(-)-Olivil and (+)-1-acetoxypinoresinol from the olive tree (Olea europaea LINNE; oleaceae) as feeding stimulants of the olive weevil (Dyscerus perforatus)

Article abstract of DOI:10.1271/bbb.67.415

Guided by a feeding stimulant activity test on the olive weevil (Dyscerus perforatus), two compounds that showed potent feeding stimulant activity were isolated from the olive tree (Olea europaea). Based on their spectral data and a literature survey, they were identified as (-)-olivil (1) and (+)-1-acetoxypinoresinol (2). The activities of these minor lignans were significantly higher for the female than for the male weevil.

Full text of DOI:10.1271/bbb.67.415

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(-)-Olivil and (+)-1-Acetoxypinoresinol from the Olive
Tree (Olea europaea LINNE; Oleaceae) as Feeding
Stimulants of the Olive Weevil (Dyscerus perforatus)
Emiko KADOWAKIa, Yasuhiro YOSHIDAc, Teruhiko NITODAa, Naomichi BABAb & Shuhei
NAKAJIMAb
a Graduate School of Natural Science and Technology, Okayama UniversityTsushimanaka,
Okayama 700-8530, Japan
b Department of Bioresources Chemistry, Faculty of Agriculture, Okayama
UniversityTsushimanaka, Okayama 700-8530, Japan
c Nippon Olive Co., Ltd.3911-10 Ushimado, Ushimado-cho, Oku-gun, Okayama 701-4394,
Japan
Published online: 22 May 2014.
To cite this article: Emiko KADOWAKI, Yasuhiro YOSHIDA, Teruhiko NITODA, Naomichi BABA & Shuhei NAKAJIMA (2003)
(-)-Olivil and (+)-1-Acetoxypinoresinol from the Olive Tree (Olea europaea LINNE; Oleaceae) as Feeding Stimulants of the
Olive Weevil (Dyscerus perforatus), Bioscience, Biotechnology, and Biochemistry, 67:2, 415-419, DOI: 10.1271/bbb.67.415
To link to this article: http://dx.doi.org/10.1271/bbb.67.415
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Biosci. Biotechnol. Biochem., 67 (2), 415–419, 2003
Note
－
＋
L
( )-Olivil and ( )-1-Acetoxypinoresinol from the Olive Tree
Olea europaea
INNE; Oleaceae) as Feeding Stimulants
of the Olive Weevil (Dyscerus perforatus
(
*
)
2
Emiko KADOWAKI,1 Yasuhiro YOSHIDA,3 Teruhiko NITODA,1 Naomichi BABA
and Shuhei NAKAJIMA
,
2,
†
1Graduate School of Natural Science and Technology, Okayama University, Tsushimanaka,
Okayama 700-8530, Japan
2Department of Bioresources Chemistry, Faculty of Agriculture, Okayama University, Tsushimanaka,
Okayama 700-8530, Japan
3Nippon Olive Co., Ltd., 3911-10 Ushimado, Ushimado-cho, Oku-gun, Okayama 701-4394, Japan
Received August 9, 2002; Accepted September 25, 2002
Guided by a feeding stimulant activity test on the
olive weevil (Dyscerus perforatus), two compounds that
showed potent feeding stimulant activity were isolated
from the olive tree (Olea europaea). Based on their spec-
tral data and a literature survey, they were identiˆed as
plant that are responsible for host selection and
attraction of the insect.
We have previously found that a secoiridoid gluco-
side (oleuropein) isolated from the olive tree stimu-
lated the feeding activity of the weevil.2) In this
present report, we describe the isolation and charac-
terization of two more feeding stimulants from the
same plant.
(
)-olivil (1) and ( )-1-acetoxypinoresinol (2). The
－ ＋
activities of these minor lignans were signiˆcantly higher
for the female than for the male weevil.
The puriˆcation of the active compound(s) was
guided by a feeding stimulant activity test on the
olive weevil.2) After extracting a sample of olive tree
with methanol, the methanol extract was evaporated
Key words: olive weevil; olive; feeding stimulant;
(„)-olivil; (+)-1-acetoxypinoresinol
The most serious pest of the olive tree in Japan, an
important plant as a source of fruit and oil produc-
tion, is now the olive weevil [Dyscerus perforatus
(ROELOFS); Coleopetera; Curculionidae] that is a
native species in Japan. This weevil originally seems
to have colonised Ligustrum japonicum Thunb. and
L. obtusifolium Sieb. et Zucc, both of which belong
to the oleacea family, like the olive. However, when
olive trees were introduced to Japan in 1908, the
weevils immediately attacked the plants and soon
preferred them to the former hosts. Unlike in the
former hosts, where the weevils lived in a low popula-
tion density, it is extraordinary high in the case of the
olive tree and the assault thereby becomes seriously
damaging for the host plant. The adult weevils have a
long life and can survive for over 900 days in a
room.1) Moreover, the females have a long egg-laying
period from spring to autumn, and the larvae attack
the bark and trunk of olive trees, weakening and
withering even adult trees as the assault progresses.
During the course of our study on the relationship
between the olive tree and olive weevil, we have been
interested in the possible chemical constituents of this
and successively partitioned with hexane water and
W
EtOAc water. Among these fractions, the EtOAc-
W
soluble fraction exhibited feeding stimulant activity
which seemed to be signiˆcantly higher for female
than for male insects. Therefore, this fraction was
further puriˆed by column chromatography and
preparative TLC on silica gel to give active com-
pound 1 as colorless needles and active compound 2
as an amorphous solid. Active compound 1 was
much more polar than 2 as indicated by its lower Rf
value on silica gel TLC (solvent system of hex-
＝
ane:EOAc 1:1).
The high-resolution EI mass spectrum (HREIMS)
of active compound 1 aŠorded a molecular ion at
m z 376.1525, indicating the molecular formula of
W
1
C20H24O7 which was consistent with the H- and 13C-
NMR data. The IR spectrum of 1 exhibited strong
absorption bands at 3400 cm„1 corresponding to a
hydroxyl group(s) and at 1605, 1520 and 824 cm„1
suggesting the presence of a trisubstituted benzene
ring. The UV spectrum (lmax 230 and 280 nm)
and positive FeCl3 test implied the presence of a
phenol chromophore. The presence of two phenolic
*
Chemical and Ecological Interrelationship Between the Olive Tree and Olive Weevil, Part II
†
To whom correspondence should be addressed. Tel Fax: +81-86-251-8302; E-mail: snaka24
＠
cc.okayama-u.ac.jp
W

416
E. KADOWAKI et al.
Fig. 1. Structures of Active Compounds 1 and 2.
b; and dH 3.60, 3.80, H-9
groups showed correlation with the quaternary car-
bon signal at dC 82.6 (C-8 ) with which the methine
?a, b) of two methylene
?
proton (dH 2.35, H-8) also showed correlation. The
HMBC spectral data also showed correlation of the
geminal proton signals at dH 2.90 and 3.00 with two
aromatic methine carbons at
and C-6 ). These data indicated another C6-C3 unit.
In addition, in the HMBC spectrum of 1, the methy-
lene proton ( H 3.60, H-9 a) showed correlation with
dC 115.1 and 124.0 (C-2?
?
d
?
the methine carbon signal at dC 86.1 (C-7) for form-
ing the ˆve-membered ring structure of this molecule.
Based on these data and a comparison with data in
the literature,3–5) active compound 1 was identiˆed as
Fig. 2. Feeding Stimulative Activities of Compounds 1 and 2
toward the Male and Female Weevils.
The dose of compounds 1 and 2 on each disk was 10
m
g. Each
20). Signiˆcantly diŠerent
-test ( 0.05). Male weevil;
*
pº
bar represents the mean
from male weevils by Student's
Female weevil.
SE (n
± ＝
4,4?,8?,9-tetrahydroxy-3,3?-dimethoxy-7,9?-cyclolig-
t
nan, („)-olivil (Fig. 1), which is a known as a minor
lignan.
The HREIMS data of active compound 2 gave a
hydroxyl groups in the molecule was suggested by the
formation of a dimethyl ether (1a, Fig. 1) prepared
by treating 1 with diazomethane.
molecular ion at m z 416.1469, revealing its molecu-
W
lar formula as C22H24O8, which is consistent with the
1H- and 13C-NMR data. The IR (3370, 1607, 1520 and
824 cm„1) and the UV (lmax 230 and 280 nm) spectra
and positive FeCl3 test also suggested the presence of
phenolic groups and a trisubstituted benzene ring(s),
as well as the ester carbonyl group (1738 cm„1). The
1H-NMR spectrum of the acetate (2a, Fig. 1) pre-
1
The H- and 13C-NMR and HMQC spectra of 1
(see the experimental section) suggested the presence
of two methoxy groups (
d
H 3.81,
d
C 56.1;
H 6.68, 6.81,
H 6.68–6.70, 6.86 for the C ring,
dH 3.82, dC
56.2), two trisubstituted benzene rings (
d
7.05 for the A ring;
d
respectively). The 1H–1H COSY spectrum showed
that a methine proton (dH 2.35, H-8) was coupled
with an oxygen-bearing methine proton (dH 4.65,
H-7) and hydroxymethylene protons (dH 3.71 and dH
3.80, H-9a, b). Furthermore, in the HMBC spec-
trum, a cross peak between the proton signal (dH
4.65, H-7) and two aromatic methine carbons (dC
111.3 and 121.3; C-2 and C-6 respectively) on ben-
zene ring A indicated the C6-C3 unit.
pared by treating 2 with acetic anhydride pyridine
W
showed the presence of two hydroxyl groups.
1
The H- and 13C-NMR data of compound 2 cor-
6)
related well with the data published by Owen et al
.
Furthermore, the EIMS data of compound 2 were
identical in all respects to those published.7) Based on
these results, the structure of 2 was identiˆed as (+)-
1-acetoxypinoresinol which is also a lignan like active
compound 1.
On the other hand, in the HMBC spectrum of 1,
pairs of geminal proton signals (dH 2.90, 3.00, H-7?a,
Figure 2 shows the feeding stimulant activities of
compound 1 and 2 toward male and female olive

Two Feeding Stimulants of the Olive Weevil
417
lignans with methylenedioxy phenyl groups such as
sesamin have a synergistic eŠect on a range of insecti-
cides.16) Furthermore, kobusin and sesamin have
been shown to inhibit the growth of silkworm
(
Bombyx mori) larvae.17) As an another example,
(„)-parabenzlactone, one of the piperolignanolides,
from Parabenzoin trilobum Nakai is known to sup-
press the feeding activity of insects.18) Thus, lignan
biosynthesis plays important roles in the host plant
defense system.
In our present study, however, the two active com-
pounds, 1 and 2, which also had a lignan structure,
did not show any defensive role against the insect
pest, but strongly stimulated their feeding behavior
(Fig. 2).
Fig. 3. EŠect of the Dose of Active Compounds 1 and 2 on
Female Weevils.
±
＝
$
Each bar represents the mean SE (
n
25).
Active com-

pound 1;
Active compound 2.
In fact, as shown in Fig. 2, isolated compounds 1
and 2 showed 30–40
z feeding stimulant activity
weevils. Both compounds showed potent feeding
stimulant activity toward the female at a dose of
toward female weevils in particular, although in the
case of males, the activity was not signiˆcant. Figure
3 show that, in the case of the female, the feeding
activity respectively increased with increasing dose of
active compounds 1 and 2.
Although we do not have a reasonable explanation
for this clear diŠerence, these two compounds appear
to play an important role in the preferential stimula-
tion by olive trees of the female weevil. This result
seems to be the ˆrst example in which feeding
stimulant activity was observed in compounds having
a lignan structure. No report describing the same
phenomenon has so far been found.
z z
10 mg disk (35.6 for 1 and 38.0 for 2, respec-
W
tively). Figure 2 also shows that the activity was sig-
niˆcantly higher for the female than for the male
weevil (
p
º
0.05). However, the activity for the male
was not signiˆcant when compared with the control
disk. Figure 3 shows the dose dependence of com-
pounds 1 and 2 on the feeding stimulant activity of
female weevils. The result shows that the activity was
dependent on the dose of 1 on the paper disk in the
range of zero-20
slope to a dose of 5
between 5 and 10
mg disk, increasing with a gentle
W
m
g disk, then by a steep slope
W
m
g, and ˆnally becoming almost
The activity of the two compounds in the lignan
family discovered in the present study might be
applied to attract the olive weevils to a limited area
where the compounds are provided as a dummy.
constant or saturated. In the case of active com-
pound 2, the maximum activity was attained at
5 mg disk after a rapid increase, this being followed
W
by a slow decrease to the same activity (
z
¿33 ) as
that of compound 1. Although a signiˆcant diŠer-
ence in their activity proˆle was observed, the feeding
stimulation was found to be totally dose-dependent.
The bark of the olive tree has been traditionally
used in the Orient as an antipyretic, antirheumatic,
tonic and remedy for scrofula,8) while olive oil and
the fruits are very important food products
nowadays. Our problem for the cultivation of this
plant in Japan is that the olive trees have been attack-
ed by the olive weevils, a typical insect pest of this
plant.
Experimental
General procedure. All the NMR experiments
were conducted with a Varian VXR500 spectrometer
(500 MHz for 1H, 125 MHz for 13C). High-resolution
electron ionization mass spectra (HREIMS) were
recorded by a JEOL SX-102A mass spectrometer,
IR (KBr) spectra were measured by a JASCO FT
W
IR-5000 spectrometer, optical rotation values were
determined with a JASCO Dip-360 digital polari-
meter, and UV spectra were measured by a Shimadzu
UV-3000 spectrophotometer.
It is well known that plants have a chemical
defense systems.9,10) One method seems to be the
synthesis of lignans when being attacked by pests.
Lignans and neolignans, which are produced through
Insect material. The weevils were ˆeld collected as
newly emerged adults from infested olive trees in
August 2000 and July 2001. Male and female weevils
a biosynthetic pathway starting from
E-coniferyl al-
cohol,11) are a widely distributed and structually
diverse phytochemical class. Most of them and their
intermediate products exhibit various biological
were separately reared in plastic containers (27 cm
×
20 cm
×
13 cm) with a piece of young branch from an
olive tree (ca. 20 cm length, 5 mm
q
) and wet cotton
9C with a 12L:12D
activities.12) For example, 7
?
-hydroxymatairesinol
under gregarious conditions at 25
photoperiod.
inhibits fungal growth,13) (+)-5
?-demethoxyepixcel-
sin, anti-HIV activity,14) and („)-trachelogemin, an
antiviral property.15) Some acyclic and furofuran
Plant material. The olive tree (Nevadillo Blanco
)

418
E. KADOWAKI et al.
was obtained from Nippon Olive Co. Ltd. in April
2001. It was cut into pieces for extraction.
152 (16), 151 (33), 137 (19), 131 (34), 103 (17);
+

HREIMS m z [M] : calcd. for C22H24O8, 416.1471;
W
×
e): 230 (1.2
found, 416.1469; UV
l
max (EtOH) nm (
10 ), 280 (4.4 10 ); IR nmax (KBr) cm„1: 3370
(–OH), 1738 (C O), 1607, 1520, 824 (aromatic);
NMR H (500 MHz, CDCl3): 1.70 (3H, s, CH3CO2–),
3.32 (1H, dt,
9.4, H-4b), 3.88 (3H, s, –OCH3), 3.91 (3H, s,
4
3
×
Extraction and puriˆcation of the plant material.
Olive trunk sections (9.1 kg) were extracted with
MeOH (26.4 l) at room temperature (r.t.) for 7 days.
The extract was ˆltered, concentrated under reduced
＝
d
＝
＝
4.9,
J
4.9, 7.6, H-5), 3.77 (1H, dd,
J
×
pressure and partitioned ˆrst with hexane (500 ml
×
＝
3) and then with EtOAc (500 ml 3) to obtain
hexane-soluble (2.6 g), EtOAc-soluble (160 g) and
aqueous (547 g) fractions. The EtOAc fraction was
separated by column chromatography on silica gel 60
(Nacalai Tesque, 230–400 mesh), successively eluting
–OCH3), 4.23 (1H, d,
J
10.7, H-8b), 4.42 (1H, dd,
10.7, H-8a), 4.74
4.9, H-6), 5.06 (1H, s, H-2), 5.74 (2H,
–OH 2), 6.85–6.86 (3H, m, H-2 , 5 , 6 ), 6.88 (1H,
), 6.91 (1H, d,
1.5, H-2 ); NMR dC (125 MHz,
CDCl3): 20.9 (CH3CO2–), 55.9 (3 , 3 –OCH3), 58.8
(C-5), 69.8 (C-4), 75.2 (C-8), 85.8 (C-6), 87.0 (C-2),
97.2 (C-1), 108.9 (C-2 ), 111.6 (C-2 ), 113.9 (C-5 ),
114.3 (C-5 ), 119.3 (C-6 ), 121.4 (C-6 ), 128.3
(C-1 ), 131.9 (C-1 ), 145.5 (C-4 ), 145.7 (C-4 ),
146.2 (C-3 ), 146.7 (C-3 ), 169.5 (CH3CO2–).
J
＝
7.6, 9.4, H-4a), 4.43 (1H, d, J
＝
＝
J
(1H, d,
×
?
?
?
＝
＝
7.9, H-5
dd,
J
1.5, 7.9, H-6
!
J
!),
＝
＝
with hexane (100
z)
ª
hexane:EtOAc 7:3
ª
1:1
ª
6.96 (1H, d,
J
!
EtOAc (100 MeOH (100
z
)
ª
z
). The feeding stimu-
?
!
latory activity was found in the MeOH fraction. This
fraction was further separated in the silica gel
!
?
?
＝
column, eluting with CHCl3:MeOH 4:1, and then
!
!
?
in another silica gel column, eluting with CHCl3:
?
!
!
?
MeOH
＝
10:0.5
ª
10:1, to aŠord two active fractions
?
!
(Fr. a and Fr. b). Fr. a (2.1 g) was further puriˆed by
preparative TLC on silica gel with EtOAc:MeOH
10:1, and then by preparative TLC on silica gel with
CHCl3:MeOH 10:1 to give active compound 1
(colorless needles, 40.5 mg, 4.5 g g of olive). Fr. b
(10.9 g) was separated by column chromatography
＝
Treatment of active compound 1 with dia-
zomethane. Active compound 1 (12.5 mg) was treat-
ed with diazomethane in ether at r.t. for 24 hr. The
dimethylether (1a, 2.1 mg) of 1 was obtained by silica
gel column chromatography, eluting with CHCl3 and
＝
m
W
＝
＝
＝
then with CHCl3:MeOH 10:1. EIMS m z: 404
(silica gel, 136 g), eluting with CHCl3:MeOH
10:0.5, and then by eluting with hexane:EtOAc
W
[M]+
, 151; NMR dH (500 MHz, CDCl3): 2.52 (1H,

1:1
7.3
ª
m
3:7
ª
0:100. Active compound
2
(66.8 mg,
q), 2.98 (1H, d), 3.08 (1H, d), 3.70 (1H, d), 3.87 (3H,
s, –OCH3), 3.88 (3H, s, –OCH3), 3.88 (3H, s,
–OCH3), 3.89 (3H, s, –OCH3), 3.86–3.90 (2H, m),
3.92 (1H, dd), 4.74 (1H, d), 6.83 (1H, d), 6.83–6.85
(3H, m), 6.93 (1H, dd), 7.26 (1H, d).
g g of olive) was obtained as an amorphous
W
solid.
Active compound
1
. Mp 111–115
9
C from EtOAc-
20
D
MeOH; [
a
]
„41.3
(2), 196 (16), 180 (9), 151 (6), 137
(100), 122 (13). HREIMS m z [M]+
: calcd. for
C20H24O7, 376.1522; found, 376.1525; UV lmax
9(c 0.91, MeOH); EIMS m z
W
(rel. int.): 376 [M]+

Acetylation of active compound 2. Active com-

pound 2 (3.3 mg) was acetylated with acetic an-
hydride-pyridine at r.t. for 12 hr, the reaction mix-
ture being worked up in the usual mannar, and the
acetate (2a) was isolated by column chromatography.
W
(EtOH) nm (e): 230 (1.2
103), 280 (4.5 102); IR
× ×
nmax (KBr) cm„1: 3400 (–OH), 1605, 1520, 1456, 824
(aromatic); NMR dH (500 MHz, CD3OD): 2.35 (1H,
NMR dH (500 MHz, CDCl3): 1.69 (3H, s, CH3CO2–),
＝
＝
q,
H-7
9.5 Hz, H-9
H-9), 3.80 (2H, m, H-9,9
3.82 (3H, s, –OCH3), 4.65 (1H, d,
J
7.6, 5.5 Hz, H-8), 2.90 (1H, d,
J
14.0 Hz,
), 3.60 (1H, d,
11.3, 5.5 Hz,
), 3.81 (3H, s, –OCH3),
7.6 Hz, H-7),
2.30 (3H, s, CH3CO2–), 2.32 (3H, s, CH3CO2–), 3.35
(1H, dt), 3.67 (1H, dd), 3.83 (3H, s, –OCH3), 3.86
(3H, s, –OCH3), 4.31 (1H, d), 4.47 (1H, dd), 4.50
(1H, d), 4.82 (1H, d), 5.11 (1H, s), 6.90–6.93 (3H,
m), 6.95 (1H, dd), 6.99 (1H, d), 7.04 (1H, d).
＝
14.0 Hz, H-7?
?), 3.00 (1H, d,
J
J
＝
?), 3.71 (1H, dd, J
＝
?
J
＝
＝
7.9 Hz, H-5), 6.68–6.70 (2H, m,
6.68 (1H, d,
H-5 ,6 ), 6.81 (1H, dd,
(1H, d, H-2 ), 7.05 (1H, d,
(125 MHz, CD3OD): 40.6 (C-7
J
＝
?
?
J
7.9, 1.8 Hz, H-6), 6.86
Bioassay. Male and female insects were precon-
ditioned in separate Petri dishes (40 mmq) containing
?
J
＝
1.8 Hz, H-2); NMR dC
?), 56.1 (–OCH3), 56.2
moistened paper disks (Advantec Toyo No. 2,
5 mm ) and were given distilled water every 12 hr for
(–OCH3), 60.7 (C-9), 61.5 (C-8), 77.7 (C-9
(C-8 ), 86.1 (C-7), 111.3 (C-2), 115.1 (C-2 ), 116.9
(C-5 ), 117.2 (C-5), 121.3 (C-6), 124.0 (C-6 ), 127.9
(C-1 ), 131.1 (C-1), 149.5 (C-4 ), 149.7 (C-4), 150.7
(C-3 ), 152.7 (C-3).
?
?
), 82.6
q
?
?
?
?
24 hr. After the 24 hours of starvation, the moistened
paper disks were replaced with paper disks contain-
ing sucrose and the active compounds. The paper dis-
ks were applied uniformly with a methanolic solution
of each sample and an aqueous solution of sucrose
?
?
20
D
Active compound
2
. [a
]
+29.2
9
(
c
1.01, EtOH);
(5 mg 10
m
l) and then air dried. A paper disk with
MeOH and sucrose was used as a control. The Petri
dishes were kept at 25 C with a 12L:12D pho-
W
+

EIMS m z (rel. int.): 416 [M] (13), 358 (1), 221 (9),
207 (16), 205 (15), 204 (100), 189 (7), 173 (6), 163 (9),
W
9

Two Feeding Stimulants of the Olive Weevil
419
7) Brenes, M., Hidalgo, F. J., Garcia, A., Rios, J. J.,
Garcia, P., Zamora, R., and Garrido, A.,
Pinoresinol and 1-acetoxypinoresinol, two new
phenolic compounds identiˆed in olive oil. J. Am. Oil
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toperiod for 48 hr. Distilled water at 20 ml disk was
W
added every 12 hr. Each test was repeated 3–5 times.
The extent of feeding was evaluated by measuring the
area of the disk bitten, and is expressed by a score
from zero to +3, in which zero is for no biting, +1 is
for a bitten track being found, +2 is for less than
50
z bitten and +3 is for more than 50z. The feed-
×
ing stimulative activity is deˆned as [(A„B) (+3
W
×
＝
z), where A the total score of the sample
C)] 100(
disks, B
＝
the total score of the control disks, and C
＝
number of insects used. The results of the test were
analyzed by Students' t-test.
Acknowledgments
11) Dinkova-Kostova, A. T., Gang, D. R., Davin, L. D.,
Bedgar, D. L., Chu, A., and Lewis, N. G., (+)-
We thank Mr. Takashi Shibata of Toyo Olive Co.
Ltd. for his help in collecting the weevils. We are also
grateful to the SC-NMR Laboratory of Okayama
University for 500 MHz NMR experiments and to
the MS Laboratory of Faculty of Agriculture at
Okayama University for the HREIMS measure-
ments.
Pinoresinol (+)-Lariciresinol reductase from For-
W
sythia intermedia. J. Biol. Chem., 271, 29473–29482
(1996).
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(1984).
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A., Hung, N. V., Cuong, N. M., Soejarto, D. D.,
Fong, H. H. S., and Pezzuto, J. M., Natural anti-
HIV agents„part I: (+)-demethoxyepiexcelsin and
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