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Isoquinoline alkaloids isolated from three Guatteria species

Article  in  Biochemical Systematics and Ecology · August 2017

DOI: 10.1016/j.bse.2017.05.002

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Biochemical Systematics and Ecology

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Isoquinoline alkaloids isolated from three Guatteria species

Anderson R. dos Santos a, *, Cassiano Pires a, Francisco A. Marques a, Adriana Q. Loba
~o b,
a
Beatriz Helena L.N.S. Maia
a
Department of Chemistry, Federal University of Parana , Centro Polit
ecnico, Curitiba, Parana, Brazil
b
Institute of Biology, Department of General Biology, Fluminense Federal University, Nitero i, Rio de Janeiro, Brazil

a r t i c l e i n f o a b s t r a c t

Article history: The chemical investigation of the aerial parts of Guatteria ferruginea collected in the National Park of
Received 9 March 2017  a
Serra dos Org ~os, Tereso
 polis, Brazil and of Guatteria latifolia and Guatteria sellowiana collected in the
Received in revised form National Park of Itatiaia, Itatiaia, Brazil resulted in the isolation and identification of six isoquinoline
7 May 2017
alkaloids, two aporphine alkaloids 3-hydroxy-nornuciferine (1), nornuciferine (2) and four oxoaporphine
Accepted 13 May 2017
alkaloids lysicamine (3), isomoschatoline (4), liriodenine (5) and O-methylmoschatoline (6). The iso-
quinoline alkaloids were found in the species G. ferruginea, G. latifolia and G. sellowiana for the first time
and they support the taxonomic position within the genus Guatteria. Isoquinoline alkaloids (5e6) can be
Keywords:
Guatteria
considered chemotaxonomic markers of the subfamily Annonoideae.
Annonaceae © 2017 Elsevier Ltd. All rights reserved.
Isoquinoline alkaloids
Chemotaxonomic marker

1. Subject and source 2. Previous work

The genus Guatteria Ruiz et Pav. belongs in the family Annona-
ceae and is found in Neotropical regions (Erkens et al., 2008) and
comprises about 2.440 species and 130 genera. The genus Guatteria
is widely found with 307 species from Southeastern Mexico to
Bolivia and Southeast Brazil with great diversity in the Amazon
(Loba~o et al., 2012). The chemical investigation of the aerial parts of
the three species of Guatteria collected in February 2011 in areas of
preservation of the Atlantic Forest was carried out. The species
G. ferruginea A. St.-Hil. (popularly known as the embuí-amarelo)
 a
was collected in the Serra dos Org ~os National Park and a voucher
specimen deposited at the Herbarium of the Botanical Garden of
Rio de Janeiro under the number RB 4444448. The species
G. latifolia (Mart.) R.E.Fr. (popularly known as embira-dura) and
G. sellowiana Schltdl. (popularly known as pindaíba-verdadeira and
pindaíba-da-mata) were collected in the Itatiaia National Park. A
voucher specimen of these species was deposited at the Herbarium
of the Botanical Garden of Rio de Janeiro under the numbers RB
518836 and RB 415016, respectively. All species were identified by
Dr. Adriana Quintella Lob~ ao, Departament of General Biology, Flu-
minense Federal University (UFF).
* Corresponding author.
E-mail address: anrogerquimica@gmail.com (A.R. dos Santos).
No chemical investigation is described on these species. The
phytochemical investigation of the genus Guatteria indicates the
presence of sesquiterpenoids (Zhang et al., 2002), prope-
nylbenzenes (Enqíques et al., 1980) and alkaloids (Costa et al., 2010)
as fixed main constituents.
3. Present study
3.1. Extraction and isolation
The aerial parts of the species G. ferruginea (590.8 g), G. latifolia
(1.300 g) and G. sellowiana (399.0 g) were air-dried and extracted
with methanol by maceration at room temperature. The extracts
were concentrated under vacuum and then the extracts
G. ferruginea (38.98 g) and G. latifolia (101.5 g) were subjected to
acid-base extraction, while half of the extractor G. sellowiana
(10.0 g) was dissolved in water/methanol (1:1) and partitioned
with solvents in order of increasing polarity, resulting in fractions
of petroleum ether (0.547 g), chloroform (1.972 g) and ethyl ace-
tate (2.327 g). The alkaloid fraction of G. ferruginea (0.343 g) was
subjected to successive purifications by column chromatography
(CC) and preparative thin layer chromatography (PTLC) over silica
gel afforded the oxoaporphine alkaloid liriodenine (5, 40.2 mg).
The alkaloid fraction of G. latifolia (0.374 g) was subjected to silica

http://dx.doi.org/10.1016/j.bse.2017.05.002
0305-1978/© 2017 Elsevier Ltd. All rights reserved.
2 A.R. dos Santos et al. / Biochemical Systematics and Ecology 73 (2017) 1e2
gel CC eluted with heptane/ethyl acetate 90%, ethyl acetate, ethyl
acetate/methanol gradient. This column afforded 110 fractions
which were evaluated and pooled by TLC analysis in seven new
fractions. Purification of fraction 4 by preparative TLC on silica gel
afforded 3-hydroxynornuciferine (1, 5.2 mg). The neutral fraction
(10.481 g) of G. latifolia after successive purifications by CC and
preparative TLC on silica gel to yield oxoaporphines alkaloids
lysicamine (3, 21.5 mg) and isomoschatoline (4, 17.3 mg), and
aporphine alkaloids nornuciferine (2, 13.5 mg). The chloroform
fraction of G. sellowiana after successive purifications by CC and
preparative TLC on silica gel afforded oxoaporphine alkaloid O-
metilmoschatoline (6, 1.9 mg) and aporphine alkaloid nornuci-
ferine (2, 14.7 mg) also found in G. latifolia. The chemical inves-
tigation of three species of Guatteria resulted in the isolation of six
isoquinoline alkaloids being two aporphines alkaloids (1, 2) and
four oxoaporphines alkaloids (3, 4, 5, 6).
3.2. Structure elucidation
The structure of the isolated compounds (Fig. 1) were deter-
mined by NMR analysis and comparison with literature data; 3-
hydroxy-nornuciferine (1) (Costa et al., 2012), nornuciferine (2)
(Dutra et al., 2012), lysicamine (3) (Siqueira et al., 1998), iso-
moschatoline (4) (Costa et al., 2011), liriodenine (5) (Siqueira et al.,
1998) and O-methylmoscatoline (6) (Silva et al., 2007).
4. Chemotaxonomic significance
The present work reports for the first time the characterization
of six isoquinoline alkaloids 1e6 of the aerial parts from three
Guatteria species (G. latifolia, G. sellowiana and G. ferruginea). The
isoquinoline derived alkaloids are very common in Guatteria and
related genera as Annona, Duguetia and Xylopia (Leboeuf et al.,
1982; Rodrigues et al., 2016; Almeida et al., 2007; Costa et al.,
2013a).
The alkaloids liriodenine (5) and O-metilmoschatoline (6) were
 pez et al.,
reported in other species of the genus as G. oliviformis (Lo
1990), G. citriodora (Rabelo et al., 2014), G. friesiana (Costa et al.,
2013b), G. tonduzii (Lopez et al., 1990), G. hispida (Costa et al.,
2010), G. blepharophylla (Costa et al., 2011) and G. pogonopus
(Santos et al., 2015) and in other genera of the same subfamily,
Annona foetida (Costa et al., 2006), Duguetia vallicola (Perez et al.,
2004), Duguetia furfuraceae (Carollo et al., 2006), Xylopia cham-
pionii (Wijeratne et al., 1996), Xylopia ferruginea (Zawawi et al.,
Fig. 1. Alkaloids isolated from Guatteria ferruginea (compound 5), G. latifolia (1, 2, 3, 4)
and G. sellowiana (2, 6).
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2012), Xylopia laevigata (Costa et al., 2013a), Fusaea longifolia
(Tavares et al., 2005), Goniothalamus tamirensis (Tran et al., 2013),
Uvaria kurzii (Lv et al., 2011), Artabotrys uncinatus (Wu et al., 1989),
Fissistigma glaucescens (Wu et al., 1990), Fissistigma oldhamii,
Uvariopsis guineensis (Leboeuf and Cave , 1972), Hornschuchia obli-
qua (Fechine et al., 2003). Our findings support the chemotaxo-
nomic evidence of the Annonaceae family and mainly the
compounds (5) and (6) and their wide occurrence in the various
genera of the subfamily Annonoideae suggests that these com-
pounds could be used as chemotaxonomic markers of this
subfamily.
Acknowledgements
The authors thank Arauc aria Foundation, CAPES and CNPq
(142141/2010-0) for financial support.
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