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Natural Products in Cyperus Species (Cyperaceae): Phytochemistry, Pharmacological Activities, and Biosynthesis

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Chemistry & Biodiversity
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The review provides an update on the traditional uses, geographical distribution, pharmacological activities, biosynthesis, and mechanisms of action of natural products derived from Cyperus species. Since 1964, a total of about 403 natural products have been isolated from 43 Cyperus species, including terpenoids (51.61%), flavonoids (17.37%), stilbenoids (6.45%), quinones (5.71%), aromatics (7.69%), coumarins (5.21%) and other compounds (5.96%). The isolated compounds displayed anticancer, antiviral, antidiabetic, antimicrobial, antidepressant, and other activities. Terpenoids and flavonoids are the most abundant class of NPs that have been isolated from Cyperus species. The biosynthesis of some terpenoids and flavonoids has been provided in the paper. Natural products isolated from Cyperus species have demonstrated interesting in vitro activities which warrant further scientific investigations.
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Chemistry & Biodiversity
REVIEW
Natural Products in Cyperus Species (Cyperaceae):
Phytochemistry, Pharmacological Activities, and
Biosynthesis
Smith B. Babiaka1,2Doris E. Ekayen3,4Conrad V. Simoben5Cyril T. Namba-Nzanguim1
Godloves F. Chi1Ndam L. Monah6Lina N. Nubed1Dieudonne L. Njimoh7Vincent de Paul N. Nziko8
Rajeev K. Singla9,10 Christopher A. Ebot-Arrey11 Emmanuel A. Asongalem11 Andrew E. Egbe4
Kennedy O. Abuga12 Rajshekhar Karpoormath13 E. Joel Loveridge14
1Department of Chemistry, Faculty of Science, University of Buea, Buea, Cameroon 2Department of Microbial Bioactive Compounds, Interfaculty Institute for
Microbiology and Infection Medicine, University of Tübingen, Tübingen, Germany 3Department of Plant Science, Faculty of Science, University of Buea, Buea,
Cameroon 4Institute of Pharmaceutical Sciences, Albert-Ludwigs-Universität Freiburg, Hermann-Herder-Straße 9, Freiburg, Germany 5Structural Genomics
Consortium, University of Toronto, Toronto, Ontario, Canada 6Agroecology Laboratory, Faculty of Agriculture and Veterinary Medicine, University of Buea,
Buea, Cameroon 7Department of Biochemistry and Molecular Biology, Faculty of Science, University of Buea, Buea, Cameroon 8Department of Chemistry,
Virginia State University, Petersburg, VA, USA 9Joint Laboratory of Artificial Intelligence for Critical Care Medicine, Department of Critical Care Medicine
and Institutes for Systems Genetics, Frontiers Science Center for Disease-Related Molecular Network, West China Hospital, Sichuan University, Chengdu,
Sichuan, China 10 School of Pharmaceutical Sciences, Lovely Professional University, Phagwara, Punjab, India 11Department of Biomedical Sciences, Faculty
of Health Sciences, University of Buea, Buea, Cameroon 12Department of Pharmaceutical Chemistry, School of Pharmacy, University of Nairobi, Nairobi,
Kenya 13Department of Pharmaceutical Chemistry, School of Chemistry, University of KwaZulu-Natal, Durban, South Africa 14Department of Chemistry,
Swansea University, Singleton Park, Swansea, UK
Correspondence: Smith B. Babiaka (babiaka.smith@ubuea.cm)E. Joel Loveridge (e.j.loveridge@swansea.ac.uk)
Received: 23 December 2024 Revised: 16 March 2025 Accepted: 25 March 2025
Funding: Smith B. Babiaka received funding from the Alexander von Humboldt Foundation for Georg Forster and Georg Forster-Bayer Research fellowships
(Ref. 3.4–CMR–1220727–GF-P) at the University of Tübingen, Germany, and Doris E. Ekayen received funding from the German Academic Exchange Service
(DAAD, Award No. 91832147).
Keywords: bioactive compounds | Cyperaceae |Cyperus species | natural products | pharmacological activities
ABSTRACT
The review provides an update on the traditional uses, geographical distribution, pharmacological activities, biosynthesis, and
mechanisms of action of potent natural products derived from Cyperus species. Cyperus species are widely distributed in the
tropical and subtropical regions across the globe. Cyperus is the second-largest genus in this family with about 950 species.
Since 1964, a total of about 403 natural products have been isolated from 43 Cyperus species, including terpenoids (51.61%),
flavonoids (17.37%), stilbenoids (6.45%), quinones (5.71%), aromatics (7.69%), coumarins (5.21%), and other compounds (5.96%). The
isolated compounds displayed anticancer, antiviral, antidiabetic, antimicrobial, antidepressant, and other activities. Terpenoids
and flavonoids are the most abundant class of natural products that have been isolated from Cyperus species. The biosynthesis of
some terpenoids and flavonoids has been provided in the paper. Natural products isolated from Cyperus species have demonstrated
interesting in vitro activities that warrant further scientific investigations.
Abbreviations: ADP-ribose, Adenosine diphosphate ribose; DNA, Deoxyribonucleic acid; DMAPP, Dimethylallyl diphosphate; ED50, Effective dose of a compound that produces a specific effect in
50% of the population that takes that dose; FPP, Farnesyl pyrophosphate; GC-MS, Gas chromatographymass spectrometry; GPP, Geranyl diphosphate; HepG2, Hepatoblastoma cell line; UHPLC,
Ultra-high-performance liquid chromatography; HPLC-PDA-ELSD,High-performance liquid chromatography-photodiode array detector-evaporative light scattering detector; HbsAg, Hepatitis B
surface antigen; H2O2, Hydrogen peroxide; IC50, Inhibitory concentration which kills 50% of whole organism or cells; IPP, Isopentenyl diphosphate; IUPAC, International Union of Pure and Applied
Chemistry; LC-MS, Liquid chromatography mass spectrometry; LD50, Lethal dose: amount of a chemical that is lethal to one-half (50%) of the experimental animals exposed to it.; µM, Micro molar;
PARP-1, Poly[ADP-ribose] polymerase 1; UV, Ultraviolet; 2D, Two dimensional; TLC, Thin layer chromatography.
© 2025 Wiley-VHCA AG, Zurich, Switzerland
Chemistry & Biodiversity, 2025; 0:e202403352
https://doi.org/10.1002/cbdv.202403352
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Summary
Overview of 403 natural products isolated from 43 Cyperus
species.
The toxicity of some Cyperus species and mechanism of
action of the potent natural products.
The biosynthesis of some terpenoids and flavonoids, the
most abundant class of compounds in the genus Cyperus.
Future prospects of metabolites derived from Cyperus
species in drug discovery
1 Introduction
Cyperaceae is a family of monocotyledonous flowering plants
known as sedges. They superficially resemble grasses and form
one of the largest and most diverse cosmopolitan angiosperm
families with 106 genera and 5500 species worldwide [1, 2].
Cyperus is the second-largest genus in this family with about
950 species. It is also the “core taxon” of the tribe Cyperaceae
which comprises approximately 950 species [3, 4]. The genus
Cyperus occurs in the tropical, subtropical and temperate regions.
These herbs have a long history of application in folk medicine
in the treatment of different diseases [5, 6]. The broad range of
pharmacological activities associated with this plant species can
be attributed to its secondary metabolites. They have proved to be
a rich source of bioactive natural products with diverse structures
and interesting biological activities. They produce both small
and complex natural products with promising bioactivities. Some
of their chemical constituents include terpenoids, flavonoids,
quinones, stilbenoids and other minor compounds [7–14]. Given
the rekindling interests of natural products from Cyperus species
arising from researchers working in drug discovery, a review of
the phytochemistry, pharmacological activities, and biosynthesis
of terpenoids and flavonoids in Cyperus species (Cyperaceae)
spanning the period 1963 to September 2023 was carried out.
To the best of our knowledge, two reviews published in 2015
reported on phenolics, nitrogenous, and terpenoids constituents
isolated from different Cyperus species growing in Egypt [15, 16].
Other reviews reported on the ethnobotanical uses of Cyperaceae
species in Brazilian traditional medicine [17], and the chem-
istry and pharmacology of Cyperaceae stilbenoids [18]. Cyperus
rotundus is the most common weeds cited in ethnobotany [19–
22]. The phytochemistry aspect of this herb has been exploited
investigated extensively [23–29]. The current review is based on
natural products derived from 43 Cyperus species and biosynthe-
sis of some potent terpenoids and flavonoids. The mechanism of
actions of the potent hits are emphasized. The study concludes
by pointing out the future prospects of natural products derived
from Cyperus species in drug discovery and development.
2 Methods
A comprehensive search was performed in reputable databases,
including PubMed, SciFinder, Science Direct, Web of Science,
Wiley Online, ResearchGate, Google Scholar, and other search
engines. The search terms Cyperus species,” Cyperaceae,”
“natural products,” “bioactive compounds,” and “pharmacolog-
ical activities” were used for data collection. The publications
included in our study were obtained from literature within the
period 1964 and September 2023. The data included in our study
were reviews, research articles, and book chapters written in
English related to pharmacological activities of crude extracts and
natural products isolated from Cyperus species. Articles based on
industrial applications and the discovery of new Cyperus species
were excluded. The 2D structures of the natural products were
generated using ChemDraw 22.0. PubChem and ChemSpider
databases were used to check the IUPAC names of the isolated
compounds.
3Ethnomedicinal Uses
The rhizomes, tubers, and roots of C.articulatus decoctions are
used in Africa and Amazon areas for treating hemorrhoids,
malaria, stomachache, constipation, and respiratory infections
[30–38]. In Africa and Asia, the aerial part of C.rotundus are
recommended for the treatment of bronchitis and fever [2, 3948].
The aerial part of C.leavigatus has been exploited as analgesic and
anthelmintic agents [14]. The tubers and leaves of C.esculentus
are used in the treatment of stomach pain, malaria, diabetes, etc.
[49–51]. The whole plant of C.longus is used as a diuretic and
tonic in Egypt [52]. The essential oils from C.scariosus are used in
perfumery and as plant growth regulators [53, 54]. The rhizomes
of C.stoloniferus are used to treat stomachache and inflammation
[55]. The whole plant of C.conglomeratus is used as a stimulant,
analgesic and anthelmintic agent [56].
4Phytochemistry
To date, our study found that approximately 406 compounds
have been isolated and identified from 43 Cyperus species. In
FIGURE 1 The distribution of Cyperus natural products by com-
pound class.
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some cases, the isolated hits were inactive despite interesting
in vitro activity demonstrated by the crude extracts. Some of
the compounds were not tested due to low yields [39, 5767].
Other studies were simply based on the isolation and structural
determination of pure compounds [11, 12, 4, 39,42, 48, 6888].
There are seven groups of compounds in our review (Figure 1):
terpenoids (1208), flavonoids (209–278), stilbenoids (279–304),
quinones (305–327), aromatics (328–358), coumarins (359–379),
and miscellaneous compounds (380–403). Molecules with potent
biological activities are shown in Figures 2–10 while the 2D
structures of natural products from these plant species are shown
in Figures S1–S24. The names, plant sources, pharmacological
activities, and references are listed in Tables 1–7.
4.1 Terpenoids
Terpenoids are the most famous natural products isolated from
nature [88–93]. Terpenoids are sometimes referred to as isoprenes
(C5unit) because of a common recurring motif in their structure.
They are the most extensive class of compounds in Cyperus
species. In this study, 208 terpenoids were found to be identified
andisolatedfromtheseCyperus species (Figure 1; Figures S1–
S10,Table1). Terpenoid subclasses in Cyperus species include
monoterpenes (C10), sesquiterpenes (C15 ), diterpenes (C20), ses-
terterpenes (C25), and triterpenes (C30 ) compounds. Among them,
sesquiterpenes constitutes about 70.00% of the natural products
isolated from these plant species [26–29].
4.2 Flavonoids
Flavonoids are an important class of organic compounds which
are widely distributed in the plant kingdom [94]. They are
secondary metabolites in plants responsible for coloring sub-
stances that contribute to the beauty and splendor of flowers
and fruits in nature. Flavonoids scaffolds have two hydroxylated
aromatic rings A and B, linked by three carbon fragments [94, 95].
Several substructures can be distinguished: chalcones, flavones,
flavonols, flavanonols, flavanes, flavanols, isoflavones, biflavones,
aurones, and anthocyanidins [96, 97]. A total of 69 flavonoids and
derivatives (209–278) have been from Cyperus species (Figures
S11–S15,Table2). Natural flavonoids are found in vegetables,
fruits, seeds, nuts, and wine [98]. Some flavonoids have important
health benefits to humans; for example, apigenin (209), luteolin
(210), quercetin (219), and the catechins [99, 100].
4.3 Stilbenoids
Stilbenes are the simplest member in the class of stilbenoids
that have been investigated extensively due to their interesting
pharmacological activities. For example, resveratrol (279)isa
component of red wine with antioxidant, anticancer, and anti-
inflammatory activity [101, 102]. The increased consumption of
red wine rich in resveratrol (279) and other flavonoids reduces the
rate of coronary heart disease due to the cardioprotective effects
of these compounds [103]. The structural scaffold of stilbenes
has two aromatic rings linked by an ethylene bridge [104]. The
stilbenoids (279–304) that were isolated from Cyperus species are
listed in Figures S16–S18 and Table 3.
4.4 Quinones
Quinones are characterized by a common basic structural pattern:
an ortho or a para substituted dione conjugated either to an
aromatic nucleus or to a condensed polycyclic aromatic system
(Figure S19,Table4). The quinones (305–327) were reported from
nine Cyperus species harvested from Australia, Portugal, Japan,
Thailand, Egypt, and Cameroon (Figure S19,Table4).
4.5 Aromatics and Coumarins
A total of 31 aromatic compounds (328–358) excluding terpenoids
have been isolated from Cyperus species (Figures S20 and S21,
Table 5). A total of 21 coumarins (359–379)isolatedfromCyperus
species harvested from North Africa (Figure S22,Table6).
4.6 Miscellaneous Compounds
A total of 21 compounds (380–403) were identified and isolated
from C. incompletes,C. rotundus,C. conglomeratus,C.alterni-
folius, C. conglomeratus, C. esculentus, C. articulatus,andC.
teneriffae (Figures S23 and S24,Table7) using silica gel column
chromatography, GC-MS, hydrodistillation, preparative HPLC,
and Sephadex LH-20 [103–111]. The natural products in this
category include aliphatics (380–397), steroidal glycosides (398–
400), cerebrosides (401–402), and aliphatic alkenoic acid (403),
respectively.
5Pharmacological Activities
The compounds isolated from this plant species are shown in
Tables 1–7. Structures of natural products with different bioactiv-
ities are shown in Figures 2–10 while Figure 11 summarizes the
reported activities.
5.1 Anticancer and Hepatoprotective Activities
Natural products in Cyperus species have shown significant
potential in both anticancer and hepatoprotective activities
(Tables 18b). In an in vitro combination therapy study, an extract
from C.rotundus with oncolytic Newcastle disease virus (NDV)
showed a synergistic cytotoxic effect on three cancer cell lines
[112]. The ethanol extract from C.articulatus L. exhibited antipro-
liferative activity with low toxicity using peritoneal macrophages
of mice and human tumor cell lines. The extract showed no
cytotoxicity in macrophages at concentrations between 12.5 and
50 mg/mL. The authors reported that treatment with this extract
reduced the activity of the enzyme arginase and proliferation
of cancer cells [113]. The essential oil from the rhizomes of C.
articulatus L. collected from the Brazilian Amazon rainforest
showed antiliver-cancer potential against five cancer cell lines
and a non-cancerous cell. The oil causes cell cycle arrest in
the G2/M phase and cell death in HepG2 cells and inhibits
tumor development in a xenograft model [114]. The n-butanol and
aqueous fractions from the rhizomes of C.rotundus demonstrated
an in vitro promising dose-dependent hepatoprotection in 2,7-
dichlrofluorescein-injured HepG2 cells [115]. The hexane extract
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TABLE 1 Terpenoids isolated from Cyperus species.
Compounds
Species, place of harvest
(VS)
Part(s), extract, measured
activity, purification
strategies References
α-Cyperene (1)C. rotundus, China Hydrocarbon, preparative
GLC and chromatography
over AgNO3-SiO2
[68]
Rotundene (2)C. scariosus, India [73]
C. rotundus, China
Cyperenol (3)C. scariosus, India Tubers, alcohol [83]
Isopatchoulenone (4) and scariodione (5) [84]
Patchoulenol (6)C. scariosus, India Tubers, hexane, GC-MS [88]
Isopatchoul-3-ene (7) Tubers, hydrocarbon, plant
growth regulation,
chromatography over SiO2
and preparative TLC
[54]
Cyperolone (8)C. rotundus, Japan Rhizomes, steam,
chromatography over SiO2
[70]
α-Rutunol (9)andβ-rutunol (10) [72]
4α,5β-Oxidoeudesm-11-en-3α-ol (11) [69]
1, cypera-2,4-diene (12), cyprotene (13), cyperotundone (14), (+)-cyperadione (15),
()-norrotundene (16), ()- isorotundene (17), γ-gurjunene (18), nootkatene (19), valencene
(20), epi-α-selinene (21), α-muurolene (22), γ-muurolene (23), ylanga-2,4-diene (24),
γ-calacorene (25), cadalene (26), α-cyperone (27), isocyperol (28), mustakone (29), cyperol
(30), and ()-cypera-2,4-diene (31)
C. rotundus, gift of K.-D.
Protzen, Paul Kadersd GmbH,
Hamburg
Rhizomes, hydrodistillation,
chromatography over SiO2,
GC-MS, and preparative TLC
[45]
Mustakone (29) and mandassidione (32) C. articulatus, Kribi (South
Cameroon
Rhizomes, hexane,
chromatography over SiO2
[35, 36]
Cyperotundone (14), 3,4-O-isopropylideneshikimic acid (33), rotundusolide A (34),
rotundusolide B (35), dehydrocostuslactone (36), (+)-alismoxide (37), sugetriol triacetate
(38), 2β-hydroxy-α-cyperone (39), eudesma-4(14),11(13)-diene-7α,8α,12-triol (40),
rotundusolide C (41), secomacrogenin B (42), and 3,4-seco-mansumbinoic acid (43)
C. rotundus/purchased from
Lanzhou Traditional Chinese
Medicine Market (No.
ZY2009C002)
Rhizomes, ethanol,
chromatography over SiO2
and preparative TLC
[79]
Mandassidione (32), cyperusol A1(44), cyperusol A2(45), cyperusol B1(46), cyperusol B2
(47), cyperusol C (48), cyperusol D (49), ()-1-p-menthene-7,8-diol (50), caryolane-1,9β-diol
(51), 3,7-epoxycaryophyllane-5α, 15-diol (52), 7,15-epoxycaryophyllane-3,5β-diol (53),
clovanediol (54), tricyclohumuladiol (55), 1β-hydroxy-10βH-guaia-4,11-dien-3-one (56),
guaidiol (57), 1,5,8,8-tetramethyl-8-bicyclo[8,1,0]-undecene-2,9-diol (58),
2,10,10-trimethyl-6-methylene-2,8-cyclodecadiene-1,5-diol (59), 1,6,6,10-
tetramethyl-4,9,14-trioxatetracyclotetradecane (60), muurolane-2α,9β-diol-3-ene (61), and
ligucyperonol (62)
C. longus, purchased in Cairo,
Egypt
Whole plants, methanol,
hepatoprotective, normal and
RP chromatography and
HPLC
[52]
(Continues)
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TABLE 1 (Continued)
Compounds
Species, place of harvest
(VS)
Part(s), extract, measured
activity, purification
strategies References
Cyperolone (8)C. rotundus, Japan Rhizomes, chromatography
over SiO2and TLC
[70]
Cyperolone (8), α-rutunol (9)andβ-rutunol (10), α-cyperone (27), mustakone (29),
(+)-nootkatone (63), 2α-(5-oxopentyl)-2β-methyl-5β-isopropenylcyclohexanone (64),
2β-(5-oxopentyl)-2β-methyl-5β-isopropenylcyclohexanone (65)
C. rotundus, Yorishima,
Okayama, Japan
Roots, methanol,
antibacterial, chromatography
over alumina and SiO2
[138]
4α,5β-Oxidoeudesm-11-en-3α-ol (11)C. rotundus, Japan Rhizomes, chromatography
over SiO2and TLC
[69]
Patchoulenone (66), 10,12-peroxycalamenene (67) and caryophyllene-α-oxide (68)C. rotundus, purchased from
Thai traditional dispensary,
Bangkok, Thailand
Tubers, hexane, antimalarial,
chromatography over SiO2
and MPLC
[136]
α-Cyperene (1), cyperol (30), eudesma-2,4,11-triene (69), eudesma-3,5,11-triene (70),
eudesma-2,4(15),11-triene (71), (-)-eudesma-3,11-dien-5-ol (72), (+)-eudesma-3,11-dien-2-one
(73), and α-cubebene (74)
C. alopecuroides, Nkolbisson
(Cameroon)
Rhizomes, hexane, GC-MS [42]
α-Corymbolol (75), and corymbolone (76)C. articulatus, Kribi (South
Cameroon
Rhizomes, hexane,
chromatography over SiO2
[35, 36]
Corymbolone (76)C. corymbosus,SantaMariade
los Guaicas, Orinoco,
Venezuela (#80524)
Rhizomes, petroleum ether,
chromatography over SiO2
[34]
Mustakone (29) and corymbolone (76)C. articulatus, Ruiri forest
Meru district of Kenya (001/
04)
Rhizomes, chloroform
antiplasmodial,
chromatography over SiO2
[137]
Cyperusol A3(77), 3β-hydroxycyperenoic acid (78), britanlin E (79), 1β,4α
-dihydroxyeudesm-11-ene (80) and 11,12-dihydroxyeudesm-4-en-3-one (81)
C. rotundus, Kyung Dong
Crude Drugs Market, Seoul,
South Korea. (CYRO1–2011)
Rhizomes, ethyl acetate,
antitumor, silica gel column
chromatography,
reversed-phase silica gel,
Sephadex LH-20, silica-MPLC,
and C18-MPLC
[119]
Valencene (20), caryophyllene-α-oxide (68), nootkatone (82), β-pinene (83), 1,8-cineole (84),
limonene (85), and 4-cymene (86)
C. rotundus, Kyung Dong
Crude Drugs Market, Seoul,
South Korea. (NM)
Rhizomes, ethanol,
antiallergic, chromatography
over SiO2and RP-C18 HPLC
[160]
(Continues)
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TABLE 1 (Continued)
Compounds
Species, place of harvest
(VS)
Part(s), extract, measured
activity, purification
strategies References
Cyperenol (3), scariodione (5), cyperotundone (14), α-cyperone (27), cyperol (30), sugetriol
triacetate (39), cyperusol C (49), cyperusol D (50), α-corymbolol (75), sugeonol (87),
cyperene-3,8-dione (88), 14-hydroxycyperotundone (89), 14-acetoxycyperotundone (90),
sugetriol-3,9- diacetate (91), cyperenoic acid (92), (4aS,7S)-7-
hydroxy-1,4a-dimethyl-7-(prop-1-en-2-yl)-4,4a,5,6,7,8- hexahydronaphthalen-2(3H)-one (93),
(4aS,7S,8R)-8-hydroxy-1,4a-dimethyl-7-(prop-1-en-2-yl)-4,4a,5,6,7,
8-hexahydronaphtha-len-2(3H)-one (94), 1β-hydroxy-α-cyperone (95),
10-epieudesm-11-ene-3β,5α-diol (96), 3β-hydroxyilicic alcohol (11(13)-eudesmene-3,4,12- triol
(97),3β,4α-dihydroxy-7-epi- eudesm-11(13)-ene (98), 2-oxo-α-cyperone (99), 7α(H),
10β-eudesm-4-en-3-one-11,12-diol (100), 2-hydroxy-14-calamenenone (101),
1-isopropyl-2,7-dimethylnaphthalene (102), rhombitriol (103), 7-epi-teucrenone (104),
α-rotunol (105), 12-hydroxynootkatone (106), oplopanone (107),
10-hydroxyamorph-4-en-3-one (108), argutosine D (109),
4,5-seco-guaia-1(10),11-diene-4,5-dioxo (110), oxyphyllol C (111), and 5-hydroxylucinone
(112)
C. rotundus, purchased from
Juhuacun (Kunming, China)
(no. 2011041101)
Rhizomes, ethanol,
antihepatitis B, and virus,
chromatography over SiO2
and UFLC-MS
[41]
Rotundine A (113), rotundine B (114), and rotundine C (115)C. rotundus, purchased from
Uchida Wakanyaku Co., Ltd.
(Tokyo, Japan) (lot. 242118)
Rhizome, methanol, standard
method for alkaloid
extraction, chromatography
over SiO2and Sephadex LH-20
[48]
Norcyperone (116)and()-clovane-2,9-diol (117)C. rotundus, Dabieshan
Mountains of Anhui Province,
P.R. China (no: 20060825)
Rhizomes, ethanol,
chromatography over SiO2
and Sephadex LH-20
[77]
Sugetriol triacetate (39) and cyperalin A (118)C. rotundus, King Abdulaziz
University campus, Jeddah,
Saudi Arabia (2014-CR110)
Rhizomes, methanol,
anti-inflammatory,
chromatography over SiO2
and RP-18 HPLC
[151]
α-Cyperene (1), cyperotundone (14), α-cyperone (27), isocyperol (28),
4α,5α-oxidoeudesm-11-en-3-one (119), and cyper-11-ene-3,4-dione (120)
C. rotundus, purchased from
Kyungdong-Yakryongsi
traditional medicine market in
Seoul, Korea
(SKKU-PH-12–50)
Rhizomes, methanol,
estrogenic, chromatography
over SiO2and RP-18 HPLC
[71]
(+)-Nootkatone (64), solavetivone (121), and aristolone (122)C. rotundus, vendor in
Trivandrum (no. 034/2011)
Rhizomes, acetone,
antioxidant, chromatography
over SiO2and RP-18 HPLC
[152]
α-Cyperone (27)C. rotundus, Bogor-Indonesia Tubers, methanol,
insecticidal, chromatography
over SiO2, preparative TLC
and RP-18 HPLC
[166]
(Continues)
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TABLE 1 (Continued)
Compounds
Species, place of harvest
(VS)
Part(s), extract, measured
activity, purification
strategies References
β-Caryophyllene (123), α-humulene (124), caryophyllene oxide (125), zerumbone (126),
(+)-dihydrocarvone (127), (R)-(+)-limonene (128), (1S)-()-verbenone (129),
(S)-()-limonene (130), ()-(E)-pinocarveol (131), (E)-carveol (132), ()-α-copaene (133),
(1R)-()-myrtenal (134), and (1R)-()-myrtenol (135)
C. rotundus, purchased from
the Boeun medicinal herb
shop (Seoul Yangnyeongsi,
Seoul, South Korea) (CR-01)
Rhizomes, methanol,
repellent, chromatography
over SiO2,preparativeHPLC
[167]
Cyperotundone (14)andα-cyperone (27)C. rotundus, supplied by
Morihiro Kinoshita (Nihon
Funmatsu Yakuhin Company,
Japan) (NM)
Rhizomes, hexane,
phytotoxicity, silica gel
column chromatography
[168]
Cyperene (1), cyperotundone (14), α-cyperone (27), cyperol (30), (+)-dihydrocarvone (127),
(1R)-()-myrtenal (134), δ-cadinene (136), β-selinene (137), β-elemene (138), caryophyllene
(139), calamenene (140), and 6-acetoxy-patchoul-4-en-3-one (141)
C. rotundus, Islands of Oahu,
Maui, Kauai and Hawaii (NM)
Tubers, hexane, chemotype,
GC-MS
[88]
Cyprotuside A (142) and cyprotuside B (143)C. rotundus, Zhanjiang,
Guangdong Province of China
(No.20090903)
Rhizomes, ethanol,
antidepressant, silica gel
column chromatography and
RP-18 HPLC
[63]
18-Epi-α-amyrin glucuronoside (144), oleanolic acid arabinoside (145), α-amyrin
glucopyranoside (146), and β-amyrin glucopyranoside (147)
C. rotundus, West Champaran,
Bihar, India (no. NISCAIR/
RHMD/Consult/-2008-
09/1114/
145)
Tubers, methanol, silica gel
column chromatography
[87]
Oleanolic acid (148), oleanolic acid-3-O-neohesperidoside (149), and β-sitosterol (150)C. rotundus, University of
Allahabad campus,
Allahabad, India (NM)
Tubers, petroleum ether and
benzene, silica gel column
chromatography
[76]
12-Methylcyprot-3-en-2-one-13-oic acid (151), stigmasterol-n-dodecanoate (152),
stigmasterol-n-tetradecanoate (153), β-sitosterol glucoside (154), and lupenyl
arabinopyranosyl oleate (155)
C. rotundus, purchased from a
Delhi market(NM)
Tubers, methanol, silica gel
column chromatography
[80]
Sitosteryl (156)C. rotundus, El-Safa and
El-Marwa, Faculty of
Agriculture, Al-Azhar
University, Assiut, Egypt
Aerial parts, methanol,
antifeedant and cytotoxic,
silica gel column
chromatography and semi
HPLC
[120]
α-Cyperene (1), α-cyperone (27), caryophyllene oxide (125), zierone (157), humulene
epoxide II (158), endesma-2,4,11-triene (159), pinocarveol (160), and germacrene D (161)
C.distans,mainroad,
Vulindlela, KwaDlangezwa,
KwaZulu-Natal, South Africa,
(Lawal, OA 03 (ZULU)
Rhizomes, hydrodistillations,
GC-MS
[82]
(Continues)
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TABLE 1 (Continued)
Compounds
Species, place of harvest
(VS)
Part(s), extract, measured
activity, purification
strategies References
Valencene (20), α-cyperone (27), caryophyllene-α-oxide (68), nootkatone (82), β-pinene (83),
1,8-cineole (84), limonene (85), and 4-cymene (86)
C. rotundus,purchasefrom
Kyung Dong Crude Drugs
Market, Seoul, South Korea.
(DKH-02561)
Rhizomes/ anti-inflammatory,
silica gel column
chromatography and
Sephadex LH-20, GC-MS
[150]
Mandassidione (32), β-sitosterol (150), sitosteryl (156), and β-sitosterol-3-O-β-D-glucoside
(162)
C. rotundus, Bahtim, Al
Qalyubiya, Egypt (CR S117)
Rhizomes, methanol,
anticancer, silica gel column
chromatography and
preparative TLC
[66]
Cyperotundone (14), cyperusol A1(24), cyperusol A2(25), sugetriol triacetate (38), cyperusol
A3(77), isocyperotundone (163), and 1,4-epoxy-4-hydroxy-4,5-seco-guain-11-en-5-one (164)
C. rotundus, purchased from
Shengru Biological
Technology Co. Ltd., Yunnan
province, China (batch
number: 121059-200706)
Rhizomes, methanol,
anti-inflammatory, silica gel
column chromatography,
Sephadex LH-20 and
semi-preparative HPLC
[153]
Cyperotundone (14), mustakone (29), 1,2-dehydro-α-cyperone (165), and sesquichamaenol
(166)
C. articulatus, Ngaoundéré,
Cameroon (reference
1256/HNC)
Rhizomes, hexane,
antiseizure, GC-MS and
HPLC-PDA-ELSD
[147]
β-Sitosterol (150)andα-amyrin (167)C. conglomerates,Jizan
territory of Saudi Arabia (NM)
Aerial parts, ethanol,
anticandidal, column
chromatography and HPLC
[139]
α-Cyperone (27)C. rotundus,Tamil Nadu,
Southern India
Rhizomes, ethanol,
antifungal, column
chromatography
[6]
Cyperotundone (14) C. sphacelatus, Mile 16, Buea,
South West Region, Cameroon
(38515/HNC)
Rhizomes, dichloromethane,
antisalmonellal, column
chromatography and HPLC
[140]
Cyperotundone (14), sugetriol triacetate (38),), cyperenoic acid (91), epi-guaidiol A (168),
guaidiol A (169), and sugebiol (170)
C. rotundus, Da-Bie-Shan
Mountains, Anhui province,
China. (No: 20060825)
Rhizomes, ethanol, silica gel
column chromatography and
Sephadex LH-20
[78]
α-Cyperone (27)C. rotundus, Kyung Dong
Crude Drugs Market, Seoul,
South Korea. (CYRO1-2011)
Rhizomes, ethanol,
anti-inflammatory, silica gel
column chromatography
[154]
Valencene (20), α-cyperone (27), nootkatone (82), β-pinene (83),1, 8-cineole (84), limonene
(85), 4-cymene (86), caryophyllene oxide (125), and β-selinene (137)
C. rotundus, Kyung Dong
Crude Drugs Market, Seoul,
South Korea. (CYRO1-2011)
Rhizomes, ethanol,
antiplatelet, column
chromatography and GC-MS
[161]
Isocyperol (28)Rhizomes, ethanol,
anti-inflammatory, silica gel
column chromatography
[155]
(Continues)
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TABLE 1 (Continued)
Compounds
Species, place of harvest
(VS)
Part(s), extract, measured
activity, purification
strategies References
Oleanolic acid (148),β-sitosterol (150), and stigmasterol (171)C. rotundus, India (KLU-1251) Rhizomes, hexane,
chloroform, and methanol,
antioxidant and anti-diabetic,
column chromatography
[129]
Cyprotuoside C (172) and cyprotuoside D (173)C. rotundus, Zhanjiang,
Guangdong Province of China
(No. 20090903)
Rhizomes, ethanol, normal
phase column
chromatography
[81]
Cyperotundone (14), mustakone (29), corymbolone (76), caryophyllene oxide (125),
copa-3-en-2α-ol (174), humulene epoxide-II (175), kobusone (176), humulene dioxide (177),
(-)-guaia-1(10),11-dien-9-one (178), and muurolane-2β,9β-diol-3-ene (179)
C. articulatus, purchased from
Kilomosso, Uíge, northern
Angola (DR050752, DR051629)
Rhizomes and roots,
methanol, anti-inflammatory,
silica gel column
chromatography, Sephadex
LH-20 and semi-preparative
HPLC
[157]
Ipolamiide (180)and6β-hydroxyipolamiide (181)C. rotundus, Al-Azhar
University campus, Assiut
Branch, Egypt (2009-CR110)
Rhizomes, methanol,
hepatoprotective, silica gel
column chromatography
[58]
Rotunduside G (182), rotunduside H (183), negundoside (184), nishindaside (185),
isooleuropein (186), and neonuezhenide (187)
C. rotundus, Zhanjiang,
Guangdong Province of China
(No. 20090903)
Rhizomes, ethanol,
antidepressant, normal phase
column chromatography and
RP-18 HPLC
[62]
Rotunduside (188), 10-O-p-hydroxybenzoyltheviridoside (189), 10-O-vanilloyltheviridoside
(190), 6″-O-(trans-p- coumaroyl)-procumbide (191), and loganic acid (192)
C. rotundus, Zhanjiang,
Guangdong Province of China
(No. 20090903)
Rhizomes, ethanol, MRB
inhibition, normal phase
column chromatography and
RP-18 HPLC
[60, 61]
Rotunduside D (193), rotunduside E (194), and rotunduside F (195)C. rotundus, Guangdong
Province of China (No.
20090903)
Rhizomes, ethanol,
antidepressant, normal phase
column chromatography and
RP-18 HPLC
[37]
Rotunduside A (196), rotunduside B (197), and 6″-O-p-coumaroylgenipin gentiobioside
(198)
C. rotundus, Zhanjiang,
Guangdong Province of China
(No. 20090903)
Rhizomes, ethanol, MRB
inhibitory, normal phase
column chromatography and
RP-18 HPLC
[60, 61]
6-O-ρ-Hydroxybenzoyl-6-epi-aucubin (199), 6-O-ρ-hydroxybenzoyl-6-epi-monomelittoside
(200), syringopicroside B (201), syringopicroside C (202),
7-O-ρ-hydroxybenzoyl-8-epi-loganic acid (203), verproside (204), senburiside I (205),
oleuropeinic acid (206), oleuroside (207), and 10-hydroxyoleuropein (208)
C. rotundus, Zhanjiang,
Guangdong Province of China
(No. 20090903)
Rhizomes, ethanol, MRB
inhibition, normal phase
column chromatography,
Sephadex LH-20 and RP-18
HPLC
[159]
Abbreviation: VS: voucher specimen number.
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TABLE 2 Flavonoids isolated from Cyperus species.
Compounds
Species, place of harvest
(VS)
Part(s), extract, measured
activity, purification
strategies References
Apigenin (209)C.cuspidatus,C.R.Dunlop5273
Mitchell River, W.A.
Leaves, methanol, column
chromatography
[8]
Apigenin (209), and luteolin (210)C. carinatus
Luteolin (210), tricin (211), and
luteolin-5-methylether (212)
C. reflexus
Apigenin (209), luteolin (210), and tricin
(211)
C.cuspidatus, K. L. Wilson 3888
& P. Sharpe, 15.5 km N.E. of Gin
Gin Rd., Queensland
Apigenin (209) and luteolin (210)
Luteolin (210)C. rotundus,K.L.Wilson3309
Denistone, N.S.W.
Luteolin (210), tricin (211), and
aureusidin (213)
C. scaber, R. Coveny 2016 North
Stradbroke Island. Queensland
Luteolin (210) and tricin (211)C. pilosus,K.L.Wilson3138
Near Lennox Head, N.S.W.
Luteolin (210), tricin (211),
quercetin-3-methylether (214),
kaempferol-3-methylether (215), and
kaempferol-3,7-dimethylether (216)
C. cunninghamii,A.A.Mitchell
453
Luteolin (210), aureusidin (213),
quercetin-3-methylether (214),
quercetin-3,7-dimethylether (217), and
quercetin-3,7,3′-trimethylether (218)
C. rigidellus,P.K.Latz5016
Luteolin (210), tricin (211), and
aureusidin (213)
C. rigidellus, A. C. Beauglehole
56179 Robinvale, Victoria
Luteolin (210), aureusidin (213),
quercetin-3-methylether (214),
kaempferol-3,7-dimethylether (216),
quercetin-3,7-dimethylether (217),and
quercetin-3,7,3′-trimethylether (218)
C. rigidellus,K.L.Wilson1634
McCallum Park, N.S.W.
Leaves, methanol, column
chromatography
[8]
Luteolin (210), tricin (211), and
aureusidin (213)
C. rigidellus,K.L.Wilson2006
Near Garah. N.S.W.
Luteolin (210), and tricin (211)C. sexflorus,P.K.Latz1406
Tanumbirini Waterhole. N.T.
Aureusidin (213), quercetin (219), and
maritimein (220)
C. squarrosus,S.T.Blake14020
Noondoo, Queensland
Worldwide
Luteolin (210), tricin (211), maritimein
(220), and 7, 3′, 4′ -trihydroxyflavone (221)
C. betchei,S.T.Blake19155
Cypress Downs, Queensland
Luteolin (210), tricin (211), aureusidin
(213), maritimein (220), and 7, 3′, 4′
-trihydroxyflavone (mariscetin) (221)
C. betchei, R. Coveny 8664 & S.
K. Roy Near Narrabri, N.S.W
Luteolin (210), tricin (211), and
aureusidin (213)
C. betchei, R. Melville 3444 Near
Jackson, Queensland
Luteolin (210), tricin (211), mangiferin
(222), and isomangiferin (223)
C. leiocaulon,K.L.Wilson3140
Near Lennox Head, N.S.W.
Luteolin (210), tricin (211), aureusidin
(213), and mariscetin (221)
C. scaber, R. Coveny 2016 North
Stradbroke Island, Queensland
(Continues)
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TABLE 2 (Continued)
Compounds
Species, place of harvest
(VS)
Part(s), extract, measured
activity, purification
strategies References
Luteolin (210), tricin (211), aureusidin
(213), mangiferin (222), and isomangiferin
(223)
C. involucratus
Luteolin (210), tricin (211),
luteolin-5-methylether (212), aureusidin
(213), quercetin (219), mangiferin (222),
isomangiferin (223), and aurone
methylether (224)
C. reflexus
Quercetin-3,3′-dimethylether (225),
quercetin-3,4′-dimethylether (226),
vicenin-2 (227), diosmetin (228), and
orientin (229)
C. alopecuroides, Mansoura,
Egypt
Inflorescences, ethanol,
estrogenic, polyamide 6S
column chromatography and
Sephadex LH-20
[162]
Luteolin (210), (+)-catechin (230), and
()-epicatechin (231)
C. longus, Egypt Whole plant, methanol,
radical scavenging, silica gel
column chromatography
[59]
Luteolin (210), (+)-catechin (230), and
()-epicatechin (231)
Whole plant, methanol,
antiallergic and radical
scavenging, silica gel column
chromatography
[158]
6,3′,4′-Trihydroxy-4-methoxy-5-
methylaurone (232)
C. capitatus, seaside near Aveiro
(NM)
Rhizomes and roots,
chloroform and methanol,
preparative TLC
[74]
6,3′,4′-Trihydroxy-4-methoxy-5-
methylaurone (232),
6,3′-dihydroxy-4,4′-dimethoxy-5-
methylaurone (233), and
4,6,3΄,4΄-tetramethoxyaurone (234)
[75]
Tamarixetin (235), ombuin (236),
5,7,3′,5′-tetrahydroxyflavanone (237), 4,6,
3′,4′-tetramethoxyaurone (238), and
3′-hydroxy-4,6, 4′-trimethoxyaurone (239)
C. teneriffae, northeast of
Tenerife ((TFC 43373)
Roots, ethanol, silica gel
column chromatography and
Sephadex LH-20
[5]
Luteolin (210), 7, 3′-dihydroxy-5,
5′-dimethoxy-8- prenylflavan (240), 5,7,
3′-trihydroxy-5΄-methoxy-8-prenylflavan
(241), and luteolin-7-methylether (242)
C. conglomeratus,Zayan,
Dakahlia, Egypt
Whole plant [56]
Luteolin (210), quercetin (219), (+)-
catechin (230), and afzelechin (243)
C. rotundus,Monastirregionin
the Center of Tunisia (Cp.10.04)
Aerial parts, water and
acetone, antioxidant and
antitumor, silica gel column
chromatography and
Sephadex LH-20
[121]
Rutin (244)C. rotundus, Al-Azhar University
campus, Assiut Branch, Egypt
(2009- CR110)
Rhizomes, methanol,
hepatoprotective, silica gel
column chromatography
[58]
Pongamone A (245) and biochanin A
(246)
C. rotundus, Zhanjiang,
Guangdong Province, China
(No.20090903)
Rhizomes, ethanol, silica gel
column chromatography,
Sephadex LH-20 and
semi-preparative HPLC
[39]
(Continues)
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TABLE 2 (Continued)
Compounds
Species, place of harvest
(VS)
Part(s), extract, measured
activity, purification
strategies References
Luteolin (210)C. rotundus, purchased from
Matsuura-Yakugyo Co. Ltd.
(Nagoya, Japan) CP-0901
Rhizomes, methanol,
antiproliferative, silica gel
column chromatography and
Sephadex LH-20
[122]
Tricin (211), isorhamnetin (247), vitexin
(248), isovitexin (249), oreintin (250),
epiorientin (251),
myricetin-3-O-β-D-galactopyranoside
(252), luteolin-7-O-β-D-
glucuronopyranoside-6΄΄-methylester
(253),
luteolin-4΄-O-β-D-glucuronopyranoside
(254), and
luteolin-7-O-β-D-glucuronopyranoside
(255)
C. rotundus, Experimental
Station of El-Safa and El-Marwa,
Al-Azhar University, Assiut,
Egypt C. rotundus
Aerial parts, methanol,
antioxidant and α-amylase,
silica gel column
chromatography and semi
HPLC
[127]
Tricin (211), and vitexin (248) Aerial parts, methanol,
antifeedant and cytotoxic,
silica gel column
chromatography and semi
HPLC
[120]
Vitexin (248), oreintin (250), cinaroside
(256),
quercetin-O-β-D-glucuronopyranoside
(257), cyperaflavoside (258), and
myricetin-3-O-β-D-glucuronopyranoside
(259)
C. rotundus, King Abdulaziz
University campus, Jeddah,
Saudi Arabia (2014-CR110)
Aerial parts, methanol,
5-Lipoxygenase inhibition,
chromatography over (silica)
SiO2and Sephadex LH-20
[151]
Luteolin (210) and aureusidin (213)C. thunbergii, Botanical Garden
of Talence (Talence, France),
(XX-0-TUEB-3630 ex JB
Tubingen)
Aerial parts/mammalian
Arginase Inhibition,
reverse-phase preparative
liquid chromatographic
[24]
C. glomeratus, Botanical Garden
of Talence (Talence, France),
(FR-0-LYJB-005964W ex JB
Lyon)
Quercetin (219)andrutin(244)C. alternifolius, Orman Garden,
Egypt
Aerial parts, ethanol,
hepatoprotective, silica gel
column chromatography,
preparative TLC and
Sephadex LH-20
[111]
(S)-5, 5′,7-Trihydroxy-2′,4′-dimethoxy-6-
methylflavanone (260), and eriodictyol
(261)
C. stoloniferus, Tien Hai, Thai
Binh,Vietnam
Rhizomes, methanol, silica
gel column chromatography
and Sephadex LH-20
[55]
(2RS,3SR)-3,4′,5,6,7,8-hexahydroxyflavane
(262)
C. rotundus, Dong Anh, Hanoi,
Vietnam
Rhizomes, methanol,
antioxidant, α-amylase and
α-glucosidase inhibition,
silica gel column
chromatography and RP-18
HPLC
[156]
(Continues)
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TABLE 2 (Continued)
Compounds
Species, place of harvest
(VS)
Part(s), extract, measured
activity, purification
strategies References
7,3′-Dihydroxy-8,4′-dimethoxyflavan
(263), 7,4′-dihydroxy-5,3′-dimethoxy-8-
methylflavan (264),
7,4′-dihydroxy-5,3′-dimethoxy-8-
prenylflavan (265),
5,4′-dihydroxy-7,3′-dimethoxyflavan
(266), and 3′,4′-dimethoxyluteolin (267)
C. conglomeratus, coastal sand
dunes (Deltaic Mediterranean
Coast) of Egypt
Aerial parts, methanol,
cannabinoid and opioid
receptor binding, silica gel
column chromatography
[148]
5-Hydroxy-7,3′,5′-trimethoxyflavan (268),
and 3′,5′-dihydroxy-6,5-dimethoxy-4′′-
prenylflavan
(269)
C. conglomeratus, East Jeddah Tubers,
petrol-diethylether-methanol,
silica gel column
chromatography and GC-MS
[86]
Luteolin (210)C. rotundus, Bahtim, Al
Qalyubiya, Egypt (CR S1-17)
Rhizomes, methanol,
cytotoxicity, silica gel column
chromatography and
preparative TLC
[66]
Luteolin (210)C. rotundus, Kyungdong Crude
Drugs Market, Seoul, Republic
of Korea (CYRO1-2011)
Rhizomes, ethanol,
antioxidative,
neuroprotective,
anti-inflammatory, and
antiamyloid-βactivities, silica
gel column chromatography,
preparative HPLC, Sephadex
LH-20 and RP-18 HPLC
[65]
Kaempferol (270)C. rotundus, India (KLU-1251) Rhizomes, hexane,
antioxidant and anti-diabetic,
column chromatography
[129]
5,7,4’-Trihydroxy-2’-methoxy-3’-
prenylisoflavone
(271)
C. rotundus, Zhanjiang,
Guangdong Province of China
(No. 20090903)
Rhizomes, ethanol,
macrophages respiratory
burst (MRB) inhibition,
normal phase column
chromatography, Sephadex
LH-20 and RP-18 HPLC
[159]
Luteolin (210), quercetin (219),
kaempferol (270), ginkgetin (272),
isoginkgetin (273), and
7,8-dihydroxy-5,6-methylenedioxyflavone
(274)
C. rotundus, Zhanjiang of
Guangdong, China (No.
20090903)
Rhizomes, ethanol,
antioxidant, silica gel column
chromatography
[64]
Ginkgetin (272), isoginkgetin (273),
amentoflavone (275), and sciadopitysin
(276)
C. rotundus, purchased from
China
Rhizomes, ethanol,
antiuterine fibroid
[57]
2R,2S-dihydroluteolin (277)C. articulatus, purchased from
Kilomosso, Uíge, northern
Angola (DR050752, DR051629)
Rhizomes and roots,
methanol, anti-inflammatory,
silica gel column
chromatography, Sephadex
LH-20 and semi-preparative
HPLC
[157]
Licoricone (278)C. rotundus, Zhanjiang,
Guangdong Province of China
(No. 20090903)
Rhizomes, ethanol, MRB
inhibition, normal phase
column chromatography,
Sephadex LH-20 and RP-18
HPLC
[159]
Abbreviations: ND: not done, NM: not mentioned, VS: voucher specimen number.
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TABLE 3 Stilbenoids isolated from Cyperus species.
Compounds Species, place of harvest (VS)
Part(s), extract, measured activity,
purification strategies References
Resveratrol (279), piceatannol (280), trans-scirpusin A
(281), trans-scirpusin B (282), cassigarol E (283), cassigarol
G(284), pallidol (285), longusone A (286), longusol A (287),
longusol B (288), and lungusol C (289)
C. longus, Egypt Whole plant, methanol, antiallergic and radical
scavenging, silica gel column chromatography
[158]
Resveratrol (279) and piceatannol (280)C. stoloniferus, Tien Hai, Thai Binh, Vietnam Rhizomes, methanol, silica gel column
chromatography and Sephadex LH-20
[55]
trans-Scirpusin A (281), scirpusin B (290),
(+)-cyperusphenol A (291), ()-(E)-cyperusphenol A (292),
(E)-mesocyperusphenol A (293), cyperusphenol C (294),
cyperusphenol B (295), and cyperusphenol D (296)
C. rotundus purchased from
Matsuura-Yakugyo Co. Ltd. (Nagoya, Japan)
CP-0901
Rhizomes, acetone, methanol, antiproliferative,
silica gel column chromatography and Sephadex
LH-20
[122]
Scirpusin B (290) and cyperusphenol B (295)C. eragrostis, Botanical Garden of Talence
(France) (IPEN code FR-0-TAL- 20070521W)
Seeds, methanol, mammalian arginase inhibition,
SPE mini-column Strata RP C18-E
[163]
4-Hydroxy-5′-methoxy-6′′,6′′-dimethylpyran[2′′,3′′: 3′,
2′]stilbene (297), 4′-hydroxy-3,5-dimethoxy-2-prenylstilbene
(298), 3′,4-dihydroxy-5′-methoxy-2′-prenylstilbene (299),
and 4,4′-dihydroxy-3,3′-dimethoxy-2′-prenylstilbene (300)
C. conglomeratus, coastal sand dunes
(Deltaic Mediterranean Coast) of Egypt
Aerial parts, methanol, cannabinoid and opioid
receptor binding, preparative GLC and
chromatography over AgNO3-Si02
[68]
Cassigarol E (283), scirpusin B (290), and scirpusin A (301)C. rotundus, Dong Anh, Hanoi, Vietnam Rhizomes, antioxidant, α-amylase and
α-glucosidase inhibition, silica gel column
chromatography and RP-18 HPLC
[156]
Scirpusin B (290), ()-(E)-cyperusphenol A (292),
(E)-mesocyperusphenol A (293), cyperusphenol D (296),
and scirpusin A (301)
C. rotundus, Yangguang drugstore, Dalian,
China (LNU-DSR-2015-1 to LNUDSR-
2015-26)
Roots, methanol, antidiabetic, LC-MS,
UHPLC-MS and Prep-RP-HPLC
[128]
Thunbergin A (302) and thunbergin B (303)C. thunbergii, Botanical Garden of Talence
(Talence, France), (XX-0-TUEB-3630 ex JB
Tübingen)
Aerial parts, methanol, mammalian Arginase
inhibition, reverse-phase preparative liquid
chromatographic
[24]
trans-Scirpusin A (281), ()-(E)-cyperusphenol A (292), and
trans-resveratrol (304)
C. glomeratus, Botanical Garden of Talence
(Talence, France), (FR-0-LYJB-005964W ex
JB Lyon)
Scirpusin B (290) and scirpusin A (301)C. rotundus, Kyungdong Crude Drugs
Market, Seoul, Republic of Korea
(CYRO1-2011)
Rhizomes, ethanol, antioxidative,
neuroprotective, anti-inflammatory, and
antiamyloid-βactivities, silica gel column
chromatography, preparative HPLC, Sephadex
LH-20 and RP-18 HPLC
[65]
Piceatannol (280), trans-scirpusin B (282), and
cyperusphenol B (295)
C. articulatus, purchased from Kilomosso,
Uíge, northern Angola (DR050752,
DR051629)
Rhizomes and roots, methanol,
anti-inflammatory, silica gel column
chromatography, Sephadex LH-20 and
semi-preparative HPLC
[157]
Abbreviation: VS: voucher specimen number.
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TABLE 4 Quinones isolated from Cyperus species.
Compounds
Species, place of harvest
(VS)
Part(s), extract, measured
activity, purification
strategies References
Cyperaquinone (305), and hydroxycyperaquinone
(306)
C. haspan, tropics of Australia Roots and rhizomes, cold
ether, column and thin layer
chromatography on silica gel
[11]
Demethylhydrocyperaquinone (307)C. compressus,tropicsof
Australia
Hydroxybreviquinone (308), and breviquinone (309)C. brevibracteatus,tropicsof
Australia
Rhizomes, chloroform. [12]
Scabequinone (310), dihydroscabequinone (311),
hydroxyscabequinone (312), and scabediol (313)
C. scaber, tropics of Australia
Scabequinone (310), dihydroscabequinone (311), and
hydroxyscabequinone (312)
C. distans, tropics of Australia
Scabequinone (310)C. distans,NaraandKyoto
Prefecture, Japan and Chiang
Mai, Thailand
Stem root, hexane,
antifeedants, silica gel column
chromatography
[13]
Hydroxycyperaquinone (306), and scabequinone (310)C. surinamensis Stem root, petroleum ether,
chlroform, cytotoxicity,
preparative thin layer
chromatography
[123]
Capiquinone A (314), capiquinone B (315),
capiquinone C (316), capiquinone D (317),
capiquinone E (318), capiquinone F (319), capiquinone
G(320), capiquinone H (321), capiquinone I (322),
capiquinone J (323), and capiquinone K (324)
C. capitatus, collected from
sandy soils on the seaboard
between Aveiro and Figueira
da Foz, Portugal
Rhizomes and roots,
chloroform, RP C18 HPLC and
preparative HPLC
[85]
Cyperaquinone (305), and remirol (325)C. nipponicus,NaraandKyoto
Prefecture, Japan and Chiang
Mai, Thailand
Basal stem, antifeedants, silica
gel column chromatography
[13]
Scabequinon-6(14)-ene (326)C. sphacelatus,Mile16,Buea,
South West Region of
Cameroon (38515/HNC)
Rhizomes, dichloromethane,
antisalmonellal, column
chromatography and HPLC
[140]
Alopecuquinone (327)C.alopecuroides, Mansoura,
Egypt
Inflorescences, ethanol,
estrogenic, polyamide 6S
column chromatography and
Sephadex LH-20
[162]
Abbreviation: VS: voucher specimen number.
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TABLE 5 Aromatics isolated from Cyperus species.
Compounds
Species, place of harvest
(VS)
Part(s), extract,
measured activity,
purification strategies References
4,7-Dimethyl-1-tetralone (328)C. rotundus, purchased from a
Thai traditional dispensary,
Bangkok, Thailand
Tubers, hexane,
antimalarial, column
chromatography and
HPLC
[136]
p-Hydroxybenzoic acid (329)C. rotundus, purchased from
Uchida Wakanyaku Co., Ltd.
(Tokyo, Japan) (lot. 242118)
Rhizomes, methanol,
standard method for
alkaloid extraction,
chromatography over SiO2
and Sephadex LH-20
[48]
Phenol (330), 1-phenylethanol
(331), chavicol (332), 3-ethoxy-
4-hydroxyallylbenzene (333),
and isoferulic acid (334)
C. conglomerates, East Jeddah
(NM)
Tubers, petrol-
diethylether-methanol,
silica gel column
chromatography and
GC-MS
[86]
Salicylic acid (335), caffeic acid
(336), protocatechuic acid
(337), and trans p-coumaric
acid (338)
C. rotundus, Experimental
Station of El-Safa and
El-Marwa, Al-Azhar
University, Assiut, Egypt C.
rotundus
Aerial parts, methanol,
antifeedant and cytotoxic,
silica gel column
chromatography and semi
HPLC
[120]
()-(E)-caffeoylmalic acid (339) Aerial parts, methanol,
antioxidant and α-amylase,
silica gel column
chromatography and semi
HPLC
[127]
Galloylquinic acid (340),
3-hydroxy-4-methoxybenzoic
acid (341) and ferulic acid (342)
C. rotundus,Monastirregionin
the Center of Tunisia
(Cp.10.04)
Aerial parts, water,
acetone, antioxidant and
antitumor, silica gel
column chromatography
and Sephadex LH-20
[121]
trans p-Coumaric acid (338)
and ellagic acid (343)
C. rotundus,purchasefrom
Kyung Dong Crude Drugs
Market, Seoul, South Korea.
(DKH-02561)
Rhizomes, hexane,
anti-inflammatory, silica
gel column
chromatography and
Sephadex LH-20, GC-MS
[150]
Preremirol (344)C. teneriffae, northeast of
Tenerife (TFC 43373)
Roots, ethanol, silica gel
column chromatography
and Sephadex LH-20
[5]
Salicylic acid (335), caffeic acid
(336), protocatechuic acid
(337), trans p-coumaric acid
(338), methoxycyperotundol
(345), and cyperotundol (346)
C. rotundus, Zhanjiang,
Guangdong Province, China
(No.20090903)
Rhizomes, ethanol, silica
gel column
chromatography, Sephadex
LH-20 and
semi-preparative HPLC
[39]
Gallic acid (347)C. alternifolius, Orman Garden,
Egypt (NM)
Aerial parts, ethanol,
hepatoprotective, silica gel
column chromatography,
preparative TLC and
Sephadex LH-20
[111]
Methyl-3,4-dihydroxybenzoate
(348)
C. rotundus, Al-Azhar
University campus, Assiut
Branch, Egypt (2009- CR110)
Rhizomes, methanol,
hepatoprotective, silica gel
column chromatography
[58]
(Continues)
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TABLE 5 (Continued)
Compounds
Species, place of harvest
(VS)
Part(s), extract,
measured activity,
purification strategies References
Chlorogenic acid (349)C. rotundus, obtained as
Organic Musta Powder
(Khandige Organic Health
Product, Bangalore, India)
(NM)
Rhizomes, ethanol,
anti-inflammatory, HPLC
[149]
Vanillin (350)C. sphacelatus, Mile 16, Buea,
South West Region of
Cameroon (38515/HNC)
Rhizomes,
dichloromethane,
antisalmonellal, column
chromatography and
HPLC
[140]
trans p-Coumaric acid (338)
and ferulic acid (342)
C. rotundus, Kyungdong Crude
Drugs Market, Seoul, Republic
of Korea (CYRO1-2011)
Rhizomes, ethanol,
antioxidative,
neuroprotective,
anti-inflammatory, and
antiamyloid-βactivities,
silica gel column
chromatography,
preparative HPLC,
Sephadex LH-20 and RP-18
HPLC
[65]
Caffeic acid (336), 4-hydroxy
cinnamic acid (338), and
4-hydroxybutyl cinnamate
(351)
C. rotundus, India (KLU-1251) Rhizomes, hexane,
antioxidant and
anti-diabetic, column
chromatography
[129]
p-Hydroxybenzoic acid (329)
and trans-p-hydoxycinnamic
acid (338)
C. articulatus, purchased from
Kilomosso, Uíge, northern
Angola (DR050752, DR051629)
Rhizomes and roots,
methanol,
anti-inflammatory, silica
gel column
chromatography, Sephadex
LH-20 and
semi-preparative HPLC
[157]
Isoaragoside (352), chionoside
A(353), and helioside C (354)
C. rotundus, Zhanjiang,
Guangdong Province of China
(No. 20090903)
Rhizomes, ethanol, MRB
inhibitory, normal phase
column chromatography
and RP-18 HPLC
[59, 60]
2S-Isopropenyl-4,8-dimethoxy-
5-methyl-2,3-dihydrobenzo-
[1,2-b;5,4-b′]difuran (355)and
2S-Isopropenyl-4,8-dimethoxy-
5-hydroxy-6-methyl-2,3-
dihydrobenzo[1,2-b;5,4-
b′]difuran (356)
C. teneriffae, northeast of
Tenerife ((TFC 43373)
Roots, ethanol, silica gel
column chromatography
and Sephadex LH-20
[5]
6’-Acetyl-3,6-diferuloylsucrose
(357) and 4’,6’-
diacetyl-3,6-diferuloylsucrose
(358)
C. rotundus, Kyungdong Crude
Drugs Market, Seoul, Republic
of Korea (CYRO1-2011)
Rhizomes, ethanol,
antioxidative,
neuroprotective,
anti-inflammatory, and
antiamyloid-βactivities,
silica gel column
chromatography,
preparative HPLC,
Sephadex LH-20 and RP-18
HPLC
[65]
Abbreviation: VS: voucher specimen number.
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TABLE 6 Coumarins isolated from Cyperus species.
Compounds Species, place of harvest (VS)
Part(s), extract, measured activity,
purification strategies References
Umbelliferone (359), scopoletin (360),
5,7-dimethoxycoumarin (361),
7,8-dimethoxycoumarin (362), 5,7,8
trimethoxyxcoumarin (363),
leptodactylone (364), prenyletin (365),
5,7-dimethoxy-8-(γ,γ-dimethylallyloxy)
coumarin (366),
7-methoxy-8-(γ,γ-methylallyloxy)
coumarin (367), and lacinartin (368)
C. incompletes, Cuzco, Peru (=175) Aerial parts, Antimicrobial [108]
Benzo-α-pyrone (369)C. rotundus,C. rotundus, Experimental
Station of El-Safa and El-Marwa,
Al-Azhar University, Assiut, Egypt C.
rotundus
Aerial parts, methanol, antifeedant and
cytotoxic, silica gel column
chromatography and semi HPLC
[120]
6,7-dimethoxycoumarin (370)C. rotundus,Monastirregioninthe
Center of Tunisia (Cp.10.04
Aerial parts, water, acetone,
antioxidant and antitumor, silica gel
column chromatography and Sephadex
LH-20
[121]
Umbelliferone (359), esculetin (371),
imperatorin (372), psoralen (373), and
xanthotoxin (374)
C.alternifolius, Orman Garden, Egypt
(NM)
Aerial parts, ethanol, hepatoprotective,
silica gel column chromatography,
preparative TLC and Sephadex LH-20
[111]
Eugenetin (375)C. teneriffae, northeast of Tenerife (TFC
43373)
Roots, ethanol, silica gel column
chromatography and Sephadex LH-20
[5]
Khellin (376), visnagin (377), ammiol
(378), and khellol-β-D-glucopyranoside
(379)
C. rotundus, El-Safa and El-Marwa,
Faculty of Agriculture, Al-Azhar
University, Assiut, Egypt
Aerial parts, methanol, antifeedant and
cytotoxicity, silica gel column
chromatography and semi HPLC
[120]
Abbreviation: VS: voucher specimen number.
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TABLE 7 Miscellaneous compounds isolated from Cyperus species.
Compounds
Species, place of harvest
(VS)
Part(s), extract,
measured activity,
purification strategies References
Succinic acid (380), myristic acid (381),
palmitic acid (382), and stearic acid
(383)
C. rotundus, upland rice field
(sandy loam soil) of Manikganj
district, Bangladesh
Tubers,water,growth
inhibition
[105]
Myristic acid (381), n-caprylic acid
(384), capric acid (385), methyl ester
palmitic (386), and linoleic methyl
ester (387)
C. conglomeratus, East Jeddah Tubers, petrol-diethylether-
methanol, silica gel column
chromatography and
GC-MS
[86]
Palmitic acid (382), stearic acid (383),
oleic acid (388), linoleic acid (389), and
linolenic acid (390)
C. esculentus, Korea Tubers, chloroform and
methanol, silicic acid
column chromatography
[107]
n-Tricont-1-ol-21-one (391)C. rotundus, West Champaran,
Bihar, India
(No.NISCAIR/RHMD/Consult/-
2008-09/1114/145)
Tubers, methanol, silica gel
column chromatography
[87]
Linoleic acid (389)C. articulatus, Sehn village,
Ndu Sub-Division in the North
West Region of Cameroon
(19450/SRF-CAM)
Rhizomes, hexane,
antionchocercal, silica gel
column chromatography
[106]
Hexadecanoic acid ethyl ester (392),
9,12-octadecadienic acid ethyl ester
(393), and 9-octadecenoic acid ethyl
ester (394)
C. articulatus, Tabocal region of
the municipality of Santarém,
Pará, Brazil (MG-207174)
Rhizomes, ethanol,
antiplasmodial,
hydrodistillation
[110]
Behenic acid (395), behenic acid
monoglyceride (396), and pinellic acid
(397)
C. rotundus, Rhizomes/Bahtim,
Al Qalyubiya, Egypt (CR S117)
Rhizomes, methanol,
cytotoxic, silica gel column
chromatography and
preparative TLC
[66]
n-Butyl-β-D-fructopyranoside (398),
ethyl-α-D-glucopyranoside (399), and
adenosine (400)
C. rotundus, Experimental
StationofEl-Safaand
El-Marwa, Al-Azhar
University, Assiut, Egypt C.
rotundus
Aerial parts, methanol,
antioxidant and α-amylase,
silica gel column
chromatography and semi
HPLC
[127]
1- O-(β-D-glucopyranosyloxy)-
(2S,3R,4E,8Z)-2-[(2′R)- 2′-
hydroxylignoceranoylamino]-4,8-
tetradecene-3-diol
(401)
C. rotundus, Shandong, China Radix, ethanol,
antiproliferation activity,
silica gel column
chromatography
[67]
2-[2-hydroxypentacosanoylamino]-1′,
3′, 4′-nonadecanetriol (402)
C. rotundus, Bahtim, Al
Qalyubiya, Egypt (CR S117)
Rhizomes, methanol,
anticancer, silica gel
column chromatography
and preparative TLC
[66]
Pinellic acid (397) and fulgidic acid
(403)
C. rotundus, Kyungdong Crude
Drugs Market, Seoul, Republic
of Korea (CYRO1-2011)
Rhizomes, ethanol,
antioxidative,
neuroprotective,
anti-inflammatory, and
antiamyloid-βactivities,
silica gel column
chromatography,
preparative HPLC,
Sephadex LH-20 and RP-18
HPLC
[65]
Abbreviation: VS: voucher specimen number.
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FIGURE 2 Chemical structures of natural products with hepatoprotective and anticancer activities.
FIGURE 3 Chemical structures of natural products with antiviral activities.
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FIGURE 4 Chemical structures of natural products with antidiabetic activities.
FIGURE 5 Chemical structures of natural products with antimicrobial activities.
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FIGURE 6 Chemical structures of natural products with antidepressant and neuroprotective activities.
of C.rotundus showed inhibition against cellular lipogenesis
and high sucrose diet (HSD)-induced steatosis. The molecular
mechanism involves the modulation of hepatic lipid metabolism
through sterol regulatory element binding protein-1c and liver X α
receptor [116]. The methanol extract of C.rotundus demonstrated
significant anticancer activity against human cancer cell lines-
breast, cervical, liver, prostate, colorectal and normal cell line
by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide
(MTT) assay. The cytotoxic effects on the tested cancer cell
lines ranged from 4.52 ±0.57 to 9.85 ±0.68 µg/mL [117].
The ethanol extract of C.rotundus L. showed inhibition on
the proliferation and induction of apoptosis in human triple-
negative breast cancer cells [118]. Compound 81 showed potent
cytotoxic activity against human ovarian cancer cells (A2780) and
endometrial adenocarcinoma cells (Ishikawa) using MTT assays
with observed IC50 values of 11.06 and 6.46 µM, respectively [119].
Visnagin (377) exhibited significant cytotoxic effect compared
to other compounds on L5178y mouse lymphoma cells with
effective doses ED50 =0.9 µg/mL [120]. The mechanisms of
actions of natural products reported in literature exhibiting
anticancer and hepatoprotective activities in the review have been
summarized and provided IN Figures 2and 12, Tables 8a and 8b
[26, 119123].
5.2 Antiviral Activity
Secondary metabolites isolated from Cyperus species have great
potentials in combating viral infections due to their diverse
bioactive compounds such as flavonoids, alkaloids, terpenoids,
and polyphenols (Figure 3,Tables1–7,Table8b). The sesquiter-
penoids, isolated from C.rotundus showed significant inhibition
against hepatitis B virus (HBV) DNA replication. The com-
pounds 96,98,100,and103 had high selectivity index (SI)
values of 250.4, 125.5, >259.6, and 127.5, respectively. Com-
pounds 78 and 92 suppressed the secretion of HBsAg effectively
[41].
5.3 Antidiabetic Activity
Phytochemicals from the genus Cyperus have exhibited sig-
nificant potential in managing diabetes through mechanisms
such as improving insulin secretion, sensitivity, reducing glucose
absorption and by antioxidant properties (Figure 4,Table8a). The
rhizomes of C.rotundus showed a dose-dependent adipogenesis
reductionwithanIC
50 value of 9.39 µg/mL. Oral administration
of this plant extract reduced weight gain in diet-induced obese
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TABLE 8 a Summary of bioactivities of the most potent compounds.
S/N Compound name Plant species
Level of
activity Bioactivity Mode of action Reference
1.Cyperol(30)C. rotundus IC50 =42.7 ±
75.9µM
Antihepatitis B virus
activity
Inhibition against
hepatitis B virus
(HBV) DNA
replication
[41, 42, 45]
2. Sugetriol triacetate (38) C. rotundus IC50 =0.15, 0.69
and 0.81µM
Inhibitory activity
against PGE2, COX-2
and LOX-5
[78, 79]
3.CyperusolC(48)rotundus IC50 =14.1 ±
71.1µM
Antihepatitis B virus
activity
Inhibition against
hepatitis B virus
(HBV) DNA
replication
[52]
4.()-1-p-Menthene-7,8-diol (50)C. logus IC50 =90 µM Hepatoprotective
activity
Inhibitory activity on
D-galactosamine-
induced cytotoxicity
in primary cultured
mouse hepatocytes
[52]
5. Caryolane-1,9β-diol (51)C. logus IC50 =100 µM[52]
6.1β-Hydroxy-10βH-guaia-4,11-dien-
3-one
(56)
C. logus IC50 =83 µM[52]
7. 1,5,8,8-Tetramethyl-8-
bicyclo[8,1,0]-undecene-2,9-diol
(58)
C. logus IC50 =70 µM[52]
8. 2,10,10-Trimethyl-6-methylene-
2,8- cyclodecadiene-1,5-diol
(59)
C. logus IC50 =27 µM[52]
9. 2,10,10-Trimethyl-6-methylene-
2,8- cyclodecadiene-1,5-diol
(59)
C. logus IC50 =41 µM[52]
10. 1,6,6,10- Tetramethyl-4,9,14-
trioxatetracyclotetradecane
(60)
C. logus IC50 =95 µM hepatoprotective
activity
Inhibitory activity on
D-galactosamine-
induced cytotoxicity
in primary cultured
mouse hepatocytes
[52]
(Continues)
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TABLE 8 a (Continued)
S/N Compound name Plant species
Level of
activity Bioactivity Mode of action Reference
11.(+)-Nootkatone (63) C. rotundus IC50 =4.81
µg/mL
DPPH radical
scavenging activity
[138]
12. 10,12-Peroxycalamenene (67), EC50 =2.33 ×
106M
Antimalarial activity [136]
13.α-Corymbolol (75)IC
50 =15.3 ±
72.7µM
Antihepatitis B virus
activity
Inhibition against
hepatitis B virus
(HBV) DNA
replication
[35, 36]
14.3β-Hydroxycyperenoic acid (78)IC
50 =46.6 ±
14.3µM
HBsAg anti secretory
activity
[119]
15. 11,12-Dihydroxyeudesm-4-en-3-
one
(81)
IC50 =11.06 µM
and IC50 =6.46
µM
Anticancer activity [119]
16. Cyperenoic acid (92)IC
50 =77.2 ±
13.0µM
HBsAg anti secretory
activity
[41]
17.1β-Hydroxy-α-cyperone (95)IC
50 =22.5 ±
71.9µM
Antihepatitis B virus
activity
Inhibition against
hepatitis
[41]
18. 10-Epieudesm-11-ene-3β,5α-diol
(96)
IC50 =13.2 ±
71.2µM
Inhibition against
hepatitis B virus
(HBV) DNA
replication
[41]
19.3β-Hydroxyilicic alcohol
(11(13)-eudesmene-3,4,12-triol)
(97)
IC50 =10.1 ±
70.7µM
[41]
20.3β,4α-Dihydroxy-7-epi-
eudesm-11(13)-ene (98)
IC50 =13.8 ±
70.9µM
[41]
21.7α(H),
10β-Eudesm-4-en-3-one-11,12-diol
(100)
IC50 =19.7 ±
72.10µM
[41]
22. Rhombitriol (103)IC
50 =11.9 ±
70.6µM
[41]
23. Cyperalin A (118) C. rotundus IC50 =0.57, 1.74
and 2.03µM,
Inhibitory activity
Against PGE2, COX-2
and LOX-5
respectiviely
Inhibition against
hepatitis B virus
(HBV) DNA
replication
[151]
(Continues)
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TABLE 8 a (Continued)
S/N Compound name Plant species
Level of
activity Bioactivity Mode of action Reference
24.10-O-Vanilloyltheviridoside (190)IC
50 =37.53 ±
2.51µM
MRB inhibitory
activity
[60, 61]
25. Rotunduside B (197)IC
50 =15.07 ±
2.51µM
[60, 61]
26. Solavetivone (121) IC50 =5.28
µg/mL
DPPH radical
scavenging activity
[152]
27. Aristolone (122) IC50 =6.82
µg/mL
[152]
28.CyprotusideA(142)IC
50 =29.1 ±
10.4, 39.4 ±17.9
Antidepressant
activity
[63]
29.CyprotusideB(143)IC
50 =31.7±11.1,
45.1±10.3
[63]
30.Sitosteryl(156)ED
50 =4.2
µg/mL
Cytotoxic activity [120]
31.SenburisideI(205)IC
50 =27.06 ±
11.33 µM
MRB inhibitory
activity
[159]
32. Luteolin (210)C. thunbergii and
C. glomeratus
IC50 =17.6 µM Arginase inhibitory
activity
[8]
33. Luteolin (210)C. rotundus IC50 =25 µg/mL Antiproliferative
activity
Inhibiting
significantly the
proliferation of K562
cells and protecting
against
H2O2/UV-photolysis
induced DNA
damage
[8, 122]
34. Luteolin (210)C. longus IC50 =3.0 µM LOX-5 Inhibitory
activity
Strong inhibition on
the release of
β-hexosaminidase
[8, 122]
35. Luteolin (210) C. rotundus IC50 =100µM Antiamyloid-β()
aggregation activity
[8, 122]
36.Aureusidin(213)C. thunbergii and
C. glomeratus
IC50 =60.6 µM Arginase inhibitory
activity
[8, 24]
(Continues)
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TABLE 8 a (Continued)
S/N Compound name Plant species
Level of
activity Bioactivity Mode of action Reference
37. Myricetin-3-O-β-D-
glucuronopyranoside
(252)
C. rotundus IC50 =2.3 µM LOX-5 Inhibitory
activity
[127]
38.(2RS, 3SR)-3, 4′, 5,
6,7,8-Hexahydroxyflavane (259)
IC50 =163.0±
12.6µM
DPPH radical
scavenging activity
[151]
39.Kaempferol(270) IC50 =3.85
µg/mL and 0.45
µg/mL
DPPH and ABTS
scavenging activities
respectively
[129]
40.Resveratrol(279)C. longus IC50 =17.0 µM LOX-5 Inhibitory
activity
Have a strong
inhibition on the
release of
β-hexosaminidase
[55, 158]
41. Piceatannol (280)C. longus IC50 =24.0 µM
42. Piceatannol (280)thunbergii and C.
glomeratus
IC50 =12.6 ±
0.6µM
Arginase inhibitory
activity
[55, 158]
43.trans-Scirpusin A (281)C. eragrostis IC50 =17.6 ±2.2
µM
[122, 158]
44.trans-Scirpusin B (282)longus SC50 =2.8 µM DPPH radical
scavenging activity
[157]
45. Cassigarol E (283)rotundus IC50 =78.6±3.7
µM
[156, 158]
46. Scirpusin B (290)C. eragrostis IC50 =22.6 ±0.9
µM
Arginase inhibition [65, 122, 156,
163]
47. Scirpusin B (290)C. rotundus IC50 =
55.1±3.8µM
DPPH radical
scavenging activity
[65, 122, 156,
163]
48. Scirpusin B (290) IC50 =100µM Antiamyloid-β()
aggregation activity
[65, 122, 156,
163]
49.()-(E)-Cyperusphenol A (292)IC
50 =1.43 ±
0.11µM
α-glucosidase
inhibitory activity
[24, 122, 128]
50.(E)-mesocyperusphenol A (293)IC
50 =1.44 ±
0.17µM
α-Glucosidase
inhibitory activity
[122, 128]
51. Cyperusphenol B (295)IC
50 =12.2 ±0.9
µM
Arginase inhibition [163, 122]
(Continues)
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TABLE 8 a (Continued)
S/N Compound name Plant species
Level of
activity Bioactivity Mode of action Reference
52. Cyperusphenol D (296)IC
50 =1.18 ±
0.11µM
α-Glucosidase
inhibitory activity
[122, 128]
53. Cyperusphenol D (296)IC
50 =26.3 µM Antiproliferative
activity
Suppress cell growth
by induction of
apoptosis
[122, 128]
54. Scirpusin A (301)IC
50 =108.3±7.2
µM
DPPH radical
scavenging activity
[65, 128, 158]
55. Scirpusin A (301) IC50 =100µM Antiamyloid-β()
aggregation activity
[65, 128, 158]
56. Thunbergin A (302)eragrostis IC50 =28.8 ±2.5
µM
Arginase inhibition [24]
57.trans-Resveratrol (304)C. eragrostis IC50 =19.4 ±1.3
µM
[24]
58. Cyperaquinone (305)C. nipponicus pED50 =6.77 Insect antifeeding
activity
[11]
59. Hydroxycyperaquinone (306)surinamensis IC50 =1.7 µM Anticancer activity Micromolar
inhibition of the 20S
catalytic core of the
20Sproteasome
[11]
60. Scabequinone (310)C. distans pED50 =8.59 Insect antifeeding
activity
[12, 13]
61.Remirol(325)C. nipponicus pED50 =6.89 [120]
62. Khellin (376)C. rotundus ED50 =4.5
µg/mL
Cytotoxic activity
63. Visnagin (377)ED
50 =0.9
µg/mL
[120]
64. 4-Hydroxy cinnamic acid (338)IC
50 =6.3 ±0.7
at 20 µg/mL and
23.5 ±1.5 at 40
µg/mL
α-Glucosidase and
α-amylase activities
respectively
[120, 150]
65. Fulgidic acid (403) IC50 =100µM Antiamyloid-β()
aggregation activity
[65]
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TABLE 8 b Summary of bioactivities of the most potent compounds.
Natural products Bioactivity Mechanisms Reference
Cyperotundone (14), valencene (20), cyperusol A2 (25),
α-cyperone (27), isocyperol (28), sugetriol triacetate (39),
(+)-nootkatone (64), cyperusol A3 (73), cyperenoic acid (92),
cyperalin A (120), solavetivone (123), aristolone (124), epioreintin
(225), myricetin-3-O-β-D-glucuronopyranoside (226),
luteolin-7-O-β-D- glucuronopyranoside-6′′ -methylester (227),
(2RS,3SR)-3,4′,5,6,7,8-hexahydroxyflavane (236), Kaempferol
(244), scirpusin B (262), trans-scirpusin A (253),
Anti-inflammatory
and antioxidant
PGE2,LPS,COX-2,LOX-5,NO,
iNOS, HO-1, ROS, free radicals
[45]
133,isorhamnetin(142), vitexin (143), isovitexin (144), oreintin
(145), epiorientin (146), myricetin-3-O-β-D-galactopyranoside
(147), luteolin-7-O-β-D-glucuronopyranoside-6΄΄-methyl ester
(148), luteolin-4΄-O-β-D-glucuronopyranoside (149), and
Luteolin-7-O-β-D-glucuronopyranoside (150)
Antioxidant PGE2, LPS, COX-2, LOX-5 [76, 87, 167]
Afzelechin (134), (+)-catechin (135), luteolin (136), quercetin
(137), galloylquinic acid (165), 3-hydroxy-4-methoxybenzoic acid
(166) and ferulic acid (167)
Antioxidant and
anticancer
K562 cells, H2O2/UV [88, 167]
Cyperol (30), 1β-hydroxy-α-cyperone (97),
10-epieudesm-11-ene-3β,5α-diol (98), 3β-hydroxyilicic alcohol
(11(13)-eudesmene-3,4,12-triol) (99), cyperusol C (49),
α-corymbolol (76), 3β,4α-dihydroxy-7-epi- eudesm-11(13)-ene
(100), 2-oxo-α-cyperone (77), 7α(H),
10β-eudesm-4-en-3-one-11,12-diol (102), and rhombitriol (105)
Antiviral HBV DNA replication, HBsAg,
HBeAg
[41, 45]
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FIGURE 7 Chemical structures of natural products with anti-inflammatory and antioxidant activities.
mice [124]. Oral administration of 500 mg/kg of C.rotundus
extract to male Sprague–Dawley rats significantly lowered the
blood glucose levels [125, 126].Compounds211,248,247,250,and
252 showed strong α-amylase inhibitory activity [120, 127]. ()-
(E)-cyperusphenol A (IC50 =1.43 ±0.11), (E)-mesocyperusphenol
A (IC50 =1.44 ±0.17), and cyperusphenol D (IC50 =1.18 ±0.11 µM)
exhibited strong in vitro α-glucosidase inhibition with acarbose as
standard [128]. Compound 338, (6.3 ±0.7 at 20 µg/mL), exhibited
mild α-glucosidase activity with acarbose as the control [129].
5.4 Antimicrobial Activity
Plants extracts and products from Cyperus species are valuable
sources of natural products capable of inhibiting microbial
growth through diverse mechanisms (Figure 5). The crude
extracts from C.rotundus rhizomes have shown antibacterial
activities against several foodborne pathogens and Salmonella
enteritidis,Staphylococcus aureus,andEnterococcus faecalis with
MIC of 0.5–5 mg/Ml, respectively [130–132]. The extracts of
C.rotundus demonstrated anthelmintic, antidiarrhoeal, and
antibacterial activities [133–135]. Compound (67), exhibited the
strongest effect (EC50)=2.33 ×106M against P. falciparum
[136]. Compounds 29 and 76 showed antimalarial activity with
IC50 values less than 2 µg/mL against P.falciparum strains
NF54 and ENT 30 [137]. Compound 8 showed moderate activity
against Bacillus subtilis at 0.5 mg [138]. β-Sitosterol (19, 250),
and α-amyrin (18 mm, 250 mg/mL) showed anticandidal activity
against Candida famata and Candida albicans, respectively [139].
Compound 14 had significant (MIC =8µg/mL) and bactericidal
(MBC =32 µg/mL) activities against a Salmonella strain [140].
5.5 Antidepressant and Neuroprotective
Potentials
Crude extracts and natural products from Cyperus species have
revealed promising antidepressant and neuroprotective poten-
tials (Figure 6) often attributed to their ability to modulate
neurotransmitter systems, reduce oxidative stress, and promote
neurogenesis. The crude extract of C.rotundus demonstrated
strong Central Nervous System (CNS) depressant, improve
amyloid β(Aβ)-induced memory impairment, neuroprotective,
anxiolytic, and acetylcholinesterase inhibitory potential [141–
146]. Compound 29 showed access to the CNS by traversing the
blood–brain barrier [147]. The flavans 263, 265, and the stilbene
derivatives 297 and 298 showed moderate activity toward μ-opioid
receptor [148].
5.6 Anti-Inflammatory and Antioxidant
Activities
Extracts and phytochemicals from Cyperus species have proven
valuable in the management and prevention of various chronic
diseases due to their anti-inflammatory and antioxidant activities.
The ethanolic extract of C.rotundus showed potent antioxidant
activity with IC50 values of 64.64 ±5.3, 85.89 ±6.3, and 8.42
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FIGURE 7 (Continued)
±0.45 mg/mL against DPPH, metal chelating, and nitric oxide
scavenging activities [145]. The topical administration of the
ethanol extract of C.rotundus showed a reduction in ear edema
and cellular infiltrate in acute and chronic skin inflamma-
tion models [149]. Valencene (20) and nootkatone (82) showed
heme oxygenase-1 (HO-1) induction [150]. The mechanisms of
actions of other compounds reported in literature exhibiting anti-
inflammatory and antioxidant activities in the review have been
summarized and provided in Figures 7and 12, and Tables 8a
and 8b [26, 151158].
5.7 Macrophages Respiratory Burst (MRB) and
Antiallergic Inhibitions
Natural products in Cyperus species influence respiratory burst
in macrophages-a rapid release of reactive oxygen species (ROS),
a process crucial for their ability to kill pathogens (Figure 8).
Through processes like immune system modulation, reduction in
the release of histamines, and other mediators involved in allergic
reactions, natural products have established their potential to
inhibit allergic responses. Senburiside I(IC50 =27.06 ±11.33)
showed significant MRB inhibitory activity with rutin (IC50 =
15.07 ±2.51) and dexamethasone (IC50 =355.14 ±45.76 µM) as ref-
erence, respectively [159]. Compounds 20, caryophyllene-α-oxide,
and 82 showed in vitro and in vivo antiallergic potential. The
sesquiterpenes demonstrated strong inhibition of 5-lipoxygenase-
catalyzed leukotrienes production in rat basophilic leukemia
(RBL)-1 cells. Valencene (20) had the highest inhibitory effect on
β-hexosaminidase release by antigen-stimulated RBL-2H3 cells.
Compounds 20 and 82 administered to mice orally at 50–300
mg/kg showed significant inhibition [160].
5.8 Estrogenic and Arginase Inhibitions
Cyperus species secondary metabolites are promising inhibitors
of estrogen production by targeting the enzyme aromatase which
converts androgens to estrogens (Figure 9). Some inhibit arginase
preventing the enzyme that converts L-arginine to L-ornithine
and urea, thus regulating nitric oxide levels. Nootkatone (82)
administered in different doses to rats showed a significant
effect on platelet aggregation ex vivo [161]. Quercetin-3,4′-
dimethylether (226) and diosmetin (228) showed weak estrogenic
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FIGURE 8 Chemical structures of natural products with macrophage respiratory burst and antiallergic activities.
FIGURE 9 Chemical structures of natural products with estrogenic and arginase inhibition.
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FIGURE 10 Chemical structures of natural products with miscellaneous activities.
FIGURE 11 Activity distribution of the different classes of compounds.
activity [162]. Cyperusphenol B (IC50 =12.2 ±0.9 µM) isolated
from C. eragrostis demonstrated significant inhibition on arginase
using Nω-hydroxy-nor-L-arginine (nor-NOHA), as a positive
control [163]. Arraki et al. [163], reported that trans-scirpusin
A (IC50 =17.6 ±2.2 µM) demonstrated significant in vitro
arginase inhibition using purified liver bovine arginase close to
piceatannol (IC50 =12.6 ±0.6 M).
5.9 Other Activities
Cyperus species have shown allelopathic, mosquito larvicidal
potential [164, 165]. α-Cyperone (27) isolated from methanol
extract of C.rotundus showed insecticidal activity [166]. Zerum-
bone (126) has shown repellency activity to the male Blattella
germanica [167]. Cyperotundone (14) and α-cyperone (27) at 100–
1000 µg/mL showed growth inhibitory effects to lettuce seedlings
(Figure 10)[168].
5.10 Safety, Preclinical Trial Data
No death was recorded when C.rotundus extracts were given
to mice at different doses [46, 139, 169]. Oral administration of
resveratrol in mouse models has been shown to be safe and non-
toxic at different doses. Also, a phase I study of the same NP was
conducted in 10 healthy individuals and no serious adverse effects
were observed [170]. Also, recent clinical trials have observed
resveratrol to be safe and well-tolerated at doses of upto 5 g/day
[170].
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FIGURE 12 Mechanism of action of some bioactive natural products isolated from Cyperus species.
FIGURE 13 Biosynthesis of bioactive terpenoids isolated from Cyperus species [171, 172].
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FIGURE 14 Biosynthesis of bioactive flavonoids isolated from Cyperus species [173–175].
6 Bioactivities and Proposed Mechanisms of
Potent Compounds
The potent secondary metabolites isolated from these plant
species have been shown in Figures 11 and 12 and Tables 8a and 8b.
7 Biosynthesis of Potent Terpenoids and
Flavonoids
We have proposed a biosynthesis (Figure 13) through the meval-
onic acid pathways of some of the potent terpenoids isolated
from these plant species [171, 172]. The flavonoids from Cype-
rus species have been derived from phenylalanine through the
phenylpropanoid pathway (Figure 14), while phenylalanine is
synthesized through the shikimate pathway [173–175].
R=H, OH, OCH3,COOH;OG=O-glycoside groups; PAL,
phenylalanine ammonia-lyase; C4H, cinnamate 4-hydroxylase;
4CL, 4-coumaroyl-CoA ligase; CHS, chalcone synthase; STS:
stilbene synthase; CHI, chalcone isomerase; F3H, flavone 3-
hydroxylase; F3′,5′H, flavonoid 3′,5′-dihydroxylase; FS, flavonol
synthase; DFR, dihydroflavonol reductase; 3GT and 5GT, 3- & 5-
glycosyl transferase; RT, rhamnosyl transferase; OMT, O-methyl
transferase.
8 Conclusions and Perspectives
Cyperus is an important genus in Cyperaceae and harbors
natural products with interesting bioactivities. In this study,
we have reported 403 compounds identified and isolated from
43 Cyperus species with terpenoids constituting the largest
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class of these products, followed by flavonoids. Other classes
of compounds found include stilbenoids, quinones, aromatics,
coumarins, and other compounds. These secondary metabolites
were found to display various activities including antioxidant,
anti-inflammatory, antitumor, antidepressant, neuroprotective,
antidiabetic, and macrophage respiratory burst (MRB) inhibitory
activities. Based on the bioactivities, some of the most promising
compounds in Cyperus species with IC50 below 10 µMfor
further development include the antihepatitis B virus (HBV)
DNA replication agents sugetriol triacetate (38) and cyperalin
A(118); the antioxidant compounds solavetivone (121), aris-
tolone (122), kaempferol (270), and trans-scirpusin B (282);
and the anti-inflammatory hits luteolin (210) and myricetin-
3-O-β-D-glucuronopyranoside (252). The anticancer quinone
hydroxycyperaquinone (306), together with the α-glucosidase
and α-amylase inhibitor 4-hydroxy cinnamic acid (338), also had
remarkable potential. The biosynthesis of some potent terpenoids
and flavonoids, the two major classes of compounds isolated from
these plant species, has been included in this study. A phase I
study of oral administration of resveratrol in healthy volunteers
and consumption of the compound at these levels did not cause
serious adverse effects. Studies on the toxicity of some of these
natural products showed no serious adverse effects though the
mechanism of action and toxicity profile of compounds from
several Cyperus species have not been extensively investigated in
in vivo models. It would be interesting in future to perform a
computational study of the potent compounds with interesting
anticancer and antiviral activities by docking them against their
target of interest.
Author Contributions
S.B.B. conceived and designed the research. All authors read and
approved the manuscript.
Acknowledgments
Smith B. Babiaka acknowledges funding from the Alexander von Hum-
boldt Foundation for Georg Forster and Georg Forster-Bayer Research
fellowships (Ref. 3.4–CMR–1220727–GF-P) at the University of Tübingen,
Germany. Doris E. Ekayen is a PhD student funded by the German
Academic Exchange Service (DAAD, Award No. 91832147).
Conflicts of Interest
The authors declare no conflicts of interest.
Data Availability Statement
Data is available in supplementary.
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