Revista Boliviana de Qumica

Rev. Bol. Quim. ISSN 0250-5460

Rev. boliv. quim. ISSN 2078-3949

Bolivian Journal of Chemistry

Vol. 33, No. 4, 2016
Abstracts list
CHEMICAL STUDY OF SEEDLINGS OF GALIPEA LONGIFLORA (EVANTA); A BIOGUIDED APPROACH

Gabriela Quiroga Selez, Carla Parra Lizarazu*, Efran Salamanca Capusiri, Esther
Flores Quisbert, Alberto Gimnez Turba

Faculty of Pharmaceutical and Biochemical Sciences, Biochemical Drug Research Institute IIFB,
Universidad
Mayor de San Andrs UMSA, P.O. Box 3239, Av. Saavedra 2224, Phone 5912229021, La Paz, Bolivia,
farbio@farbio.edu.bo

Keywords: seedlings, quinoline alkaloids, leishmanicidal activity, PAT.

ABSTRACT
The active principles (quinolinic alkaloids) from Galipea longiflora (Evanta) were isolated and characterized .
These alkaloids showed low toxicity and a good in vitro activity against Leishmania strains. Seedlings of
different ages of this medicinal species were developed. The work has been focused on the analysis of variations
of quinolinic alkaloids present in extracts of the seedlings and the variation of the antiparasitic activity compared
with each other and with the total alkaloids in adult specimens.
Five common major quinolinic alkaloids were identified in the adult-age tree and in the seedlings. Fourteen
alkaloids were identified in the seedlings, compounds such as Shikimina, and 2-(3`,4`-metoxiphenylquinoline)
appear when the seedlings get older.
As a rule the PAT shows better biological activity than CAT with an IC50 of 13,41,2g/mL on L.
amazonensis and 7,20.55g/mL on L. braziliensis . This comparison between the variation of the antiparasitic
activity against the variation of seedling size and chemical composition of PAT give us a pattern of which
molecules will have influence in the biological activity.
*Corresponding author: mgqs88.mgqs@gmail.com

RESUMEN

Spanish title: Estudio qumico biodirigido de plantines de Galipea longiflora (Evanta). Los principios
activos (alcaloides quinolinicos) de Galipea longiflora (Evanta) fueron aislados y caracterizados. Estos alcaloides
mostraron baja toxicidad y una buena actividad in vitro frente a cepas de Leishmania. Se han realizado estudios
sobre plantines de diferentes edades de Galipea longiflora. El trabajo se centr en el anlisis de variaciones de la
mezcla de los alcaloides quinolnicos presentes en los extractos de plantines y la variacin de la actividad
antiparasitaria; comparados entre s y con alcaloides totales de corteza de especmenes adultos.
Se identificaron 5 alcaloides mayoritarios comunes en el rbol en edad adulta y plantines. En los plantines se
identificaron hasta 14 alcaloides, llegando a reportarse compuestos como la: Shikimanina, y 2(metoxifeniletilquinolina) cuando los plantines representan mayor edad.
En general, los PAT, presentan mejor actividad biolgica con una IC50 de 13,41,2g/mL sobre L. amazonensis
y 7,20.55g/mL sobre L. braziliensis que el CAT. Esta comparacin entre la variacin de la actividad
antiparasitaria frente a la variacin del tamao del plantin y a la composicin qumica de los PAT, nos da una
pauta de cules seran las molculas que influyen en la actividad biolgica.

SELECTION OF FILAMENTOUS FUNGI CAPABLE OF BIOTRANSFORMING THE

COMPOUND 2-PHENYLQUINOLINE
Carla Parra Lizarazu*, Gabriela Quiroga Selaez, Alberto Gimnez Turba
Faculty of Pharmaceutical and Biochemical Sciences, Biochemical Drug Research Institute IIFB,
Pharmaceutical Chemistry Area, Universidad Mayor de San Andrs UMSA, P.O. Box 3239, Av. Saavedra
2224, Phone 5912229021, La Paz, Bolivia, farbio@farbio.edu.bo

Keywords: Biotransformation, 2phenylquinoline, filamentous fungi.

ABSTRACT
Eighty strains, previously preserved by lyophilization, from the fungi collection of the Instituto de
Investigaciones Farmaco Bioquimicas-IIFB, part of the Major San Andres University, were activated. Ten strains
were preselected based on its ability to show development in an Agar medium with 2-phenylquinoline as the only
substrate. To evaluate the biotransformation process of the alkaloid, batch cultures were established in two
different media; Sabouraud broth and Basal Medium for fungi. Analysis by thin layer chromatography allowed to
select 6 strains which showed the formation of different products. Out of all the strains analyzed, strain 114QD
was the one that showed products of interest in both media.
*Corresponding author: mgqs88.mgqs@gmail.com

RESUMEN
Spanish title: Seleccin de hongos filamentosos capaces de biotransformar el compuesto 2fenilquinolina. Se activaron 80 cepas, procedentes del cepario del Instituto de Investigaciones FrmacoBioqumicas IIFB de la UMSA, en estado de conservacin por la tcnica de liofilizado, 10 de estas fueron
preseleccionadas por su capacidad de desarrollar en un medio solido de Agar Agar y 2-fenilquinolina como
nico sustrato. La evaluacin del proceso de biotransformacin del alcaloide se llev a cabo mediante el
establecimiento de cultivos Batch en dos medios de cultivo; Medio Sabouraud y Medio Basal para hongos, un
anlisis por cromatografa en capa fina permiti seleccionar a 6 cepas las cuales mostraron la formacin de
distintos productos siendo la cepa 114QD la nica que mostro productos de inters en ambos medios.

CHEMICAL AND BIOLOGICAL CHARACTERIZATION OF THE PRODUCTS OBTAINED

FROM THE BIOTRANSFORMATION OF 2-PHENYLQUINOLINE (2FQ) BY
ASPERGILLUS SPP

Carla Parra Lizarazu*, Gabriela Quiroga Selaez , Efran Salamanca Capusiri,

Esther Flores Quisbert, Alberto Gimnez Turba

Faculty of Pharmaceutical and Biochemical Sciences, Biochemical Drug Research Institute IIFB,
Universidad
Mayor de San Andrs UMSA, P.O. Box 3239, Av. Saavedra 2224, Phone 5912229021, La Paz, Bolivia,
farbio@farbio.edu.bo

Keywords: Biotransformation, 2-phenylquinoline, Aspergillus spp, Basal Medium.

ABSTRACT
Microorganisms such as filamentous fungi have been widely used in biotransformation studies of drugs and
complex molecules of plants.
The alkaloid 2-phenylquinoline obtained from the medicinal plant Galipea longiflora was the substrate in
biotransformation processes by 114QD, strain identified as Aspergillus spp. Chemical characterization was
carried out by thin layer chromatography (TLC), high performance liquid chromatography (HPLC) and gas
chromatography (GC). These techniques allowed to detect the presence of a product derived from a
biotransformation. Such product showed to be a more polar compound than the original substrate and exhibited
an UV absorption spectrum different from that of the substrate which has a bathochromic shift of the absorption
bands due to the replacement by OH. An analysis coupled to mass spectroscopy permitted identify the
hydroxylation of the quinoline ring by showing in its mass spectrum a molecular ion at 221 m/z compared to 205
m/z of the 2-phenylquinoline. Chromatographic techniques also allowed establishing that after 360 hours of
incubation in Basal Medium, approximately 78% of the substrate was bio-transformed. The analysis of the areas
in function of time showed an increase up to 10 times for the product formed regarding the early hours of culture.
Biological activity against promastigotes of Leishmania evaluated by XTT showed IC 50 values different
from those of the original substrate.
*Corresponding author: carlitaden2309@gmail.com

RESUMEN
Spanish title: Caracterizacin qumica y biolgica de los productos derivados de la biotransformacin
del alcaloide leishmanicida 2-fenilquinolina (2FQ) por Aspergillus spp. Los microorganismos, como los
hongos filamentosos han sido utilizados ampliamente en estudios de biotransformacin de frmacos y molculas
complejas provenientes de plantas.
El alcaloide 2-fenilquinolina obtenido de la planta medicinal Galipea longiflora, fue el sustrato en procesos de
biotransformacin por la cepa 114QD, identificada como Aspergillus spp. La caracterizacin qumica fue
realizada por cromatografa en capa fina (CCF), cromatografa lquida de alta resolucin (HPLC) y cromatografa
de gases (CG). Estas tcnicas permitieron detectar la formacin de un producto de biotransformacin, el cual
tiene como caracterstica una mayor polaridad con un espectro de absorcin UV diferente al del sustrato original.
Dicho producto presenta un desplazamiento batocrmico de las bandas de absorcin por sustitucin por OH, un
anlisis (HPLC y GC) acoplado a espectroscopia de masas identific de manera inequvoca la hidroxilacin del
anillo quinolnico al mostrar en su espectro de masas un in molecular con el pico a m/z 221 comparado con m/z
205 de la 2-fenilquinolina. Las tcnicas cromatogrficas permitieron adems determinar que luego de 360 horas
de incubacin en Medio Basal para hongos, aproximadamente un 78% de sustrato fue biotransformado. El
anlisis de las reas en el tiempo para el producto formado mostr su aumento de hasta 10 veces ms al hallado
durante las primeras horas de cultivo.