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Chemical Analysis and Biological Evaluation of Tropical Plants: Goetzea elegans and Pimenta racemosa

Jaymie M. Rivera Gutirrez Dr. Claudia Ospina1, Dr. Mayra Pagn1 and Prof. Augusto Carvajal2
1Chemistry

Department University of Puerto Rico at Cayey 2Biology Department, University of Puerto Rico at Cayey

Aims:
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Main:
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The development and application of bioassay for the research of antitumor activity on tropical plants extract.

Specifics:
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Studying cytotoxic properties of tropical species. Chemotaxonomic study of tropical plants in Puerto Rico

Introduction
Since ancient times, in Puerto Rico some plants have been used to treat diseases like colds, coughs, diarrhea, respiratory infections, skin lesions and others. Unfortunately, it is estimated that only a few group of endemic and native plants have been studied around entire world. In Puerto Rico, we are at risk of losing the ancestral knowledge of the healing properties of plants.

Melndez, 2006

Plant-based anticancer molecules


OH O O O O O O O O O G lu

O O

O O

P o d o p h y ll o t o x in L ig n a n is o la t e d f r o m P o d o p h y llu m p e lta tu m

E t o p o s id e S y n th e tic D r u g

N O N N O OH O OH N O O HO N O

C a m p t o t h e c in A lk a lo id e x t r a c te d fr o m C a m p o th e c a a c u m in a ta

T o p o te c a n S y n th e tic D r u g

Srivastava, 2005

GENERAL STRATEGY: Selection of the Organism


The species that we chose for this study were:
Pimenta Racemosa (P.R.) antiseptic and astringent properties; against headache, sore throat, stomach pain reliever and it helps to regulate the digestion.

Goetzea Elegans (G.E. - endemic) Has not been reported any healing power yet.

Alain, 2006

GENERAL STRATEGY: Collection


Ro Piedras, Puerto Rico Goetzea Elegans

February 23, 2008: A collection expedition was organized taking in consideration the distribution and abundance of the organisms in a specific area

Cidra, Puerto Rico

Pimenta Racemosa

GENERAL STRATEGY: Methodology


P la n t D ry in g a n d M a c e ra tio n w ith a m ix tu re o f C H 2 C l2/M e O H (1 :1 ) C r u d e E x tr a c t

S u s p e n d e d in W a te r a n d E x tra c te d w ith s o lv e n ts o f d iffe re n t p o la rity

H exan e

C h lo r o fo r m

E th y l A c e ta te

B u t a n o l*

W a te r

* S o m e t im e s , b u t a n o l e x t r a c t io n is r e q u ir e d

GENERAL STRATEGY:
Methodology
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Rotovaporation of the samples

Results and Discussion


-GeneralSolvent name Hexane P.R. 279.66 Chloroform Ethyl Acetate Buthanol Aqueous Hexane G.E. 270.10 Chloroform Ethyl Acetate Aqueous Leaves dry Plant Weight (g) 0.02g Solvent (mL) 400 300 300 300 175 400 450 300 200 25.10 17.76 Crude extract dry weight (g) 0.02

GENERAL STRATEGY: Methodology


Biological evaluation:
Bioassay
Serial dilutions of extracts are made in wells of 96-wells microplates in triplicate in 100L sea water. A suspension of nauplii containing 10-15 brine shrimp larvae are added to each microwell plate incubated at room temperature for 24 hours.

GENERAL STRATEGY: Methodology

Bioassay

Results and Discussion


-Biological evaluationExtract P.R.Crude P.R.Hexane P.R.CHCl3 G.E.Crude G.E.Hexane G.E.CHCl3 LC50 (g/mL) 1.6x104 68.9 92.0 6.2x104 171.0 4.1x102

Three of the six extracts were active with a LC50 200 g/mL. These extracts were obtained after partition with solvents of different polarities. The crude extracts of these species were inactive with a LC50 200 g/mL.

Results and Discussion


-Chemical analysis1H

NMR spectrum of Pimenta Racemosa in CD3OD

The functional groups for the crude extract of P.R. are aliphatic carbons under the 1-2 ppm region, aromatics in 67.1ppm, and double bonds at 5pmm. The high peaks under 3.5-4.8ppm is the methanol-d used as solvent.

Results and Discussion


-Chemical analysis1H

NMR of chloroform extract of Pimenta Racemosa

The corresponding compound for this NMR is eugenol and the corresponding molecule is:

Results and Discussion


-Chemical analysis1H

NMR spectrum of Goetzea Elegans in CDCl3

The functional groups for the crude extract of G.E. are aliphatic protons under the 0.6-2.4 ppm region, and double bonds at 5pmm.

GENERAL STRATEGY: Methodology


Chemical analysis:
TLC Analysis: A mixture of different concentrations of solvents was prepared as the liquid phase. We took drops of the corresponding samples of G.E. crude, G.E. hexane extract and G.E. chloroform extract and settled in the stationary phase.

GENERAL STRATEGY: Methodology

TLC

Results and Discussion


-Chemical analysisA
Where A is the crude extract, B is the hexane extract and C is CHCl3 extract for G.E.

TLC analysis: B C
Better mixture of solvents to purify the compounds 9.0mL Hexane with 1.0mL AcoEt

GENERAL STRATEGY: Methodology


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Chemical analysis:
z

Separation by column:
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We made a separation by columns using the best mixture of solvents with different polarities based on the results of the TLC.

GENERAL STRATEGY: Methodology

Column and the six fractions.

Results and Discussion


-Chemical analysisA
Where A is the crude extract, B is fraction #1 , C is the fraction #2 and D is the fraction #3 for the hexane extract for G.E.

TLC analysis: B C D
Mixture of solvents :9.5mL Hexane with 0.5mL AcoEt

Results and Discussion


-Chemical analysis1H

NMR of the third fraction of G.E. hexane extract.

The possible functional groups for the hexane extract of G.E. are aliphatic carbons under the 1-2 ppm region, aromatics in 7-8ppm, and double bonds at 5pmm.

Future Work:
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Extracts purification and separation will be based on the bioactivity results. NMR for the third fraction of G.E. hexane extract.

{ 13C

Sam, et Al, 2007

Acknowledgments:
Dr. Claudia Ospina { Isamar Ortiz, Karla Claudio and Janibeth Hernandez { Biominds Program { Chemistry and Technicians Department { Interdisciplinary Investigation Institute { RISE Program
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Chemical Analysis and Biological Evaluation of Tropical Plants: Goetzea elegans and Pimenta racemosa
Jaymie M. Rivera Gutirrez Dr. Claudia Ospina1, Dr. Mayra Pagn1 and Prof. Augusto Carvajal2
1Chemistry

Department University of Puerto Rico at Cayey 2Biology Department, University of Puerto Rico at Cayey

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