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molecules
Review
Allamanda cathartica: A Review
of the Phytochemistry, Pharmacology,
Toxicology, and Biotechnology
Vera L. Petricevich and Rodolfo Abarca-Vargas *
Facultad de Medicina de la Universidad Autónoma del Estado de Morelos (UAEM), Calle, Leñeros,
esquina Iztaccíhuatl s/n. Col. Volcanes, Cuernavaca, C.P. Morelos 62350, Mexico; vera.petricevich@uaem.mx
*Correspondence: rodolfo.abarca@uaem.mx; Tel.: +52-777-361-2155
Academic Editor: Ericsson Coy-Barrera
Received: 20 February 2019; Accepted: 23 March 2019; Published: 29 March 2019
Abstract:
In this work, we explore the current knowledge about the phytochemistry and
in vitro
and
in vivo
evaluations of the extracts and, where appropriate, the main active components
characterized and isolated from the Allamanda cathartica. Of the 15 Allamanda species, most
phytochemical, pharmacological, and toxicological studies have focused on A. cathartica. These plants
are used for the treatment of various health disorders. Numerous phytochemical investigations
of plants from the A. cathartica have shown the presence of hydrocarbons, alcohols, esters, ethers,
aldehydes, ketones, fatty acids, phospholipids, volatile compounds, phenolic compounds, flavonoids,
alkaloids, steroids, terpenes, lactones, and carbohydrates. Various studies have confirmed that
extracts and active substances isolated from the A. cathartica have multiple pharmacological activities.
The species A. cathartica has emerged as a source of traditional medicine used for human health.
Further studies on the phytochemical, pharmacological, and toxicological properties and their
mechanisms of action, safety, and efficacy in the species of A. cathartica is recommended.
Keywords: Allamanda cathartica; phytochemistry; pharmacology; toxicology and biotechnology
1. Introduction
The plant Allamanda is a very widespread group throughout the world. It belongs to the family
Apocynaceae and, according to the “The Plant List,” contains approximately 15 species (A. augustifolia,
A. blanchetti,A. caccicola,A. cathartica,A. doniana,A. laevis,A. martii,A nobilis,A. oenotherifolia,
A. polyantha,A. puberula,A. schottii,A. setulosa,A. thevetifolia, and A. weberbaueri) [
1
]. The objective of this
work is to present complete information about the current research on the distribution, phytochemistry,
pharmacology, toxicity, and biotechnology of Allamanda cathartica; to identify its therapeutic potential;
and to direct future research opportunities. The most relevant data were searched using the keyword
“Allamanda cathartica” in “Google Scholar”, “PubMed”, “ScienceDirect”, “Scopus”, “Taylor & Francis”,
“Web of Science”, and “Wiley”. The taxonomy was validated using the “The Plant List”.
2. Ethnobotany
2.1. Botanical Characterization
The genus Allamanda is endemic to South America [
2
]. The genus is named after the Swiss
botanist Jean Frédéric-François Louis Allamand, who collected seeds in Suriname and sent them to
Carlos Linnaeus to be named in 1771 [
3
]. A. cathartica plants are robust shrubs growing up to 6 m tall.
The leaves are elliptical to obovate, opposite, or in whorls. The flowers are yellow and trumpet-shaped,
with corolla tubes. The flowers are similar in size to the leaves. The fruits are capsules with spins,
Molecules 2019,24, 1238; doi:10.3390/molecules24071238 www.mdpi.com/journal/molecules
Molecules 2019,24, 1238 2 of 22
and the seeds are compressed and winged. The shrubs, with their beautiful yellow flowers, are popular
ornamentals [
4
]. The species flowers grow all year round, and fruits grow from April to July and in
October. In botanical texts, A. cathartica is reported to have a wide global distribution in warm climates
(Figure 1) [
2
]. Based on these data, a more exhaustive analysis of the scientific literature was performed.
Molecules 2019, 24, x FOR PEER REVIEW 2 of 21
The leaves are elliptical to obovate, opposite, or in whorls. The flowers are yellow and trumpet-
shaped, with corolla tubes. The flowers are similar in size to the leaves. The fruits are capsules with
spins, and the seeds are compressed and winged. The shrubs, with their beautiful yellow flowers, are
popular ornamentals [4]. The species flowers grow all year round, and fruits grow from April to July
and in October. In botanical texts, A. cathartica is reported to have a wide global distribution in warm
climates (Figure 1) [2]. Based on these data, a more exhaustive analysis of the scientific literature was
performed.
Figure 1. Allamanda cathartica.
2.2. Distribution
A. cathartica plants are distributed in tropical and subtropical areas of many countries, including
the United States, México, Belize, Honduras, Nicaragua, Costa Rica, Panama, Venezuela, Bolivia,
Ecuador, Guyana, French Guyana, Paraguay, Peru [2], Guatemala [5], El Salvador [6], Puerto Rico [7],
Trinidad and Tobago [8], Surinam [9], Cuba [10], Martinique [11], Colombia [12], Brazil [3], Hawaii
[13], India [14], the Andaman islands [15], Bangladesh [16], Pakistan [17], Malaysia [18], Indonesia
[19], The Philippines [20], Thailand [21], Singapore [22], Hong Kong [14], Myanmar [11], Nepal, Sri
Lanka [23], China [24], Australia [25], Kuwait [26], Ghana [18], the Republic of Mauritius [27],
Cameroon, Madagascar [2], Nigeria [28] Zimbabwe [29], and France [20].
2.3. Synonyms
Synonyms of Allamanda cathartica include Echites verticillata Sessé and Moç, Orelia grandiflora
Aublet, Allamanda grandiflora (Aublet) Poiret in Lam, and Allamanda hendersonii W. Bull ex Dombrain
[30], as well as Allamanda schotti (Pohl) [31]. In the various countries where Allamanda is found, other
popular names have been attributed to it.
The following are synonyms: (in Australia) Allamanda [25]; (in Bangladesh) Allamanda [32],
Allokananda [23], and Fok Kaia [33]; (in Brazil) Buiussu, Carolina [34], Alamanda, Cipó-de-leite,
Dedal-de-dama, Alamanda-amarela, Alamanda-de-flor-grande, Guissú, Quatro-patacas-amarelas
[35], Golden trumpet, Yellow Bell, and Buttercup flower [30]; (in Cuba) Flor de barbero, Barbero loco,
Flor de mantequilla, Jazmín de la tierra [10], and Jazmín de Cuba [36]; (in El Salvador) San José [6,37];
(in France) Jasmin dÁmarilla [20]; (in French Guiana) Orélie de la Guyana [20]; (in Guatemala)
Amanda, Butter cup, and Campana [5]; (in Hawaii) Lani-ali’I and Allamanda [13]; (in India)
Jaharisontakka, Pilikaner, Pivikanher [20], Almanda, golden trump vine, [38], Haldhia phool [39],
Ghonta phool [40], and Golden trumpet [41]; (in Indonesia) Bunga Terompet [16]; (in Malaysia)
Jamaican sunset [42]; (in Mexico) Berta, Cuernos de chivo, Chicliyo [2], and San José [6,37]; (in
Figure 1. Allamanda cathartica.
2.2. Distribution
A. cathartica plants are distributed in tropical and subtropical areas of many countries, including
the United States, México, Belize, Honduras, Nicaragua, Costa Rica, Panama, Venezuela, Bolivia,
Ecuador, Guyana, French Guyana, Paraguay, Peru [
2
], Guatemala [
5
], El Salvador [
6
], Puerto Rico [
7
],
Trinidad and Tobago [
8
], Surinam [
9
], Cuba [
10
], Martinique [
11
], Colombia [
12
], Brazil [
3
], Hawaii [
13
],
India [
14
], the Andaman islands [
15
], Bangladesh [
16
], Pakistan [
17
], Malaysia [
18
], Indonesia [
19
],
The Philippines [
20
], Thailand [
21
], Singapore [
22
], Hong Kong [
14
], Myanmar [
11
], Nepal, Sri Lanka [
23
],
China [
24
], Australia [
25
], Kuwait [
26
], Ghana [
18
], the Republic of Mauritius [
27
], Cameroon,
Madagascar [2], Nigeria [28] Zimbabwe [29], and France [20].
2.3. Synonyms
Synonyms of Allamanda cathartica include Echites verticillata Sesséand Moç, Orelia grandiflora
Aublet, Allamanda grandiflora (Aublet) Poiret in Lam, and Allamanda hendersonii W. Bull ex
Dombrain [
30
], as well as Allamanda schotti (Pohl) [
31
]. In the various countries where Allamanda
is found, other popular names have been attributed to it.
The following are synonyms: (in Australia) Allamanda [
25
]; (in Bangladesh) Allamanda [
32
],
Allokananda [
23
], and Fok Kaia [
33
]; (in Brazil) Buiussu, Carolina [
34
], Alamanda, Cipó-de-leite,
Dedal-de-dama, Alamanda-amarela, Alamanda-de-flor-grande, Guissú, Quatro-patacas-amarelas [
35
],
Golden trumpet, Yellow Bell, and Buttercup flower [
30
]; (in Cuba) Flor de barbero, Barbero loco,
Flor de mantequilla, Jazmín de la tierra [
10
], and Jazmín de Cuba [
36
]; (in El Salvador) San José[
6
,
37
];
(in France) Jasmin dÁmarilla [
20
]; (in French Guiana) Orélie de la Guyana [
20
]; (in Guatemala) Amanda,
Butter cup, and Campana [
5
]; (in Hawaii) Lani-ali’I and Allamanda [
13
]; (in India) Jaharisontakka,
Pilikaner, Pivikanher [
20
], Almanda, golden trump vine, [
38
], Haldhia phool [
39
], Ghonta phool [
40
],
and Golden trumpet [
41
]; (in Indonesia) Bunga Terompet [
16
]; (in Malaysia) Jamaican sunset [
42
];
(in Mexico) Berta, Cuernos de chivo, Chicliyo [
2
], and San José[
6
,
37
]; (in Nigeria) Allamonda, Yellow
allamanda, Golden trumpet [
43
], Nkutu [
44
], and Ako-dodo [
45
]; and (in Thailand) Golden trumpet [
21
].
Molecules 2019,24, 1238 3 of 22
2.4. Traditional Medical Use
In traditional medicine, A. cathartica is indicated for various treatments in many parts of
the world: as an antifungal (United States, Caribe [
3
], and Bangladesh [
23
]), antiviral (United States
and Caribbean [
3
]), anticancer (Malaysia [
46
]), and cathartic (India [
20
] and Bangladesh [
23
]) or to
treat colic (India [
47
]) or diabetes (India [
48
]). It is also used as a diuretic and an emetic (India [
38
]);
for the treatment of fever (India [
39
] and Brazil [
34
]), hydragogue ascites (India [
20
] and Bangladesh [
23
]),
hypertension (the Philippines [
49
] and Bangladesh [
23
]); to improve blood circulation (Indonesia [
16
]);
and to reduce inflammation (Nigeria [
43
]). It is also used to treat jaundice (Suriname [
8
], Brazil [
34
],
and Malaysia [
46
]), laxative (India [
38
], Suriname [
8
], and Nigeria [
44
]), and Malaria (Nigeria [
45
],
Suriname, [
8
], Philipphines [
20
], Malaysia [
46
], and Brazil [
34
]). The milky sap is used for lead colic
(Mexico and El Salvador [
36
]), parasitosis (Brazil [
34
]), rheumatism (Bangladesh [
33
]), scabies and lice
elimination (Brazil [
34
]), snake bites (Bangladesh [
23
], Colombia [
12
], and India [
20
]), and splenomegaly
(Suriname [
8
] and Brazil [
34
]). The plant parts used most frequently, in decreasing order, are the leaves,
stem bark, flowers, roots, stem, sap, seeds, and branches.
3. Phytochemistry
The chemical constituents of A. cathartica have been extensively studied since 1954 [
14
].
Preliminary chemical studies showed the presence of alkaloids [
13
], anthraquinones [
50
],
anthocyanins [
51
], carbohydrates [
52
], carotenoids [
21
], coumarin [
53
], flavonoids [
54
], glycosides [
28
],
hydrocarbon [
52
], lignin [
51
], lipids [
50
,
52
], phenolic compounds [
54
], quinones [
53
], saponins [
28
,
54
],
steroids [
54
], tannins [
28
,
54
], and terpenes [
53
,
54
] from various extracts, mainly leaves, flowers, stems,
stem bark, roots, and shoots.
Only these groups of chemical compounds have been isolated and identified, and no
anthraquinones, anthocyanins, coumarin, quinones, or lignins have been found. The Marvin program
was used to draw the structures of organic chemical compounds [55].
In an analysis of the inorganic composition by atomic absorption spectrophotometry from flowers,
the following elements were detected at the following concentrations: Fe (12.21
±
0.038
µ
g/g),
Mn (1.338
±
0.049
µ
g/g), Ni (0.593
±
0.014
µ
g/g), Cu (0.348
±
0.006
µ
g/g), Cr (0.181
±
0.032
µ
g/g),
Pb (0.104 ±0.024 µg/g), and Co (0.089 ±0.010 µg/g) [56].
3.1. Hydrocarbons
The presence of 3 hydrocarbons has been confirmed in A. cathartica flowers (Table 1and Figure 2).
Table 1. The hydrocarbons from A. cathartica.
No. Compound’s Name Parts Used Reference
(1)n-Heneicosane Flowers [10]
(2)n-Tricosane Flowers [10]
(3)n-Pentacosane Flowers [10]
Molecules 2019, 24, x FOR PEER REVIEW 3 of 21
Nigeria) Allamonda, Yellow allamanda, Golden trumpet [43], Nkutu [44], and Ako-dodo [45]; and
(in Thailand) Golden trumpet [21].
2.4. Traditional Medical Use
In traditional medicine, A. cathartica is indicated for various treatments in many parts of the
world: as an antifungal (United States, Caribe [3], and Bangladesh [23]), antiviral (United States and
Caribbean [3]), anticancer (Malaysia [46]), and cathartic (India [20] and Bangladesh [23]) or to treat
colic (India [47]) or diabetes (India [48]). It is also used as a diuretic and an emetic (India [38]); for
the treatment of fever (India [39] and Brazil [34]), hydragogue ascites (India [20] and Bangladesh [23]),
hypertension (the Philippines [49] and Bangladesh [23]); to improve blood circulation (Indonesia
[16]); and to reduce inflammation (Nigeria [43]). It is also used to treat jaundice (Suriname [8], Brazil
[34], and Malaysia [46]), laxative (India [38], Suriname [8], and Nigeria [44]), and Malaria (Nigeria
[45], Suriname, [8], Philipphines [20], Malaysia [46], and Brazil [34]). The milky sap is used for lead
colic (Mexico and El Salvador [36]), parasitosis (Brazil [34]), rheumatism (Bangladesh [33]), scabies
and lice elimination (Brazil [34]), snake bites (Bangladesh [23], Colombia [12], and India [20]), and
splenomegaly (Suriname [8] and Brazil [34]). The plant parts used most frequently, in decreasing
order, are the leaves, stem bark, flowers, roots, stem, sap, seeds, and branches.
3. Phytochemistry
The chemical constituents of A. cathartica have been extensively studied since 1954 [14].
Preliminary chemical studies showed the presence of alkaloids [13], anthraquinones [50],
anthocyanins [51], carbohydrates [52], carotenoids [21], coumarin [53], flavonoids [54], glycosides
[28], hydrocarbon [52], lignin [51], lipids [50,52], phenolic compounds [54], quinones [53], saponins
[28,54] , steroids [54], tannins [28,54], and terpenes [53,54] from various extracts, mainly leaves,
flowers, stems, stem bark, roots, and shoots.
Only these groups of chemical compounds have been isolated and identified, and no
anthraquinones, anthocyanins, coumarin, quinones, or lignins have been found. The Marvin program
was used to draw the structures of organic chemical compounds [55].
In an analysis of the inorganic composition by atomic absorption spectrophotometry from
flowers, the following elements were detected at the following concentrations: Fe (12.21 ± 0.038 µg/g),
Mn (1.338 ± 0.049 µg/g), Ni (0.593 ± 0.014 µg/g), Cu (0.348 ± 0.006 µg/g), Cr (0.181 ± 0.032 µg/g), Pb
(0.104 ± 0.024 µg/g), and Co (0.089 ± 0.010 µg/g) [56].
3.1. Hydrocarbons
The presence of 3 hydrocarbons has been confirmed in A. cathartica flowers (Table 1 and Figure
2).
Table 1. The hydrocarbons from A. cathartica.
No. Compound’s Name Parts Used Reference
(1) n-Heneicosane Flowers [10]
(2) n-Tricosane Flowers [10]
(3) n-Pentacosane Flowers [10]
(1) (2)
(3)
Figure 2. The structures of the hydrocarbons from A. cathartica.
3.2. Alcohol, Ester, Ether, Aldehyde, and Ketone
Seven alcohol compounds were identified, as well as 9 esters, 1 ether, 6 aldehydes, and 1 ketone
in various extracts of flowers, leaves, and stems (Table 2 and Figure 3).
Figure 2. The structures of the hydrocarbons from A. cathartica.
3.2. Alcohol, Ester, Ether, Aldehyde, and Ketone
Seven alcohol compounds were identified, as well as 9 esters, 1 ether, 6 aldehydes, and 1 ketone
in various extracts of flowers, leaves, and stems (Table 2and Figure 3).
Molecules 2019,24, 1238 4 of 22
Table 2. The alcohols, esters, ethers, aldehydes, and ketones from A. cathartica.
No. Compound’s Name Parts Used Reference
(4) 1-Hexanol Flowers [10]
(5) 1-Hexadecanol Flowers [10]
(6) Glycerin Leaves and stem [57]
(7) (Z)-3-Hexenol Flowers [10]
(8) Nerol Flowers [35]
(9) Geraniol Flowers [35]
(10) (E)-Nerolidol Flowers [35]
(11) Hexanoic acid, ethyl ester Leaves and stem [57]
(12) Octanoic acid, ethyl ester Leaves and stem [57]
(13) Decanoic acid, ethyl ester Leaves and stem [57]
(14) Hexadecanoic acid, ethyl ester Leaves and stem [57]
(15) Octadecanoic acid, ethyl ester Leaves and stem [57]
(16) Nonadecanoic acid, ethyl ester Leaves [57]
(17) 9,12-Octadecadienoic acid, ethyl ester Leaves and stem [57]
(18)
9,12,15-octadecatrienoic acid, ethyl ester, (Z,Z,Z)-
Leaves and stem [43,57]
(19) Methyl linoleate Flowers [10]
(20) Propane, 1,1,3-triethoxy- Leaves and stem [57]
(21) Hexanal Flowers [10]
(22) Heptanal Flowers [10]
(23) Octanal Flowers [10]
(24) (E)-2-Heptenal Flowers [10]
(25)Cis,cis,cis-7,10,13-hexadecatrienal Leaves [57]
(26) 2-furancarboxaldehyde, 5-(hydroxymethyl)- Stem [57]
(27) 6,10,14-Trimethyl-2-pentadecanone Flowers [10]
Molecules 2019, 24, x FOR PEER REVIEW 4 of 21
Table 2. The alcohols, esters, ethers, aldehydes, and ketones from A. cathartica.
No. Compound’s Name Parts Used Reference
(4) 1-Hexanol Flowers [10]
(5) 1-Hexadecanol Flowers [10]
(6) Glycerin Leaves and stem [57]
(7) (Z)-3-Hexenol Flowers [10]
(8) Nerol Flowers [35]
(9) Geraniol Flowers [35]
(10) (E)-Nerolidol Flowers [35]
(11) Hexanoic acid, ethyl ester Leaves and stem [57]
(12) Octanoic acid, ethyl ester Leaves and stem [57]
(13) Decanoic acid, ethyl ester Leaves and stem [57]
(14) Hexadecanoic acid, ethyl ester Leaves and stem [57]
(15) Octadecanoic acid, ethyl ester Leaves and stem [57]
(16) Nonadecanoic acid, ethyl ester Leaves [57]
(17) 9,12-Octadecadienoic acid, ethyl ester Leaves and stem [57]
(18) 9,12,15-octadecatrienoic acid, ethyl ester, (Z,Z,Z)- Leaves and stem [43,57]
(19) Methyl linoleate Flowers [10]
(20) Propane, 1,1,3-triethoxy- Leaves and stem [57]
(21) Hexanal Flowers [10]
(22) Heptanal Flowers [10]
(23) Octanal Flowers [10]
(24) (E)-2-Heptenal Flowers [10]
(25) Cis,cis,cis-7,10,13-hexadecatrienal Leaves [57]
(26) 2-furancarboxaldehyde, 5-(hydroxymethyl)- Stem [57]
(27) 6,10,14-Trimethyl-2-pentadecanone Flowers [10]
(4) (5) (6) (7) (8) (9)
(10) (11) (12) (13)
(14) (15) (16)
(17) (18) (19)
(20) (21) (22) (23) (24)
(25) (26) (27)
Figure 3. The structures of the alcohols, esters, ethers, aldehydes, and ketones from A. cathartica.
3.3. Fatty Acids and Phospholipids
A fatty acid composition analysis resulted in the identification of 37 compounds and a
compound of very unusual structure (59). Two phospholipids were also identified. The flowers,
leaves, and stems were used for the isolation of these compounds (Table 3 and Figure 4).
Figure 3. The structures of the alcohols, esters, ethers, aldehydes, and ketones from A. cathartica.
3.3. Fatty Acids and Phospholipids
A fatty acid composition analysis resulted in the identification of 37 compounds and a compound
of very unusual structure (
59
). Two phospholipids were also identified. The flowers, leaves, and stems
were used for the isolation of these compounds (Table 3and Figure 4).
Molecules 2019,24, 1238 5 of 22
Table 3. The fatty acids and phospholipids from A. cathartica.
No. Compound’s Name Parts Used Reference
(28) Dodecanoic acid Flowers, leaves, and stem [52,57]
(29) Tetradecanoic acid Flowers, leaves, and stem [7,52,57]
(30) Pentadecanoic acid Leaves and flowers [7,57]
(31) Hexadecanoic acid Flowers, leaves, and stem [7,43,52,57]
(32) Heptadecanoic acid Flowers [7]
(33) Octadecanoic acid Flowers and leaves [7,52]
(34) Nonadecanoic acid Flowers [7]
(35) Eicosanoic acid Flowers and leaves [7,52]
(36) Heneicosanoic acid Flowers [7]
(37) Docosanoic acid Flowers [7]
(38) Tetracosanoic acid Flowers [7]
(39) Pentacosanoic acid Flowers [7]
(40) Hexacosanoic acid Flowers [7]
(41) 2-Hydroxyhexadecanoic acid Flowers [7]
(42) 2-Hydroxyoctadecanoic acid Flowers [7]
(43) 2-Hydroxyeicosanoic acid Flowers [7]
(44) 2-Hydroxydocosanoic acid Flowers [7]
(45) 2-Hydroxytricosanoic acid Flowers [7]
(46) 2-Hydroxytetracosanoic acid Flowers [7]
(47) 2-Hydroxydocosenoic acid Flowers [7]
(48) 2-Hydroxytetracosenoic acid Flowers [7]
(49) 7-Eicosenoic acid Flowers [7]
(50) 9-Hexadecenoic acid Flowers [7]
(51) 9-Octadecenoic acid Flowers, leaves, and stem [7,52,57]
(52) 9-Nonadecenoic acid Flowers [7]
(53) 11-Octadecenoic acid Flowers [7]
(54) 11-Eicosenoic acid Flowers [7]
(55) 13-Eicosenoic acid Flowers [7]
(56) 13-Docosenoic acid Flowers [7]
(57) 15-Docosenoic acid Flowers [7]
(58) 5,9-Nonadecadienoic acid Flowers [7]
(59) 17-Methyl-5,9-octadecadienoic acid * Flowers [7]
(60) 11,14-Eicosadienoic acid Flowers [7]
(61) 9,12-Octadecadienoic acid Flowers and leaves [7,52]
(62) 9,12-Octadecadienoic acid (Z,Z)- Stem [57]
(63) 9,12,15-Octadecatrienoic acid Flowers [7]
(64) 9,12,15-Octadecatrienoic acid (Z,Z,Z)- Leaves and Stem [44,57]
(65) Phosphatidylinositol Flowers [7]
(66) Phosphatidycholine Flowers [7]
Note: * Not reported in nature.
Molecules 2019,24, 1238 6 of 22
Molecules 2019, 24, x FOR PEER REVIEW 6 of 21
(28) (29) (30)
(31) (32) (33)
(34) (35)
(36) (37)
(38) (39)
(40) (41)
(42) (43)
(44) (45)
(46) (47)
(48) (49)
(50) (51)
(52) (53) (54)
(55) (56)
(57) (58)
(59) (60) (61)
(62) (63) (64)
(65) (66)
Figure 4. The structures of the fatty acids and phospholipids from A. cathartica.
3.4. Volatile Compounds
A total of 43 volatile compounds have also been identified, mostly in flowers and leaves (Table
4 and Figure 5).
Figure 4. The structures of the fatty acids and phospholipids from A. cathartica.
3.4. Volatile Compounds
A total of 43 volatile compounds have also been identified, mostly in flowers and leaves (Table 4
and Figure 5).
Molecules 2019,24, 1238 7 of 22
Table 4. The volatile compounds from A. cathartica.
No. Compound’s Name Parts Used Reference
(67) (E)-β-ocineme Flowers [10]
(68) (E)-β-Farnesene Flowers [10]
(69) (E,E)-α-Farnesene Flowers [10]
(70) (Z)-β-ocimene Flowers [10]
(71) (E,E)-Geranyl linaool Flowers [10]
(72) (Z,Z)-Farnesol Flowers [10]
(73) 1-Octen-3-ol Flowers [10]
(74) 2-Butooxyethanol Flowers [10]
(75) 1,8-cineole Flowers [10]
(76) 2-Phenylethanol Flowers [10]
(77) Benzaldehyde Flowers [10]
(78) Benzoic acid, 2-hydroxy-, methyl ester Leaves [57]
(79) Benzyl isothiocyanate Flowers [35]
(80) Phenylacetonitrile Flowers [35]
(81) Bicyclogermacrene Flowers [35]
(82) Trans-Linalool oxide Flowers [35]
(83) Cis-sabinehydrate Flowers [10]
(84) Germacrene D Flowers [35]
(85) Indole Flowers [10]
(86) Linalool Flowers [35]
(87) Myrcene Flowers [10]
(88) Limonene Flowers [10]
(89)γ-Terpinene Flowers [10]
(90)α-Terpinene Flowers [10]
(91)p-cyneme Flowers [10]
(92) Terpinolene Flowers [10]
(93)α-Terpineol Flowers [10,35]
(94) Terpinen-4-ol Flowers [10]
(95) 3,7,11,15-tetramethyl-2-hexadecen-1-ol N.R. [58]
(96) Cumin alcohol Flowers [35]
(97) Phenylacetaldehyde Flowers [10,35]
(98)α-Thujene Flowers [10]
(99)α-Copaene Flowers [35]
(
100
)
α-Cubebene Flowers [35]
(
101
)
β-Cubebene Flowers [35]
(
102
)
δ-Cadinene Flowers [35]
(
103
)
α-Humulene Flowers [35]
(
104
)
α-Pinene Flowers [10]
(
105
)
β-Pinene Flowers [10]
(
106
)
Camphene Flowers [10]
(
107
)
Isoborneol Flowers [10]
(
108
)
β-Caryophyllene Flowers [10,35]
(
109
)
β-Elemene Flowers [35]
Note: N.R. = Not reported.
Molecules 2019,24, 1238 8 of 22
Molecules 2019, 24, x FOR PEER REVIEW 8 of 21
(67) (68) (69) (70) (71)
(72) (73) (74) (75) (76) (77) (78)
(79) (80) (81) (82) (83) (84) (85)
(86) (87) (88) (89) (90) (91) (92) (93) (94) (95)
(96)
OH
(97) (98) (99) (100) (101) (102) (103)
(104) (105) (106) (107) (108) (109)
Figure 5. The structures of the volatile compounds from A. cathartica.
3.5. Phenolic Compounds and Flavonoids
From the flowers and stems, 5 phenolic compounds and 6 flavonoids have been identified (Table
5 and Figure 6).
Table 5. The phenolic compounds and flavonoids from A. cathartica.
No. Compound’s Name Parts Used Reference
(110) Protocatechuic acid Flowers [24]
(111) Gallic acid Flowers [24]
(112) 1-(3-(4-Allyl-2,6-dimethoxyphenoxy)-4-methoxyphenyl)propane-
1,2,diol Stem [59]
(113) Glabridin Stem [59]
(114) 2-phenanthrenecarboxaldehyde, 1,2,3,4,4a,4b,5,6,7,8,8a,9-dodecahydro-
7-hydroxy-2,4b,8,8-tetramethyl-
Leaves and
stem [57]
(115) Epicatechin Flowers [24]
(116) Naringenin Stem [59]
(117) Kaempferol Stem [59]
(118) Quercetin Flowers [60]
(119) Quercitrin Flowers [60]
(120) Rutin Flowers [61]
(110) (111) (112) (113) (114)
(115) (116) (117) (118)
(119) (120)
Figure 6. The structures of the phenolic compounds and flavonoids from A. cathartica.
Figure 5. The structures of the volatile compounds from A. cathartica.
3.5. Phenolic Compounds and Flavonoids
From the flowers and stems, 5 phenolic compounds and 6 flavonoids have been identified (Table 5
and Figure 6).
Table 5. The phenolic compounds and flavonoids from A. cathartica.
No. Compound’s Name Parts Used Reference
(
110
)
Protocatechuic acid Flowers [24]
(
111
)
Gallic acid Flowers [24]
(
112
)
1-(3-(4-Allyl-2,6-dimethoxyphenoxy)-4-methoxyphenyl)propane-1,2,diol
Stem [59]
(
113
)
Glabridin Stem [59]
(
114
)
2-phenanthrenecarboxaldehyde,
1,2,3,4,4a,4b,5,6,7,8,8a,9-dodecahydro-7-hydroxy-2,4b,8,8-tetramethyl- Leaves and stem [57]
(
115
)
Epicatechin Flowers [24]
(
116
)
Naringenin Stem [59]
(
117
)
Kaempferol Stem [59]
(
118
)
Quercetin Flowers [60]
(
119
)
Quercitrin Flowers [60]
(
120
)
Rutin Flowers [61]
Molecules 2019, 24, x FOR PEER REVIEW 8 of 21
(67) (68) (69) (70) (71)
(72) (73) (74) (75) (76) (77) (78)
(79) (80) (81) (82) (83) (84) (85)
(86) (87) (88) (89) (90) (91) (92) (93) (94) (95)
(96)
OH
(97) (98) (99) (100) (101) (102) (103)
(104) (105) (106) (107) (108) (109)
Figure 5. The structures of the volatile compounds from A. cathartica.
3.5. Phenolic Compounds and Flavonoids
From the flowers and stems, 5 phenolic compounds and 6 flavonoids have been identified (Table
5 and Figure 6).
Table 5. The phenolic compounds and flavonoids from A. cathartica.
No. Compound’s Name Parts Used Reference
(110) Protocatechuic acid Flowers [24]
(111) Gallic acid Flowers [24]
(112) 1-(3-(4-Allyl-2,6-dimethoxyphenoxy)-4-methoxyphenyl)propane-
1,2,diol Stem [59]
(113) Glabridin Stem [59]
(114) 2-phenanthrenecarboxaldehyde, 1,2,3,4,4a,4b,5,6,7,8,8a,9-dodecahydro-
7-hydroxy-2,4b,8,8-tetramethyl-
Leaves and
stem [57]
(115) Epicatechin Flowers [24]
(116) Naringenin Stem [59]
(117) Kaempferol Stem [59]
(118) Quercetin Flowers [60]
(119) Quercitrin Flowers [60]
(120) Rutin Flowers [61]
(110) (111) (112) (113) (114)
(115) (116) (117) (118)
(119) (120)
Figure 6. The structures of the phenolic compounds and flavonoids from A. cathartica.
Figure 6. The structures of the phenolic compounds and flavonoids from A. cathartica.
Molecules 2019,24, 1238 9 of 22
3.6. Alkaloids
Two alkaloids present in the stems are the only ones reported in the literature [
38
] (Table 6
and Figure 7).
Table 6. The alkaloids from A. cathartica.
No. Compound’s name Parts Used Reference
(
121
)
6,7-dimethylthieno(2,3-b) quinolin-3-ylamine Stem [57]
(
122
)
Heptanediamide, N,N0-di-benzoyloxy- Stem [57]
Molecules 2019, 24, x FOR PEER REVIEW 9 of 21
3.6. Alkaloids
Two alkaloids present in the stems are the only ones reported in the literature [38] (Table 6 and
Figure 7).
Table 6. The alkaloids from A. cathartica.
No. Compound’s name Parts Used Reference
(121) 6,7-dimethylthieno(2,3-b) quinolin-3-ylamine Stem [57]
(122) Heptanediamide, N,N’-di-benzoyloxy- Stem [57]
(121) (122)
Figure 7. The structures of the alkaloids from A. cathartica.
3.7. Steroids and Terpenes
Carotenoids are terpene compounds. They can be yellow, orange, or red in pigment, and they
are widely distributed in nature. In plants, they play an important role in photosynthesis and in the
colouring of flowers and fruits [62]. A. cathartica carotenoids have been found in flowers, leaves, and
stems (Table 7 and Figure 8).
(123) (124) (125)
(126) (127)
(128)
(129) (130)
(131) (132)
(133)
Figure 8. The structures of the steroids and terpenes from A. cathartica.
Figure 7. The structures of the alkaloids from A. cathartica.
3.7. Steroids and Terpenes
Carotenoids are terpene compounds. They can be yellow, orange, or red in pigment, and they
are widely distributed in nature. In plants, they play an important role in photosynthesis and in
the colouring of flowers and fruits [
62
]. A.cathartica carotenoids have been found in flowers, leaves,
and stems (Table 7and Figure 8).
Molecules 2019, 24, x FOR PEER REVIEW 9 of 21
3.6. Alkaloids
Two alkaloids present in the stems are the only ones reported in the literature [38] (Table 6 and
Figure 7).
Table 6. The alkaloids from A. cathartica.
No. Compound’s name Parts Used Reference
(121) 6,7-dimethylthieno(2,3-b) quinolin-3-ylamine Stem [57]
(122) Heptanediamide, N,N’-di-benzoyloxy- Stem [57]
(121) (122)
Figure 7. The structures of the alkaloids from A. cathartica.
3.7. Steroids and Terpenes
Carotenoids are terpene compounds. They can be yellow, orange, or red in pigment, and they
are widely distributed in nature. In plants, they play an important role in photosynthesis and in the
colouring of flowers and fruits [62]. A. cathartica carotenoids have been found in flowers, leaves, and
stems (Table 7 and Figure 8).
(123) (124) (125)
(126) (127)
(128)
(129) (130)
(131) (132)
(133)
Figure 8. The structures of the steroids and terpenes from A. cathartica.
Figure 8. The structures of the steroids and terpenes from A. cathartica.
Molecules 2019,24, 1238 10 of 22
Table 7. The steroids and terpenes from A. cathartica.
No. Compound’s Name Parts Used Reference
(
123
)
β-sitosterol Leaves and stem [63]
(
124
)
β-Amyrin Leaves and stem [63]
(
125
)
Ursolic acid Leaves and stem [14,63]
(
126
)
Phytol Flowers, leaves, and stem [10,57]
(
127
)
Squalene Leaves [57]
(
128
)
Vitamine E Leaves [57]
(
129
)
Zeaxanthin Flowers [21]
(
130
)
b-Carotene Flowers [21]
(
131
)
Lutein Flowers [21]
(
132
)
Neoxanthin Flowers [21]
(
133
)
Violaxanthin Flowers [21]
3.8. Lactones
The mechanisms for recovering compound (
145
) from ethanol and ethyl acetate extracts have been
established, with ethanol showing the greatest yield [
64
]. The most commonly used plant parts for
the isolation and identification of compounds are flowers, roots, leaves, root bark, and bark (inner part)
(Table 8and Figure 9).
Table 8. The lactones from A. cathartica.
No. Compound’s Name Parts Used Reference
(
134
)
4H-Pyran-4-one,
2,3-dihydro-3,5-dihydroxy-6-methyl- Leaves and stem [57]
(
135
)
Vitamine C Leaves [14]
(
136
)
Dendrolasin Flowers [35]
(
137
)
Allamandin Root bark [65]
(
138
)
Plumericin
Leaves, root, stem, leaves, flowers, bark,
and root bark [9,18,65,66]
(
139
)
Isoplumericin Leaves, root, root bark, stem, and bark [9,18,65,66]
(
140
)
Acetylallamandin Root bark [65]
(
141
)
Allamdin Root bark [65]
(
142
)
Allamandicin Root bark [65]
(
143
)
Penta-acetylplumieride coumarate Root [66]
(
144
)
Octa-acetylplumieride coumarate Root [66]
(
145
)
Plumieride Root, stem, leaves, flowers, bark,
and bark (inner part) [18]
(
146
)
Plumieride coumarate Root, stem, leaves, flowers, bark,
and bark (inner part) [18,66]
(
147
)
Plumieride coumarate glucoside Root, stem, leaves, flowers, bark,
and bark (inner part) [18,66]
Molecules 2019,24, 1238 11 of 22
Molecules 2019, 24, x FOR PEER REVIEW 11 of 21
(134) (135) (136) (137) (138)
(139) (140) (141) (142)
(143) (144)
(145) (146) (147)
Figure 9. The structures of the lactones from A. cathartica.
3.9. Carbohydrates
The presence of 6 carbohydrates in the leaves, stems, and nectar has been shown (Table 9 and
Figure 10).
Table 9. The carbohydrates from A. cathartica.
No. Compound’s Name Parts Used Reference
(148) 1-Deoxy-D-mannitol Leaves [57]
(149) 3-O-methyl-D-glucose Leaves and stem [43,57]
(150) Glucose Nectar [67]
(151) Rhamnose Nectar [15]
(152) Fructose Nectar [67]
(153) β-L-arabinopyranoside, methyl Leaves [57]
(148) (149) (150)
(151) (152) (153)
Figure 10. The structures of the carbohydrates from A. cathartica.
4. Pharmacological Activity
A. cathartica has been reported in traditional medicine, and the first biological and
pharmacological studies were documented in 1943 [68]. A more general view of the pharmacological
investigations on various crude extracts and isolated chemical compounds of the species are
described below.
Figure 9. The structures of the lactones from A. cathartica.
3.9. Carbohydrates
The presence of 6 carbohydrates in the leaves, stems, and nectar has been shown (Table 9
and Figure 10).
Table 9. The carbohydrates from A. cathartica.
No. Compound’s Name Parts Used Reference
(
148
)
1-Deoxy-D-mannitol Leaves [57]
(
149
)
3-O-methyl-D-glucose Leaves and stem [43,57]
(
150
)
Glucose Nectar [67]
(
151
)
Rhamnose Nectar [15]
(
152
)
Fructose Nectar [67]
(
153
)
β-L-arabinopyranoside, methyl Leaves [57]
Molecules 2019, 24, x FOR PEER REVIEW 11 of 21
(134) (135) (136) (137) (138)
(139) (140) (141) (142)
(143) (144)
(145) (146) (147)
Figure 9. The structures of the lactones from A. cathartica.
3.9. Carbohydrates
The presence of 6 carbohydrates in the leaves, stems, and nectar has been shown (Table 9 and
Figure 10).
Table 9. The carbohydrates from A. cathartica.
No. Compound’s Name Parts Used Reference
(148) 1-Deoxy-D-mannitol Leaves [57]
(149) 3-O-methyl-D-glucose Leaves and stem [43,57]
(150) Glucose Nectar [67]
(151) Rhamnose Nectar [15]
(152) Fructose Nectar [67]
(153) β-L-arabinopyranoside, methyl Leaves [57]
(148) (149) (150)
(151) (152) (153)
Figure 10. The structures of the carbohydrates from A. cathartica.
4. Pharmacological Activity
A. cathartica has been reported in traditional medicine, and the first biological and
pharmacological studies were documented in 1943 [68]. A more general view of the pharmacological
investigations on various crude extracts and isolated chemical compounds of the species are
described below.
Figure 10. The structures of the carbohydrates from A. cathartica.
4. Pharmacological Activity
A. cathartica has been reported in traditional medicine, and the first biological and pharmacological
studies were documented in 1943 [
68
]. A more general view of the pharmacological investigations on
various crude extracts and isolated chemical compounds of the species are described below.
Molecules 2019,24, 1238 12 of 22
4.1. Analgesic
In a previous study conducted in our laboratory, it was observed that the ethanol extract from
the aerial parts of A. cathartica showed an analgesic activity in the murine model.
4.2. Anti-Inflammatory
The inhibition of haemolysis in human erythrocytes by an aqueous fraction from a methanol
extract was evaluated, with rates of 69.49
±
0.49% compared to the positive control acetyl salicylic
acid (0.1 mg/mL), which showed a 72.79% inhibition [
69
]. In another study, the compound (
119
)
obtained from fresh A. cathartica flowers was evaluated for anti-inflammatory activity using an
in vitro
haemolytic membrane stabilization study. The effect of inflammation was studied using erythrocytes
exposed to a hypotonic solution. The results indicated that the obtained compound showed
a membrane stabilizing activity, which was highest with 75
µ
g [
70
]. In an
in vivo
model, the compound
(
145
) from a flower ethanol extract was evaluated for activity against ulcerative colitis induced by
dextran sulfate sodium (DSS) in female mice. As a standard control, 5-Amino-Salicylic Acid was
used, and the mice were administered either compound at the same dose (100 mg/kg/day for 7 days).
Treatment with the (
145
) compound resulted in less shortening of the colon, improved histological
damage, and less mucin depletion of the intestinal mucosa compared to the group only treated with
the vehicle [71].
4.3. Antidepressant
The antidepressant activity of the compound (
145
) was evaluated in Swiss Webster female mice
(0.5, 1, and 2
µ
g/kg i.p). Doses of 1 and 2
µ
g/kg showed a significant difference p< 0.001 with respect
to the negative control. Imipramide (20 mg/kg i.p.) was used as a positive control [61].
4.4. Antidiabetic
Aqueous extracts from the aerial parts of A. cathartica (400 mg/kg for 28 days) reduced blood
glucose levels in diabetic rats with streptozotocin, compared to glibenclamide (5 mg/kg) as a standard,
with a statistical significance p< 0.001 [48].
4.5. Antihyperlipidaemic
An ethanolic flower extract of A. cathartica (100, 150, and 300 mg/kg, p.o.) and the compound
(
145
) (0.5, 1, and 2 mg/kg, i.p.) decreased the total and High Density Lipoprotein (HDL) cholesterol
levels, with significant differences of p< 0.001 and p< 0.05, respectively, in female Swiss Webster mice
at the two highest doses tested [61].
4.6. Antifertility
The oral administration of aqueous leaf extracts of A. cathartica (150 mg/kg/day for 14, 28,
and 42 days) induced infertility and changes in various male reproductive endpoints in Parkes
strain mice. Histologically, the testes from the extract-treated mice showed nonuniform degenerative
changes in the seminiferous. The treatment also had adverse effects on motility, viability, morphology,
and the number of spermatozoa in the cauda epididymides. The fertility of the extract-treated males
was also suppressed [
72
]. The oral administration of (
145
) (15 mg/rat/day for 60 days) in male
Wistar rats significantly reduced the weight of the testes, epididymides, seminal vesicles, and prostate
compared to the negative controls, and the mobility of the sperm and Sertoli cells also decreased
significantly and without systemic side effects. The number of mature Leydig cells was decreased,
and a complete suppression of fertility was observed. The content of protein and sialic acid in the testes,
epididymides, seminal vesicle, and prostate, as well as the glycogen content of the testes and fructose
in the seminal vesicles were reduced. However, testicular cholesterol was elevated [73].
Molecules 2019,24, 1238 13 of 22
4.7. Wound Healing
Aqueous leaf extracts of A. cathartica (150 mg/kg/day for 14 days) promoted the wound healing
activity in Sprague–Dawley rats. Compared to the controls, treated rats had higher rates of wound
contraction, decreased periods of epithelialisation, a higher skin breaking strength, a significantly
higher weight of the granulation tissue, and more hydroxyproline content. Histological studies
of the granulation tissue in treated rats showed less inflammatory cells and increased collagen
formation [8].
4.8. Thrombolysis
A. cathartica leaves were extracted with methanol and subsequently partitioned with hexane,
carbon tetrachloride, chloroform, and water. The thrombolytic activity of the resulting preparation
was evaluated
in vitro
with the concentration of extract at 0.1 mg/100
µ
L. As a positive control,
streptokinase was used. All extracts showed thrombolytic activity with respect to the negative control
with a significant difference of p< 0.001. The chloroform-partitioned extract presented the highest rate
of clot lysis (34.51%) [30].
4.9. Purgative Effect
The purgative effect of the aqueous leaf extract of A. cathartica was evaluated at different doses
(20, 40, 80, 160, and 320 mg/kg orally). As a positive control, the Senna extract was used under the same
conditions and the saline solution was used as a negative control; the extract showed a dose-dependent
effect [28].
4.10. Tyrosinase
The tyrosinase inhibitory activity of the methanol stem powder extracts of A. cathartica was
examined, and compound (
113
) was identified as having the highest inhibitory activity against
tyrosinase (IC
50
: 2.93
µ
M), which was 15 times stronger than the kojic acid used as a positive control
(IC50: 43.7 µM) [59].
4.11. Amylase
In leaves extracted with ethanol 50% (v/v), Allotides were identified as being proline-rich
and having an α-amylase inhibitory activity [22].
4.12. Antiviral
Through an in silico method, it was determined that some compounds present in A. cathartica
have an antiviral activity against human hepatitis B viral capsid protein [
58
]. The antirabic activity of
methanol and aqueous extracts of leaves was evaluated; however, the extracts did not inhibit the rabies
virus at the concentrations evaluated [31].
4.13. Antimicrobial
The methods most commonly used to evaluate antimicrobial activity are carried out by plaque,
disk, and dilution methods. Table 10 describes the different studies carried out with extracts obtained
from different parts of A. cathartica.
Molecules 2019,24, 1238 14 of 22
Table 10. The effect of A. cathartica extract on a microorganism.
Microorganism Used Part Extract/Fraction Reference
Gram Positive
Agrobacterium tumefaciens
Flowers and leaves Bound and free flavonoids, steroids,
and alkaloids [74]
Bacillus cereus Leaves
TCM [75]
EtOAc [69]
MeOH, PE, TCM, EtOAc, and Dia-Ion [76]
Bacillus megaterium Leaves TCM [75]
EtOAc [69]
Bacillus subtilis
Flowers and Leaves Bound and free flavonoids and steroids [74]
Leaves TCM [75]
Water * [77]
Sarcina lutea Leaves TCM [75]
Staphylococcus aureus
Flowers Water * [78]
MeOH 90% [79]
Flowers and leaves Free flavonoids, alkaloids, bound
flavonoids, and steroids [74]
Leaves MeOH, PE, TCM, EtOAc, and Dia-Ion [76]
TCM [77]
Root MeOH, EtOAc, and PE [80]
All plant N.E. [68]
Staphylococcus aureus ** Leaves MeOH, EtOH, EtOAc, TCM, and PE [81]
Streptococcus pneumonia Root MeOH, EtOAc [80]
Gram Negative
Acinetobacter baumannii **
Flowers EtOH [82]
Acinetobacter sp ** Leaves MeOH, EtOH, EtOAc, Water, and PE [81]
Bacillus subtillis Leaves Bound flavonoids [74]
Escherichia coli
Flowers Water * [78]
Flowers and leaves Bound flavonoids and steroids [74]
Flowers MeOH 90% [79]
Leaves TCM [75]
MeOH, PE, TCM, EtOAc, and Dia-Ion [76]
Root EtOAc [80]
Escherichia coli ** Leaves Water and PE [81]
Water [32]
Klebsiella pneumoniae
Root MeOH and EtOAc [80]
Flowers Water * [78]
Flowers and leaves Bound and free flavonoids [74]
Leaves Water * [77]
Klebsiella pneumoniae ** Leaves Water [32]
Proteus mirabilis ** Leaves Water [32]
Proteus sp ** Leaves PE [81]
Proteus vulgaris Leaves MeOH, PE, TCM, EtOAc, and Dia-Ion [76]
Pseudomonas aeruginosa Leaves TCM [75]
Water * [77]
Pseudomonas aeruginosa **
Leaves Water [32]
MeOH, EtOAc, TCM, and PE [81]
Salmonella paratyphi Leaves TCM [75]
EtOAc [69]
Salmonella typhi Leaves TCM [75]
EtOAc [69]
Molecules 2019,24, 1238 15 of 22
Table 10. Cont.
EtOAc [69]
Salmonella typhimurium Flowers Water * [78]
Shigella boydii Leaves TCM [75]
Shigella dysenteriae Leaves TCM [75]
Vibrio mimicus Leaves TCM [75]
Vibrio parahemolyticus Leaves TCM [75]
Fungi
Aspergillus flavus Leave and Flowers MeOH [83]
Aspergillus flavus Leaves MeOH:Water (2:1 v/v) [84]
Water * [77]
Aspergillus niger Leaves TCM [75]
Water * [77]
Candida albicans
Leaves
EtOH 99.8% [85]
TCM [75]
MeOH [34]
Leave and Flowers MeOH [83]
Flowers MeOH 90% [79]
Candida albicans ** Leaves EtOH [81]
Carvularia lunata Leaves PE and TCM [40]
Epidermophyton floccosum Leaves MeOH [86]
Microsporum gypseum Leaves MeOH [86]
Pityrosporum ovale Leaves EtOH 99.8% [85]
Sacharomyces cerevaceae Leaves TCM [75]
Plant Fungi
Colletotrichum
gloeosporioides Leaves TCM [42]
Colletotrichum
lidemuthianum Leaves PE and TCM [40]
Curvularia luunata Leaves Water * [77]
Fusarium oxysporum Leaves PE and TCM [40]
MeOH, EtOH, EtOAc, and EtOH 50% [87]
Fusarium oxysporum
f.sp. capsici Leave MeOH [16]
Phomopsis vexans Leaves MeOH, EtOH, EtOAc, and EtOH 50% [87]
Phytophthora capsici Leaves MeOH, EtOH, EtOAc, and EtOH 50% [87]
Rhizopus arrhizus Leaves Water * [77]
Rhizotonia solani Leaves MeOH, EtOH, EtOAc, and EtOH 50% [87]
Sclerotium rolsfsii Leaves MeOH, EtOH, EtOAc, and EtOH 50% [87]
Note: * Used with silver nanoparticles (AgNPs), ** Clinical isolates, TCM = Chloroform, PE = Petroleum ether,
MeOH = Methanol, EtOH = Ethanol, and EtOAc = Ethyl acetate.
4.14. Antimalarial
In an
in vivo
model in albino rats, the antimalarial activity of a leaf ethanol extract from
A. cathartica was evaluated at different doses (50, 100, and 200 mg/mL). As a positive control,
the compound (
128
) was used (200 mg/kg), and the extract showed an effect similar to (
128
) that was
dose-dependent [88].
4.15. Nematicide
Bark methanol extracts were evaluated on Bursaphelenchus xylophilus (pinewood nematode),
where a minimum effective dose (MED) of 5 mg/cotton ball was found [
19
]. Fractions of hexane
extracts of the leaves and stem from A. cathartica were evaluated
in vitro
for nematicidal activity at 0.06,
Molecules 2019,24, 1238 16 of 22
0.1, and 0.2 mg/mL against juvenile larvae of Meloidogyne incognita. The extract showed a nematicidal
activity from the first hours of exposure with a rate of 16.87% [89].
4.16. Pesticidal
Aqueous extracts of leaves and flowers from A. cathartica showed pesticidal properties against
Oligonychus coffeae [
90
]. Extractions using petroleum ether, chloroform, and methanol showed
pesticidal effects on Tribolium castaneum exposed for 24, 48, and 72 h. The LD
50
values at these
time points were 684,376, 319,028, and 225,205
µ
g/cm
2
for petroleum ether; 34,289.35, 4,308,567,
and 804,082
µ
g/cm
2
for chloroform; and 445,092.10, 38,709.10, and 9,906.21
µ
g/cm
2
for methanol,
respectively [76].
4.17. Antihaemorrhagic
Extracts of 96% ethanol made from the leaves, branches, and stems of A. cathartica were evaluated
for an
in vitro
haemorrhagic neutralization activity using the blood of a Swiss Webster mouse
with 10
µ
gBothrops atrox venom, and the results obtained showed a neutralization of 72
±
8%.
However, it was not clear if the parts of the plant were evaluated together or separately [12].
4.18. Cytotoxicity
The methanolic extract and subsequent fractions (methanol, chloroform, hexane, and carbon
tetrachloride) from A. cathartica leaves were evaluated for their toxic effects on brine shrimp.
The chloroform-, hexane-, and carbon tetrachloride-soluble fractions showed a significant cytotoxic
activity against nauplii brine shrimp, with LC
50
values of 1.45, 5.00, and 5.24
µ
g/mL, respectively [
30
].
The methanol and aqueous extracts of leaves at concentrations of 10, 5, 2.5, 1.25, and 0.6 mg/mL did
not show a cytotoxic activity on BHK-21 cells [
31
]. In another study of methanol extracts from leaves,
an IC
50
of 85
µ
g/mL was found for P388 leukaemia cells [
86
]. The use of silver nanoparticles (AgNO
3
)
with aqueous latex extracts of A. cathartica showed a dose-dependent effect against human mononuclear
blood cells [
91
]. The methanol, ethyl acetate, petroleum ether, and chloroform extracts from leaves
of A. cathartica showed LD
50
values of 111.61, 131.14, 332.42, and 47.86
µ
g/mL, respectively, against
Artemia salina [
76
]. Compounds (
142
), (
139
), and (
138
) obtained from 95% ethanol leaf extracts showed
a significant tumour suppression
in vitro
against human nasopharnyx carcinoma (KB) cells with
an LD50 of 2.1, 2.6, and 2.7 µg/mL, respectively [65].
4.19. Antioxidants
The antioxidant activity of A. cathartica was evaluated
in vitro
using the FRAP and TEAC
methods with Methanol:Acetic acid:Water extracts (50:3.7:46.3 v/v/v) as well as the water-soluble
and fat-soluble fraction from flowers, which showed antioxidant activities via FRAP of 18.95
±
0.34
and 4.56
±
0.11
µ
mol Fe (II)/g, respectively. By the TEAC method, the antioxidant activity was
7.35
±
0.26 and 1.46
±
0.21
µ
mol Trolox/g, respectively [
24
]. The ethanol extracts from the leaves had
an antioxidant activity (based on the DPPH method) that was dose-dependent at concentrations of
0.5, 1, 2, and 5 mg/mL [
92
]. The methanol extracts from the flowers showed an antioxidant activity
by the DPPH method at a concentration of 0.6 mg/mL [
93
]. Different plant parts were analysed for
their antioxidant activity
in vitro
where it was higher in shoot > root > leaves > flowers. The relative
peroxidase and superoxide dismutase (SOD) activities were in the order of root > shoot > leaves >
flowers [
17
]. The relative
in vitro
antioxidant activity of various leaf extracts of A. cathartica was in
the following order: butylated hydroxyl toluene (BHT) > Dia-Ion resin Absorbed > Chloroform > Ethyl
acetate (EtOAc) > Methanol (MeOH) > Petroleum ether (PE) [
76
]. The carbon tetrachloride fraction
from a methanol extract from the leaves had an IC
50
of 47.5
±
0.11
µ
g/mL in the DPPH model [
69
].
In the study of isolated compounds, (
145
) (100 mg/kg orally) administered to female Swiss mice
significantly decreased the levels of lipid hydroperoxides (LOOH) and reduced the glutathione (GSH)
levels and SOD activity, whereas the catalase (CAT) activity remained unchanged compared with
Molecules 2019,24, 1238 17 of 22
the untreated group. The standard drug 5-ASA reduced the LOOH content and increased the SOD
activity compared to the vehicle (VEH) group, whereas treatment with (
145
) promoted a complete
improvement of the oxidative unbalance, restoring all the parameters [
71
]. In an
in vivo
model
using albino rats, the antioxidant activity of the ethanol extract of leaves (50, 100, and 200 mg/mL)
was evaluated, and as a positive control, the compound (
128
) was used (200 mg/kg), showing
a significant increase in TBARS, with a decrease in GSH and CAT levels [88].
5. Toxicity
A. cathartica is reported to be a venomous plant due to the presence of a cardiotoxic glycoside [
25
].
All parts of the plant cause dermatitis [
29
]. It has been reported that the leaves and sap produce persistent
diarrhoea with high consumption rates. Also, skin irritation has been reported, but the responsible
compounds have not been identified [
3
]. Studies have been carried out on the cytotoxicity
and genotoxicity of hexane extracts of leaves of A. cathartica. It was demonstrated that a concentration
of 315 mg/mL is cytotoxic to lymphocytes with a 79% cellular viability. In HeLa cells, an IC
50
of 13.5 mg/mL was found. These results showed a genotoxicity (p< 0.01) for both cell types, which led
the authors to suggest that A. cathartica not be used as a medicinal plant [
94
]. However, it is necessary
to standardize the HPLC samples for at least one compound present in the plant. In the evaluation
of acute toxicity (i.p.) in mice, it was observed that the LD
50
was 1320
±
15 mg/kg [
28
]. The oral
administration of 2 mg/kg of ethanolic extract of flowers and the compound (
145
) in Swiss Webster
mice administered as a single dose and evaluated at 14 days showed no toxic effects, no changes in
biochemical or haematological parameters, and no genotoxic effects [
61
]. The toxicological evaluation of
the petroleum ether extract of leaves in albino mice showed no toxicity at doses of 100 to 1000 mg/kg
p.o. for 72 h [81].
6. Biotechnological Use
The effects of 2,4-dichlorophenoxyacetic acid (2,4-D) and 6-benzylaminopurine (BAP)
on the induction of callus from leaf and stem explants were investigated. The regeneration of plants
from the nodal explants was achieved. The explants were cultured in a Murashige and Skoog (MS)
medium, supplemented with different concentrations of 2,4-D (0.5 and 1.0 mg/L) or in combinations
of 2,4-D (0.5, 1.0, and 1.5 mg/L) with BAP (0.5, 1.0, and 1.5 mg/L). In the study of plant regeneration,
the nodal explants were cultivated in an MS medium supplemented with BAP at 1.0, 3.0, or 5.0 mg/L
for the multiplication of shoots. The MS basal medium was used as a control and was also used
for the elongation of the shoots. All cultures were incubated under a photoperiod of 16 h of light
and 8 h of darkness. For callus induction, the explants of leaves and stems grown at 1.0 mg/L
of 2,4-D and 1.0 mg/L of BAP gave the best callus response (100%). For the multiplication of shoots,
the MS medium supplemented with 5 mg/L of BAP gave the best response (100%) with multiple buds
formed [46].
7. Conclusions
This review details the ethnomedical, phytochemical, pharmacological, toxicological,
and biotechnological uses of A. cathartica. Although there have been several studies on the pharmacological
activity of A. cathartica, the potential of this plant is as an analgesic, anti-inflammatory, antidepressant,
antidiabetic, antihyperlipedaemic, antifertility agent, wound healing, trombolytic, purgative, tyrosine,
amylase, antimicrobial, antimalarial, nematicide, antioxidant, etc. agent.
Author Contributions:
All authors contributed to this work, prepared the manuscript, and approved this version
of the article.
Funding:
This work was supported by Secretaría de Educación Publica (SEP-PROMEP) and Consejo Nacional de
Ciencia y Tecnología (CONACyT), México under number ON.551–6/18–7513.
Molecules 2019,24, 1238 18 of 22
Conflicts of Interest:
The authors declare that they have no conflict of interest. The funding sponsors contributed
the scholarship payment and had no role in the study design, collection, analysis, or interpretation of the data;
in the writing of the manuscript; or in the decision to publish the results.
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