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State Key Laboratory of Natural and Biomimetic Drugs,
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Natural Product Communications
Chemical Composition of Diterpenes from the Brown Alga
Canistrocarpus cervicornis (Dictyotaceae, Phaeophyceae)
2008
Vol. 3
No. 9
1469 - 1472
Aline Santos de Oliveiraa, Diana Negrão Cavalcantia, Éverson Miguel Biancob,
Joel Campos de Paulac, Renato Crespo Pereiraa, Yocie Yoneshigue-Valentind and
Valéria Laneuville Teixeiraa,*
a
Departmento de Biologia Marinha, Instituto de Biologia, Universidade Federal Fluminense,
P.O. Box 100.644, Niterói, RJ, Brazil, 24001-970
b
Programa de Pós-Graduação em Química Orgânica, Instituto de Química,
Universidade Federal Fluminense, Niterói, RJ, Brazil, 24020-015
c
Departamento deBiologia Vegetal, Instituto de Biologia Roberto AlcântaraGomes,
Universidade do Estado do Rio de Janeiro, RJ, Brazil, 20550-013
d
Departamento de Botânica, Instituto de Biologia, Universidade Federal do Rio de Janeiro, RJ,
Brazil, 21941-590
[email protected]
Received: June 11th, 2008; Accepted: June 26th, 2008
Specimens of two populations of Canistrocarpus cervicornis were collected from two different localities on the Brazilian coast
about 2000 kilometers apart. The CH2Cl2 extracts were analyzed by 1H NMR and HRGC-MS techniques. A total of fourteen
diterpenes were detected, eight dolastanes (1-8) and five secodolastanes (9-13). The results obtained revealed a typical pattern
for C. cervicornis, which did not vary according to the geographical region.
Keywords: Canistrocarpus cervicornis, diterpenes, dolastane, secodolastane, chemical variation, HRGC-MS, NMR.
Brown algae (Phaeophyceae) are generally dominant
along the coast of Brazil in terms of biomass, but
present a smaller number of species in comparison
with the red (Rhodophyceae) and green algae
(Chlorophyceae) [1,2]. Two orders in particular are
important for Brazilian coasts, the Fucales and
Dictyotales (e.g. Dictyota Lamouroux) [2].
Canistrocarpus De Paula et De Clerck, and
Rugulopteryx De Clerck et Coppejans. The genus
Canistrocarpus includes the old species Dictyota
cervicornis Kützing, D. crispata Kützing and
D. magneana De Clerck et Coppejans.
The Dictyotales consists of the large family
Dictyotaceae Lamouroux, in which some 20 genera
are currently recognized, and two small families,
Dictyotopsidaceae and Scoresbyellaceae [3].
As we have a great interest in the diterpenes from
algae of the family Dictyotaceae [e.g. 4,5], we
examined the chemical variation in these compounds
from Canistrocarpus cervicornis collected from two
widely different localities along the Brazilian coast
by using NMR and HRGC-MS techniques.
The Dictyotaceae is subdivided into two tribes,
Dictyoteae and Zonarieae. Recently, De Clerck
and collaborators [3] published a revised
classification of the Dictyoteae based on rbcL
and 26S ribosomal DNA sequence analysis. In this
study, the authors proposed the separation of
Dictyoteae into three genera, Dictyota Lamouroux,
In previous investigations of this alga (as Dictyota
cervicornis Kützing) collected in Brazil, 11 dolastane
and 4 secodolastane diterpenes were isolated [6-9].
The populations of C. cervicornis presented dolastane
and secodolastane diterpenes as major metabolites,
which result from a first cyclization of geranylgeraniol between positions 1 and 11 [4,10-11]. Many
1470 Natural Product Communications Vol. 3 (9) 2008
OH
OH
Oliveira et al.
Table 1: Presence of the diterpenes in two populations in the two
treatments.
OH
OH
RO
HO
HO
1
2R=H
4R=H
5 R = Ac
3 R = Ac
OH
O
OH
OH
O
AcO
RO
6R=H
7 R = Ac
OH
R
OAc
8
9R=H
10 R = OH
11 R = Oac
O
O
RO
O
O
OH
12 R = H
13 R = Ac
OH
Compds
1
2
3
4
5
6
7
8
9
10
11
12
13
14
others
Bahia
Rio de Janeiro
crude extract after filtration crude extract after filtration
tr
nd
nd
tr
nd
+
+
+
tr
+
nd
+
+
nd
+
tr
+
nd
+
nd
tr
nd
+
tr
tr
nd
+
nd
+
tr
+
nd
nd
nd
tr
tr
+
+
+
+
+
+
+
+
tr
tr
+
+
+
+
+
+
tr
tr
+
+
+
+
+
+
+ present, tr = trace amounts (<5% of the crude extract), nd = not detected
OH
14
of these diterpenes were isolated from other
populations of this species and also from populations
of C. crispatus (as Dictyota crispata) from Brazil
[12]. In this context, the populations named Dictyota
divaricata and D. linearis from the Caribbean Sea
[13,14] and Japan [15-18], D. dichotoma [19-22] and
D. indica from Pakistan [23-24], D. furcellata from
Australia [25] and Dictyota sp. from the Canary
Islands [26] could be considered as C. cervicornis.
The two extracts of C. cervicornis presented similar
profiles on TLC analysis on silica gel layers
(CH2Cl2/EtOAc 4:1 as eluent). The 1H NMR spectra
of the extracts of the two populations revealed the
presence of 8 as the major diterpene, followed by the
dolastane 6 and the secodolastane diterpene 10.
The dolastanes 1, 3 and 5 and secodolastane
diterpenes 9, 12 and 14 were either absent or present
in the crude extract as either minor or trace
components (Table 1). The 1H NMR spectra of the
two extracts after filtration on silica gel with
CH2Cl2/EtOAc (9:1) revealed the presence of 2 and 3
as major diterpenes, but either the absence or a small
amount of 6 and 8.
The crude extract of the Bahia population
presented the dolastane diterpene 4,7-diacetoxy-14hydroxydolastane-1(15),8-diene (8) as the major
metabolite, forming more than 50% of the crude
extract. However, the dolastane diterpene 6, the
secodolastane diterpenes isolinearol (10) and
isolinearol acetate (13) were also encountered in
great quantity.
In the crude extract of the population from northern
Rio de Janeiro, dolastane 8 was again the major
metabolite, present along with dolastanes 2, 4-8 and
the six secodolastanes diterpenes 10-14. About ten of
the diterpenes identified in this population were
related to those of C. cervicornis from Angra dos
Reis, Rio de Janeiro [6-8,27]. This similarity
confirmed an important role of the diterpenes as
taxonomic and biogeographic markers.
The HRGC/MS analysis corroborated the NMR
results, after filtration (see Supplementary Data).
Although the HRGC-MS technique is suitable for the
analysis of algal extracts [28], the heating procedure
resulted in the formation of artifacts (2 and 3)
generated by dehydration of the diterpenes.
Therefore, the use of less acid organic solvent in
extraction (such as n-hexane), caution in drying the
biological material, and NMR qualitative and
quantitative analysis indicated that further
investigation of the diterpene composition would be
of value.
Finally, the results obtained revealed that this species
has a chemical pattern that suffers little variation
resulting from geographic location.
Experimental
Algal material: Specimens of C. cervicornis were
collected during February 2005 in Praia da Penha,
Vera Cruz, Bahia (lat. 12°58’22”S, long.
038°30’45”W) and in Praia do Saco do Céu, Ilha
Grande, Rio de Janeiro (lat. 23°00’24”S, long.
044°19’05”W). These places are approximately 2000
km. apart. The algae were collected at depths varying
from 2 to 5 meters. Voucher specimens are deposited
Diterpenes from Canistrocarpus cervicornis
in the Herbarium of the Universidade do Estado do
Rio de Janeiro (HRJ).
Extraction: The air-dried algae were extracted with
CH2Cl2 at room temperature (25°C). The solvent was
evaporated under reduced pressure yielding brownish
residues. Aliquots of the crude extracts (20 mg for
each population) were filtered through silica gel with
30 mL of CH2Cl2 /EtOAc (9:1).
NMR analysis: 1H NMR (300 MHz) spectra were
recorded on a Varian Unity Plus 300 spectrometer
using CDCl3 as solvent and TMS as internal standard.
Chemical shifts were reported in δ (ppm) and
coupling constants (J) in Hz.
Gas chromatographic analysis (HRGC): The
preliminary HRGC analysis was carried out using an
HP 5890 CG equipped with an SE-54 glass capillary
column (15 m x 0.25 mm; film thickness 0.25 µm)
and a FID detector.
HRGC/MS analysis: An aliquot of the extract was
diluted with an appropriate volume of ethyl acetate
and analysed by HRGC-MS on a HP 6890 series GC
system, coupled to a HP 5973 mass selective detector
in the electron impact mode (70 eV), equipped with a
Natural Product Communications Vol. 3 (9) 2008 1471
HP-1 MS capillary column (30 m x 0.25 mm; film
thickness 0.25 µm). Injector and detector
temperatures were set at 270oC and 290oC,
respectively. The temperature program was kept at
160oC, then programmed to 260oC at a rate of 4o
C/min and finally raised at a rate of 15oC/min to
290oC for 15 min. Hydrogen was the carrier gas at a
flow rate of 1 mL/min. Diluted sample were injected
manually in the split mode (1/10 or 1/20). Data were
obtained from Frd area percent data. The chemical
components were identified based on comparison of
their mass spectra with those of standards and/or
literature data, by co-injection technique in HRGC,
and with Wiley 275 library data of the HRGC/MS
system. Silica gel GF254 (Merck) was used for TLC.
Supplementary data: Mass spectral data of isolated
diterpenes (1-5, 8-10 and 11) is presented (Table 2).
Acknowledgments - We are grateful to CNPq for
financial support and for Productivity Fellowships to
YYV, RCP and VLT. EMB also thanks CNPq for a
Doctor’s degree fellowship. DNC and ASO
appreciate CAPES for providing ProDoc and Master
degree fellowships, respectively. The authors are also
grateful to Dr Claudia Rezende and Angelo Pinto for
use of the HRGC and HRGC-MS equipment.
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A New Biflavanone from Ochna lanceolata
Shaik I. Khalivulla, Nimmanapalli P. Reddy, Bandi A.K. Reddy, Ramireddy V.N. Reddy,
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Extraction Methods Play a Critical Role in Chemical Profile and Biological Activities of Black Cohosh
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Natural Product Communications
2008
Volume 3, Number 9
Contents
Page
Anti-tuberculosis Compounds from two Bolivian Medicinal Plants, Senecio mathewsii and
Usnea florida
Qi Hong, David E. Minter, Scott G. Franzblau and Manfred G. Reinecke
1377
Natural Products from Polygonum perfoliatum and their Diverse Biological Activities
Chi-I Chang, Fei-Jane Tsai and Chang-Hung Chou
1385
Phytochemical Characterization of the Australian (Aboriginal) Medicinal Plant Dolichandrone
heterophylla and Influence of Selected Isolated Compounds on Human Keratinocytes
Thomas Dzeha, Kristian Wende, Manuela Harms, Ju Ju (Burriwee) Wilson, Jim Kohen, Subra Vemulpad,
Joanne Jamie and Ulrike Lindequist
1387
Analysis of Saponin Mixtures from Alfalfa (Medicago sativa L.) Roots using Mass Spectrometry
with MALDI Techniques
H. Ewa Witkowska, Zbigniew Bialy, Marian Jurzysta and George R. Waller
1395
Control of Allantoin Accumulation in Comfrey
Paulo Mazzafera, Kátia Viviane Gonçalves and Milton Massao Shimizu
1411
Trigonelline (N-methylnicotinic acid) Biosynthesis and its Biological Role in Plants
Hiroshi Ashihara
1423
Biosynthesis and Catabolism of Purine Alkaloids in Camellia Plants
Misako Kato and Hiroshi Ashihara
1429
A View on the Active Site of Firefly Luciferase
Franklin R. Leach
1437
Study on the Chemical Constituents of Premna integrifolia L.
Nguyen Thi Bich Hang, Pham Thanh Ky, Chau Van Minh, Nguyen Xuan Cuong, Nguyen Phuong Thao
and Phan Van Kiem
1449
Τ-Cadinol Nerolidol Ether from Schisandra chinensis
Asmita V. Patel, Gerald Blunden, Peter D. Cary, Lubomír Opletal, Markéta Beránkova, Kersti Karu,
David E. Thurston and Milan Pour
1453
Bioactive Semisynthetic Derivatives of (S)-(+)-Curcuphenol
Helena Gaspar, Cristina Moiteiro, João Sardinha and Azucena González-Coloma
1457
Eco-contribution to the Chemistry of Perezone, a Comparative Study, Using Different Modes of
Activation and Solventless Conditions
Joel Martínez, Benjamín Velasco-Bejarano, Francisco Delgado, Rocío Pozas,
Héctor M. Torres Domínguez, José G. Trujillo Ferrara, Gabriel A. Arroyo and René Miranda
1465
Chemical Composition of Diterpenes from the Brown Alga Canistrocarpus cervicornis
(Dictyotaceae, Phaeophyceae)
Aline Santos de Oliveira, Diana Negrão Cavalcanti, Éverson Miguel Bianco, Joel Campos de Paula,
Renato Crespo Pereira, Yocie Yoneshigue-Valentin and Valéria Laneuville Teixeira
1469
Cembranoid Diterpenes from the Soft Corals Sarcophyton sp. and Sarcophyton glaucum
Daniela Grote, Kamel H. Shaker, Hesham S. M. Soliman, Muhammmad M. Hegazi and Karlheinz Seifert
1473
Dolabellane Diterpenes from Cleome droserifolia
Hoda M. Fathy, Mohamed I. Aboushoer, Fathallah M. Harraz, Abdallah A. Omar, Gilles Goetz and
Rafael Tabacchi
(Continued inside back cover)
1479