|Zephyranthes; Amaryllidaceae alkaloids; Ceramides;
Anticancer; Acetylcholinesterase inhibition.
|Zephyranthes is a genus of bulbous perennials belonging to family
Amaryllidaceae. This family is one of the top 20 most widely used
plant families well known for its ornamental value. The plants of this
family are used by native peoples of different countries for treating
various diseases. The genus Zephyranthes is one amongst 75 genera
under this family [1,2]. It consists of about 90 species and out of
which few have been studied for their chemical constituents [3,4]. The
phytochemical work on this genus revealed the diversity of compounds
especially alkaloids having various pharmacological activities. The
name Zephyranthes is derived from word ‘Zephyrus’ means the Greek
God of west wind that reawakened nature each spring and ‘anthos’
meaning flower. Common name for the species in this genus are fairy
lily, rain flower, zephyr lily, magic lily, rain lily . The present review
summarises the phytochemical and pharmacological studies within the
|The genus Zephyranthes is native to western hemisphere and to
the higher altitudes like Mexico, Argentina where the species possesses
greatest cold hardiness potential. The genus has been naturalised and
cultivated as ornamental plant in places like India, Hawaii, Indonesia,
Thailand etc. Some species of this genus are widespread whereas some
are confined to small geographical area. Broadly these plants are
distributed in temperate to tropical areas of the world [6,7].
|Morphology and taxonomy
|The genus Zephyranthes vary in bulb, flower and leaf characteristics
i.e. size, color etc. The species belonging to this genus are perennial
bulbs which tolerate many natural habitats i.e. from wet soil to dry
conditions. Bulbs are covered with dark brown or black tunica and
contractile roots. Bulbs size varies from 2.5 to 5cm in diameter .
The leaves are deciduous with sheathing basis and have linear blades.
The size of leaves varies from tiny to broad. Flowers are funnel shaped
having six petals and more often appears in spring and summer. These
have general tendency to bloom after a heavy rain therefore named as
rain lily. The flowers of this genus are solitary, declinate, point straight
upward and have equal stamen length [3,7,8]. Seeds are D-shaped or wedge shaped. Zephyranthes bulbs can flower several times during one
season and the flower last after one to two days. Leaves may or may
not be present during flowering. Beautiful flowers of this genus have
increased its ornamental value. Flower color ranges from white, yellow,
pink, sometimes contains various tints of yellow to sulphur. Some
species have sweet fragrant flowers [9,10].
|Zephyranthes genus is scientifically classified under phylum
Angiospermae, order Asparagales, family Amaryllidaceae and tribe
Hippeastreae. This genus comprises about 90 species according to
World checklist of selected plant families out of which few have been
studied phytochemically [7,4].
|The genus Zephyranthes has been used as folk medicine in many
countries. Plant parts like bulbs and leaves have been used for the
treating various diseases. In the history of Peru Z. parulla had been
used for the treatment of tumors, in China Z. rosea used for treatment
of breast cancer. The leaves of Z. candida have been used by indigenous
peoples in Africa for treatment of diabetes mellitus. In India bulb
extracts of Z. rosea and Z. flava had been used for variety of therapeutic
purposes, e.g. treatment of diabetes, for ear and chest ailments and
against viral infections. Traditional usage of this genus from very
simple health problems like head ache, cough and cold, boils to very
complicated diseases like breast cancer, tuberculosis, rheumatism,
tumors shows its importance in treatment of various diseases [2,11,12].
|The family Amaryllidaceae is known to contain characteristic
alkaloids known as Amaryllidaceae alkaloids (AAs) mainly responsible
for different pharmacological activities [1-2]. Phytochemical
investigation on Zephyranthes has been initiated in 19th century.
Different researchers have reported many compounds from this
genus which includes alkaloids, flavonoids, flavans, gibberllins,
phospholipids, sterols, lectins, terpenoids and ceramides [13-39] but
most of the reports focused on alkaloids. The skeleton types of AAs
reported from this genus are lycorine, homolycorine, crinine and
haemanthamine, tazettine, pancratistatin, galanthamine types. Table 1
summarize the chemical constituents reported in different species of
this genus. Figure 1 shows the chemical structure of the compounds
isolated from the genus. To the best of our knowledge about seventy
alkaloids have been isolated from this genus.
|The initial phytochemical investigation had been done in 1940s
by Greathouse, and he reported the presence of an alkaloid ‘lycorine’
already reported from plants of Amaryllidaceae family, in bulbs and
root tissues of Z. texana . Later on in 1950s Boit et al., reported
AAs from different species of Zephyranthes i.e. lycorine, nerinine,
haemanthamine, tazettine from Z. candida; lycorenine, galanthine,
haemanthamine from Z. citrina; lycorine, galanthine, tazettine,
haemanthamine from Z. carinata, lycorine, galanthamine from Z. rosea; haemanthamine and galanthamine from Z. andersoniana [14-16]. In 1960s, a flavonoids, rutin and alkaloids lycorine, tazettine,
nerinine, haemanthidine and zephyranthine were reported from the
petals and bulbs of Z. candida respectively [17-20]. In the same decade,
Dopke et al., reported a new alkaloid tubispacin along with lycorine,
powellin, nerispin from the bulbs of Z. tubispatha and Maheshwari
et al., reported a gibberellin like substance from Z. lancasteri during
seed development [21-22]. At the end of this decade Rao reported lycorine and haemanthamine from Z. robusta .Thereafter different
groups had investigated this genus and in 1970s the presence of
AAs, pretazettine, carinatine, lycorine, galanthine, haemanthamine,
maritidine in bulbs of Z. carinata, Z. robusta and Z. sulphurea; a
flavonoid glycoside, kaempferol-3-O-rhamnoglucoside in flowers of Z. candida was reported [24-27].
|In 1980s Pettit et al., and Ghosal et al., reported alkaloids,
pancratistatin, (+)-epimaritidine, crinamine and haemanthamine,
maritidine, ungeremine, criasbetaine, zefbetaine, zeflabetaine,
alkaloidal phospholipids, two lactam alkaloid, three glucosyloxy
alkaloid; flavans, 7-hydroxy-3’,4’-methylenedioxyflavan and its
glycoside, 7,4’-dihydroxy-3’-methoxyflavan and 7-methoxy-
2’-hydroxy-4’,5’-methylenedioxyflavan from bulbs and flowers
of different species [28-32]. In 1990s, Pettit et al., Kojima et al.,
reported trans-dihydronarciclasine: an antineoplastic compound,
1-O-(3-hydroxybutyryl) pancratistatin and 1-O-(3-O-β-dglucopyranosylbutyryl)
pancratistatin from Z. carinata and Z. candida
[33,34]. In 2001 Nagatsu et al., Herrera et al., and Mutsuga et al., reported
alkaloids oxomaritidine, maritidine, hemanthamine, haemanthidine,
vittatine, lycorine, galanthine, narcissidine, 4,5-ethano-2,8-dimethoxy-
9-hydroxy-phenantridine, 1-O-(3-hydroxybutyryl) pancratistatin ,
1-O-(3-O-β-d-glucopyranosylbutyryl) pancratistatin, pancratistatin,
tortuosine, galanthine, carinatine, trispharidine, hamayne from Z. citrina and Z. carinata [33-37]. In 2006, a novel mannose binding lectin
was purified from bulbs of Z. candida .
|In 2009-10, three reports showed the presence of ceramides in
the genus. This was the first report of ceramides from this family. The
ceramides: zephyranamide A, zephyranamide B, zephyranamide C,
zephyranamide D, candidamide A and candidamide B were isolated from the bulbs of Z.candida [39-41]. During this decade flavans,
sterols were also reported from the same species . In past five
years, the work on this genus was accelerated with isolation of
new alkaloids by different researchers, Reyes-chilpa et al., in 2011
reported chlidanthine, galanthamine, galanthamine-N-oxide
from bulbs of Z.concolor , Luo et al., in 2012 reported seven
new alkaloids, N-methylhemeanthidine chloride, N-methyl-5,6-
ine, N-ethoxycarbonyl propylcrinasiadine, N-phenethylcrinasiadine,
N-isopentylcrinasiadine from whole plant of Z. candida ; in 2013
Katoch et al., reported Zephgrabetaine, a new betaine alkaloid from
bulbs of Z. grandiflora ; in 2014 Shitara et al., reported a new
homolycorine type alkaloid 2-hydroxyalbomaculine along with three
new crinine type alkaloid 6α-hydroxyhippeastidine, 10-deoxy-6α-
hydroxyhippeastidine and 6β-hydroxyhippeastidine from aerial part of
Z. candida  and revised NMR for an alkaloid from Z. robusta given
by Safratova et al., for 9-O-demethylgalanthamine . To the best of
our knowledge different compounds reported till August 2015 in this
genus are compiled in this review.
|Along with isolation of pure compounds different researchers
have applied modern hyphenated techniques like GC/MS, LC/MS
for chemical profiling of extracts. Compounds mainly alkaloids were
identified on the basis of their characteristic mass fragmentation
pattern. Reports showing GC/MS based chemical profiling, identified
galanthamine, lycoramine, vittatine, nerbowdine, haemanthamine,
tazettine, galanthine in bulbs of Z. robusta and galanthamine,
lycoramine, vittatine, nerbowdine, haemanthamine, tazettine,
galanthine in bulbs of Z. grandiflora [47-48]. However, chemical
profiling of Z. grandiflora bulbs by UPLC/MS identified AAs: lycorine,
lycoramine, dihydrovittatine, lycoramine-N-oxide, galanthine,
hamayne, zaiden, ambelline, crinamidine, haemanthamine, vittatine,
zefbetaine, ungeremine, 1-O-(3-hydroxybutyryl)-pancratistatin,
|A number of pharmacological studies have been reported from
different species of Zephyranthes. Pharmacological activities of these
species are mainly because of alkaloids present in these plants i.e. AAs.
Different activities reported by various research groups are:
|Greathouse in 1941 investigated the resistance to root rot caused
by Phymatotrichum omnivorum in Z. texana and Cooperia pedunculata
and suggested that the toxicity, quantity and localization of the AAs
indicate that alkaloid content of these plants may contribute to the
immunity of bulbs from root rot . In 2009 Wu et al., evaluated the
antimicrobial activity i.e. antibacterial activities against Staphylococcus
aureus and Escherichia coli and antifungal activities against Aspergillus
niger, Candida albicans and Trichophyton rubrum against Penicillin G
and ketoconazole as positive control for bacteria and fungi respectively
and reported that candidamide A and candidamide B showed moderate
|In 2010 Singh et al., reported the significant antifungal activity of
AAs isolated from Z. citrina against Alternaria solani, A. Triticina,
Curvularia lunata, C. Maculans, Cercospora malvacearum, Fusarium
udum, Helminthosporium pisi, H. Speciferum, Erysisphe sp. and Ustilago
|In 2014 Oluyemisi et al., reported antiviral activity of lycorine,
trisphaeridine and 7-hydroxy-3’,4’-methylenedioxyflavan. However
lycorine was most active as compared to trisphaeridine and 7-hydroxy-
|In 1964, bulb extract of Z. candida displayed activity against
human epidermoid carcinoma of the nasopharynx, KB system in
the US national cancer Institute research programs [18-20]. In 1966,
Fransworth in his review on biological and phytochemical screening of
plants reported 19 species of Amaryllidaceae family to be active as tumor
inhibitor and Z. carinata and Z. texana were among these plants . In
1986 Ghosal et al., reported significant antitumour activity of ungeremine,
criasbetaine, zefbetaine, zeflabetaine in P-388 and KB systems and caused
cytolysis of Sarcoma 180 ascites tumor cells. In 1990 Pettit et al., found
the principal cytostatic (P-388) compound trans-dihydronarciclasine from
bulbs of Z. candida using active extract .
|In 1978, Furmanowa et al., studied the effect of haemanthamine,
lycorine and extracts from Z. robusta on dividing cells and result
suggest that antimitotic activity exhibited by Z. robusta may be caused
by lycorine and haemanthamine .
|In 1984 and 1990 Pettit et al., reported two antineoplastic compounds,
pancratistatin from Z. grandiflora and trans-dihydronarciclasine from Z. candida bulbs using the P-388 lymphocytic leukemia bioassay [31,33].
|In 1998 Kojima et al., compared the cytotoxicity of 1-O-(3-
hydroxybutyryl) pancratistatin, 1-O-(3-O-β-d-glucopyranosylbutyryl)
pancratistatin and pancratistatin against KB, HeLa and P388-D1 cells
and found that cytotoxicity of 1-O-(3-hydroxybutyryl) pancratistatin
is three times higher than pancratistatin on these cells. Their result
indicates significant difference in activity could be related to structure
. In 2001 Mutsuga et al., evaluated the cytotoxicity of isolated
alkaloids against human epidermoid carcinoma KB cells and showed
that pancratistatin and its derivative showed significant activity
. In 2012 Luo et al., alkaloids from Z. candida were evaluated invitro
cytotoxicity against five human cancer cell lines (HL-60, K562,
A549, HepG2, HT-29) and beas-2B immortalized human bronchial
epithelial cell line which showed that lycorine, haemanthamine,
N-methylhemeanthidine chloride, N-phenethylcrinasiadine are more
potent than positive control (cisplatin) . In 2013 Katoch et al.,
studied in-vitro cytotoxicity of alkaloids from Z. grandiflora against
C-6 (rat glioma cells) and CHO-K1 (Chinese hamster ovary cells) and
reported a dose dependent cytotoxic effect with prominent activity
exhibited by lycorine and haemanthamine .
|In 2011 Reyes-Chilpa et al., reported acetylcholinesterase activity
of Chlidanthine and galanthamine N-oxide isolated from bulbs of Z.
concolor to be five times less active than galanthamine. The alkaloids
chlidanthine, galanthamine, galanthamine-N-oxide showed poor
inhibitory activity of HIV-1 replication and cytotoxicity against human
MT-4 cells . In 2011 Cahlikova et al., reported the promising
cholinesterase inhibitory activities of alkaloid extract of bulbs of Z. grandiflora against human blood acetylcholinesterase and human
plasma butyrylcholinesterase . In 2013 Kulhankova et al., reported 8-O-demethylmaritidine, alkaloid from Z. robusta Baker showed
significant acetylcholinesterase inhibition activity and indicates that
this activity is mainly related with galanthamine- and lycorine-type
skeleton and galanthamine type skeleton are more active inhibitor than
other skeletons of AAs. However, crinine alkaloids showed mainly
cytotoxicity but not acetylcholinesterase inhibition activity. These
alkaloids were also screened for antioxidant activity but were found to
be inactive .
|The different pharmacological activities reported on Zephyranthes
includes antifungal, antiviral, cytotoxicity, acetylcholinesterase
inhibitor, anticancer, antimitotic activities and these were broadly
related with isolated AAs and extracts. Among the different skeleton
types of AAs lycorine, pancratistatin, haemanthamine and crinine
type skeletons were reported to be active against cancer whereas
galanthamine type skeletons were reported to be more active inhibitor
|The genus Zephyranthes has immense potential for exploring the
chemical compounds for identification as well as isolation for different
pharmacological activity. Many species are known but only few are
investigated for their phytochemical constituents. The information
compiled in this review will help the researchers to use this genus for
|The authors are grateful to Director, CSIR-IHBT, Palampur for their support
during work. A financial support received from Department of Science and
Technology, New Delhi is highly acknowledged.
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