Pharmaceutical Biology

2001, Vol. 39, No. 3, pp. 161169

1388-0209/01/3903-161$16.00
Swets & Zeitlinger

Alkaloid Screening of Herbarium Samples of Rubiaceae from

Panama

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Antonio Soto-Sobenis, Berenice Castillo, Alcibiades Delgado, Aida Gonzlez and Roberto Montenegro
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Panama, Estafeta Universitaria,
Panama, Republic of Panama

Abstract
In an effort to study plants of the Rubiaceae from Panama,
299 herbarium samples, representing 133 species, were subjected to alkaloid screening. From this total, 234 samples
(78%) afforded a positive test for alkaloids, and 99 samples
(33%) gave a positive reaction for indole alkaloids; 109
species (82%) contain alkaloids and 58 (44%) produce indole
alkaloids. This is the first time that 102 (94%) and 52 (90%)
species are reported as alkaloid and indole alkaloid bearing,
respectively. The results of 10 out of 15 species, that is 67%,
corroborate earlier studies. The richest indole alkaloid
species were: Hamelia patens, Hamelia xerocarpa, Hoffmannia morii, Hoffmannia unguis-canceris, Deppea grandiflora, Elaeagia nitidifolia, Rondeletia secunda, Simira
maxonii, Uncaria tomentosa, Gonzalagunia rosea, Isertia
haenkeana, Isertia laevis, Posoqueria latifolia and Cinchona
pubescens.

The relationship between the Rubiaceae, Apocynaceae

and Loganiaceae, as far as alkaloids are concerned, has been
widely recognized. It is interesting that some of these alkaloids, e.g., vincristine and vinblastine, are important drugs in
modern medicine. The stability of alkaloids in plants preserved for long periods is well known. Therefore, herbaria
are good sources of material for chemical and biological
studies (Phillipson, 1982).
For these reasons, we decided to carry out alkaloid screening of native species of Rubiaceae to select alkaloid rich
plants for further phytochemical and pharmacological
studies.

Keywords: Alkaloids, herbarium samples, Panama, Rubiaceae, screening.

Leaf, flower, fruit or seed samples were provided by Mireya

Correa, Director of the Herbarium of the University of
Panama (PMA).

Materials and Methods

Plant material

Introduction
Rubiaceae is the largest plant family in Panama, with about
425 species in 87 genera, which represent about 20% of the
known genera in the world (Dwyer, 1980). There are 87
species of the subfamily Cinchonoideae, which grow only
in Panama and neighbouring countries (Dwyer, 1980).
However, little scientific research has been done to discover
the presence of any phytoconstituents systematically. In addition, it should be noted that there are discrepancies in the
taxonomic classification of many genera and tribes of this
family (Burger & Taylor, 1993; Dwyer, 1980; Phillipson et
al., 1982). Therefore, chemical screening should be useful
from the taxonomic point-of-view.

Screening of alkaloids
Less than 1 g of samples was moistened with diluted 10%
ammonia, shaken with chloroform for 24, and brought to
acid-base extraction to yield the alkaloid extracts. The
extracts were redissolved in 1 ml of chloroform, and 15 drops
of the extract were spotted on a filter paper. For comparison,
5, 10 and 15 drops of 0.5 mg/ml emetine hydrochloride were
spotted on the same filter paper. Then, the paper was sprayed
with Dragendorffs reagent. A positive test for alkaloids was
recorded when an orange colour ranging from light (+) to
very deep (++++) developed. A score of four crosses (++++)
means that the color reaction of the sample is more intense

Accepted: May 20, 2000

Address correspondence to: Antonio Soto-Sobenis, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy,
University of Panama, Estafeta Universitaria, Panama, Republic of Panama. E-mail: aymsoto@cwp.net.pa

162

A. Soto-Sobenis et al.

than 15 drops of 0.15 mg/ml emetine-HCl solution. The positive samples, were also chromatographed on Silica gel TLC
plates with authentic samples of emetine, cephaeline and
methylpsychotrine. Finally, the plates were sprayed with Dragendorffs and FeCl3/HClO4 reagents to detect the presence
of indole alkaloids (Phillipson & Hemingway, 1975).

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Results
A total of 299 samples (some belonging to the same species),
which represents 133 species of 48 genera, was examined.
Samples of most species belong to the tribes Cinchoneae,
Condamineae, Gardenieae, Hamelieae, Mussaendeae,
Naucleae, Oldenlandieae and Rondeletieae, and some
species belong to the tribes Chiococceae and Psychotrieae.
The results demostrated that 234 samples (109 species)
contain alkaloids, and 99 (58 species) also rendered a positive test for indole alkaloids. Table 1 summarizes these
results. The species that gave the strongest positive test for
indole alkaloids were: Hamelia patens Jacq., Hamelia
xerocarpa Kuntze, Hoffmannia morii Dwyer, Hoffmannia
unguis-canceris Dwyer, Deppea grandiflora Schlecht.,
Elaeagia nitidifolia Dwyer, Rondeletia secunda Standl.,
Simira maxonii (Standl.) Steyerm., Uncaria tomentosa
(Willd. ex Roem. & Schult.) DC., Gonzalagunia rosea
Standl., Isertia haenkeana DC., Isertia laevis (Triana)
B.M.Boom, Posoqueria latifolia (Rudge) Roem. & Schult.
and Cinchona pubescens Vahl.

Discussion
It is well known that there are variations in the alkaloid
content of different samples of the same species, possibly
due to climatic (rainy/dry season), topographic (altitude),
age variations, or other factors, like the existence of botanical varieties or chemical races. Nevertheless, some comments about the alkaloid distribution in the Rubiaceae can be
made.
The tribe Condamineae is unique among the tribes analyzed, because all the genera and species gave positive results
for alkaloids. However, it is also a very small tribe, since
only four genera and seven species grow in Panama. Rustia
panamensis has been recently classified as R. costaricensis
(Burger & Taylor, 1993). The freeze-dried sap of Pogonopus
speciosus has yielded the antitumour and cytotoxic
indole alkaloid tubulosine and the isoquinoline alkaloid
psychotrine (Ma et al., 1990). There is no work reported
on the other three genera insofar as alkaloid production is
concerned.
Results obtained with samples of the tribe Hamelieae
suggest that the four genera found in Panama, i.e., Bertiera,
Hamelia, Hoffmannia and Xerococcus, produce alkaloids.
Hamelia patens has been cited in the literature for the
production of indole alkaloids like maruquine, palmirine,
pteropodine and speciophylline (Borges del Castillo et al.,

1981, 1982). Surprisingly, the isoquinoline alkaloid ephedrine has also been isolated from this plant (Chaudhuri &
Thakur, 1991). The genus Hoffmannia is very large in
Panama with 28 species, which are difficult to differentiate
from a taxonomic point-of-view (Dwyer, 1980). Furthermore, Burger and Taylor (1993) have made a revision of
Rubiaceae that includes changes in the genus Hoffmannia
and even the only species of the genus Xerococcus (X. congestus) analyzed has been classified as Hoffmannia congesta
(Table 2). The analysis of 16 species showed variation in the
alkaloid content. Some species, i.e., H. morii and H. unguiscanceris, rendered a strong positive test for alkaloids and
indole alkaloids. On the other hand, H. areolata, H. manussatani and H. subauriculata, lack alkaloids according to our
results. Between these extremes, we have H. pittieri, H.
woodsonii and H. xerococcoides that afforded less intense
color reaction with Dragendorff and rendered a positive test
for indole alkaloids; and others, i.e., H. vesiculifera and H.
woodsonii ssp. montivaga, that rendered a positive test for
alkaloids, but lack indole alkaloids. It is interesting that the
tribe Hamelieae is placed in the subfamily Rubioideae by
other authors (Phillipson et al., 1982).
Although the tribe Oldenlandieae has two genera only,
Arcytophyllum (one species) and Oldenlandia (three
species), completely different results were found in the alkaloid screening. Our results with O. corymbosa confirm other
reports, since no alkaloid has been isolated from this plant,
but caffeine (Freise, 1935). This plant contains monoterpenes, triterpenes and steroids (Khastgir et al., 1960; Otsuka
et al., 1991). On the other hand, African and Asian species
of this genus, O. affinis and O. auricularia, have yielded
indole alkaloids (Gran, 1973; Purushothaman & Sarada,
1981).
The Rondeletieae is a very complex tribe insofar as alkaloid production is concerned. Unfortunately, there are no
herbarium specimens of the genera Limnosipanea and Lindenia, so it was impossible to test samples of these genera
for a better discussion of the tribe. The genera Deppea and
Elaeagia are closely related, and surprisingly there is variation between them. It should be mentioned that D. panamensis has recently been classified as E. myriantha (Burger
& Taylor, 1993). The other genera, Bathysa, Simira,
Warsewiczia and Rondeletia, are botanically related and the
first three have chemical similarity, since they rendered
positive results. The genus Simira has been recorded in the
literature for alkaloid production (Castro & Lopez, 1986;
Hasbun et al., 1989; Hegnauer, 1973). On the other hand,
Rondeletia has interspecific variety, some species gave negative results, and others gave positive ones with different
intensities. R. secunda is interesting because it was the only
one in this genus to afford a positive test for indole alkaloids.
The bark of R. panamensis has cytotoxic constituents of
diterpene nature (Koike et al., 1980).
In Panama, there is a single species belonging to the tribe
Naucleae, namely Uncaria tomentosa, which gave a strong
positive test for alkaloids and for indole alkaloids. These

Alkaloid screening of Rubiaceae from Panama

163

Table 1. Alkaloid presence in Panamanian species of Rubiaceae.

TEST FOR
TRIBE SPECIES
CONDAMINEAE
Chimarrhis parviflora Standl.

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Condaminea corymbosa (R.&P.) DC.

Pogonopus speciosus (Jacq.) Schum. in

Mart
Rustia occidentalis (Benth) Hemsl.

Rustia panamensis Dwyer

HAMELIEAE
Bertiera guianensis Aubl.

PLANT
PART

lf
lf
fl
fr
lf
lf, fl
fr

fl
fr

ALKALOIDS

INDOLES

04/11/82

04/0112/78
02/18/82
04/0112/78
11/29/71

+++
++++
+
++

NT
NT
NT

Garwood 704
Garwood, Gibby,
Hampshire &
Humphries 10
DArcy & Hammel 12238
Mori & Kallunki 3869

02/2224/77
01/04/83

++
+++

NT
NT

10/07/78
12/20/74

++
-

NT
NT

05/18/76

NT

06/23/77
09/25/69
02/18/85
09/19/65
1967
07/09/75
06/09/76

+++
+++
++++
++
+
++++
-

+
+
+
+
NT
+
NT

10/13/81
01/11/77
04/06/77
04/24/82
08/02/84
08/11/77
04/11/79

++
+++
+
++++
+
+

NT
NT
NT
NT
+
+
NT

07/02/71
07/1020/77
05/12/77
04/02/77
01/19/80

+
+
++++
+

NT
NT
NT
+
-

01/01/83
05/13/77

++
++

+
-

COLLECTION NUMBER

Knapp, Mallet & Huft

4586
Garwood 802
Whitefoord & Eddy 237
Garwood 802
Aguilera 17

Hoffmannia bullata L.O.Wms.

Hoffmannia cercidifolia Dwyer
Hoffmannia coclensis Dwyer
Hoffmannia manussatani Dwyer
Hoffmannia morii Dwyer
Hoffmannia pittieri Standl.
Hoffmannia psychotriifolia (Benth. in
Oerst.) Griseb.

lf
lf
lf, fl
br
lf
lf
lf

Hoffmannia rexmontis Dwyer

Hoffmannia subauriculata Standl.
Hoffmannia umbrella-medusae Dwyer
Hoffmannia unguis-canceris Dwyer
Hoffmannia vesiculifera Standl.

lf
lf
lf
lf
lf

Hoffmannia woodsonii Standl.

Hoffmannia woodsonii Standl. ssp.
montivaga Dwyer
Hoffmannia xerococcoides Dwyer
Xerococcus congestus Oerst.

lf
lf

Correa, Mendieta &

Mayo 2035
Folsom 3871
Correa & Dressler 1652
McDade 714
Blum & Tyson 607
Kirkbride & Elias 258
Mori 7086
Correa, Escobar &
Mendoza 2182
Knapp 1557
Folsom 1245
Folsom & Kauke 2654
Knapp & Schmalzel 4785
Churchill 5927
Bliz 211
DArcy, Hammel, Hill,
Schwartz & Wolcott
13261
Croat 15920
Folsom 4210
Folsom 3143
Folsom & Robinson 2360
Correa, Taylor, Salazar,
Mendoza, Bliz &
Vergara 3279
Stein & Hamilton 1150
Folsom 3220

lf
lf

Knapp 5001
Folsom & Robinson 2346

05/09/82
04/02/77

+
+

+
+

lf

Bliz & Salazar 320

04/08/78

+++

lf
lf

Correa & Aranda 4729

Correa, Mendieta &
Mayo 2028

12/13/86
05/18/76

NT
NT

Hamelia axillaris Sw.

Hamelia calycosa J.D.Sm.
Hamelia patens Jacq.
Hamelia patens Jacq. var. patens Jacq.
Hamelia sanguinea Elias
Hamelia xerocarpa Kuntze var. xerocarpa
Hoffmannia areolata Standl.

OLDENLANDIEAE
Arcytophyllum lavarum K.Schum. ex
Standl.
Oldenlandia corymbosa L.
Oldenlandia lancifolia (Schumach.) DC.

lf, fr

DATE OF
COLLECTION

lf
lf
lf
lf
lf
lf
lf

164

A. Soto-Sobenis et al.

Table 1. Continued.
TEST FOR
TRIBE SPECIES

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RONDELETIEAE
Bathysa panamensis Dwyer
Bathysa veraguensis Dwyer
Deppea grandiflora Schlecht.
Deppea panamensis Dwyer
Elaeagia auriculata Hemsl.

PLANT
PART

fr
infl
fr
lf, fl
lf
lf

Elaeagia nitidifolia Dwyer

fl
lf

Rondeletia amoena (Planch.) Hemsl.

lf

Rondeletia bertieroides Standl.

Rondeletia buddleioides Benth.
Rondeletia buddleioides Benth. var.
buddleioides Benth.
Rondeletia chiriquiana Lorence

Rondeletia cooperi Standl.

Rondeletia hamelifolia Dwyer & Hayden
Rondeletia kirkbridei Dwyer
Rondeletia panamensis DC.
Rondeletia platysepala Standl.
Rondeletia salicifolia Dwyer & Hayden
Rondeletia secunda Standl.
Simira maxonii (Standl.) Steyerm
Warszewiczia coccinea (Vahl) Kl.
NAUCLEAE
Uncaria tomentosa (Willd. ex Roem. &
Schult.) DC.
MUSSAENDEAE
Coccocypselum guianense (Aubl.)
K.Schum. in Mart.
Coccocypselum herbaceum P.Br.
Coccocypselum hirsutum Bartl. ex DC.
var. glabrum (DC.) L.O.Wms.
Coccocypselum hirsutum Bartl. ex DC.
var. hirsutum Bartl. ex DC.
Coccocypselum hispidulum Standl.
Gonzalagunia bracteosa (J.D.Sm.)
B.L.Rob.
Gonzalagunia kallunki Dwyer
Gonzalagunia ovatifolia (J.D.Sm.)
B.L.Rob.
Gonzalagunia panamensis (Cav.)
K.Schum.in Mart.

fr
lf
lf, fr
lf
lf

lf
lf, fl
lf
lf
lf
lf
lf
lf
fl
lf

COLLECTION NUMBER

Hammel 4685
Hammel 4685
Folsom 5248
Hammel 6455
Mori & Kallunki 4965
Correa, Dressler,
Salazar, Mendieta,
Garibaldi, Farnum &
Bliz 2885
McPherson 6784
DeNevers & Herrera
4266
Van der Weff & Herrera
7082
Huft 1840
Knapp & Dressler 4925
Folsom 3814
Wilbur, Luteyn &
Armond 11927
Correa, Dressler,
Salazar, Mendieta,
Garibaldi, Farnum &
Bliz 2698
Knapp 3710
Churchill 5721
Croat & Folsom 34064
Vergara 32
Dwyer & Lallathin 8682
Folsom & Kauke 2639
DArcy 13652
Foster 2345
Foster 2345
Nee 7113

DATE OF
COLLECTION

ALKALOIDS

INDOLES

09/09/78
09/09/78
09/10/77
03/17/79
03/07/75
09/26/76

++
+++
++
++++
+
-

+
+
+
+
NT

03/11/85
11/15/84

++++

NT
+

02/26/85

NT

04/15/82
04/28/82
06/22/77
05/29/70

+++
+
+
-

NT
NT
NT
NT

09/24/76

NT

02/21/82
07/20/84
04/04/76
11/18/73
07/14/68
04/16/77
04/28/80
07/17/71
07/17/71
09/24/73

+
++++
++++
++++
+++

NT
NT
NT
NT
NT
NT
+
+
+
-

lf

Gentry 6051

09/18/72

++++

lf

03/24/69

++

lf
lf

Dwyer, Durkee &

Castilln 4137
Antonio 1915
Him & Gordon 13

09/18/79
02/13/81

++
+

+
+

lf

Him & Gordon 142

03/19/81

++

lf
lf

Nee 11299
DArcy 10613

04/13/74
09/10/76

++
++

+
+

lf

03/23/85

+++

NT

lf

Hampshire & Whitefoord

905
Folsom 3653

06/11/77

+++

lf

Foster 1489

01/31/70

++

NT

Alkaloid screening of Rubiaceae from Panama

165

Table 1. Continued.
TEST FOR
TRIBE SPECIES
Gonzalagunia rosea Standl.
Gonzalagunia rudis (Standl.) Standl.
Gonzalagunia veraguensis Dwyer

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Isertia haenkeana DC.

Isertia hypoleuca Benth.

Isertia laevis (Triana) B.M.Boom

Pentagonia brachyotis (Standl.) Standl.
Pentagonia gymnopoda (Standl.) Standl.
Pentagonia macrophylla Benth.
Pentagonia nana Dwyer
Pentagonia nuciformis Dwyer
Pentagonia pinnatifida Seem.
Pentagonia veraguensis Dwyer
Pentagonia wendlandii Hook.
Raritebe blumii Dwyer
Raritebe euryphyllum (Standl.) Dwyer
Raritebe palicoureoiodes Wernh.
ssp. dwyeranum Kirkbr.
Raritebe panamensis (Dwyer) Dwyer
Raritebe trifoliatum (Dwyer &
Hayden) Dwyer
Sabicea panamensis Wernh.
Sabicea villosa Willd. ex Roem. &
Schult.
Sabicea villosa Willd. ex Roem. &
Schult. var. adpressa (Wernh.) Standl.
Schradera blumii Dwyer & Hayden
Sommera donnell-smithii Standl.
GARDENIEAE
Alibertia edulis (L.C.Rich.) A.Rich. ex
DC.
Alibertia garapatica K. Schum in Mart.
Amaioua corymbosa H.B.K.

Amaioua magnicarpa Dwyer

PLANT
PART
lf
lf
lf

COLLECTION NUMBER

DATE OF
COLLECTION

ALKALOIDS

INDOLES

09/10/82
11/12/77
08/16/76

++++
++
+++

+
NT
+

10/14/72
08/01/83
03/06/82
04/13/71
01/05/83

++++
++++
++++
+++
+++

+
+
+
+
+

07/25/83

++++

04/28/80
08/08/82
03/11/74
02/72
04/15/82
05/16/75
03/24/78
04/16/82
10/25/80
07/07/85
03/27/74
04/27/73
04/22/81
11/11/80
11/11/80
02/12/86

+
+
+++
++
++
+
+
++
+
+
+++

NT
NT
NT
NT
+
+
NT
NT
NT
NT
NT
NT
+
NT
+
+

lf
lf
fr
fl
fr
fl
lf
fl
lf
fl
lf
fl
fr
lf
fr
fr

DArcy 15036
Folsom 6231
Correa, Dressler &
Garibaldi 2516
Lombardo 15
Miller & Miller 927
Whitefoord & Eddy 386
Lao & Holdridge 10
Garwood, Gibby,
Hampshire &
Humphries
Miller, Miller, Hamilton
& Kraeger 821
DArcy 13638
Hamilton 544
Nee 10528
Taymes 126
Knapp & Mallet 4617
Mori & Kallunki 6128
Hammel 2309
Knapp & Mallet 4626
Sytsma 1905
deNevers 5959
Nee & Tyson 10918
Dressler 4362
Sytsma 4094
Stevens 18275
Stevens 18275
McPherson 8421

lf
fr
fr

Stein 1033
McPherson 7912
Sytsma 3778

12/28/82
12/31/85
03/12/81

++
++
++

+
+
+

Folsom 3650
Correa, Taylor, Salazar,
Mendoza, Bliz &
Vergara 3391
Whitefoord & Eddy 157

06/11/77
01/19/80

+
+

+
+

02/12/82

02/15/84

+++

03/20/77
06/27/77

+
+++

+
+

10/15/74
06/30/71
08/14/77

+++
+++
+++

NT
NT
NT

11/18/73
07/16/66

++
++

NT
NT

10/15/73
03/11/77

++
+

NT
NT

02/14/85

+++

NT

lf, fl
fl
fr
fl
fr

lf, fl

lf
lf, fl

lf, fl
lf
lf
fr
lf
fl
lf
lf
fl
fr
lf
fr

Churchill, deNevers &

Stockwell 4594
Folsom 2200
Folsom 3976
DeLen 10
Webster 16802
Folsom, Small & Robbins
4740
Fernndez 128
Tyson, Dwyer, Blum &
Duke 4741
Rodrguez 10
Folsom, Gentry & Daley
1976
deNevers 4871

166

A. Soto-Sobenis et al.

Table 1. Continued.
TEST FOR
TRIBE SPECIES
Amaioua pedicellata Dwyer

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Borojoa panamensis Dwyer

Genipa americana L.
Posoqueria grandifolia Standl.
Posoqueria latifolia (Rudge) Roem. &
Schult.
Randia aculeata L.
Randia armata (Sw.) DC.
Randia diversiloba Standl.
Randia formosa (Jacq.) Schum.
Randia cf. karstenii Polak.

PLANT
PART
lf, fl
fr
lf
lf
fl
fl
lf
fl
sd
lf
lf
fl
lf
lf
lf

Randia lasiantha (Standl.) Standl.

Randia megalocarpa Dwyer
Randia mira Dwyer
Randia pepoformis Dwyer
Stachyarrhena dichroa Standl.

lf
lf
lf
lf
lf

Tocoyena pittieri (Standl.) Standl

fl

CINCHONEAE
Alseis blackiana Hemsl.
Calycophyllum candidissimum (Vahl) DC.

lf
lf

Cinchona pubescens Vahl

Cosmibuena skinneri (Oerst) Hemsl.
Coutarea hexandra (Jacq.) K.Schum. in
Mart.
Exostema mexicanum A.Gray
Hillia chiapensis Standl.

fl
fr
lf
lf, fl
fl
sd
lf
lf, st

Hillia chiapensis Standl. ssp.

grandifolia Dwyer
Hillia chiriquiensis Dwyer
Hillia ligulifolia Dwyer

lf, st

Hillia palmana Standl.

Hillia panamensis Standl.

lf
lf, st

Hillia tetrandra Sw.

lf, st

Joosia panamensis Dwyer

Ladenbergia aurantiaca Dwyer
Ladenbergia bullata (Wedd.) Standl.
Ladenbergia macrocarpa (Vahl) Kl. in
Hayne
Macrocnemum glabrescens (Benth.)
Wedd.

lf
lf
lf
lf
fl, pd
lf

lf
lf

DATE OF
COLLECTION

ALKALOIDS

INDOLES

McPherson 9685
Folsom 1290
Kennedy & Foster 2197
VonChong 45
Saldaa 50
Folsom 5238
Escobar 9
McPherson 9010
McPherson 8774
Antonio 2574
Nee 8123
DArcy 13639
Garwood 1001
Knapp 3237
Carasquilla & Mendoza
1339
Foster 3921
Nee 8865
Nee 10535
McPherson 9955
Lao, Holdridge &
Gentry 4
Garwood, Gibby,
Hampshire &
Humphries 292

06/25/86
01/14/77
01/19/73
12/28/72
05/24/70
09/10/77
11/24/69
04/25/86
03/10/86
11/21/79
11/18/73
04/28/80
04/29/80
01/28/82
03/29/80

+++
+++
+
++++
+++
+++
++
++++
+
+++
++
+++
++
+

NT
+
NT
NT
NT
NT
+
+
+
NT
NT
NT
+
NT
+

06/16/82
12/18/73
03/11/74
08/22/86
08/10/71

+
++
++

NT
NT
NT
NT
+

01/14/83

++

Foster 863
Wilbur, Teer & Foster
12891
Medina 17
Knapp 3249
Mori & Bolten 7410
Miller & Miller 999
Foster 1074
Mori & Kallunki 4079a
Foster 3920
Correa, Dressler &
Webster 1770
Knapp, Kress & Hammel
4161
Antonio 1534
Hampshire & Whitefoord
140
McPherson 7138
Folsom, Small &
Robbins 4785
Hampshire & Whitefoord
174
Folsom 3240
Mori & Kallunki 5501
Dressler 3505
McPherson 9800
McPherson 7025
Churchill & deNevers
4230

05/20/69
01/10/71

+
+

NT
-

09/29/73
01/29/82
07/23/75
08/03/83
07/06/69
12/26/74
06/16/82
06/09/71

++
++
++++
++
++
+++
++

+
NT
+
+
+
NT
+
NT

03/13/82

+++

NT

07/26/79
02/27/85

+
+

NT
NT

10/11/85
08/14/77

++
+

NT
NT

02/28/85

NT

05/18/77
04/07/75
05/21/68
07/24/86
03/29/85
01/11/84

+++
++
+++
++
++
+++

NT
+
+
+
NT

COLLECTION NUMBER

Alkaloid screening of Rubiaceae from Panama

167

Table 1. Continued.
TEST FOR
PLANT
PART

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TRIBE SPECIES

DATE OF
COLLECTION

ALKALOIDS

INDOLES

Foster & Kennedy 1984

Sytsma, Knapp &
Andersson 4852
Correa, Taylor, Salazar,
Mendoza, Bliz &
Vergara 3436
Antonio 4105
Mori 7001

11/15/70
05/26/81

+
-

NT
NT

01/20/80

NT

04/09/80
07/07/75

+++
+++

+
+

lf
lf
lf
lf

Hammel 6086
Folsom 2149
Sytsma & Anderson 4592
Folsom & Page 5962

02/09/79
03/19/77
05/14/81
10/20/77

++
+++
-

+
NT
+
NT

lf
lf

Gentry & Mori 13787

Folsom 4869

01/22/75
08/16/77

NT
NT

lf
lf
lf
lf

Puga 5
Correa & Dressler 467
Sytsma 1490
Hamilton & Krager 3873

10/07/72
11/16/67
10/08/80
07/13/83

NT
NT
NT
NT

Manettia coccinea (Aubl.) Willd. in L.

Manettia flexilis Brandeg.

lf
lf

Manettia reclinata Mutis in L.

lf

Ravnia triflora Oerst.

Wittmackanthus stanleyanus (Schomb.)
Kuntze
PSYCHOTRIEAE
Palicourea bella (Standl.) Dwyer
Palicourea fastigiata Benth. in H.B.K
Palicourea ochnoides Dwyer
Palicourea rigidifolia (Dwyer & Hayden)
Dwyer
Palicourea tumidonodosa Dwyer
Palicourea veraguensis Dwyer
CHIOCOCCEAE
Chiococca alba (L.) Hitchc.
Chiococca durifolia Dwyer
Chiococca jefensis Dwyer
Chiococca phaenostemon Schlecht.

lf
lf, fl

COLLECTION NUMBER

Table 2. Comparison of the classification of the species from the

genus Hoffmannia according to Dwyer (1980) and Burger and
Taylor (1993).
Dwyer1

Burger & Taylor3

Hoffmannia morii Dwyer

Hoffmannia vesiculifera
Standl.
Hoffmannia nesiota J.D. Smith

Hoffmannia nicotianifolia
(Mart. & Gal.) Williams
Hoffmannia rex-montis Dwyer
Hoffmannia woodsonii
Standley
Xerococcus congestus Oerst.

Hoffmannia pallidiflora
Standl.
Hoffmannia longipetiolata
Polak.
Hoffmannia congesta (Oerst.)
Dwyer

results were expected since this species and others from the
same genus have been extensively studied and several indole
alkaloids have been isolated (Hemingway & Phillipson, 1980;
Phillipson et al., 1982; Wagner et al., 1985). For these results,
some authors have classified this genus with Mitragyna as a
subtribe in the tribe Cinchoneae (Phillipson et al., 1982).
The results obtained with samples from the tribe Mussaendeae showed that all the genera of this tribe produce alkaloids. Genera Gonzalagunia, Isertia and Raritebe are closely
related and this is confirmed by our results, since samples

from these genera gave a positive test for indole alkaloids.

The genus Isertia has been reported in the literature as
alkaloid producer (Bruix et al., 1993; Esterl et al., 1983;
Hemingway & Phillipson, 1980), and our results showed likewise. The classification of Isertia hypoleuca as I. laevis
(Burger & Taylor, 1993) is well supported by our results. It is
interesting that all the species from the genera Coccocypselum, Sabicea, Schradera and Sommera rendered positive results for both alkaloids and indole alkaloids. According
to Burger and Taylor (1993), Coccocypselum hispidulum is in
fact C. herbaceum. On the other hand, the samples from the
genus Pentagonia gave results either slightly positive or negative, except P. macrophylla and P. nana that gave positive test
for indole alkaloids. However, the samples analyzed consisted
of different parts of the plants, which could be a reason for
the difference in our results.
In relation to the tribe Gardenieae, only one genus
afforded negative results for alkaloids, i.e., Borojoa, but it
should be mentioned that just one species, B. panamensis,
was analyzed. Genera Alibertia and Amaioua rendered positive results for alkaloids, confirming the close taxonomic
relationship between them, although Amaioua pedicellata
was the only one that seems to produce indole alkaloids. Our
results suggest that Genipa americana produces alkaloids,
however, according to the literature, its main constituents are
monoterpenes (Tallent, 1964; Ueda et al., 1991). It is interesting that caffeine has been isolated from the seeds (Freise,

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168

A. Soto-Sobenis et al.

1935). The two analyzed species of the genus Posoqueria

gave strong positive tests for alkaloids, but only P. latifolia
gave a positive test for indole alkaloids. The only chemical
constituents so far isolated from P. latifolia are monoterpenes
of iridoid nature (Chao & Svoboda, 1980). The genus Randia
also showed variations insofar as alkaloid distribution is concerned. Only R. diversiloba and R. karstenii rendered positive tests for indole alkaloids. Burger and Taylor (1993)
classified Randia karstenii as R. aculeata, Randia pepoformis as R. altiscandens, and R. formosa as Rosenbergiodendron formosum. The stem bark of the latter has yielded
monoterpenes, but no alkaloid has been isolated (Sainty et
al., 1982).
As far as the tribe Cinchoneae is concerned, all the
analyzed genera rendered positive tests for alkaloids. The
botanical relationship among the genera Cinchona, Joosia,
Macrocnemum and Ladenbergia was confirmed by our
results, since samples from the four genera gave strong
positive tests for alkaloids. Cinchona pubescens is widely
known for the production of quinine, and its leaves also yield
indole alkaloids (Zeches et al., 1980). It is interesting that
Ladenbergia aurantiaca has been recently classified as L.
macrocarpa (Burger & Taylor, 1993), since both samples
gave the same results. L. hexandra, a non-Panamanian
species, has yielded the indole alkaloid yohimbine (Holker
et al., 1964). The genera Coutarea and Exostema gave
positive tests for indole alkaloids, which confirms earlier
reports (Hemingway & Phillipson, 1980). Nevertheless, C.
hexandra is known for its coumarin constituents, but no
alkaloid has been isolated so far (Delle Monache et al., 1983,
1990; Reher et al., 1983). Similarly, Exostema mexicanum
contains coumarins and triterpenes (Mata et al., 1990),
but no alkaloid has been reported. On the other hand,
there is no report about the alkaloid presence in the genera
Alseis, Cosmibuena and Ravnia, although all three rendered
positive tests for alkaloids. Regarding Cosmibuena skinneri,
it has been recently classified as C. grandiflora (Burger &
Taylor, 1993). The results of Ravnia triflora are remarkable,
because this species afforded a strong positive test for
alkaloids and indole alkaloids. However, the classification of
this species as Hillia triflora (Burger & Taylor, 1993) is not
supported by our results, since three samples of this species
gave very different results compared with those of any
sample of Hillia spp. All the samples belonging to the
genus Hillia afforded similar results insofar as alkaloid
content is concerned. The isoquinoline alkaloids cephaeline
and emetine have been isolated from a non-Panamanian
species of this genus, Hillia illustris (Willaman & Schubert,
1961). Burger and Taylor (1993) classified Hillia ligulifolia
and H. chiriquiensis as Cosmibuena valerii, Hillia palmana
and H. tetrandra as H. maxonii and H. chiapensis as H.
panamensis. Genus Manettia showed variation among the
analysed species. M. coccinea and M. reclinata gave slight
positive results, which support the classification of M. coccinea as M. reclinata (Burger & Taylor, 1993). This genus
has previously been reported as an alkaloid producer in the

literature (Hemingway & Phillipson, 1980; Willaman &

Schubert, 1961).
Genus Palicourea (tribe Psychotrieae) has been reported
as an alkaloid producer (Hemingway & Phillipson, 1980;
Morita et al., 1989; Nakano & Martin, 1976; Stuart & WooMing, 1974; Woo-Ming & Stuart, 1975), however, the
analyses of six species showed that alkaloid distribution was
uneven in the genus. The related species, P. bella and P.
ochnoides, afforded strong positive tests, whereas the others
gave either slight positive or negative results. Palicourea veraguensis has been recently classified as P. lasiorrhachis
(Burger & Taylor, 1993).
In the tribe Chiococceae, the four species of the genus
Chiococca analyzed gave negative results for alkaloids.
These findings are supported by the literature survey, which
shows for Chiococca alba the production of coumarins,
triterpenes and other compounds, but no alkaloids
(Bhattacharyya & Cunha, 1992; El-Hafiz et al., 1991).
Our results do not support the classification of Chiococca
jefensis as Elaeagia nitidifolia (Burger & Taylor, 1993), since
both samples gave completely different results.

Acknowledgement
We are grateful to the International Foundation for Science
(IFS) for financing the research project F-0991; Dr. Mahabir
Gupta, of the Pharmacognosy Research Centre (CIFLORPAN) for allowing us the use of some laboratory facilities;
the University of Illinois at Chicago for allowing Dr. Guptas
access to NAPRALERT; and Prof. Mireya Correa, Director
of the Herbarium of the University of Panama for providing
the plant material.

References
Bhattacharyya J, Cunha EVL (1992): A triterpenoid from the
root-bark of Chiococca alba. Phytochemistry 31: 2546
2547.
Borges del Castillo J, Manresa-Ferrero MT, Rodriguez-Luis F
(1981): Oxindole alkaloids from Hamelia patens Jacq.
In: Atanasova B, ed., Proc. 1st Int. Conf. Chem. Biotechnol.
Biol. Act. Nat. Prod., Bulgarian Acad. Sci. Sofia 3: 70
73.
Borges del Castillo J, Manresa-Ferrero MT, Martin-Ramon JL,
Rodriguez-Luis F, Vazquez-Bueno P (1982): Salvadorian
flora. 5. Study of alkaloids from Hamelia patens Jacq. An
Quim Ser C 78: 180183.
Bruix M, Rumbero A, Vazquez P (1993): Apodihydrocinchonamine, an indole alkaloid from Isertia haenkeana.
Phytochemistry 33: 12571261.
Burger W, Taylor CM (1993): Family #202 Rubiaceae. In:
Burger W, ed., Flora Costaricensis. Fieldiana. Botany 33.
Castro O, Lopez UJ (1986): Harman, the principal alkaloid in
roots of Simira maxonii Standley (Rubiaceae). Ing Cienc
Quim 10: 5657.

Pharmaceutical Biology Downloaded from informahealthcare.com by The University of Manchester on 12/08/14

For personal use only.

Alkaloid screening of Rubiaceae from Panama

Chao PDL, Svoboda GH (1980): Two new iridoids from Posoqueria latifolia. J Nat Prod 43: 571576.
Chaudhuri PK, Thakur RS (1991): Hamelia patens: a new
source of ephedrine. Planta Med 57: 199.
Delle Monache G, Botta B, Neto AS, Alves de Lima R (1983):
4-arylcoumarins from Coutarea hexandra. Phytochemistry
22: 16571658.
Delle Monache G, Botta B, Vinciguerra V, Moura Pinheiro R
(1990): 4-Arylcoumarins from Coutarea hexandra. Phytochemistry 29: 39843986.
Dwyer JD (1980): Family Rubiaceae. Part I. In: Woodson RE,
Schery RW, eds., Flora of Panama. Ann Missouri Bot
Garden 67: 1256.
El-Hafiz MAA, Weniger B, Quirion JC, Anton R (1991): Ketoalcohols, lignans and coumarins from Chiococca alba. Phytochemistry 30: 20292031.
Esterl A, Gab S, Bieniek D (1983): On the constituents of Isertia
hypoleuca. Planta Med 49: 244245.
Freise FW (1935): The ocurrence of caffeine in Brazilian medicinal plants. Pharm Zentralhalle Dtschl 76: 704706.
Gran L (1973): Oxcytocic principles of Oldenlandia affinis.
Lloydia 36: 174178.
Hasbun CP, Calderon M, Castro O, Gacs-Baitz E, Delle
Monache G, Delle Monache F (1989): Maxonine, a novel
alkaloid from Simira maxonii. Tetrahedron Lett 30:
61996202.
Hegnauer R (1973): Chemotaxonomie der Pflanzen. Volume 6.
Basel, Leiden, Birkhuser Verlag, pp. 130, 149.
Hemingway SR, Phillipson JD (1980): Alkaloids in the Rubiaceae. In: Phillipson JD, Zenk MH, eds., Indole and Biogenetically Related Alkaloids, London, Academic Press,
p. 63.
Holker JSE, Ross WJ, Whalley WB, Raffauf RF (1964): The
Alkaloids of Ladenbergia hexandra. Phytochemistry 3:
361362.
Khastgir HN, Sengupta SK, Sengupta P (1960): The constituents
of the Indian medicinal plant Oldenlandia corymbosa.
J Amer Pharm Assoc Sci Ed 49: 562563.
Koike K, Cordell GA, Farnsworth NR, Freer AA, Gilmore CJ,
Sim GA (1980): Potential anticancer agents. XII. New cytotoxic diterpenes from Rondeletia panamensis (Rubiaceae).
Tetrahedron 36: 11671172.
Ma WW, Anderson JE, McKenzie AT, Byrn SR, McLaughlin JL
(1990): Tubulosine, an antitumor constituent of Pogonopus
speciosus. J Nat Prod 53: 10091014.
Mata R, Albor C, Pereda-Miranda R, McLaughlin JL (1990):
Cytotoxic constituents of Exostema mexicanum. Planta
Med 56: 241.

169

Morita H, Ichihara Y, Takeya K, Watanabe K, Itokawa H,

Motidome M (1989): A new indole alkaloid glycoside from
the leaves of Palicourea marcgravii. Planta Med 55:
288289.
Nakano T, Martn A (1976): Studies on the alkaloids of Palicourea fendleri. Planta Med 30: 186188.
Otsuka H, Yoshimura K, Yamasaki K, Cantoria MC (1991): Isolation of 10-O-acyl iridoid glucosides from a Philippine
medicinal plant, Oldenlandia corymbosa L. (Rubiaceae).
Chem Pharm Bull 39: 29492952.
Phillipson JD (1982): Chemical investigations of herbarium
material for alkaloids. Phytochemistry 21: 24412456.
Phillipson JD, Hemingway SR (1975): Chromatographic and
spectroscopic methods for the identification of alkaloids
from herbarium samples of the genus Uncaria. J Chromatog 105: 163178.
Phillipson JD, Hemingway SR, Ridsdale CE (1982): The chemotaxonomic significance of alkaloids in the Naucleeae s. l.
(Rubiaceae). J Nat Prod 45: 145162.
Purushothaman KK, Sarada A (1981): Structure of auricularine,
a bis-indole alkaloid from Hedyotis auricularia. Phytochemistry 20: 351352.
Reher G, Kraus LJ, Sinnwell V, Konig WA (1983): A new
flavonoid from Coutarea hexandra (Rubiaceae). Phytochemistry 22: 15241525.
Sainty D, Delaveau P, Bailleul F, Moretti C (1982): 10-Caffeoyl
deacetyldaphylloside, a new iridoid from Randia formosa.
J Nat Prod 45: 676678.
Stuart KL, Woo-Ming RB (1974): Palicourea alkaloids: The
structure of palinine. Tetrahedron Lett 1974: 3853.
Tallent WH (1964): Two new antibiotic cyclopentanoid
monoterpenes of plant origin. Tetrahedron 20: 1781
1787.
Ueda S, Iwahashi Y, Tokuda H (1991): Production of antitumor
promoting iridoid glucosides in Genipa americana and its
cell cultures. J Nat Prod 54: 16771680.
Wagner H, Kreutzkamp B, Jurcic K (1985): Alkaloids of
Uncaria tomentosa and their phagocytosis enhancement
activity. Planta Med 51: 419423.
Willaman JJ, Schubert BG (1961): Alkaloid-bearing plants
and their contained alkaloids. ARS, USDA, Tech. Bull.
1234, Supt. Documents, Govt. Print. Off., Washington,
DC.
Woo-Ming RB, Stuart KL (1975): Calycanthine from Palicourea
albina. Phytochemistry 14: 2529.
Zeches M, Richard B, Thepenier P, Le Men-Olivier L, Le Men
J (1980): Alcalides des feuilles du Cinchona ledgeriana.
Phytochemistry 19: 24512454.