Secondary metabolites from the leaves of Feijoa sellowiana Berg.

Article abstract of DOI:10.1016/j.phytochem.2004.06.038

The investigation of the lipid extract of leaves of Feijoa sellowiana cultivated along the east coast of Sicily has yielded in addition to the widespread secondary metabolites: α-tocopherol, flavone, stigmasterol and β-carotene, an inseparable mixture of tyrosol esters of lignoceric (1a), cerotic (1b) and montanic (1c) acids, and a novel galactolipid identified as (2S)-1,2,6′-tri-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl] -3-O-β-d-galactopyranosyl glycerol (2).

Full text of DOI:10.1016/j.phytochem.2004.06.038

PHYTOCHEMISTRY
Phytochemistry 65 (2004) 2947–2951
www.elsevier.com/locate/phytochem
Secondary metabolites from the leaves of Feijoa sellowiana Berg.
a,
b
Giuseppe Ruberto *, Corrado Tringali
a
Istituto del C.N.R. di Chimica Biomolecolare – Sezione di Catania, Natural Products and Food Chemistry,
Via del Santuario 110, I-95028 Valverde CT, Italy
`
Dipartimento di Scienze Chimiche, Universita degli Studi di Catania, Viale A. Doria 6, I-95125 Catania, Italy
b
Received 1 April 2004; received in revised form 3 June 2004
Available online 20 August 2004
Dedicated to Prof. Dr. Kurt Hostettmann on the occasion of his 60th birthday
Abstract
The investigation of the lipid extract of leaves of Feijoa sellowiana cultivated along the east coast of Sicily has yielded in addition
to the widespread secondary metabolites: a-tocopherol, flavone, stigmasterol and b-carotene, an inseparable mixture of tyrosol
esters of lignoceric (1a), cerotic (1b) and montanic (1c) acids, and a novel galactolipid identified as (2S)-1,2,60-tri-O-
[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]-3-O-b-D-galactopyranosyl glycerol (2).
ꢀ 2004 Elsevier Ltd. All rights reserved.
Keywords: Feijoa sellowiana; Myrtaceae; Leaves; Lipid extract; Tyrosol derivatives; Acyl-monogalactodiacyl glycerol
1. Introduction
reason it is also called Ôpineapple guavaÕ. Furthermore,
there is a large variety of industrialized products on
the market, particularly in the Australian area, in the
form of jam, paste, syrup, liqueur and crystallized fruits.
Notwithstanding literature reports on the antimicro-
bial, antioxidant and antitumoral activities of F. sel-
lowiana crude extracts (Basile et al., 1997; Koshimizu
et al., 1988; Vuotto et al., 2000), the chemistry of this
plant has not been extensively investigated. The deter-
mination of some basic components (Romero-Rodri-
guez et al., 1994a,b), flavonoids (Ferrara et al.,
1999a,b), and volatile components (Binder and Flath,
1989; Shaw et al., 1989, 1990) are the only available
phytochemical data.
Feijoa sellowiana Berg. (syn. Acca sellowiana) is an
evergreen bush belonging to the Myrtaceae family na-
tive to southern of South America, where it is widely dis-
tributed. Owing to its easy adaptability in subtropical
regions, nowadays it is extensively cultivated in Califor-
nia and mainly in New Zeland, where the fruits are pop-
ular. In the Mediterranean basin, this species was
introduced at the end of 19th century, initially as an
ornamental plant. Subsequently, feijoa plantations were
established in North Africa, Spain, France, Portugal
and Italy, as well as in the Caucasian region of southern
Russia (Morton, 1987).
The fresh fruit is appreciated for its characteristic fla-
vour and aroma, which are similar to pineapple, for this
As part of our current interest in wild and cultivated
Sicilian plant species, we wish to report here the results
of a study on the lipid extract of leaves of F. sellowiana
cultivated along the east coast of Sicily. In addition to
well-known components, namely a-tocopherol, flavone,
stigmasterol and b-carotene, some unreported long-
chain esters of tyrosol and a novel galactolipid have
been isolated and characterized.
*
Corresponding author. Tel.: +39-0957212136; fax: +39-
0957212141.
E-mail addresses: giuseppe.ruberto@icb.cnr.it (G. Ruberto), ctrin-
gali@unict.it (C. Tringali).
0031-9422/$ - see front matter ꢀ 2004 Elsevier Ltd. All rights reserved.
doi:10.1016/j.phytochem.2004.06.038

2948
G. Ruberto, C. Tringali / Phytochemistry 65 (2004) 2947–2951
2. Results and discussion
The molecular formula of the metabolite 2 was deter-
mined as C63H102O11 by HRFABMS, which exhibited
significant peaks at m/z 1057 [M + Na]+ and 1035
[M + H]+. The IR spectrum of the compound showed
absorption bands at 3450 and 1741 cmꢀ1 ascribable to
hydroxyl and ester functions.
Repeated chromatography on polyamide and silica
diol of the methylene chloride extract obtained from
the leaves of F. sellowiana revealed six compounds.
Among them, four were easily identified as the wide-
spread a-tocopherol, flavone, stigmasterol and b-caro-
tene, on the basis of their spectral properties and
comparison with authentic samples. A further two iso-
lates proved to be novel metabolites.
The 1H, 13C NMR and DEPT spectra showed a num-
ber of deshielded signals assignable to oxymethines and
oxymethylenes, and further signals at higher fields sug-
gesting the presence of polyunsaturated long chains. A
careful analysis of the 1D NMR spectra was accom-
plished on the basis of 2D NMR experiments, namely
COSY, HSQC and HMBC. A complex multiplet cen-
tered at d 5.30 was HSQC-correlated to a group of sig-
nals in the 13C NMR spectrum between 131.9 and 127.1
ppm assignable to olefinic methines. Further signals
indicated the presence of a glucopyranosyl moiety whose
Isolate 1 did not give a well-defined molecular weight
from its EI mass spectrum. It showed typical absorp-
tions for hydroxyl (3610 cmꢀ1) and ester (1737 cmꢀ1
)
1
functionalities in the IR spectrum. The H NMR spec-
trum confirmed the presence of a para-substituted ben-
zene ring appearing as an AAÔXXÕ system (d 7.07 and
6.76, each 2H, d). The aliphatic region showed an iso-
lated A2X2 system (d 4.23 and 2.85, each 2H, t) con-
firmed by COSY mutual correlations, and further
signals assignable to a saturated long chain, whose exact
length could not be determined by integral analysis (d
2.28, t; d 1.62, m; d 1.25, bs; d 0.87, bt). The 13C NMR
spectrum (see Section 3), as well as HSQC and HMBC
experiments, indicated the presence of a tyrosol moiety
and suggested that the primary alcoholic function was
esterified with a saturated long chain fatty acid.
Although isolate 1 could not be separated into its con-
stituents, it was apparent from the above data that it
was a mixture of tyrosol esters with acyl residues of dif-
ferent lengths. Such mixtures have been isolated from
Sideritis javalambrensis (Alcaraz et al., 1989) and Pilio-
stigma thonningi (Baratta et al., 1999). As a confirma-
tion, the methanolysis of this mixture gave the methyl
esters of lignoceric (C24), cerotic (C26) and montanic
(C28) acids (identified through GC-MS), accounting
for over 90% of the mixture. Therefore, the mixture
was characterized as a combination of the three tyrosol
derivatives 1a–1c.
1
b-anomeric H and 13C resonances appeared at d 4.22
(d, J = 7.5 Hz) and d 103.6 (d), and four oxymethines
and one oxymethylene between d 4.37 and 3.60 (1H)/d
73.1 and 62.3 (13C). Two further oxymethylenes and
an oxymethyne signal at d 62.3, 68.0 and 70.0, respec-
tively, as resulted by the DEPT experiments, associated
1
with signals in the H NMR spectrum at d 4.28 (CH2),
3.98 and 3.69 (CH2), and 5.27 (CH) accounted for a
1
glycerol moiety. The remaining signals in both H and
13C NMR spectra were assigned to different kinds of
methylenes, namely bis-allylic (whose 13C chemical
shifts were typical for a cis geometry of the vicinal dou-
ble bonds) (Wenkert et al., 1975), allylic, saturated, and
to terminal methyl groups, thus confirming the presence
of all-cis-polyunsaturated alkyl chains. Finally, three
13C NMR quaternary carbon signals at d 173.7, 173.5
and 173.7 were ascribed to three different carbonyl
esters.
All the above data strongly suggest the structure as a
galactolipid. A literature search showed a close similar-
ity of metabolite 2 with a galactolipid isolated from dif-
ferent plant species and the cyanobacterium Phormidium
tenue, namely (2S)-1,2-di-O-[(9Z,12Z,15Z)-octadeca-
O
n
9,12,15-trienoyl]-3-O-b-
D
-galactopyranosyl
glycerol
O
HO
(Larsen et al., 2003; Murakami et al., 1991; Wegner
et al., 2000). The difference with the compound isolated
from F. sellowiana was the presence, in this latter, of a
third polyunsaturated alkyl chain (as testified by MS
and NMR spectral data), which had to be allocated on
the sugar moiety.
This assumption was corroborated by the HMBC
correlations between the three carbonyl signals and
one oxymethylene and the oxymethine of the glycerol
moiety, and the oxymethylene of the sugar unit. Finally,
alkaline hydrolysis of 2 afforded compound 3 identical
1a n = 20; 1b n = 22; 1c n = 24
O
1''''
O
HO
4'
6'
O
O
5'
3
2'
O
OH1'
HO
3'
2
1
1'''
O
O
1''
O
2
OH
HO
HO
O
O
1
in all respects to (2R)-1-O-glyceryl-b-D-galactopyrano-
OH
2
side. This established the absolute configuration of the
C-2 stereogenic center in 2 as S (according to priority
rules), confirmed the sugar unit to be galactose, and that
3
OH
OH
3

G. Ruberto, C. Tringali / Phytochemistry 65 (2004) 2947–2951
2949
the further polyunsaturated alkyl chain was bound
at the C-60 hydoxyl group of galactose as evidenced by
and heteronuclear multiple-bond correlation (HMBC),
were performed at constant temperature (27 ꢁC) in deu-
terochloroform or deuteromethanol, using the software
supplied by the manufacturer.
Gas chromatographic (GC) analyses were run on a
Hewlett-Packard gas-chromatograph model 5890 con-
nected with an electronic integrator. Gas-chromatogra-
phy-mass spectrometry (GC-MS) was carried out on
the same gas-chromatograph connected to a Hewlett-
Packard mass spectrometer model 5971A, with an ioni-
zation voltage of 70 eV, electron multiplier 1700 V, a ion
source temperature 180 ꢁC.
1
the shift of 6-H2 signals in the H NMR spectra from
d 4.37/4.29 in 2 to d 3.73/3.68 in 3. On the other hand,
the gas chromatographic analysis of the organic layer
of the alkaline hydrolysis gave only the methyl ester of
a-linolenic acid.
All these data, together with analysis of HMBC
correlations, establish compound 2 as the novel galacto-
lipid: (2S)-1,2,60-tri-O-[(9Z,12Z,15Z)-octadeca-9,12,15-
trienoyl]-3-O-b-D-galactopyranosyl glycerol.
Galactolipids such as monogalactosyldiacyl glycerol
(MGDG) and digalactosyldiacylglycerol (DGDG) rep-
resent the main membrane lipids in leaves of higher
plants, whereas the occurrence of acylated galactolipids
at the C-60 position is very limited (Do¨rmann and Ben-
ning, 2002). On the contrary, both MGDG and DGDG
with an acyl group at C-60 position of the sugar moiety
are fairly widespread in several kinds of micro-organ-
isms such as actinomycetes (Gamian et al., 1996), cyano-
bacteria (Murakami et al., 1991, 1993, 1992),
dinoflagellates (Daranas et al., 1999; Kobayashi et al.,
1992; Murakami et al., 1992), and bacteria (Bultel-
Thin layer chromatography (TLC) and preparative
thin layer chromatography (PTLC) were carried out
using glass-packed pre-coated silica gel F254 plates
(Merck); flash chromatography used Diol and LiChro-
prep (Merck).
3.2. Plant material
Fresh leaves of F. sellowiana were collected from the
‘‘San Matteo’’ farm, Giarre CT, Italy in January 2003.
A voucher specimen (FS1) has been deposited in the
Herbarium of the Department of Botany, University
of Catania, Italy.
´
Ponce et al., 1997). About 75% of total membrane lipids
comprise galactolipids. However, it has been suggested
that they may have other specific functions beyond their
role as membrane building blocks (Do¨rmann and Ben-
ning, 2002). Furthermore, the interest towards these
compounds is due to their antitumour-promoting prop-
erties and anti-inflammatory effects (Larsen et al., 2003;
Murakami et al., 1995).
3.3. Extraction and purification
Fresh leaves were freeze-dried to obtain 540 g of
dried material, which was ground and extracted three
times with methylene chloride at room temperature with
continuous stirring. After concentration, 16 g of extract
was obtained. This was subjected to chromatography
over MN Polyamide SC6 < 0.07 mm. Elution with step-
wise gradient from 100% hexane to 100% ethyl ether,
and successively acetone and methanol, gave 10 frac-
tions (A–L). Some of these fractions (A, D–F, H–L)
were disregarded in the present study, on the basis of
a preliminary TLC, GC-MS or NMR analysis. In fact,
these fractions contained essentially ubiquitary constitu-
ents such as fats, carotenoids, chlorophylls, or were very
complex mixtures of many minor constituents.
Fraction B (1.2 g) was applied to a Diol (40–63 lm)
flash chromatography column using eluents of increas-
ing polarity from 100% hexane to 100% diethyl ether.
This separation yielded 16 fractions, the sixth consisting
of a-tocopherol (19 mg), whereas the ninth was rechro-
matographated over Diol (40–63 lm), using a gradient
from 20% to 50% of diethyl ether in hexane to give fur-
ther four fractions. The first one was subjected to PTLC
(silica, 0.5 mm thickness) using 30% of diethyl ether/hex-
ane as the eluant, to give flavone (33 mg) and stigma-
sterol (5 mg).
3. Experimental
3.1. General methods
Optical rotations were determined on a Jasco DIP-
370 digital polarimeter in chloroform. The mass spectra,
including high-resolution mass spectra (HREIMS,
HRFABMS), were recorded on
instrument.
a Kratos M50S
Infrared (IR) spectra in chloroform were measured
on a Perkin–Elmer model Spectrum BX spectrophotom-
eter. Ultraviolet (UV) spectra of ethanolic solutions
were recorded using a Perkin–Elmer model Lambda 25
spectrophotometer.
1H NMR spectra were measured on a Varian INOVA
operating at 500 MHz and a Bruker Avance 400 at 400
MHz, whereas 13C NMR spectra were run at 100 MHz
on a Bruker Avance 400 instrument. Multiplicities of
13C NMR resonances were determined by DEPT exper-
iments. All NMR experiments, including two-dimen-
sional spectra, i.e., correlation spectroscopy (COSY),
heteronuclear multiple-quantum correlation (HMQC),
Fraction C (632 mg) was purified by flash chroma-
tography over Diol (40–63 lm) by gradient elution of
ethyl acetate in methylene chloride; seven fractions

2950
G. Ruberto, C. Tringali / Phytochemistry 65 (2004) 2947–2951
were obtained (C1–C7). Fractions C1 and C2 were
pooled and rechromatographated over Diol (40–63
lm) using a mixture of 25% ethyl acetate in methylene
chloride to obtain 143 mg of p-hydroxyphenylethanol
esters (1a–1c).
Fraction G (1.2 g), coming from the initial polyamide
column, was subjected to flash chromatography over sil-
ica gel LiChroprep (40–63 lm), by gradient elution of
30–100% diethyl ether in hexane, and then from 100%
of diethyl ether to 100% of methanol to yield b-carotene
and compound 2.
3.3.7. (2S)-1,2,60-Tri-O-[(9Z,12Z,15Z)-octadeca-9,12,-
15-trienoyl]-3-O-b- -galacto pyranosyl glycerol (2)
D
Oil (55 mg, 0.0102% dry wt.). [a]D = +6.9ꢁ (c, 1.11 in
EtOH); IR mmax (CHCl3): 3450, 2880, 1741 cmꢀ1; HRF-
ABMS m/z 1057.7303 (calc. for C63H102O11Na
1
1057.7313); H NMR (500 MHz, CDCl3): d 3.98 (1H,
dd, J = 11.0, 6.0 Hz, H-1a), 3.69 (1H, m, H-1b), 5.27
(1H, m, H-2), 4.28 (2H, m, H-3), 4.22 (1H, d, J = 7.5
Hz, H-10), 3.60 (1H, m, H-20), 3.62 (1H, m, H-30), 3.89
(1H, dd, J = 3.3, 1.0 Hz, H-40), 3.67 (1H, m, H-50),
4.37 (1H, dd, J = 12.3, 6.0 Hz, H-60a), 4.29 (1H, dd,
J00=00 12.3, 3.5 Hz, H-60b), 2.32 (6H, m, H-200, H-2000, H-
2 ), 1.61 (12H, m, H-300, 3000, 30000 and H-700, H-7000, H-
70000), 1.31 (18H, m, H-300/3000/30000, H-400/4000/40000 and 5-H00/
5000/50000), 2.03 (6H, m, H-80, H-800, H-8000), 5.30 (18H, m,
H-900/9000/90000, H0-01000/10000/100000, H-1200/12000/120000, H-1300/
13000/130000, H-15 /15000/150000 and H-1600/16000/160000), 2.81
(12H, m, H-1100/H-11000/H-110000 and H-1400/14000/140000),
2.06 (6H, m, H-1700, H-17000, H-170000), 0.98 (9H, t,
J = 7.5 Hz, H-1800, H-18000, H-180000); 13C NMR (100
MHz, CDCl3): ppm 68.0 (t, C-1), 70.0 (d, C-2), 62.3 (t,
C-3), 103.6 (d, C-10), 73.1 (d, C-20), 68.1 (d, C-30), 72.4
(d, C-40), 71.4 (d, C-50), 62.3 (t, C-60), 173.5 (s, C-100),
173.3 (s, C-1000), 173.7 (s, C-10000), 34.1 (t, C-200, C-2000, C-
20000), 24.8 (t, C-300, C-3000, C-30000), 30.1-29.6 (t, C-400/4000/
40000, C-500/5000/50000, C-600/6000/60000), 28.8 (t, C-700, C-7000, C-
70000),00020 7.2 (t, C-800, C-8000, C-80000), 131.9-127.1 (d, C-900/
9000/9 00 , C-1000/10000/100000, C-1200/12000/12000, C-1300/13000/13000,
C-15 /15000/150000, C-1600/16000/160000), 25.6 (t, C-1100, C-11000,
C-110000), 25.5 (t, C-1400, C-14000, C-140000), 20.5 (t, C-1700,
C-17000, C-170000), 14.1 (q, C-1800, C-18000, C-180000).
3.3.1. a-Tocopherol
Oil (19 mg, 0.0035% dry wt.). Identical in all respects
to an authentic sample.
3.3.2. Flavone
Amorphous solid (33 mg, 0.0061% dry wt.). Identical
in all respects to an authentic sample.
3.3.3. Stigmasterol
Amorphous solid (5 mg, 0.0009% dry wt.). Identical
in all respects to an authentic sample.
3.3.4. b-Carotene
Amorphous solid (14 mg, 0.0026% dry wt.). Identical
in all respects to an authentic sample.
3.3.5. Tyrosol derivatives (1a–1c)
Oil (143 mg, 0.0265% dry wt.); IR mmax (CHCl3):
1
3610, 2880, 1737 cmꢀ1; H NMR (400 MHz, CDCl3):
d 7.07 (2H, d, J, 8.3 Hz), 6.76 (2H, d, J, 8.3 Hz), 4.23
(2H, t, J, 7.0 Hz), 2.85 (2H, t, J, 7.0 Hz), 2.28 (2H, t,
J, 7.4 Hz), 1.62 (m), 1.25 (bs), 0.87 (3H, t, J, 6.0 Hz);
13C NMR (100 MHz, CDCl3): ppm 174.0 (s), 154.4
(s), 130.0 (d), 130.0 (d), 115.3 (d), 115.3 (d), 129.8 (s),
65.1 (t), 34.3 (t), 34.2 (t), 31.9 (t), 29.1 (t), 22.7 (t),
14.1 (q).
3.3.8. Alkaline hydrolysis of 2
A solution of 2 (30 mg) in THF (2 ml) was treated
with 2.8% NaOMe–MeOH (2 ml) and the mixture was
refluxed for 30 min. The reaction mixture was neutral-
ized with diluted HCl and partitioned into n-hexane/
H2O mixture. Evaporation of the aqueous phase gave
a residue which was chromatographed on silica gel to
yield 3 (8 mg). The organic phase was evaporated to dry-
ness to give a residue which was subjected to gas chro-
matographic analysis, with the following analytical
conditions: DB-5 MS capillary column (30 m · 0.25
mm · 0.25 lm), helium as carrier gas; injection in split
mode (1:50), injected volume 1 ll, injector and detector
temperature 300 ꢁC; the oven temperature was pro-
grammed from 80 to 300 ꢁC at 5 ꢁC/min. A single peak
was detected and identified as a-linolenic acid methyl
ester in comparison with an authentic sample.
3.3.6. Alkaline hydrolysis of 1a–1c
A solution of the mixture of 1a–1c (25 mg) in THF (2
ml) was treated with 2.8% NaOMe–MeOH (2 ml) and
the mixture was refluxed for 30 min. The reaction mix-
ture was neutralized with diluted HCl and partitioned
into a n-hexane/H2O mixture. The organic phase was
evaporated to dryness to give a residue, which was sub-
jecetd to GC-MS. Analytical conditions: DB-5 MS cap-
illary column (30 m · 0.25 mm · 0.25 lm), helium as
carrier gas; injection in split mode (1:50), injected vol-
ume 1 ll, injector and detector temperature 300 ꢁC.
The oven was programmed from 80 to 300 ꢁC at 5 ꢁC/
min.
3.3.9. (2R)-1-O-Glyceryl-b- -galactoside 3
D
Amorphous white powder. [a]D = ꢀ7.5ꢁ (c, 0.90 in
H2O); HREIMS m/z 254.0991 (calc. for C9H18O8
254.0996); 1H (500 MHz, CD3OD): d 3.90 (1H, dd,
J = 10.4, 5.2 Hz, H-1a), 3.70 (1H, dd, J = 10.4, 4.5 Hz,
H-1b), 3.79 (1H, m, H-2), 3.62 (1H, dd, J = 11.2, 5.6
The methyl esters of lignoceric (C25H50O2 [M]+ 382,
21.4%), cerotic (C27H54O2 [M]+ 410, 32.8%) and mon-
tanic (C29H58O2 [M]+ 438, 33.3%) acids were
identified.

G. Ruberto, C. Tringali / Phytochemistry 65 (2004) 2947–2951
2951
Kobayashi, M., Hayashi, K., Kawazoe, K., Kitagawa, I., 1992. Marine
natural products XXIX. Heterosigma-glycolipids I, II, III and IV,
four diacylglycolipids possessing x-3-polyunsaturated fatty acid
residues, from raphidophycean dinoflagellate Heterosigma aka-
shiwo. Chem. Pharm. Bull. 40, 1404–1410.
Hz, H-3a), 3.56 (1H, dd, J = 11.2, 5.6, H-3b), 4.25 (1H,
d, J = 7.5 Hz, H-10), 3.56 (1H, m, H-20), 3.50 (1H, m, H-
30), 3.83 (1H, dd, J = 3.2, 1.0 Hz, H-40), 3.53 (1H, m,
H-50), 3.73 (1H, dd, J = 10.4, 4.4 Hz, H-60a), 3.68 (1H,
dd, J = 10.4, 4.4 Hz, H-60b); 13C NMR (100 MHz,
CD3OD): ppm 72.0 (t, C-1), 72.2 (d, C-2), 64.1 (t, C-
3), 105.3 (d, C-10), 72.6 (d, C-20), 74.9 (d, C-30), 70.3
(d, C-40), 76.8 (d, C-50), 62.5 (t, C-60).
Koshimizu, K., Ohigashi, H., Tokuda, H., Kondo, A., Yamaguchi, K.,
1988. Screening of edible plants against possible antitumor
promoting activity. Cancer Lett. 39, 247–257.
Larsen, E., Kharazmi, A., Christensen, L.P., Brøgger Christensen, S.,
2003. An anti-inflammatory galactolipid from rose hip (Rosa
canina) that inhibits chemotaxis of human peripheral blood
neutrophils in vitro. J. Nat. Prod. 66, 994–995.
Acknowledgements
Morton, J.F., 1987. Fruit of Warm Climates. Florida Flair Books,
Miami, FL.
Murakami, A., Nakamura, Y., Koskimizu, K., Ohigashi, H., 1995.
`
The authors are grateful to Dr. Pierlucio Magrı for
Glyceroglycolipids from Citrus hystrix,
a traditional herb in
his valuable contribution to this work whilst preparing
his degree thesis. Thanks are also due to Mrs. Concetta
Rocco (ICB-CNR – Sezione di Catania) for conducting
the NMR experiments and to Mr. Carlo Limone (‘‘San
Matteo’’ farm, Giarre CT) for the generous gift of plant
material.
Thailand, potently inhibit the tumor-promoting activity of 12-O-
tetradecanoylphorbol 13-acetate in mouse skin. J. Agric. Food
Chem. 43, 2779–2783.
Murakami, N., Morimoto, T., Imamura, H., Ueda, T., Nagai, S.,
Sakakibara, J., Yamada, N., 1991. Studies on glycolipids. III.
Glyceroglycolipids from an axenically cultured cyanobacterium
Phormidium tenue. Chem. Pharm. Bull. 39, 2277–2281.
Murakami, N., Shirahashi, H., Nagatsu, A., Sakakibara, J., 1993.
Studies on glycolipids VI. New acyl-distributed glyceroglycolipids
from the nitrogen-fixing cyanobacterium Anabaena flos-aquae f.
flos aquae. Chem. Pharm. Bull. 41, 1177–1179.
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