Volume 4. Issue 3. Pages 307-456.

2009
ISSN 1934-578X (printed); ISSN 1555-9475 (online)
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 NPC Natural Product Communications
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EDITORS
PROFESSOR ALESSANDRA BRACA ADVISORY BOARD
Dipartimento di Chimica Bioorganicae Biofarmacia,
Universita di Pisa, Prof. Berhanu M. Abegaz Prof. Hartmut Laatsch
via Bonanno 33, 56126 Pisa, Italy Gaborone, Botswana Gottingen, Germany
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PROFESSOR YOSHIHIRO MIMAKI
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NPC Natural Product Communications
Novel Macrolide from Wild Strains of the Phytopathogen
Fungus Colletotrichum acutatum
Gabriela Mancilla, Daniel Jiménez-Teja, Marienca Femenía-Ríos, Antonio J. Macías-Sánchez,
Isidro G. Collado and Rosario Hernández-Galán
Organic Chemistry Department, Faculty of Sciences, University of Cádiz s/n, Apdo 40,
11510 Puerto Real, Cádiz, Spain
rosario.hernandez@uca.es
Received: November 12th, 2008; Accepted: February 12th, 2009
Three wild strains of C. acutatum have been investigated for their phytotoxic secondary metabolites involved in anthracnose
disease. In addition to known compounds, a new macrolide 6 has been isolated and characterized by spectroscopic analysis.
Keywords: Colletotrichum, anthracnose, macrolide.
Species of the anamorphic genus Colletotrichum
(teleomorph Glomerella) are implicated in plant
diseases, generally referred to as anthracnoses,
throughout the world [1]. In fact, the various
Colletotrichum species comprise the most destructive
post-harvest pathogens of a wide range of plants,
including cereals, legumes, fruits, and vegetables.
Strawberries are a particularly susceptible host,
suffering a variety of Colletotrichum-triggered
diseases, including wilts, rots, and anthracnose [2].
The symptoms of anthracnose are stunting and
chlorosis and the appearance of dark and necrotic
spots and yellow-orange masses of spores on plant
tissues. This pathogen is present in many important
areas around whole the world, Colletotrichum
produces important losses in France, [3a] in southern
Europe, specially in Huelva, Spain [3b].
Work is in progress with the aim to develop a rapid
diagnostic test for Colletotrichum species, especially
those associated with strawberry diseases [3c,3d].
Colletotrichum acutatum, one of the species
implicated, is subject to a statutory quarantine
requirement (EC Directive 77/93). An essential
prerequisite to the development of a diagnostic test is
the unambiguous characterization of the different
species and populations, so that the various taxa
implicated can be properly defined [3d].
2009
Vol. 4
No. 3
395 - 398
With this in mind chemical characterization of
secondary metabolites isolated from different species
may help shed further light on the identification of
different species and populations of this
phytopathogenic genus and could clarify the role that
secondary metabolites play in the infection
mechanism. The latter issue has been the focus of
previous studies [3e]. It is well documented, that
Colletotrichum sp. are known to produce phytotoxic
metabolites, which induce symptoms similar to those
of the pathogens themselves. Some of these
metabolites have been used to screen for resistance
and have shown to play a significant role in the
pathogenesis [4a-4d].
This work investigates the secondary metabolites
from three wild strains of Colletotrichum acutatum:
IMI 348489, IMI 364856 and UCA 1028.
Fresh mycelium of the C. acutatum strains, obtained
from Petri dishes incubated for 7 days, were
inoculated in Erlenmeyer flasks each containing PDB
medium and fermented in an orbital shaker as
described. The extracts obtained from different
fermentations were subjected to chromatography
(silica gel) and the fractions obtained (F1-F8) were,
where appropriate, further purified by HPLC yielding
compounds 1-6 (Table 1). The chemical structures of
these compounds were elucidated on the basis of
extensive 1 and 2D NMR and MS spectra.
396 Natural Product Communications Vol. 4 (3) 2009
Table 1: Compounds isolated from C. acutatum.
Strain Compounds isolated (Fractions)
IMI 348489 4 (F2, F3, F5, F8)
IMI 364856 1, 2 (F5, F6); 3 (F3, F4, F5), 4 (F6, F7), 6 (F6)
UCA1028 1, 4, 5, 6 (F5)
5 1'
OH
6 4
2'
1 3
HO 2 HO
1 2
OH O OH
8 8
1 1
4 4a
5 OH
5
4 OH
3 OH
O
6
HO
HO 6' 1 4
5 2 OH
5
4 3
5
Compounds 1 and 2, isolated from C. acutatum IMI
364856, corresponded to known fungal metabolites
tyrosol 1 and 4-hydroxybenzylic alcohol 2 [5a].
Fractions F-3, F-4 and F-5 yielded a compound
whose spectroscopic data and optical rotation [α]D25 =
-9 (c, 1.5 mg/mL CHCl3), were coincident with that
reported for (4R)-4,8-dihydroxy-α-tetralone 3 ((-)-
isosclerone) [5a,5b].
Compound 4 was isolated from the three strains as
yellow oil, presenting physical and spectroscopic
constants identical to those showed by the
melanin biosynthetic intermediate, 4-hydroxy-6-
deoxyscytalone 4. The coupling constant between
protons H-3 and H-4 (J = 2,9 Hz) in conjunction with
a positive optical rotation ([α]D25 = +2 (CHCl3)),
suggested an axial-equatorial arrangement coincident
with data reported for (3R, 4S)-4-hydroxy-6-
deoxyscytalone [5c]. Review of the data of this
compound indicated some confusion over
configurational assignments. Different values
of the optical rotation have been reported for the
same absolute configuration [5b,5d]. This compound,
also named 3,4-dihydro-3,4,8-trihydroxy-1(2H)-
naphthalenone, 3-hydroxyisosclerone and 3,4,8-
trihydroxytetralone (3,4,8-THT) has been reported as
a phytotoxic substance originally isolated from
Pyricularia [5c,5e].
2,5-dihydroxymethylfurane 5 was isolated from the
F-5 of C. acutatum UCA 1028 via column
Mancilla et al.
chromatography and subsequent HPLC. The
metabolite showed characteristic signals pattern
in the 13C-NMR for a C-2, C-5 substituted furan ring
(δ 57.4; 109.7; 152.0). The singlet at δ 4.58(s, 4H)
was assigned to two hydroxymethyl groups. From
this data structure 5 was inferred, identical to a
OH
dihydromethyl furan produced by Xylaria and
Phellinus [5f,6a].
The study of F-6 and F-5 of the strains of
O
C. acutatum 364856 and C. acutatum UCA 1028
8a
respectively led the isolation of 6 as a white solid.
4 The IR spectral bands (3377, 1713, 1630, 1330 cm-1),
all strong, indicated the presence of a hydroxyl
O group, double bonds and an α,β-unsaturated
14
2
1
O ester/lactone. The mass spectra indicated a molecular
3
13
12
formula C14H20O4 with 5 degrees of unsaturation.
11
6
7
8 9 10
The 13C-NMR spectra and DEPT experiments
OH
showed a methyl group, 3 methylene, 3 methine
6 carbons proximal to an oxygenated function, three
vinyl carbons and a carbonyl carbon belonging to the
ester/lactone group. From these data, along with a
quaternary carbon (δC 166.4 ppm), a monocyclic
lactone with 3 double bonds structure 6 was inferred.
A signal at δH 7.02 ppm for a vinylic C-H indicated
that the double bond was conjugated with the
carbonyl group. The relative arrangement of the other
two double bonds and the hydroxyl groups of 6 were
confirmed on studying the g-COSY, g-HSQC,
g-HMBC and TOCSY spectra. The correlation
between the signal at δH 7.02 and a vinyl proton at δH
5.90 (H-2) and with a proton joined to a hydroxylic
carbon at δH 5.27 (H-4) was determined in g-COSY.
The proton H-4 was also correlated with another
double bond at δH 5.53, δC 132.0 and δH 5.46, δC131.2
ppm respectively in g-HMBC spectra. Both protons
were correlated in g-COSY and g-HMBC spectra
with a signal of a proton geminal to a hydroxyl group
at δH 4.81 and δC 70.6 ppm, which correlated it with
another double bound at δH 5.48, δH 5.85, δC 130.2
and δC 131.4 respectively. A signal of a methyl
group at δH 1.24 coupled with a proton at δH = 4.75
was observed. This last proton also showed coupling
with the carbonyl group of the lactone at δC 166.4 in
g-HMBC spectra and with 3 CH2 groups in TOCSY
spectra. All these data indicated a –CH2-CH2-CH2-
CH(CH3)-O-CO- fragment in the molecule. In
conclusion, a structure of 4,7-dihydroxy-13-
tetradeca-2,5,8-trienolide was proposed for the
compound 6.
Secondary metabolites from wild strains of Colletotrichum acutatum
The comparison of spectroscopy data with the
literature indicated that 6 should be an isomer of
known lactones mutolide [6b] and nigrosporolide
[6c] the principal difference being the configuration
of double bonds which were determined for
compound 6 as 2E, 5Z and 8E by inspection of
coupling constants (J2-3 = 15.6, J5-6 = 11.4 and J8-9 =
15.2 Hz).
The study of the nOe spectra showed a cis disposition
for the hydroxyl groups. The irradiation of the signal
corresponding to H-3 produced a nOe effect in the
signals of the protons H-4, H-7 and H-9, while the
irradiation of H-7 produced a positive effect in H-4,
H-9 and H-3. Irradiation of H-13, produced a unique
nOe effect on geminal methyl group.
Unfortunately 6 was isolated in insufficient amount
to determinate the absolute configuration of the three
chiral centers of the molecule.
Experimental
General experimental procedures: IR spectra were
recorded on a Perkin-Elmer FT-IR System Spectrum
BX spectrophotometer. The NMR spectra were
recorded CDCl3 on a Varian Inova-400 MHz
spectrometer or a Varian Inova-600 MHz
spectrometer. Chemical shifts were expressed in
δ values relative to a solvent resonance lines.
Mass spectra were determinate with a Voyager
(Termoquest) spectrometer. TLC was performed on
Merck Kiesegel 60 F254, 0.2 mm thick Silica gel
60PF254 (60-100 mesh, Merck) was used for column
chromatography. HPLC was performed with a
Hitachi/Merck L-6270 apparatus equipped with an
UV-VIS detector (L 4250) and a differential
refractometer detector (RI-71), using a silica gel
column (Hibar 60, 7 m, 1 cm wide, 25 cm long). All
solvents used were freshly distilled.
Organism and Culture Conditions: In this study
three independent wild strains, C. acutatum IMI
348489, C. acutatum IMI 364856 and C. acutatum
UCA 1028 were used. The strains C. acutatum IMI
348489 and IMI 364856 were isolated from
strawberry plants in France and Spain respectively
[3d]. Strain C. acutatum UCA 1028 was isolated
from strawberry growing in Conil, Cádiz. This
culture of C. acutatum is deposited in the University
of Cádiz, Science Faculty Mycological Herbarium.
Each strain of C. acutatum was cultured in Petri
dishes containing potato dextrose agar (PDA) and
incubated (7 days) with permanent diffuse light from
Natural Product Communications Vol. 4 (3) 2009 397
fluorescent lamps at 25ºC. After this period, fresh
mycelium was inoculated and cultured in Erlenmeyer
flasks each containing potato dextrose broth medium.
The Erlenmeyers were incubated and fermented for 7
days in orbital shaker at 140 rpm and 25ºC, with
permanent diffuse light from fluorescent lamps.
Extraction and Isolation: Resultant broths were
filtered (Nylon 200 µm) and the culture liquid (2-3 L)
was saturated (NaCl), and the aqueous phase was
then extracted (EtOAc). This extract was washed
(H2O) and then dried (anh. Na2SO4). Evaporation of
the solvent in vacuo gave a yellow oil that was
separated by column chromatography (silica gel with
ethyl acetate/petroleum ether of increasing polarity;
10, 20, 30, 40, 50, 60, 80 and 100 % ethyl acetate) to
obtain eight fractions F-1 to F-8.
The fractions were collected and purified by normal
phase high-pressure liquid chromatography (HPLC)
[LiChrospher Si-60 analytical silica column (0,4x25
cm), refraction index and UV detectors, λ=254 nm, 1
mL/min.], yielding to: from C. acutatum IMI 348489
compound 4 (10.4 mg), C. acutatum IMI 364856 1
(6.3 mg), 2 (0.5 mg), 3 (6.3 mg), 4 (1.4 mg), 6 (0.7
mg) and C. acutatum UCA 1028 1 (11 mg), 4 (8.4
mg), 5 (7 mg) and 6 (0.4 mg). The chemical structure
of these compounds was elucidated on the basis of
1 and 2D NMR and MS spectra.
(3R,4S)-cis-4-hydroxy-6-deoxyscytalone (4)
[α]D23: +2 (c 2.2 mg/mL, CHCl3).
IR (KBr): 3382, 1720, 1639, 1456 cm-1.
1
H NMR (400 MHz, CDCl3): 2.87 (1H, dd,
J2a-2b = 17.38, J2a-3 = 3.71 Hz, H-2a), 3.08 (1H, dd,
J2b-2a = 17.38, J2b-3 = 7.42 Hz, H-2b), 4.36 (1H, ddd,
J3-2b = 7.42, J3-4 = 2.71 Hz, H-3), 4.90 (1H, d, J4-3 =
2.71 Hz, H-4), 6.94 (1H, dd, J5-6 = 8.40, J5-7 = 0.98
Hz, H-5), 7.52 (1H, dd, J6-5 = 8.40, J6-7 = 7.62 Hz,
H-6), 7.09 (1H, dd, J7-6 = 7.62, J7-5 = 0.98 Hz, H-7).
13
C NMR (100 MHz, CDCl3): 42.6 (CH2), 69.1 (CH),
70.1 (CH), 118 (CH), 119 (CH), 137.2 (CH), 142.4
(C), 202 (C).
EIMS m/z (%): 194 [M+] (22), 176 [M-H2O]+ (9), 150
(23), 121 (100), 93 (17); 65 (45).
2,5-dihydroxymethylfurane (5)
IR (KBr): 3339, 1010 cm-1.
1
H NMR (400 MHz, CDCl3): 4.58 (4H, s, H-6 and
H-6´), 6.23 (2 H, s, H-3 and H-4).
13
C NMR (100 MHz, CDCl3): 57.4 (CH2), 109.7
(CH), 152 (C).
398 Natural Product Communications Vol. 4 (3) 2009 Mancilla et al.

4,7-dihydroxy-13-tretradeca-1,5-dienolide (6) 72.09 (CH), 118.3 (CH), 130.2 (CH), 134.4 (CH),
[α]D23: -4.4 (c 0.4 mg/mL, CHCl3). 131.2 (CH), 132.0 (CH), 148.1 (CH), 166.4 (C).
IR (KBr): 3377, 2925, 1713, 1330, 1175 cm-1. EIMS m/z (%): 252 [M+] (3), 243 (35), 169 (33); 131
1
H NMR (400 MHz, CDCl3): 7.02 (1H, dd, J3-2 = 15.6 (100); 69 (48).
Hz, J3-4 = 1.7 Hz, H-3), 5.90 (1H, d, J2-4 = 1.7 Hz, J2-3
Acknowledgments - This research was supported by
= 15.6 Hz, H-2), 5.85 (1H, ddd, J9-8 = 15.2 Hz, J9-10 =
grants from MEC, AGL2006-13401-C02-01/AGR,
9.5 Hz, J9-10 ’= 5.3 Hz, H-9), 5.53 (1 H, dd, J5-6 = 11.4
and the Junta de Andalucía, PAI05-FQM-00489. G.
Hz, J5-4 = 4.4 Hz, H-5), 5.46 (1H, m, H-6), 5.48 (1H,
M. thanks CONACYT (Mexico) and the Fundación
m, H-8), 5.27 (1H, m, H-4), 4.81 (1 H, t, J = 8.3 Hz,
Carolina (Spain) and D. J. T thanks the Foundation
H-7), 2.09 (1H, m, H-10), 1.97 (1H, m, H-10’), 1.82
Ramón Areces for both studentships. Sincere thanks
(1H, m, H-12), 1.76 (1H, m, H-11), 1.51 (1H, m,
are also due to E. Montes who supply us with isolates
H-11’), 1.26 (3H, d, J15-14 = 6.75 Hz, H-15), 1.10 (1H,
Colletotrichum acutatum IMI 348489 and IMI
m, H-11’).
13 364856 used in this study.
C NMR (100 MHz, CDCl3): 20.2 (CH3), 24.4
(CH2), 32.8 (CH2), 34.5 (CH2), 68.4 (CH), 70.6 (CH),

References
[1] Bailey JA, Jeger MJ. [Eds.] (1992) Colletotrichum: Biology, Pathology and Control. CAB International, Wallingford, UK.
[2] Cannon PF, Bridge PD, Montes E. (2000) Linking the past, present and future of Colletotrichum systematics. In Host specificity,
pathology and host-pathogen interaction of Colletotrichum. Ed. Dov Prusky, Stanley Freeman and Marty Dickman. APS Press: St.
Paul, Minnesota.
[3] (a) Denoyes B, Baudry A. (1996) Species identification and pathogenicity study of French Colletotrichum strains isolated from
strawberry using morphological and cultural characteristics. Phytopathology, 85, 53–57; (b) De los Santos B, de Paredes G,
Romero Munoz F. (1999) Occurrence of Colletotrichum acutatum, causal organism of strawberry anthracnose in southwestern
Spain. Plant Disease, 83, 301; (c) Garcia Muñoz JA, Suarez MB, Grondona I, Montes E, Buddie AG, Bridge PD, Cannon PF.
(2000) A physiological and biochemical approach to the systematics of Colletotrichum species pathogenic to strawberry.
Mycologia, 92, 488-498; (d) Buddie AG, Martinez-Culebras Bridge PD, García MD, Querol A, Cannon PF, Montes E. (1999)
Molecular characterization of Colletotrichum strains derived from strawberry. Mycological Research, 103, 385-394; (e) García-
Pajón CM, Collado IG. (2003) Secondary metabolites isolated from Colletotrichum species. Natural Product Reports, 20, 426–431.
[4] (a) Frantzen KA, Johnson LB, Stuteville DL. (1982) Partial characterization of phytotoxic polysaccharides produced in vitro by
Colletotrichum trifolii. Phytopathology, 72, 568-573; (b) (a) Amusa NA. (1994) Production, partial purification and bioassay of
toxic metabolites of three plant pathogenic species of Colletotrichum in Nigeria. Mycopathologia, 128, 161-166; (c) Amusa, NA.
(2001) Screening of cassava and yam cultivars for resistance to anthracnose using toxic metabolites of Colletotrichum species.
Mycopathologia, 150, 137-142; (d) Barjau M, Druet D, Comeau LC. (1995) Purification and partial characterization of phytotoxic
glycopeptides secreted by Colletotrichum gloeosporioides. Applied Microbiology and Biotechnology, 43, 217-221.
[5] (a) Machida K, Matsuoka E, Kasahara T, Kikuchi M. (2005) Studies on the constituents of Juglans species. I. Structural
determination of (4S)- and (4R)-4-hydroxy-α-tetralone derivatives from the fruit of Juglans mandshurica MAXIM. var. sieboldiana
MAKINO. Chemical & Pharmaceutical Bulletin, 53, 934-937; (b) Iwasaki S, Muro H, Nozoe S, Okuda S. (1972) Isolation of 3,4-
dihydro-3,4,8-trihydroxy-1(2H)-napthalenone and tenuazonic acid from Piricularia oryzae. Tetrahedron Letters, 13-16; (c) Krohn
K, Biele K, Drogies K H, Steingröver K, Aust H J, Graeger S, Schulz B. (2002) Biologically active secondary metabolites from
fungi. 18. Fusidilactones, a new group of polycyclic lactones from an endophyte, Fusidium sp. European Journal of Organic
Chemistry, 2331-2336; (d) Inácio ML, Silva GH, Helder LT, Trevisan HC, Cavalheiro AJ, Bolzani VS, Young MCM, Pfenning
LH, Aráujo AR. (2006) Antifungal metabolites from Colletotrichum gloeosporioides, an endophytic fungus in Cryptocarya
mandioccana Nees (Lauraceae). Biochemical Systematics and Ecology, 34, 822-824; (e) Gremaud G, Tabacchi, R. (1996)
Antifungal metabolites from Colletotrichum gloeosporioides, an endophytic fungus in Cryptocarya mandioccana Nees
(Lauraceae). Phytochemistry, 42, 1547-1549; (f) Schneider G, Anke H, Sterner O. (1996) Xylaramide, a new antifungal compound,
and other secondary metabolites from Xylaria longipes. Zeitschrift fuer Naturforschung, C: Biosciences, 51, 802-806.
[6] (a) Song KS, Cho SM, Ko KS, Han MW, Yoo ID. (1994) Secondary metabolites from the mycelial culture broth of Phellinus
linteus. Han'guk Nonghwa Hakhoechi, 37, 100-104; (b) Bode HB, Walker M, Zeeck A. (2000) Secondary metabolites by chemical
screening. 42 Cladospirones B to I from Sphaeropsidales sp. F-24'707 by variation of culture conditions. European Journal of
Organic Chemistry, 1451-1456; (c) Harwood J S, Cutler H G, Jacyno J M. (1995) Nigrosporolide, a plant growth-inhibiting
macrolide from the mold Nigrospora sphaerica. Natural Product Letters, 6, 181-185.
Novel Macrolide from Wild Strains of the Phytopathogen Fungus Colletotrichum acutatum
Gabriela Mancilla, Daniel Jiménez-Teja, Marienca Femenía-Ríos, Antonio J. Macías-Sánchez,
Isidro G. Collado and Rosario Hernández-Galán 395
Fatty Acid Profile and in vitro Antioxidant and Antibacterial Activities of Red Grape
(Vitis vinifera L. cvs. Öküzgözü and Boğazkere) Marc Extracts
Bilge Çıbık, Zuhal Özaydın, Nazlı Böke, Ülkü Karabay, Murat Pekmez, Nazlı Arda and
Süheyla Kırmızıgül 399
Fatty Acid Derived Compounds – The Dominant Volatile Class of the Essential Oil Poor
Sonchus arvensis subsp. uliginosus (Bieb.) Nyman
Niko Radulović, Polina Blagojević and Radosav Palić 405
Analysis of Essential Oil from Teucrium maghrebinum Greuter et Burdet Growing Wild in Algeria
Carmen Formisano, Daniela Rigano, Felice Senatore, Malik R. Y. Al-Hillo, Franco Piozzi and
Sergio Rosselli 411
The Essential Oil of Thymus aureopunctatus (Beck) K. Malý
Sanja Ćavar, Milka Maksimović and Danijela Vidic 415
Essential Oil Constituents of Eclipta prostrata (L.) L. and Vernonia amygdalina Delile
Akinola O. Ogunbinu, Guido Flamini, Pier L. Cioni, Isiaka A. Ogunwande and Sunday O. Okeniyi 421
Chemical Composition of the Leaf Essential Oil of Casimiroa edulis La Llave & Lex. (Rutaceae)
from Monteverde, Costa Rica
Sarah L. Miller, William A. Haber and William N. Setzer 425
Essential Oil Composition of Three Peperomia Species from the Amazon, Brazil
Patrícia Natália B. de Lira, Joyce Kelly R. da Silva, Eloisa Helena A. Andrade, Pergentino José C. Sousa,
Nayla N. S. Silva and José Guilherme S. Maia 427
Composition and Antimicrobial Activity of Marrubium incanum Desr. (Lamiaceae) Essential Oil
Silvana Petrović, Milica Pavlović, Zoran Maksimović, Marina Milenković, Maria Couladis, Olga Tzakou
and Marjan Niketić 431

Review/Account
The Flavonoids and Phenolic Acids of the Genus Silphium and Their Chemosystematic Value
Jeffrey D. Williams, Małgorzata Wojcińska, Lalita M. Calabria, Klaus Linse, Jennifer A. Clevinger and
Tom J. Mabry 435
Solvent Derived Artifacts in Natural Products Chemistry
Federica Maltese, Frank van der Kooy and Robert Verpoorte 447
 Natural Product Communications
2009
Volume 4, Number 3

Contents

Original Paper Page

Sesquiterpene and Acyclic Diterpenes from Hyptis verticillata Jacq.

Duanne A. C. Biggs, Roy B. R. Porter and William F. Reynolds 307
Minor Chemical Constituents of Caesalpinia bonduc
Athar Ata, Chibuike C. Udenigwe, Elikana M. Gale and Radhika Samarasekera 311
Three New Spongian Diterpenes from the Fijian Marine Sponge Spongia sp.
Harald Gross, Anthony D. Wright, Uwe Reinscheid and Gabriele M. König 315
A New Rearranged Abietane Diterpene and other Constituents from Clerodendrum philipinum
Ha Van Oanh, Pham Xuan Sinh, Nguyen Thai An, Ta Manh Hung, Tran Thi Lan Huong,
Do Thi Nguyet Que, Nguyen Phuong Thao, Nguyen Xuan Cuong, Nguyen Tien Dat,
Chau Van Minh and Phan Van Kiem 323
Antimicrobial Evaluation of Clerodane Diterpenes from Polyalthia longifolia var. pendula
Koneni V. Sashidhara, Suriya P. Singh and P.K. Shukla 327
Antifouling Sesterterpenes from the New Zealand Marine Sponge Semitaspongia bactriana
Michael Stewart, Craig Depree and Karen J Thompson 331
Genetic and Withaferin A Analysis of Iranian Natural Populations of Withania somnifera and
W. coagulans by RAPD and HPTLC
Mohammad Hossein Mirjalili, Seyyed Mohammad Fakhr-Tabatabaei, Houshang Alizadeh,
Alireza Ghassempour and Fateme Mirzajani 337
Cytotoxic and HLE-inhibitory Tetramic Acid Derivatives from Marine-derived Fungi
Kerstin Neumann, Stefan Kehraus, Michael Gütschow, and Gabriele M. König 347
Murrayakoeninol- A New Carbazole Alkaloid from Murraya koenigii (Linn) Spreng
Mumu Chakraborty, Sudipta Saha and Sibabrata Mukhapadhyay 355
Alkaloid Synthesis and Accumulation in Leucojum aestivum in vitro Cultures
Strahil Berkov, Atanas Pavlov, Vasil Georgiev, Jaume Bastida, Monique Burrus, Mladenka Ilieva and
Carles Codina 359
Exudate Flavonoids of Primula spp: Structural and Biogenetic Chemodiversity
Karin M. Valant-Vetschera, Tshering Doma Bhutia and Eckhard Wollenweber 365
Antioxidant and Antimicrobial Effects of the Mangrove Tree Heritiera fomes
Helle Wangensteen, Huong Cam Thi Dang, Shaikh Jamal Uddin, Mahiuddin Alamgir and
Karl Egil Malterud 371
Possibility for Selective Accumulation of Polyphenolics in Tissue Cultures of
Senno (Lychnis senno Siebold et Zucc.)
Shinjiro Ogita, Junko Miyazaki, Toshinari Godo and Yasuo Kato 377
Phenolic Glucosides from Flacourtia indica
Swati Madan, Steve T. Pannakal, Seru Ganapaty, Gyanendra N. Singh and Yatendra Kumar 381
Antimicrobial Phenolic Compounds from Anabasis aphylla L.
Hua Du, Ye Wang, Xiaojiang Hao, Chun Li, Youliang Peng, Jihua Wang, Hao Liu and Ligang Zhou 385
Aureobasidin, New Antifouling Metabolite from Marine-Derived Fungus Aureobasidium sp.
Ahmed Abdel-Lateff, Ehab S. Elkhayat, Mostafa A. Fouad and Tatsufumi Okino 389

Continued inside back cover