Industrial Crops and Products 91 (2016) 358–376

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Industrial Crops and Products

journal homepage: www.elsevier.com/locate/indcrop

Chemical constituents of the oilseed crop Ricinus communis and their

pharmacological activities: A review
Paulo R. Ribeiro a,b,∗ , Renato D. de Castro b , Luzimar G. Fernandez b
a
Departamento de Química Orgânica, Instituto de Química, Universidade Federal da Bahia, Rua Barão de Jeremoabo s/n, 40170-115, Salvador-BA, Brazil
b
Laboratório de Bioquímica, Biotecnologia e Bioprodutos, Departmento de Bioquímica e Biofísica, Universidade Federal da Bahia, Avenida Reitor Miguel
Calmon s/n, 40160-100, Salvador-BA, Brazil

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

Article history: Ricinus communis L. agronomic importance has stimulated a diverse set of studies related to pharmaco-
Received 25 March 2016 logical activities of extracts and compounds isolated from this plant. Phytochemical studies have shown
Received in revised form 6 June 2016 that this species possesses a wide diversity of chemical compounds that presents relevant pharmaco-
Accepted 11 July 2016
logical activities. This review discusses 83 compounds that were isolated from different tissues of R.
communis, which includes alkaloids, terpenoids, flavonoids, benzoic acid derivatives, coumarins, toco-
Keywords:
pherols, terpenoids and fatty acids. The potential to inhibit or prevent bacterial and fungal growth is the
Bioactive compounds
most extensively studied pharmacological activity of R. communis extracts, but many other activities are
Castor bean
Medicinal plants
attributed to them, such as cytotoxicity, antioxidant, insecticidal, antiasthmatic, anti-inflammatory, and
Traditional medicine many others. Pharmacological activities of R. communis extracts and isolated compounds are discussed
herein, and structure–activity relationships are presented when appropriate.
© 2016 Elsevier B.V. All rights reserved.

Contents

1. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 359
2. Pharmacological studies of R. communis extracts . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 359
2.1. Antimicrobial activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 359
2.1.1. Genus Bacillus . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 359
2.1.2. Escherichia coli . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 361
2.1.3. Genus Aspergillus . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 362
2.1.4. Candida albicans . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 362
2.2. Cytotoxic activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 362
2.3. Antioxidant activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 362
2.4. Insecticidal activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 362
2.5. Other activities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 363
3. Chemical constituents of Ricinus communis and their pharmacological activities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 363
3.1. Alkaloids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 363
3.2. Flavonoids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 363
3.3. Benzoic acid derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 373
3.4. Coumarins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 373
3.5. Tocopherols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 373

Abbreviations: CK1␣, casein kinase 1 alpha; CoA, coenzyme A; EC50 , The concentration of a compound or extract capable giving half-maximal response; 11␤-HSD, 11-
Beta hydroxysteroid dehydrogenase; IC50 , The concentration of a compound or extract capable giving half-maximal inhibition; LD, Lethal Dose; LC50 , The concentration of a
compound or extract capable of killing 50% of the tested (micro)organism; MES, Maximal electroshock seizure; MIC, minimal inhibitory concentration; TFC, Transcriptional
transactivation partner.
∗ Corresponding author at: Departamento de Química Orgânica, Instituto de Química, Universidade Federal da Bahia, Rua Barão de Jeremoabo s/n, 40170-115 Salvador,
Brazil.
E-mail addresses: paulodc3@gmail.com, pauloribeiro@ufba.br (P.R. Ribeiro).

http://dx.doi.org/10.1016/j.indcrop.2016.07.010
0926-6690/© 2016 Elsevier B.V. All rights reserved.
 P.R. Ribeiro et al. / Industrial Crops and Products 91 (2016) 358–376 359

3.6. Terpenoids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 373

3.6.1. Monoterpenoids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 373
3.6.2. Diterpenoids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 373
3.6.3. Sterols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 373
3.6.4. Triterpenoids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 373
3.7. Fatty acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 373
3.8. Other compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 374
4. Concluding remarks . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 374
Conflict of interest . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 374
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 374

1. Introduction confers the medicinal properties of this species (Scarpa and Guerci,
1982). Since then, several authors have dedicated their efforts to
Ricinus communis L. belongs to the Euphorbiaceae family and is investigate different biological activities of R. communis extracts.
mainly cultivated in tropical and subtropical regions worldwide. Its In this review, we summarized the most recent papers describ-
seeds contain high levels of toxic compounds, such as the ribosome- ing pharmacological activities of R. communis extracts and isolated
inactivating protein ricin and the alkaloid ricinine (Ogunniyi, 2006; compounds. Pharmacological activities of R. communis extracts and
Severino et al., 2012). R. communis is a xerophytic and heliophile isolated compounds are discussed herein, and structure–activity
plant that presents a deep taproot system, simple (i.e., lobed or relationships are presented when appropriate.
unlobed but not separated into leaflets) and denticulate leaves, with
great phenotypic variability in its morphological characteristics. Its 2. Pharmacological studies of R. communis extracts
phenotypic diversity is quite wide, with variations in growth habits,
color of the leaves, stem and seeds, and oil content (Savy Filho R. communis is an important oilseed crop and pharmacological
et al., 2007). Additionally, it present variation in plant size (shrub activities of extracts and isolated compounds have been extensively
or tree height), annual or casually biennial cycle, and great vari- studied. Leaf was, by far, the most well-studied part of the plant.
ability in appearance and biometric parameters of the seeds (Chan Pharmacological activities of leaf extracts were reported in around
et al., 2010; Nobre et al., 2012). Some cultivars have annual average 50% of the papers, followed by extracts from seeds (16%) and roots
cycle of 150 days, which is more suitable for mechanical harvest- (11%) (Fig. 1a). This is in line with the fact that several ethnob-
ing due to homogeneous maturation of the seeds. The long-cycle otanical studies describe leaf as one of the most used part of the
varieties (180–210 days) are better suited to tropical regions, and plant in the traditional medicine (Abe and Ohtani, 2013; Cunha
have increased tolerance to biotic and abiotic stresses, and there- Lima et al., 2012; Rashid et al., 2015). The main extraction method
fore most recommended for producers using low-tech resources used by these studies was maceration (55%), followed by soxhlet
(Severino and Auld, 2013; Severino et al., 2012). (21%) (Fig. 1b). Methanol and ethanol were used by 28 and 26% of
R. communis is an important oilseed crop and its agronomic the papers, respectively, followed by water (15%) and ethyl acetate
importance stimulated not only a diverse set of studies related (9%) (Fig. 1c). The pharmacological activities attributed to these
to pharmacological activities of extracts and compounds isolated extracts are summarized in Table 1.
from this plant (subject of this review), but also molecular research
related to seed maturation (Kim et al., 2014), plant development 2.1. Antimicrobial activity
(Cabral-de França et al., 2013; Hierl et al., 2012; Schurr et al., 2000),
and responses to biotic and abiotic stresses (de Araújo Silva et al., The potential to inhibit or prevent bacterial and fungal growth
2015; Huang et al., 2016; Moraes et al., 2015; Pal et al., 2013; Patel is the most extensively studied pharmacological activity of R.
et al., 2015; Ribeiro et al., 2014a, 2015a, 2015d). communis extracts. The identification of plant extracts and pure
R. communis has been used worldwide due to its medicinal prop- compounds which presents antimicrobial properties is essential to
erties (Scarpa and Guerci, 1982). In particular, the oil extracted the advance of new drugs and, ultimately, in the healthcare system
from its seeds has a peculiar chemical composition which make worldwide. Antifungal and antibacterial activities of R. communis
it a good choice for many pharmaceutical and industrial applica- extracts were assessed against thirty three different microorgan-
tions (Ogunniyi, 2006; Severino et al., 2012). In a pioneer study, isms (Table 2). Further details of some of the most well studied
Scarpa and Guerci (1982) described the medicinal uses of R. com- microorganisms are provided in the following sub-sections.
munis in several communities worldwide. Although the results
showed that this plant is extensively used throughout the world, 2.1.1. Genus Bacillus
the authors concluded that further phytochemical and pharmaco- Khafagi (2007) produced extracts from callus cultures of two
logical studies were required in order to reveal which compounds varieties of R. communis and evaluated the antimicrobial activity

Fig. 1. Tissues, extraction methods and solvents used during phytochemical and pharmacological studies of R. communis.
Table 1
Pharmacological activities, tissues, extraction methods, solvents and compounds described in phytochemical studies of R. communis.

360
Activity Tissue Extraction method Solvent Compound detected References

antimicrobial leaves maceration methanol, ethanol and water NT Naz and Bano (2012)
leaves maceration methanol and ethyl acetate alkaloids, coumarins, flavanoids, tannins and phenols Rampadarath et al. (2014)
leaves maceration methanol tannins, phlobatannins, flavonoids, terpenoids and Oyewole et al. (2010)
cardiac glycosides
leaves and stem maceration methanol and water amino acids and carbohydrates Habib Naqvi et al. (2011)
leaves and seeds maceration methanol tannins, alkaloids, cardiac glycosides, terpenoids, Vandita et al. (2013)
flavonoids and steroids
leaves, stems, roots, maceration methanol alkaloids and cardiac glycosides Ibraheem and Maimako (2014)
seeds and capsules
callus maceration ethanol and ether quercetin, kaempferol and ricinine Khafagi (2007)
leaves soxhlet ethanol and methanol saponins, cardiac glycosides, tannins, flavonoids and Christy Jeyaseelan and Justin
terpenoids Jashothan (2012)
leaves hydrodistillation – ␣-thujone, 1,8-cineole, ␣-pinene, camphor and Zarai et al. (2012)
camphene
acaricidal leaves maceration and ethanol, hexane, choloroform, quercetin, gallic Ghosh et al. (2013)
partition n-butanol and water acid, flavone and kaempferol

P.R. Ribeiro et al. / Industrial Crops and Products 91 (2016) 358–376

analgesic root bark soxhlet water alkaloids, flavonoids, saponins, steroids and glycosides Rajeshkumar et al. (2013)
antiasthmatic roots soxhlet ethanol steroids, saponins, alkaloids, flavonoids and glycosides Taur and Patil (2011)
anticonvulsant seeds maceration ethanol alkaloids, steroids, flavonoids, glycosides and phenolics Tripathi et al. (2011)
antidiabetic (hypoglycemic) leaves maceration ethanol NT Mann et al. (2013)
antihelmintic callus maceration ethanol and ether quercetin, kaempferol and ricinine Khafagi (2007)
bark soxhlet ethanol and water NT Rana et al. (2013)
antihemolytic leaves, stems, roots, maceration methanol alkaloids and cardiac glycosides Ibraheem and Maimako (2014)
seeds and capsules
antihistamine and root soxhlet ethanol NT Lomash et al. (2010)
anti-inflammatory
antinociceptive leaves soxhlet methanol saponins, steroids and alkaloids Taur et al. (2011)
antioxidant leaves hydrodistillation – ␣-thujone, 1,8-cineole, ␣-pinene, camphor and Kadri et al. (2011)
camphene
leaves, stems, roots, maceration methanol alkaloids and cardiac glycosides Ibraheem and Maimako (2014)
seeds and capsules
roots and leaves maceration methanol phenols, flavonoids, and condensed tannins Wafa et al. (2014)
contraceptive stem bark maceration petroleum ether, ethyl acetate, NT Nath et al. (2013)
acetone and water
contractile (rabbit uterine strips) root bark hot extraction ethanol and water NT Kaingu et al. (2012)
cytotoxic leaves hydrodistillation – ␣-thujone, 1,8-cineole, ␣-pinene, camphor and Zarai et al. (2012)
camphene
leaves maceration hexane, dichloromethane, – Nemudzivhadi and Masoko (2014)
acetone, and methanol
leaves maceration ethanol flavonoids, alkaloids, saponins, and phytosterols Rondon et al. (2011)
growth, survival and disease leaves maceration methanol NT Sankar et al. (2011)
resistance in the black tiger
shrimp (Penaeus monodon)
immunomodulatory (human leaves soxhlet methanol tannins Kumar et al. (2011)
neutrophils)
insecticidal seeds and leaves reflux methanol, hexane and ethyl ricinine, linolenic acid and linoleic acid Ramos-López et al. (2012, 2010)
acetate
seeds hydraulic extractor ethanol NT Babarinde et al. (2011)
leaves maceration methanol and ethyl acetate alkaloids, coumarins, flavanoids, tannins and phenols Rampadarath et al. (2014)
leaves maceration ethanol ricinine and its carboxylic acid derivative Wachira et al. (2014)
3-carboxy-4-methoxy-N-methyl-2-pyridone
larvicidal roots and leaves maceration methanol phenols, flavonoids, and condensed tannins Wafa et al. (2014)
seeds hydraulic extractor ethanol NT Babarinde et al. (2011)
seeds maceration acetone NT Mandal (2010)
parasite mortality leaves soxhlet hexane, chloroform, ethyl epicatechin Zahir et al. (2012)
(Paramphistomum cervi) acetate, acetone and methanol
toxicity of pollen to honeybees pollen dried pollen – NT de Assis Junior et al. (2011)

NT = not tested.
 P.R. Ribeiro et al. / Industrial Crops and Products 91 (2016) 358–376 361

Table 2
Microorganisms, solvents, tissues, and compounds described in antibacterial studies of R. communis extracts.

Microorganism Solvent Extract Tissue Compound Detected References

Aspergillus fumigatus water leaves and stems free amino acids and sugars Habib Naqvi et al. (2011), Naz and
Bano (2012)
water leaves – Naz and Bano (2012)
methanol leaves –
Aspergillus niger water stem – Habib Naqvi et al. (2011), Vandita
et al. (2013)
Aspergillus niger methanol leaves tannins, alkaloids, cardiac Vandita et al. (2013)
glycosides, terpenoids, flavonoids
and steroids.
Aspergillus flavus methanol leaves – Naz and Bano (2012)
Bacillus algicola ethyl acetate and methanol leaves alkaloids, coumarins, flavanoids, Rampadarath et al. (2014)
tannins and phenols
Bacillus cereus ethyl acetate and methanol leaves alkaloids, coumarins, flavanoids, Rampadarath et al. (2014), Zarai
tannins and phenols et al. (2012)
essential oil leaves ␣-thujone and 1,8-cineole Zarai et al. (2012)
␣-pinene camphor and camphene
Bacillus subtilis ethanol callus cultures alkaloids, flavonoids, anthocyanin, Khafagi (2007), Naz and Bano
terpenes, tannins and glycosides (2012), Oyewole et al. (2010),
Vandita et al. (2013), Zarai et al.
(2012)
methanol, ethanol and water leaves – Naz and Bano (2012)
methanol – – Oyewole et al. (2010)
methanol leaves tannins, alkaloids, cardiac Vandita et al. (2013)
glycosides, terpenoids, flavonoids
and steroids.
essential oil leaves ␣-thujone and 1,8-cineole, Zarai et al. (2012)
␣-pinene camphor and camphene
Botrytis cinerea essential oil leaves ␣-thujone and 1,8-cineole, Zarai et al. (2012)
␣-pinene camphor and camphene
Candida albicans methanol callus – Khafagi (2007), Rampadarath et al.
(2014), Vandita et al. (2013)
methanol and ethyl acetate leaves alkaloids, coumarins, flavanoids, Rampadarath et al. (2014)
tannins and phenols
methanol leaves – Vandita et al. (2013)
Enterobacter cloacae essential oil leaves ␣-thujone and 1,8-cineole, Zarai et al. (2012)
Enterococcus faecalis ␣-pinene camphor and camphene
Escherichia coli
Escherichia coli methanol and ethanol leaves saponins, cardiac glycosides, Christy Jeyaseelan and Justin
tannins, flavonoids and terpenoids Jashothan (2012)
methanol leaves and stem – Habib Naqvi et al. (2011)
methanol callus – Khafagi (2007)
methanol leaves tannins, alkaloids, cardiac Vandita et al. (2013)
glycosides, terpenoids, flavonoids
and steroids.
methanol and ethyl acetate leaves alkaloids, coumarins, flavanoids, Rampadarath et al. (2014)
tannins and phenols
Klebsiella pneumoniae essential oil leaves ␣-thujone and 1,8-cineole, Zarai et al. (2012)
Micrococcus luteus ␣-pinene camphor and camphene
Penicillium digitatum
Pseudomonas aeruginosa
Staphylococcus aureus methanol, ethanol leaves saponins, cardiac glycosides, Christy Jeyaseelan and Justin
tannins, flavonoids and terpenoids Jashothan (2012)

of these extracts. These extracts showed inhibition zones against
B. subtilis that varied from 5 to 10 mm. Many classes of secondary
metabolites were detected in these extracts, including alkaloids and
phenolic compounds (Table 2) (Khafagi, 2007). Naz and Bano (2012)
showed that R. communis methanol, ethanol and aqueous extracts
exhibited relative percentage inhibition against B. subtilis of 74.9%,
70.0% and 51.3%, respectively. Penicillin was used as reference drug
for the determination of the relative percentage inhibition (Naz and
Bano, 2012). Oyewole et al. (2010) investigated the antimicrobial
properties of leaf extracts and reported that these extracts showed
inhibition zones against B. subtilis of 7 mm. They also reported the
presence of several phenolic compounds, cardiac glycosides and
terpenoids (Table 2) (Oyewole et al., 2010). Similarly, Vandita et al.
(2013) assessed the antibacterial activity of methanol leaf extract
against B. subtilis. This extract showed inhibition zones of 6 mm
(Vandita et al., 2013).
Zarai et al. (2012) studied the antimicrobial activity of R. com-
munis essential oil against B. subtilis and B. cereus. The essential
oil showed minimal inhibition concentration (MIC) of 480 and
300 ␮g/mL against B. subtilis and B. cereus, respectively (Zarai et al.,
2012). Two monoterpenes, ␣-thujone and 1,8-cineole, comprised
more than 60% of the essential oil, whereas ␣-pinene, camphor
and camphene summed up to 37% of the essential oil (Table 2).
Rampadarath et al. (2014) evaluated the chemical composition
and antimicrobial activity of extracts from R. communis growing in
Mauritius. Ethyl acetate and methanol leaf extracts showed mini-
mal inhibitory concentrations that varied from 1 to 75 ␮g/L against
B. algicola and B. cereus. Alkaloids, coumarins, flavanoids, tannins
and phenols were detected in the extracts (Table 2) (Rampadarath
et al., 2014).
362 P.R. Ribeiro et al. / Industrial Crops and Products 91 (2016) 358–376
2.1.2. Escherichia coli
Christy Jeyaseelan and Justin Jashothan (2012) evaluated the
antibacterial activity of leaf extracts of R. communis against E. coli
and Staphylococcus aureus. To obtain the extracts, they used ethanol
and methanol in two conditions: hot and cold extraction. Their
results shows that all extracts showed inhibition against the tested
microorganisms. Extracts obtained by hot solvents showed MIC
of 80 mg/mL against E. coli, whereas cold solvents showed MIC
of 160 mg/mL. Therefore, hot extraction enhanced the concen-
tration of active compounds in the extracts (Christy Jeyaseelan
and Justin Jashothan, 2012). These authors failed, however, to
justify the relatively high extract concentrations which they con-
sidered as “active”. Nevertheless, these results were included in
this review. Habib Naqvi et al. (2011) reported that R. communis
methanol extracts obtained from the leaves and stem showed an
inhibition zone of 8 and 9 mm against E. coli, whereas the cal-
lus extracts showed inhibition zone that varied between 20 and
30 mm (Khafagi, 2007). Vandita et al. (2013) described that the leaf
methanol extract showedd an inhibition zone of 18 mm against E.
coli. Rampadarath et al. (2014) reported that a MIC of 2.7 ␮g/L for
the methanol extract and a MIC of 3.6 ␮g/L for the ethyl acetate
extract, both obtained from R. communis leaves. R. communis essen-
tial oil showed minimal inhibition concentration of 430 ␮g/mL
against E. coli.
2.1.3. Genus Aspergillus
Habib Naqvi et al. (2011) studied the antifungal activity of
extracts obtained from different tissues of R. communis against
Aspergillus niger and A. fumigates. Extracts were obtained using
methanol and water as extraction solvents. Regardless of the tis-
sue used, methanol extracts did not show any antifungal activity
against the tested fungal species. Similarly, the majority of the
water extracts showed no effectiveness, except the extract obtained
from R. communis stem, which exhibited an inhibition zone of 6 mm
against A. niger. Curiously, 20% water extract of R. communis leaves
and stems inhibited A. fumigatus growth (10 mm inhibition zone).
In contrast to the results of Habib Naqvi et al. (2011), the methanol
extract of R. communis leaves showed considerable activity against
A. niger (23 mm) (Vandita et al., 2013). Additionally, Vandita et al.
(2013) reported the phytochemical analysis of the extracts and
showed the presence of tannins, alkaloids, cardiac glycosides, ter-
penoids, flavonoids and steroids (Table 2). Naz and Bano (2012)
investigated the in vitro antimicrobial activities of R. communis leaf
extract in different solvents. The methanol extracts inhibited fungal
growth of A. fumigatus and A. flavus by 59.5% and 56.3%, respec-
tively. Water extracts inhibited fungal growth of A. fumigatus and
A. flavus by 55.7% and 51.3%, respectively. Taken together, these
results shows that R. communis leaves constitute a good source of
bioactive compounds against species of Aspergillus genus.
2.1.4. Candida albicans
The antifungal activity against Candida albicans was tested for
R. communis leaf (Rampadarath et al., 2014; Vandita et al., 2013)
and callus extracts (Khafagi, 2007). In the study of Vandita et al.
(2013), methanol extract of R. communis leaves showed an inhi-
bition zone of 20 mm, whereas in the study of Rampadarath et al.
(2014), the methanol and ethyl acetate extracts obtained from the
leaves showed a MIC of 7.25 and 10.88 ␮g/L. None of the callus
extracts showed activity against C. albicans (Khafagi, 2007). Fre-
quently, it is not possible to make a direct comparison between
different studies that report the same antibacterial activities due
to the fact that authors use different protocols and, therefore, their
results are presented in different ways. Nevertheless, taking all
these results together it is possible to conclude that R. communis
constitute a good source of bioactive compounds.
2.2. Cytotoxic activity
Zarai et al. (2012) studied the cytotoxicity of R. communis essen-
tial oil on HeLa (cervical cancer) cell (Table 2). HeLa cells were
killed by about 30% when 3 mg/mL extracts were used, whereas at
4 mg/mL nearly all cells were killed. Synergism between ␣-pinene
and other compounds was accounted responsible for the observed
cytotoxicity (Shunying et al., 2005; Zarai et al., 2012).
Nemudzivhadi and Masoko (2014), studied the cytotoxic activ-
ity of leaf extracts obtained from different solvents against Bud-8
(Human Caucasian skin fibroblast) cell lines (Table 2). The tested
concentrations ranged from 100 to 500 ␮g/mL. Crude extracts were
only toxic to Bud-8 cell line at the highest concentration. Methanol
extract (784 ␮g/mL) had the highest LC50 after 24-h exposure, fol-
lowed by hexane (629.3 ␮g/mL), dichloromethane (573.6 ␮g/mL),
and acetone (544.6 ␮g/mL) (Nemudzivhadi and Masoko, 2014).
Interestingly, the authors reported that the morphology of cells
was also altered from its normal shape of fibroblast to oval shape,
because of the toxic effect of R. communis extracts to the cells
(Nemudzivhadi and Masoko, 2014).
Rondon et al. (2011) evaluated the in vitro cytotoxicity on the
murine monocytic cells (RAW264.7). The cytotoxicity test demon-
strated that the ethyl acetate fraction (100 ␮g/mL) was the least
toxic, resulting in 83.5% cell viability. However, the chloroform and
methanol fractions resulted in 52.1 and 61.2% cell viability at the
same concentration (Rondon et al., 2011).
2.3. Antioxidant activity
Ibraheem and Maimako (2014) studied the antioxidant activity
of leaf, stem, root, capsule and seed extracts. In this study, a specific
protocol was used to obtain extracts enriched in alkaloids and car-
diac glycosides. For the alkaloid-enriched extracts, the antioxidant
activity was 19.51% for the seeds, 32.54% for the capsule, 33.38%
for the stems and 57.61% for the leaves. For the cardiac glycoside-
enriched extracts, the antioxidant activity was 17.65% for the roots,
32.81% for the capsule and 33.83% for the stems (Ibraheem and
Maimako, 2014). It was suggested that if the concentration of alka-
loids and cardiac glycosides in the extracts were two times higher,
they would be as effective as the control ascorbic acid (Ibraheem
and Maimako, 2014).
R. communis essential oil antioxidant activity was evaluated by
three different approaches: 1,1-diphenyl-2-picrylhydrazyl (DPPH),
␤-carotene bleaching and reducing power assays (Kadri et al.,
2011). The antioxidant activity of the essential oil was found
to be 7–8 times lower than the control, butylated hydroxy-
toluene (BHT). The activity measured by the bleaching of the
␤-carotene-linoleate system shows that at 70 ␮g/mL, the oil had
lower linoleic acid inhibition activity than BHT (39.47 ± 2.00% vs.
77.50 ± 1.00% for essential oil and BHT, respectively). Additionally,
it was reported that the reducing power value at the same con-
centration were 0.804 ± 0.010, which is slightly lower than that
of BHT (1.051 ± 0.010). The EC50 value of R. communis essential
oil was 39.32 ␮g/mL, which was about three times higher than
BHT (13.80 ␮g/mL). 1,8-Cineole, ␣-pinene and camphene were held
responsible for the observed activity (Kadri et al., 2011).
Wafa et al. (2014) studied the antioxidant activity (DPPH rad-
ical scavenging assay) of leaf and root extracts and essential
oil of Tunisian R. communis. The EC50 values varied between
0.65–3.91 ␮g/mL and 1.03–5.78 ␮g/mL, for the leaves and root
extracts, respectively. This results are in agreement with those of
Singh et al. (2009) that showed the methanol extract as the most
active one with EC50 ranging between 0.65 and 3.91 ␮g/mL.
 P.R. Ribeiro et al. / Industrial Crops and Products 91 (2016) 358–376
2.4. Insecticidal activity
R. communis L. extracts possess insecticidal activity against pests
that affects several important crops (Mandal, 2010; Ramos-López
et al., 2012; Ramos-López et al., 2010; Rampadarath et al., 2014;
Wafa et al., 2014; Zahir et al., 2012). Rampadarath et al. (2014)
evaluated effect of R. communis crude extracts on Bactrocera zonata
and B. cucurbitae. The larvae of these two fruit fly species are very
adaptable to different climates and have the capacity to survive
on different host plants. This may cause serious economic losses
on fruit crop production (Rampadarath et al., 2014). The methanol
extract showed higher insecticidal activity than the ethyl acetate
extract on both larvae species. The LC50 against B. cucurbitae was
0.22 mg/mL for the methanol extract and 1.93 mg/mL for the ethyl
acetate extract. The LC50 of the methanol extract against B. zonata
was 2.88 mg/mL, whereas the ethyl acetate extract did not lead
to any mortality of the larvae (Rampadarath et al., 2014). Wafa
et al. (2014) investigated effect of aqueous extracts obtained from
R. communis seeds and leaves against Culex pipiens larvae. The
LC50 values for the seed extracts varied from 0.57 to 2.14 mg/mL,
whereas the leaves extracts ranged from 1.30 to 3.03 mg/mL.
Mandal (2010) assessed the larvicidal activity and adult emergence
inhibition seed extracts against Anopheles stephensi, Culex quinque-
fasciatus and Aedes albopictus. R. communis seed extracts exhibited
LC50 values of 7.10 ␮g/mL for Cx. quinquefasciatus, 11.64 ␮g/mL for
An. stephensi and 16.84 ␮g/mL for Ae. albopictus.
Ramos-López et al. (2010) assessed the of R. communis extracts
on Spodoptera frugiperda. This insect species has been identified as a
pest of many crops, especially maize causing losses as high as 57%
(Cruz et al., 1999; Nagoshi and Meagher, 2004). The LC50 values
varied from 0.75 × 103 to 1.97 × 103 ppm for the seed extracts and
from 4.83 × 103 to 10.01 × 103 ppm for the extract of leaves. This is
in accordance with the results of Wafa et al. (2014) who showed
that the leaves extracts screened for larvicidal activity against Cx.
pipiens were less effective as compared to seeds extracts.
Wachira et al. (2014) assessed the effect of methanol extracts
and two compounds identified from R. communis methanol leaf
extracts on Anopheles gambiae. Feeding time (exposure) showed
a strong effect on the toxicity of the extracts: mosquito that were
allowed to fed on the extracts for 3 days, showed significantly lower
than the mortality (LC50 of 8.69 mg/mL) than mosquito that were
allowed to fed on the extracts for 7 days (LC50 of 2.56 mg/mL). The
effect of the extracts on Anopheles gambiae larvae survival was also
assessed. High mortality was observed after 24 h of exposure (LC50
value of 0.40 mg/mL), similar to the positive control (Wachira et al.,
2014). Additionally, larval mortality after 72 h of exposure was sig-
nificantly higher than after 24 h of exposure with LC50 values of
0.18 mg/mL.
2.5. Other activities
Additionally, R. communis extracts were tested for acaricidal
(Rhipicephalus (Boophilus)) (Ghosh et al., 2013), antidiabetic (hypo-
glycemic) (Mann et al., 2013), antinociceptive (Taur et al., 2011),
antiasthmatic (Taur and Patil, 2011), anthelmintic (Rana et al.,
2013), antihistamine and anti-inflammatory (Lomash et al., 2010),
immunomodulatory (Kumar et al., 2011), contraceptive (Nath
et al., 2013), analgesic (Rajeshkumar et al., 2013), anticonvulsant
(Tripathi et al., 2011), contractile (rabbit uterine strips) (Kaingu
et al., 2012) activities, parasite mortality (Paramphistomum cervi)
(Zahir et al., 2012) and toxicity of R. communis pollen to honeybees
(de Assis Junior et al., 2011) (Table 1).
363
3. Chemical constituents of Ricinus communis and their
pharmacological activities
Eighty-three compounds were identified from R. communis
seeds, leaves, roots and stem extracts. This includes some alkaloids,
terpenoids, flavonoids, benzoic acid derivatives, coumarins, toco-
pherols, terpenoids and fatty acids. In the following sections, these
compounds are listed and their pharmacological activities dis-
cussed. Moreover, structure–activity relationships are presented
when appropriate.
3.1. Alkaloids
Alkaloids are a chemically diverse group of secondary metabo-
lites exploited due to their pharmacological activities (Facchini,
2001; Ndagijimana et al., 2013). Five alkaloids have been isolated
from R. communis (Table 3). Ricinine (1) has been found in R. com-
munis seeds, roots, cotyledons, leaves, flowers, fruits and stem (Bigi
et al., 2004; Ferraz et al., 1999; Kang et al., 1985; Khafagy et al., 1979;
Ohishi et al., 2014; Ribeiro et al., 2014b, 2015b; Singh et al., 2013;
Tang et al., 2012; Tripathi et al., 2011; Wachira et al., 2014). This
alkaloid is probably the most well-studied compound produced by
R. communis. Wachira et al. (2014) described the toxicity and lar-
vicidal activity of 1 and its carboxylic acid derivative (2) on the
vector of malaria (Anopheles gambiae) and they reported that both
compounds reduced survival levels when mosquito were fed with
these compounds as compared to the control. It seems, however,
that the substitution of the cyano group at carbon 3 of ricinine by a
carboxyl group has increased the survival time of female Anopheles
gambiae maintained on a 0.04 mg/mL solution of these compounds,
therefore reducing the toxicity and larvicidal activity of 2 when
compare to ricinine (Wachira et al., 2014). Ricinine (1) showed
anticonvulsant activity in mice (Tripathi et al., 2011), insecticidal
activity against Atta sexdens rubropilosa (Bigi et al., 2004), and anti-
inflammatory activity (Singh et al., 2013). It also showed stimulant
effects on the central nervous system of mices (Ferraz et al., 1999).
N-demethylricinine (3) was isolated from R. communis leaves,
but no pharmacological activity was evaluated (Kang et al., 1985).
Rumape et al. (2014) described the isolation of the compounds (4)
and (5) from R. communis seeds and their antifeedant effects on Epi-
lachna varivestis larvae. Compounds 4 inhibited Epilachna varivestis
larvae feeding by 58%, whereas compound 5 were able to inhibited
by 79%.
3.2. Flavonoids
Flavonoids comprises an important group of plant secondary
metabolites and can be classified in several subgroups (Falcone
Ferreyra et al., 2012). These compounds are produced from the
reaction between one molecule of cinnamoyl-CoA and three
molecules of malonyl-CoA (Falcone Ferreyra et al., 2012).
The flavonol quercetin (6) was isolated from roots and leaves
and showed antioxidant activity (DPPH radical-scavenging)
(Singh et al., 2009, 2013). Compound 6 possesses high DPPH
radical-scavenging ability with IC50 equal to 4.62 ␮g/mL. Four
quercetin derivatives were isolated from flowers, roots and
leaves: quercetin-3-O-␤-d-galactoside (7), quercetin-3-O-␤-
d-glucopyranoside (8), quercetin-3-O-␤-d-rutinoside (9) and
quercetin-3-O-␤-d-xylopyranoside (10). Compound 9 showed
higher DPPH radical-scavenging activity (IC50 = 9.46 ␮g/mL) than
its aglycone 6 (IC50 = 4.62 ␮g/mL). It is generally accepted that
the number of free hydroxyl groups is reduced by glycosylation.
These free hydroxyl groups are, however, crucial for the antioxi-
dant activity of phenolic compounds. Three kaempferol glycosyl
derivatives were isolated from R. communis leaves: kaempferol-
3-O-␤-d-glucopyranoside (11), kaempferol-3-O-␤-d-rutinoside
Table 3

364
Compounds, chemical structures, pharmacological activities, and tissues described in phytochemical and pharmacological studies of R. communis.

Number Compound Structure Activity tissue References

1 ricinine anti-inflammatory, root, leaves, Bigi et al. (2004), Ferraz

anticonvulsant, cotyledons, flowers, et al. (1999), Kang et al.
insecticidal (Atta fruits, stem (1985), Khafagy et al.
sexdens rubropilosa, (1979), Ohishi et al.
central nervous system (2014), Ribeiro et al.
stimulant effects, (2014b, 2015b), Singh
involved in the Wnt et al. (2013), Tang et al.
signaling pathway, (2012), Tripathi et al.
insecticidal and (2011), Wachira et al.
toxicity (Anopheles (2014)
gambiae)

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2 3-carboxy-4-methoxy- toxicity (Anopheles leaves Wachira et al. (2014)
N-methyl-2-pyridone gambiae)

3 N-demethylricinine NT leaves Kang et al. (1985)

4 methyl 5-(3-cyano-1- antifeedant (Epilachna seeds Rumape et al. (2014)

methyl-2-oxo-1,2- varivestis larvae)
dihydropyridine-4-il)
pentanoate

5 1-methyl-4-(4- antifeedant (Epilachna seeds Rumape et al. (2014)

metilpentiloksi) varivestis larvae)
pyridine-2 (1H)-on

6 quercetin anti-inflammatory, root, leaves Singh et al. (2009,

DPPH 2013)
radical-scavenging

7 quercetin-3-O-␤-d- NT flowers Khafagy et al. (1979)

galactoside

8 quercetin-3-O-␤-d- NT leaves Kang et al. (1985)

glucopyranoside
Table 3 (Continued)

Number Compound Structure Activity tissue References

9 quercetin-3-O-␤-d- DPPH roots, leaves and Kang et al. (1985),

rutinoside radical-scavenging flowers Khafagy et al. (1979),
Singh et al. (2009),
Wafa et al. (2014)

10 quercetin-3-O-␤-d- NT leaves Kang et al. (1985)

xylopyranoside

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11 kaempferol-3-O-␤-d- NT leaves Kang et al. (1985)
glucopyranoside

12 kaempferol-3-O-␤-d- NT leaves Kang et al. (1985)

rutinoside

13 kaempferol-3-O-␤-d- NT leaves Kang et al. (1985)

xylopyranoside

14 catechin NT roots and leaves Wafa et al. (2014)

15 epicatechin DPPH leaves Singh et al. (2009),

radical-scavenging, Zahir et al. (2012)
parasite mortality
(Paramphistomum
cervi)

16 luteolin NT roots Tang et al. (2012)

365
 366
Table 3 (Continued)

Number Compound Structure Activity tissue References

17 vitexin NT roots and leaves Wafa et al. (2014)

18 ellagic acid DPPH leaves Singh et al. (2009)

radical-scavenging

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19 gallic acid DPPH roots and leaves Singh et al. (2009),
radical-scavenging Tang et al. (2012), Wafa
et al. (2014)

20 gentisic acid DPPH roots and leaves Singh et al. (2009),

radical-scavenging Wafa et al. (2014)

21 vanillic acid NT roots and leaves Wafa et al. (2014)

22 3,4-dimethoxy-6,8- NT flowers Khafagy et al. (1979)

dihydroxy
coumarin

23 isofraxidine NT leaves Bigi et al. (2004)

24 scopoletin NT leaves Bigi et al. (2004)

25 ␣-tocopherol involved in roots and cotyledons Ribeiro et al. (2014b)

temperature tolerance

26 ␤-tocopherol involved in roots and cotyledons Ribeiro et al. (2014b)

temperature tolerance
Table 3 (Continued)

Number Compound Structure Activity tissue References

27 ı-tocopherol involved in roots and cotyledons Ribeiro et al. (2014b)

temperature tolerance

28 -tocopherol involved in roots and cotyledons Ribeiro et al. (2014b)

temperature tolerance

29 (2R,4aR,8aR)-3,4,4a,8a- NT leaves Tan et al. (2009)

tetrahydro-4a-
hydroxy-2,6,7,8a-
tetramethyl-2-(4,8,12-

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trimethyltridecyl)-2H-
chromene-5,8-dione

30 ␣-thujone NT leaves Kadri et al. (2011)

31 1,8-cineole NT leaves Kadri et al. (2011)

32 ␣-pinene NT leaves Kadri et al. (2011)

33 camphor NT leaves Kadri et al. (2011)

34 camphene NT leaves Kadri et al. (2011)

35 ficusic acid inhibition of leaves Li et al. (2014)

11␤-hydroxysteroid
dehydrogenase
(diabetes)

36 phytol inhibition of roots, leaves and Li et al. (2014), Ribeiro

11␤-hydroxysteroid cotyledons et al. (2014b)
dehydrogenase
(diabetes)

37 callyspinol inhibition of leaves Li et al. (2014)

11␤-hydroxysteroid
dehydrogenase
(diabetes)

367
 368
Table 3 (Continued)

Number Compound Structure Activity tissue References

38 (+)-beyerene NT whole seedlings Robinson and West

(1970a,b)

39 (+)-cembrene NT whole seedlings Robinson and West

(1970a,b)

40 (−)-kaurene NT whole seedlings Robinson and West

(1970a,b)

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41 (+)- NT whole seedlings Robinson and West
sandaracopimaradiene (1970a,b)

42 (−)-trachylobane NT whole seedlings Robinson and West

(1970a,b)

43 casbene NT whole seedlings Sitton and West (1975)

44 (3E,7Z,11E)-19- NT leaves Tan et al. (2009)

hydroxycasba-3,7,11-
trien-5-one

45 6a-hydroxy- NT leaves Tan et al. (2009)

10bmethoxy-7a,8a-
epoxy-5-oxocasbane-
20,10-olide

46 campesterol involved in roots and cotyledons Ribeiro et al. (2014b)

temperature tolerance
Table 3 (Continued)

Number Compound Structure Activity tissue References

47 ␤-sitosterol involved in roots and cotyledons Ribeiro et al. (2014b)

temperature tolerance

48 stigmasterol involved in roots and cotyledons Ribeiro et al. (2014b),

temperature tolerance Tang et al. (2012)

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49 3-O-␤-d- involved in the Wnt leaves and stem Bigi et al. (2004),
glycosylsitosterol signaling pathway Ohishi et al. (2014)

50 7-oxo-␤-sitosterol involved in the Wnt stem Ohishi et al. (2014)

signaling pathway

51 stigmasterol arachidate NT roots Mittal and Ali (2012)

52 stigmasterol oleate NT roots Mittal and Ali (2012)

53 stigmasterol stearate NT roots Mittal and Ali (2012)

54 stigmast4-en-3-one inhibition of leaves Li et al. (2014)

11␤-hydroxysteroid
dehydrogenase
(diabetes)

369
 370
Table 3 (Continued)

Number Compound Structure Activity tissue References

55 stigmast-4-en-6␤-ol- inhibition of leaves Li et al. (2014)

3-one 11␤-hydroxysteroid
dehydrogenase
(diabetes)

56 stigmast4-en-3,6- inhibition of leaves Li et al. (2014)

dione 11␤-hydroxysteroid
dehydrogenase
(diabetes)

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57 3-O-␤-d- NT leaves Bigi et al. (2004)
glycosylstigmasterol

58 erandone anti-inflammatory roots Srivastava et al. (2014)

59 lupeol anti-inflammatory roots, stem and Li et al. (2014), Ohishi

cotyledons et al. (2014), Ribeiro
et al. (2014b),
Srivastava et al. (2014),
Tang et al. (2012)

60 30-nor-lupan-3␤-ol- inhibition of leaves Li et al. (2014)

20-one 11␤-hydroxysteroid
dehydrogenase
(diabetes)

61 lup-20(29)-en-3␤,15␣- inhibition of leaves Li et al. (2014)

diol 11␤-hydroxysteroid
dehydrogenase
(diabetes)
Table 3 (Continued)

Number Compound Structure Activity tissue References

62 acetylaleuritolic acid inhibition of leaves Li et al. (2014)

11␤-hydroxysteroid
dehydrogenase
(diabetes)

63 lup-20(29)-en-15␣-ol- NT leaves Tan et al. (2009)

3-one

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64 3-O-[␤-d- antibacterial seeds Acharya and Khan
glucuronopyranosyl- (2013)
(1->3)-␣-l-
rhamnopyranosyl-(1-
>2)␤-d-
glucopyranosyl]-
4␣,20␣-
di(hydroxymethyl)olean-
12-en-28-oic
acid

65 ricinoleic acid NT seeds, roots and leaves Oloyede (2012), Wafa

et al. (2014)

66 linoleic acid insectistatic and roots, leaves and seeds Oloyede (2012),
insecticidal (Spodoptera Ramos-López et al.
frugiperda) (2012), Wafa et al.
(2014)

67 linolenic acid insectistatic and seeds Ramos-López et al.

insecticidal (Spodoptera (2012)
frugiperda)

68 palmitic acid NT seeds, roots and leaves Ramos-López et al.

(2012), Ribeiro et al.
(2014b), Tang et al.
(2012), Wafa et al.
(2014)

69 stearic acid NT roots, leaves and seeds Ramos-López et al.

(2012), Wafa et al.
(2014)

70 methyl ricinoleate NT seeds Oloyede (2012)

371
Table 3 (Continued)

372
Number Compound Structure Activity tissue References

71 methyl linoleate NT seeds Oloyede (2012)

72 aleuritic acid NT roots Tang et al. (2012)

73 gondoic acid NT roots and leaves Wafa et al. (2014)

74 oleic acid NT roots and leaves Wafa et al. (2014)

75 1-palmitic acid glycerol NT leaves Bigi et al. (2004)

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ester

76 1-palmitic acid NT leaves Bigi et al. (2004)

glycerol-2,3-
dimethylketal
ester

77 n-heptacosanyl oleate NT roots Mittal and Ali (2012)

78 triricinolein NT roots Tang et al. (2012)

79 arachidoyl arabinoside NT roots Mittal and Ali (2012)

80 n-butyl NT roots Mittal and Ali (2012)

ricicommunioate

81 ethyl NT roots Tang et al. (2012)

brevifolincarboxylate

82 n-hexatriacont-14-ene NT roots Mittal and Ali (2012)

83 methyl communisoate NT roots Mittal and Ali (2012)

NT = not tested.
 P.R. Ribeiro et al. / Industrial Crops and Products 91 (2016) 358–376
(12) and kaempferol-3-O-␤-d-xylopyranoside (13) (Kang et al.,
1985). The flavanols catechin (14) and epicatechin (15) were
isolated from R. communis roots and leaves (Singh et al., 2009;
Wafa et al., 2014; Zahir et al., 2012). The DPPH radical-scavenging
activity of 15 (IC50 = 5.82 ␮g/mL) is reported by (Singh et al., 2009).
Compound 15 has the same number of hydroxyl groups than 6,
but the absence of the 2,3-double bond conjugated with the 4-oxo
function justifies the higher IC50 of 15. Additionally, compound
15 showed anti-parasitic activity against Paramphistomum cervi
(Zahir et al., 2012). The flavones luteolin (16) and vitexin (17) were
isolated R. communis roots and leaves. Compounds 7, 8, 10–13, 16
and 17 were not tested for any pharmacological activity.
3.3. Benzoic acid derivatives
Ellagic (18), gallic (19), gentisic (20) and vanillic acids (21) were
isolated from R. communis roots and leaves. Compounds 18, 19 and
20 showed high DPPH radical-scavenging activity with IC50 equal
to 2.52, 3.15 and 2.92 ␮g/mL, respectively. The observed activity
is due to the presence of the o- and p-dihydroxybenzene system,
which is an enhancer of the antioxidant activity (Cai et al., 2006;
Singh et al., 2009).
3.4. Coumarins
Three coumarins were isolated from R. communis: 3,4-
dimethoxy-6,8-dihydroxy coumarin (22) from the flowers
(Khafagy et al., 1979) and isofraxidine (23) and scopoletin
(24) from the leaves (Bigi et al., 2004). Compounds 22–24 were
not tested for any pharmacological activity.
3.5. Tocopherols
␣-, ␤-, ␦-, and ␥-Tocopherol (25–28) were identified in R.
communis roots and cotyledons (Ribeiro et al., 2014b). These com-
pounds have been associated with the biochemical responses of this
species to environmental stresses. In the cotyledons, ␣-tocopherol
(25) levels increased at high temperatures (35 ◦ C), whereas in the
roots, no variation was observed in response to temperature. ␤- and
␦-tocopherol (26–28) showed a similar behavior, but to a lesser
extent. These compounds act by protecting cells from oxidative
damages caused by high temperature. Compound 29 was isolated
from R. communis leaves, but no activity is reported.
3.6. Terpenoids
Terpenoids comprises a chemically rich and diverse group natu-
ral products and are originate from the C5 substrates dimethylallyl
diphosphate (DMAPP) and isopentenyl diphosphate (IPP). Geranyl
diphosphate (GPP), farnesyl diphosphate (FPP), and geranylgeranyl
diphosphate (GGPP) are formed by the condensation of DMAPP
with one or more IPP molecules (Oldfield and Lin, 2012). DMAPP
and IPP can be produced by the mevalonate (Miziorko, 2011) and
methylerythritol phosphate (MEP) (Rohmer, 2008) pathways. The
mevalonate pathway in mostly present in eukaryotes, archaea, and
some eubacteria (Miziorko, 2011), whereas methylerythritol phos-
phate pathway is found in most eubacteria (Rohmer, 2008). Sterols
and triterpenes are produced by the mevalonate pathway, whereas
hemi-, mono-, di- and tetraterpenes are produced by the MEP path-
way (Miziorko, 2011; Oldfield and Lin, 2012; Rohmer, 2008).
3.6.1. Monoterpenoids
␣-Thujone (30), 1,8-cineole (31), ␣-pinene (32), camphor (33)
and camphene (34) were identified in the essential oil obtained
from R. communis leaves (Kadri et al., 2011), whereas ficusic acid
(35) was obtained from the methanol extracts R. communis leaves
373
(Li et al., 2014). Compound 35 showed significant in vitro inhibitory
activity and good selectivity against 11-beta hydroxysteroid dehy-
drogenase (11␤-HSD) of mouse and human (Li et al., 2014).
3.6.2. Diterpenoids
Phytol (36) was detected in R. communis roots, leaves and cotyle-
dons (Li et al., 2014; Ribeiro et al., 2014b). Callypsinol (37) was
obtained from the methanol extract of R. communis leaves and
together with 36 showed significant in vitro inhibitory activity
and good selectivity against 11␤-HSD of mouse and human (Li
et al., 2014). (+)-Beyerene (38), (+)-cembrene (39), (−)-kaurene
(40), (+)-sandaracopimaradiene (41) and (−)-trachylobane (42)
were identified in a pioneer study conducted by Robinson and
West (1970a,b) in which soluble enzyme preparations from 60-h-
old R. communis converted mevalonate into a mixture of diterpenes
38-42. Casbene (43) was produced from mevalonic acid by 2.5-day-
old seedlings exposed to cultures of Rhizopus stolonifer, Aspergillus
niger and Fusurium monilijkme. Casbene (43) is reported to act as a
phytoalexin (Sitton and West, 1975). Compounds 44 and 45 were
isolated from R. communis leaves, but no activity is reported (Tan
et al., 2009).
3.6.3. Sterols
Campesterol (46), ␤-sitosterol (47) and stigmasterol (48) were
detected in the roots and cotyledons of young R. communis
seedlings growing in different temperatures (Ribeiro et al., 2014b).
3-O-␤-d-glycosylsitosterol (49) and 7-oxo-␤-sitosterol (50) were
isolated from R. communis leaves and stem (Bigi et al., 2004; Ohishi
et al., 2014). Stigmasterol arachidate (51), stigmasterol oleate (52)
and stigmasterol stearate (53) were isolated from the roots of R.
communis (Mittal and Ali, 2012), whereas stigmast4-en-3-one (54),
stigmast-4-en-6␤-ol-3-one (55), stigmast4-en-3,6-dione (56) and
3-O-␤-d-glycosylstigmasterol (57) were isolated from the leaves
(Bigi et al., 2004; Li et al., 2014). Compounds 54–56 showed in vitro
inhibitory activity against 11␤-HSD of mouse and human (Li et al.,
2014).
3.6.4. Triterpenoids
Srivastava et al. (2014) reported the isolation and identification
of two triterpenes from the root of R. communis: a new diketone
pentacyclic triterpene (58) and one known compound, lupeol (59).
These compounds showed moderate anti-inflammatory activity,
compound 58 being the most active compound (Srivastava et al.,
2014). 30-nor-lupan-3␤-ol-20-one (60), lup-20(29)-en-3␤,15␣-
diol (61) and acetylaleuritolic acid (62) were isolated from R.
communis leaves and showed in vitro inhibitory activity against
11␤-HSD of mouse and human (Li et al., 2014).
Lup-20(29)-en-15␣-ol-3-one (63) was isolated from R. commu-
nis leaves (Tan et al., 2009), whereas compound 64, a new oleanene
triterpenoid, was isolated from seeds (Acharya and Khan, 2013).
Compound 64 showed MIC of 260 ␮g/mL against E. coli, 235 ␮g/mL
against Klebsiella pneumoniae and 350 ␮g/mL against Staphylococ-
cus aureus.
3.7. Fatty acids
Ricinoleic acid (12-hydroxyoctadeca-9-enoic acid) (65) is an
hydroxylated fatty acid of particular interest to the chemical indus-
try (Bafor et al., 1991). R. communis endosperm accumulates over
80% of this fatty acid. Although, 65 is mainly found in R. communis
endosperm it was also isolated from its roots and leaves (Oloyede,
2012; Wafa et al., 2014).
Four fatty acids were detected in the hexane leaf and seed
extracts of R. communis by GC–MS: linoleic acid (66), linolenic acid
(67), palmitic acid (68), and stearic acid (69) (Ramos-López et al.,
374 P.R. Ribeiro et al. / Industrial Crops and Products 91 (2016) 358–376
2012; Ribeiro et al., 2015b, 2015c). The insectistatic and insecti-
cidal activities of compounds 66 and 67 was assessed Spodoptera
frugiperda. The larval viability fifty (LV50 ) values were 849 ppm for
compound 66 and 857 ppm for compound 67. The double bond
between C15 and C16 of linolenic acid (67) seems to have increased
the LV50 as compared to linoleic acid (66). Compounds 66–69 were
also isolated from R. communis roots and seeds (Oloyede, 2012;
Ribeiro et al., 2014b; Tang et al., 2012; Wafa et al., 2014). Oloyede
(2012) reported the identification of methyl ricinoleate (70) and
methyl linoleate (71) from R. communis seeds, but it is mostly
likely that these compounds are an artifact product of the extrac-
tion procedure, in which methanol was used. Aleuritic acid (72)
was isolated from R. communis roots (Tang et al., 2012) and gon-
doic acid (73) and oleic acid (74) were detected in the leaves and
roots (Wafa et al., 2014). 1-Palmitic acid glycerol ester (75) and 1-
palmitic acid glycerol-2,3-dimethylketal ester (76) were isolated
from R. communis leaves (Bigi et al., 2004). n-Heptacosanyl oleate
(77) and triricinolein (78) were isolated from R. communis roots
(Mittal and Ali, 2012; Tang et al., 2012). No pharmacological activity
is reported for compounds 65, 68–78.
3.8. Other compounds
Arachidoyl arabinoside (79), n-butyl ricicommunioate (80),
ethyl brevifolincarboxylate (81), n-hexatriacont-14-ene (82) and
methyl communisoate (83) were isolated from R. communis roots
(Mittal and Ali, 2012; Tang et al., 2012), but no pharmacological
activity is reported.
4. Concluding remarks
This review presented 83 compounds isolated from R. com-
munis, including alkaloids, terpenoids, flavonoids, benzoic acid
derivatives, coumarins, tocopherols, terpenoids and fatty acids.
Leaf was the most well-studied part of the plant, followed by
extracts from the seeds and roots. Maceration and soxhlet were
the extraction methods chosen by 76% of the studies, whereas
methanol, ethanol, water and ethyl acetate were used in 78% of
the studies. Antibacterial activity was the most extensively studied
pharmacological activity of R. communis extracts, but many other
activities are attributed to R. communis extracts, such as cytotox-
icity, antioxidant, insecticidal, antiasthmatic, anti-inflammatory,
and many others. Therefore, R. communis presents a great chemi-
cal diversity which is reflected in the pharmacological activity of
the extracts obtained from this plant, as well as of the isolated
compounds. Several factors contribute to R. communis importance,
including its worldwide geographic distribution, long history of
use in traditional medicine, and the abundance and diversity of
secondary metabolites with promising pharmacological activities.
Taken together, this factors stimulated an increasing interest in the
isolation and identification of R. communis compounds. The phar-
macological activities of some of the isolated compounds have not
been investigated and, therefore, a comprehensive investigation of
these compounds is still necessary. In this context, this species is
a promising candidate as an alternative source of bioactive com-
pounds to be used in studies aiming at developing new natural
product based drugs.
Conflict of interest
The authors declare that they have no conflict of interest.
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