silica gel F254. The
plates were visualized with vanillin-H2SO4 and warming.
Research Note
Ragasa et al.: Terpenoids and Sterols from Philippine
Trees, Ficus pseudopalma and F. ulmifolia
Philippine Journal of Science
Vol. 138 No. 2, December 2009
Figure 1. Terpenoids and Sterols from Ficus ulmifolia (1-10) and Ficus pseudopalma (1-5).
206
Plant Material
The plant samples were collected from around Lake Buhi,
Camarines Sur in September 2007. They were identified
as Ficus pseudopalma and Ficus ulmifolia by Noe Gapas
of the Philippine National Museum who also collected
the samples. Ficus pseudopalma (voucher specimen #
132) and Ficus ulmifolia (voucher specimen # 133) were
deposited at the Chemistry Department, De La Salle
University – Manila.
H
RH
H
RH
H
RH
OH
3
]
[[]
n
CH
2
OH
1 a R =
CH
3
(CH
2
)nCOO
1b R = OAc
1c R = O 2 c R = O
OAc
2b R =
CH
3
(CH
2
)nCOO
2 a R =
3c R = O
OAc
3b R =
CH
3
(CH
2
)nCOO
3 a R =
4
5
6
OH
HO
7
8
HH
HO
H
9
10
H
HO
H H
Isolation
The dichloromethane extract of the air-dried leaves of F.
pseudopalma (1.9 kg) was chromatographed on a silica
gel column using increasing proportions of acetone in
dichloromethane at 10% increment. The 10% acetone
in dichloromethane fraction was rechromatographed
in petroleum ether. The less polar fractions afforded 4
after rechromatography in petroleum ether. The more
polar fractions were rechromatographed (7x) in 2.5%
Ragasa et al.: Terpenoids and Sterols from Philippine
Trees, Ficus pseudopalma and F. ulmifolia
Philippine Journal of Science
Vol. 138 No. 2, December 2009
207
is α to a carbonyl, and a methyl triplet at δ 0.88 for 1a,
an acetoxy methyl was detected at δ 2.01 for 1b. The
13C NMR spectrum for 1a gave resonances for the long
chain fatty acid methylene carbons centered at δ 29.7,
carbonyl carbon of the ester at δ 173.7, and the methyl
carbon at the end of the fatty acid chain at δ 14.1. These
resonances for 1a were replaced in 1b by the resonances
for the acetoxy carbons at δ 171.0 and 21.3. Ursenone
1c, oleanone 2c, and lupenone 3c have similar 1H NMR
resonances to -amyrin acetate 1b, β-amyrin acetate 2b, and
lupeol acetate 3b, respectively, except in the regions where
their structures differ, e.g., around C-3 where the acetates
were replaced by carbonyls. Thus, the resonances at δ
2.01 for the acetoxy methyl and δ 4.40 for the oxymethine
protons of 1b, 2b, and 3b were not found in 1c, 2c, and
3c. The 13C NMR resonances for the acetoxy carbons at
δ 171.0 and 21.3, and the carbinyl carbon resonances at
δ 80.9 for 1b, 2b, and 3b were replaced by the carbonyl
carbon resonances at δ 217.9 for 1c, 2c, and 3c (Hisham
et al. 1995; Clen et al. 1998).
Although bioassays were not conducted on the isolated
compounds, there were previous studies that reported
on their biological activities. α-Amyrin acetate has been
reported to possess hypoglycemic activity (Narrender et al.
2009), while lupeol exhibited antiurolithiatic and diuretic
activity (Vidya et al. 2002). α-Amyrin acetate may be one
of the active constituents in the anti-diabetes property of F.
pseudopalma. Lupeol prevented the formation of vesical
calculi and reduced the size of the preformed stones in
rats (Anand et al. 1994). This indicates that lupeol may
be one of the active constituents in the treatment of kidney
stones by F. pseudopalma. α-Amyrin and β-amyrin were
reported to posses anti-inflammatory activity (Recio et al.
1995; Madeiros et al. 2007), while α-amyrin, β-amyrin,
and the 3-O-acyl derivatives of α-amyrin and -amyrin
exhibited analgesic property (Otuki et al. 2005; Soldi
et al. 2008). Squalene significantly suppresses colonic
ACF formation and crypt multiplicity. This strengthens
the hypothesis that squalene possesses chemopreventive
activity against colon carcinogenesis (Rao et al. 1998).
Squalene has cardioprotective effect which is related to
inhibition of lipid accumulation by its hypolipidemic
properties and/or its antioxidant properties (Farvin et
al. 2006). Lutein and zeaxanthin may have roles in
protecting against age-related macular degeneration
(Mozaffarieh et al. 2003). β-Sitosterol has been shown
to inhibit proliferation and induce apoptosis in human
solid tumors such as colon and breast cancers (Park et al.
2007). Stigmasterol lowers plasma cholesterol levels,
inhibits intestinal cholesterol and plant sterol absorption,
and suppresses hepatic cholesterol and classic bile acid
synthesis in Winstar as well as WKY rats (Batta et al.
2006). A polyprenol from the ethanol extract of Coccinia
ethyl acetate in petroleum ether. The less polar fractions
afforded a mixture of 1c, 2c, and 3c, followed by a
mixture of 2a and 3a. The more polar fractions were
rechromatographed in 5% ethyl acetate in petroleum
ether to yield a mixture of 1b and 2b from the less polar
fractions, while 5 was obtained from the more polar
fractions.
The dichloromethane extract of the air-dried leaves of
F. ulmifolia (742 g) was chromatographed on a silica
gel column using increasing proportions of acetone in
dichloromethane at 10% increment. The 10% acetone
in dichloromethane fraction was rechromatographed in
petroleum ether. The less polar fractions afforded 4 and
7. The more polar fractions were rechromatographed
by gradient elution technique. The column was first
eluted with 2.5% ethyl acetate in petroleum ether to
afford a mixture of 1b, 2b, and 3b, followed by 5% ethyl
acetate in petroleum ether to afford a mixture of 1a and
2a. The 20% acetone in dichloromethane fraction was
rechromatographed in 10% ethyl acetate in petroleum
ether to afford 5. The 40% acetone in dichloromethane
fraction was rechromatographed in dichloromethane to
afford 6. The 50% acetone in dichloromethane fraction
was rechromatographed in dichloromethane:diethyl
ether:acetonitrile (8:1:1) to afford a mixture of 9 and 10
after washing with petroleum ether. The 60% acetone
in dichloromethane fraction was rechromatographed
in dichloromethane:diethyl ether: acetonitrile (8:1:1)
to afford 8 after washing with petroleum ether, then
diethyl ether.
RESULTS AND DISCUSSION
The dichloromethane extracts of the air-dried leaves
of Ficus pseudopalma and Ficus ulmifolia afforded
terpenoids and sterols by silica gel chromatography.
These compounds were identified by comparison of their
13C NMR spectral data with those of -amyrin fatty acid
ester 1a (Menezes et al. 1998), β-amyrin fatty acid ester
2a (Menezes et al. 1998; Wang 2007; Barreiros et al.
2002), β-amyrin acetate 2b (Derome 1987), lupeol fatty
acid ester 3a (Wang 2007), lupeol acetate 3b (Derome
1987), squalene 4 (Brown & Martens 1977), polyprenol
5 (Rideout et al. 2003), phytol 6 (Ragasa et al. 2003),
lutein 7 (Largo et al. 1997), β-carotene 8, stigmasterol
9, and sitosterol 10 (Cayme and Ragasa 2004) reported in
the literature. The structure of α-amyrin acetate 1b was
deduced by comparison of its 1H NMR and 13C NMR
spectral data with those of α-amyrin fatty acid ester
1a. Instead of the long chain fatty acid at δ 1.25 for the
methylene protons, a methylene triplet at δ 2.30 which
Ragasa et al.: Terpenoids and Sterols from Philippine
Trees, Ficus pseudopalma and F. ulmifolia
Philippine Journal of Science
Vol. 138 No. 2, December 2009
208
grandis showed significant triglyceride and cholesterol
lowering effects in dyslipidemic hamster model (Singh
et al. 2007).
ACKNOWLEDGMENT
A rese ar ch grant fr om the Un iversity Re se ar ch
Coordination Office and the Science Foundation of De
La Salle University is gratefully acknowledged. The plant
samples were collected by Noe Gapas of the Philippine
National Museum.
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... The folkloric practice of using fig leaves to decoct for the treatment of kidney stones and diabetes is recently validated by a study on the antioxidant and antiurolithic properties of F. pseudopalma leaves [2,9] . The dichloromethane extract of the air-dried leaves of F. pseudopalma afforded squalene, polyprenol, β-amyrin fatty acid ester, α-amyrin acetate and β-amyrin acetate, lupeol fatty acid ester, lupenone, oleane, and ursenone [10] . Despite recent studies are on the biological activities of F. pseudopalma leaf extracts, its antimicrobial properties have not yet been investigated. ...
... Phytochemical screening on the dichloromethane leaf extract of F. pseudopalma revealed the presence of squalene, polyprenol, β-amyrin fatty acid ester, α-amyrin acetate and β-amyrin acetate, lupeol fatty acid ester, lupenone, oleanone, and ursenone [10] . The presence of lupeol, a pentacyclic triterpene, was identified in the acetone:methanol fraction from the crude ethanolic leaf extract [18] , in the crude ethanolic leaf extract and in its chloroform and ethylacetate fractions [19] and in the ethyl acetate fraction from the crude dichloromethane extract [2] of F. pseudopalma through HPLC analysis. ...
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... The use of fig leaves for the treatment of kidney stones and diabetes in folkloric medicine [3] has been recently validated in a study where the anti-urolithiatic and antioxidant properties of the leaves of the plant were demonstrated by promoting free radical scavenging activity, inhibition of lipid peroxidation, and reduction of calcium oxalate crystal deposit in renal tissues [4]. Phytochemical screening of air-dried leaves of FP revealed the presence of ursenone and lupeol [5]. ...
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The protective effect of squalene on membrane function and mineral status was examined in isoproterenol-induced myocardial infarction in male albino rats. The pretreatment with squalene at 2% level along with feed significantly reduced the isoproterenol-induced rise in the levels of plasma diagnostic marker enzymes (ALT, AST, LDH and CPK). It counteracted isoproterenol-induced lipid peroxidation in plasma and heart tissue, and maintained the level of reduced glutathione in the heart tissue at near normalcy. Supplementation of squalene also exerted membrane stabilizing action against isoproterenol-induced myocardial infarction by maintaining the activities of membrane-bound ATPases (Na+, K+ ATPase and Ca2+ ATPase) in heart tissue and the mineral status (sodium, potassium and calcium) in plasma and heart tissue at near normal levels. The cardioprotective effect of squalene might be ascribable to its antioxidant nature and membrane stabilizing property.
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Ficus racemosa belongs to the family of Moraceae and is commonly known as 'Gular' in north India. Bio-activity guided isolation work on the fruits of F. racemosa resulted in the identification of antidiabetic active principle, a-amyrin acetate 7. Compound 7 lowered the blood glucose levels by 18.4 and 17.0% at 5 and 24 h, respectively, in sucrose challenged streptozotocin induced diabetic rat (STZ-S) model at the dose of 100 mg/kg body weight. Fifteen novel derivatives viz, 9–21, 24, 25 of a-amyrin 8 were prepared and their antihyperglycemic activity profile was assessed. The p-chlorobenzoic acid derivative 9 and nicotinic acid derivative 14 showed potent antihyperglycemic activity at 100 mg/kg body weight. Ó 2008 Elsevier Masson SAS. All rights reserved.
Article
The 13C NMR of squalene in tetrahydrofuran-d8 is sufficiently resolved for T1 measurements (by the inversion-recovery method) to permit the derivation of relative mobilities along the chain On addition of water, no detectable changes occur to the point of saturation, consistent with the absence of conformational changes (coiling) with change in solvent polarity. On the basis of silver-ion induced carbon chemical shifts, complexation occurs unselectively at all three double bonds in THF, but with some preference for the terminal double-bond in part-aqueous solutions. Squalane shows similar mobility to the unsaturated compound but complications from line overlap are apparent. In squalene-2,3-glycol, the polar end of the molecule is of lower mobility, and this difference is accentuated on addition of water consistent with specific association of water at the OH terminus.
Article
A mixture containing a new triterpene, chamaedrydiol (urs-12-ene-2α,3β-diol), and three known triterpenes (lup-20(29)-ene-2α,3β-diol, castanopsol and epigermanidiol) was isolated from Marsypianthes chamaedrys. The components in the mixture were identified using spectroscopic methods. In addition, a mixture of four less polar known triterpenes consisting of α-amyrin, β-amyrin, lupeol and germanicol, was also isolated.
Article
β-Sitosterol is the main dietary phytosterol found in plants and has been shown to inhibit proliferation and induce apoptosis in human solid tumors such as colon and breast cancers. However, the mechanism by which β-sitosterol induces apoptosis is not completely understood in leukemic cells. This study investigated the mechanism of apoptosis induced by β-sitosterol in human leukemic U937 cells. β-Sitosterol induced cytotoxicity and apoptosis in U937 cells in a concentration dependent manner, as measured by hemocytometer counts, fluorescence microscopy, agarose gel electrophoresis, and flow cytometry analysis. The increase in apoptosis induced by β-sitosterol was associated with down-regulation of Bcl-2, degradation of poly-(ADP-ribose) polymerase (PARP) and phospholipase C (PLC)-γ1 protein, and activation of caspase-3. β-Sitosterol induced apoptosis was not associated with changes in the expression of Bcl-xL, Bax, or inhibitor of apoptosis proteins (IAPs). z-DEVD-fmk, a caspase-3 specific inhibitor, blocked caspase-3 activation and PARP degradation, and significantly attenuated β-sitosterol-induced apoptosis. This suggests that caspase-3 activation is partially essential for β-sitosterol-induced apoptosis. Bcl-2 overexpression also significantly blocked caspase-3 activation and the decrease in PARP cleavage by β-sitosterol, and effectively attenuated the apoptotic response to β-sitosterol. These results show that β-sitosterol potently induces apoptosis in U937 cells and that β-sitosterol-induced apoptosis is related to the selective activation of caspase-3 and induction of Bax/Bcl-2 ratio.
Book
This book presents an introduction to modern NMR methods at a level suited to organic and inorganic chemists engaged in the solution of structural and mechanistic problems. The book assumes familiarity only with the simple use of proton and carbon spectra as sources of structural information and describes the advantages of pulse and Fourier transform spectroscopy which form the basis of all modern NMR experiments. Discussion of key experiments is illustrated by numerous examples of the solutions to real problems. The emphasis throughout is on the practical side of NMR.
Article
In the traditional Indian system of medicine Crateva nurvala (Hindi: Varuna) constitutes a major ingredient of formulations used to treat urinary disorders including urolithiasis. In an earlier study we confirmed the antiurolithiatic activity in the crude extract of the plant, and further fractionation led to the isolation of the active constituent lupeol (Lup-20(29)-en-3β-ol). Antiurolithiatic activity of lupeol was assessed in rats by observing the weight of the stone, biochemical analysis of serum and urine, and histopathology of bladder and kidney. Lupeol not only prevented the formation of vesical calculi but also reduced the size of the preformed stones.