Industrial Crops and Products: Paulo R. Ribeiro, Renato D. de Castro, Luzimar G. Fernandez
Industrial Crops and Products: Paulo R. Ribeiro, Renato D. de Castro, Luzimar G. Fernandez
Industrial Crops and Products: Paulo R. Ribeiro, Renato D. de Castro, Luzimar G. Fernandez
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
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
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.
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 Zarai et al. (2012) studied the antimicrobial activity of R. com-
B. subtilis that varied from 5 to 10 mm. Many classes of secondary munis essential oil against B. subtilis and B. cereus. The essential
metabolites were detected in these extracts, including alkaloids and oil showed minimal inhibition concentration (MIC) of 480 and
phenolic compounds (Table 2) (Khafagi, 2007). Naz and Bano (2012) 300 g/mL against B. subtilis and B. cereus, respectively (Zarai et al.,
showed that R. communis methanol, ethanol and aqueous extracts 2012). Two monoterpenes, ␣-thujone and 1,8-cineole, comprised
exhibited relative percentage inhibition against B. subtilis of 74.9%, more than 60% of the essential oil, whereas ␣-pinene, camphor
70.0% and 51.3%, respectively. Penicillin was used as reference drug and camphene summed up to 37% of the essential oil (Table 2).
for the determination of the relative percentage inhibition (Naz and Rampadarath et al. (2014) evaluated the chemical composition
Bano, 2012). Oyewole et al. (2010) investigated the antimicrobial and antimicrobial activity of extracts from R. communis growing in
properties of leaf extracts and reported that these extracts showed Mauritius. Ethyl acetate and methanol leaf extracts showed mini-
inhibition zones against B. subtilis of 7 mm. They also reported the mal inhibitory concentrations that varied from 1 to 75 g/L against
presence of several phenolic compounds, cardiac glycosides and B. algicola and B. cereus. Alkaloids, coumarins, flavanoids, tannins
terpenoids (Table 2) (Oyewole et al., 2010). Similarly, Vandita et al. and phenols were detected in the extracts (Table 2) (Rampadarath
(2013) assessed the antibacterial activity of methanol leaf extract et al., 2014).
against B. subtilis. This extract showed inhibition zones of 6 mm
(Vandita et al., 2013).
362 P.R. Ribeiro et al. / Industrial Crops and Products 91 (2016) 358–376
364
Compounds, chemical structures, pharmacological activities, and tissues described in phytochemical and pharmacological studies of R. communis.
365
366
Table 3 (Continued)
367
368
Table 3 (Continued)
369
370
Table 3 (Continued)
66 linoleic acid insectistatic and roots, leaves and seeds Oloyede (2012),
insecticidal (Spodoptera Ramos-López et al.
frugiperda) (2012), Wafa et al.
(2014)
371
Table 3 (Continued)
372
Number Compound Structure Activity tissue References
NT = not tested.
P.R. Ribeiro et al. / Industrial Crops and Products 91 (2016) 358–376 373
(12) and kaempferol-3-O--d-xylopyranoside (13) (Kang et al., (Li et al., 2014). Compound 35 showed significant in vitro inhibitory
1985). The flavanols catechin (14) and epicatechin (15) were activity and good selectivity against 11-beta hydroxysteroid dehy-
isolated from R. communis roots and leaves (Singh et al., 2009; drogenase (11-HSD) of mouse and human (Li et al., 2014).
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). 3.6.2. Diterpenoids
Compound 15 has the same number of hydroxyl groups than 6, Phytol (36) was detected in R. communis roots, leaves and cotyle-
but the absence of the 2,3-double bond conjugated with the 4-oxo dons (Li et al., 2014; Ribeiro et al., 2014b). Callypsinol (37) was
function justifies the higher IC50 of 15. Additionally, compound obtained from the methanol extract of R. communis leaves and
15 showed anti-parasitic activity against Paramphistomum cervi together with 36 showed significant in vitro inhibitory activity
(Zahir et al., 2012). The flavones luteolin (16) and vitexin (17) were and good selectivity against 11-HSD of mouse and human (Li
isolated R. communis roots and leaves. Compounds 7, 8, 10–13, 16 et al., 2014). (+)-Beyerene (38), (+)-cembrene (39), (−)-kaurene
and 17 were not tested for any pharmacological activity. (40), (+)-sandaracopimaradiene (41) and (−)-trachylobane (42)
were identified in a pioneer study conducted by Robinson and
3.3. Benzoic acid derivatives West (1970a,b) in which soluble enzyme preparations from 60-h-
old R. communis converted mevalonate into a mixture of diterpenes
Ellagic (18), gallic (19), gentisic (20) and vanillic acids (21) were 38-42. Casbene (43) was produced from mevalonic acid by 2.5-day-
isolated from R. communis roots and leaves. Compounds 18, 19 and old seedlings exposed to cultures of Rhizopus stolonifer, Aspergillus
20 showed high DPPH radical-scavenging activity with IC50 equal niger and Fusurium monilijkme. Casbene (43) is reported to act as a
to 2.52, 3.15 and 2.92 g/mL, respectively. The observed activity phytoalexin (Sitton and West, 1975). Compounds 44 and 45 were
is due to the presence of the o- and p-dihydroxybenzene system, isolated from R. communis leaves, but no activity is reported (Tan
which is an enhancer of the antioxidant activity (Cai et al., 2006; et al., 2009).
Singh et al., 2009).
3.6.3. Sterols
3.4. Coumarins
Campesterol (46), -sitosterol (47) and stigmasterol (48) were
detected in the roots and cotyledons of young R. communis
Three coumarins were isolated from R. communis: 3,4-
seedlings growing in different temperatures (Ribeiro et al., 2014b).
dimethoxy-6,8-dihydroxy coumarin (22) from the flowers
3-O--d-glycosylsitosterol (49) and 7-oxo--sitosterol (50) were
(Khafagy et al., 1979) and isofraxidine (23) and scopoletin
isolated from R. communis leaves and stem (Bigi et al., 2004; Ohishi
(24) from the leaves (Bigi et al., 2004). Compounds 22–24 were
et al., 2014). Stigmasterol arachidate (51), stigmasterol oleate (52)
not tested for any pharmacological activity.
and stigmasterol stearate (53) were isolated from the roots of R.
communis (Mittal and Ali, 2012), whereas stigmast4-en-3-one (54),
3.5. Tocopherols
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
␣-, -, ␦-, and ␥-Tocopherol (25–28) were identified in R.
(Bigi et al., 2004; Li et al., 2014). Compounds 54–56 showed in vitro
communis roots and cotyledons (Ribeiro et al., 2014b). These com-
inhibitory activity against 11-HSD of mouse and human (Li et al.,
pounds have been associated with the biochemical responses of this
2014).
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 3.6.4. Triterpenoids
␦-tocopherol (26–28) showed a similar behavior, but to a lesser Srivastava et al. (2014) reported the isolation and identification
extent. These compounds act by protecting cells from oxidative of two triterpenes from the root of R. communis: a new diketone
damages caused by high temperature. Compound 29 was isolated pentacyclic triterpene (58) and one known compound, lupeol (59).
from R. communis leaves, but no activity is reported. These compounds showed moderate anti-inflammatory activity,
compound 58 being the most active compound (Srivastava et al.,
3.6. Terpenoids 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.
Terpenoids comprises a chemically rich and diverse group natu- communis leaves and showed in vitro inhibitory activity against
ral products and are originate from the C5 substrates dimethylallyl 11-HSD of mouse and human (Li et al., 2014).
diphosphate (DMAPP) and isopentenyl diphosphate (IPP). Geranyl Lup-20(29)-en-15␣-ol-3-one (63) was isolated from R. commu-
diphosphate (GPP), farnesyl diphosphate (FPP), and geranylgeranyl nis leaves (Tan et al., 2009), whereas compound 64, a new oleanene
diphosphate (GGPP) are formed by the condensation of DMAPP triterpenoid, was isolated from seeds (Acharya and Khan, 2013).
with one or more IPP molecules (Oldfield and Lin, 2012). DMAPP Compound 64 showed MIC of 260 g/mL against E. coli, 235 g/mL
and IPP can be produced by the mevalonate (Miziorko, 2011) and against Klebsiella pneumoniae and 350 g/mL against Staphylococ-
methylerythritol phosphate (MEP) (Rohmer, 2008) pathways. The cus aureus.
mevalonate pathway in mostly present in eukaryotes, archaea, and
some eubacteria (Miziorko, 2011), whereas methylerythritol phos- 3.7. Fatty acids
phate pathway is found in most eubacteria (Rohmer, 2008). Sterols
and triterpenes are produced by the mevalonate pathway, whereas Ricinoleic acid (12-hydroxyoctadeca-9-enoic acid) (65) is an
hemi-, mono-, di- and tetraterpenes are produced by the MEP path- hydroxylated fatty acid of particular interest to the chemical indus-
way (Miziorko, 2011; Oldfield and Lin, 2012; Rohmer, 2008). try (Bafor et al., 1991). R. communis endosperm accumulates over
80% of this fatty acid. Although, 65 is mainly found in R. communis
3.6.1. Monoterpenoids endosperm it was also isolated from its roots and leaves (Oloyede,
␣-Thujone (30), 1,8-cineole (31), ␣-pinene (32), camphor (33) 2012; Wafa et al., 2014).
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from R. communis leaves (Kadri et al., 2011), whereas ficusic acid extracts of R. communis by GC–MS: linoleic acid (66), linolenic acid
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