Cyperus Species (Part I): Phenolics and Nitrogenous

Available online on www.ijppr.com International Journal of Pharmacognosy and Phytochemical Research 2015; 7(1); 51-67

ISSN: 0975-4873 Research Article

A Review: Compounds Isolated From Cyperus Species (Part I): Phenolics and Nitrogenous

Mohamed A. Gamal1, Kamal M. K. Hani2, Elhady S. Sameh3, *Ibrahim R. M. Sabrin4

1Pharmacognosy Department, Faculty of Pharmacy, Al-Azhar University, Assiut Branch, Assiut 71524, Egypt. 2Biomedical Technology, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia. 3Department of Natural Products and Alternative Medicine, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia. 4Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut, 71526 Egypt.

Available Online: 1st February, 2015

ABSTRACT Species belonging to the family Cyperaceae are an important source of active constituents with biological activity. Cyperaceae is a family of monocotyledonous known as sedges, which superficially resemble grasses or flowering plants rushes. The family comprises about 4000 species described in about 90 genera. These species are widely distributed in tropical Asia and tropical South America. While, sedges may be found growing in all types of soils, many are associated with wet lands or poor soils. The genus Cyperus includes about 600 species, some of which are used in folk medicine, the most important one is Cyperus rotundus L. In this review we focused on the phenolics and nitrogenous constituents isolated from different Cyperus species growing in Egypt.

Keywords: Cyperacae, Cyperus species, Phenolics, Nitrogenous compounds.

INTRODUCTION activity16,17. While, the ethanolic extract of the Family Cyperaceae (Sedge family) includes grass like inflorescences showed a moderate oestrogenic activity18. plants which grow mostly in marshy places. It comprises The essential oil displayed significant antimicrobial and about 4000 species within 90 genera1-5. There are twenty cytotoxic activities15. Methanolic extract and some one species of Cyperus in Egypt6. Many Cyperus species isolated compounds of C. alopecuroides showed are used as food or medicines. The tubers of C. esculentus antioxidant, cytotoxic, and α-amylase inhibitory19. C. are edible and used as spermatogenic, aphrodisiac, articulatus L. are used in the perfume industry20. C. galactogogue, emollient7, digestive, tonic, diuretic and alternifolius showed signifiant hepatoprotective activity 8 21 promotes menstruation . C. rotundus L. (Nut grass; Nut against CCl4 induced hepatotoxicity in rats . C. scariosus sedge, Magessa, Zible El-Meize, Sed El-Homar) 6,7 was have been widely used as anti-inflammatory, analgesic, well known to the ancient. It grew in Egypt during the astringent, hypotensive, hepatoprotective, and stone age in moist soils. Its tubers were used by the antidiabetic22. Several reports were traced in the current ancient Egyptians in embalming and perfumes9. Also, literature concerning the previous phytochemical studies they are widely used as diaphoretic, astringent, of different Cyperus species. The main phenolics and demulcent, liver remedy, antidysentric, and antimalarial10, nitrogenous compounds isolated from different Cyperus antioxidant, cytotoxic, and α-amylase inhibitory11,12. The species are summarized as following table: plant was also used for treatment of cough and 5 psychosomatic diseases13. Moreover, rhizomes OR constituents might be of therapeutic benefit for the OR4 prevention of platelet-associated cardiovascular R1 diseases14. C. alopecuroides Rottb. (Samar; Foxtail 2 Sedge; Mat Sedge, Aloob es-sultaan) is cultivated in R O O some regions of the Nile Delta6,7. In Faiyum, it is cultivated in limited areas for mat and chair making7. It is used as a raw material for perfumes15. The ethanolic extract of the aerial parts of C. alopecuroides Rottb. 3 O produced signs of pain and allergy on rabbit’s skin16, OR revealing that the extract contained histamine or histamine like substance16. Also, the ethanolic and Fig 1: Flavanoids ethereal extracts of the aerial parts showed antimicrobial

*Author for Correspondence Gamal et.al. / A Review: Compounds isolated from…

Table 1: Main phenolic constituents isolated from different Cyperus species. Compound name Structure Plant source Organ Ref.

OR5

OR4 1 R 1. Flavonoids: R2O O

OR3 O Leaves and Luteolin R1 = R2 = R3 = R4 = R5 = H in about 120 species 23-27 inflorescence Luteolin 3`-methyl R1 = R2 = R3 = R4 = H Tubers and C. rotundus L. 23 ether R5 = Me aerial parts C. alopecuroides Luteolin 4´methyl R1 = R2 = R3 = R5= H Rottb. Inflorescence [19] ether R4 = Me

C. alopecuroides Leaves 26 Rottb. Leaves and C. aquatilis R. Br. 24 inflorescence C. alternifolius L. Leaves 26 C. articulatus L. Leaves 26 C. compressus L. Leaves and 24 inflorescence C. conglomeratus Leaves 26 Rottb. C. cyperinus Retz. Leaves 24 C. disjunctus C.B. Leaves and 24 Clarke inflorescence R1 = R2 = R4 = R5 = H C. fenzelianus Leaves 26 Luteolin 5methyl ether R3 = Me C. flaccidus R. Br. Leaves 24 C. flavescens L. Leaves 24 C. laevigatus L. Leaves 24,26 C. lucidus R. Br. Leaves 24 C. maculatus Boeck Leaves 24 C. polystachyos Leaves 24 Rottb. C.reflexus Vahl Leaves 24 C. Leaves 24 sanguinolentusVahl C. subulatus R. Br. Leaves 24 C. tenuiculmis Leaves 24 Boeck. C. trinervis R. Br. Leaves 25 Luteolin 7, 3`-dimethyl R1 = R3 = R4 = H C. rotundus L. Areal parts [11] ether R2 = R5 = Me Luteolin 5, 3`-dimethyl R1 = R2 = R4 = H C. rotundus L. Areal parts [11] ether R3 = R5 = Me C. alternifolius L. Leaves 26 C. bulbosus Vahl Leaves 26 Luteolin 7glucuronide 1 3 4 5 R = R = R = R = H C.conglomeratus Leaves 26 2 52 R = Glucuronic acid Rottb. C. compressus L. Leaves 26 C. digitatus Roxb. Leaves 26 Page

C. difformis L. Leaves 26

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C. esculentus L. Leaves 26 C. fenzelianus Leaves 26 C. fuscus L. Leaves 26 C. imbricatus R. Br. Leaves 26 C. laevigatus L. Leaves 26 C. maculatus Boeck Leaves 26 C. microbolbos C. Leaves 26 B.Cl. C. michelianus L. Leaves 26 C. papyrus L. Leaves 26 C. rotundus L. Leaves 11,26 C. alopecuroides 26 Leaves Rottb. C. articulatus L. Leaves 26 R1 = R3 = R4 = R5 = H C. alternifolius L. Leaves 26 Luteolin 7glucoside R2 = Glc C. esculentus L. Leaves 26 C. laevigatus L. Leaves 26 C. schimperianus Leaves 26 Steud. Luteolin4`glucoside R1 = R2 = R3 = R5 = H C. rotundus L. Areal parts 11 R4 = Glc Orientin R1 = Glc C. alopecuroides Infloresc- 28 R2 = R3 = R4 = R5 = H Rottb. ences C. alopecuroides Leaves 26 Rottb. C. bulbosus Vahl Leaves 26 C. difformis L. Leaves 26 R1 = R3 = R4 = R5 = H C. esculentus L. Leaves 26 Luteolin 7diglucoside R2 = GlcGlc C. maculatus Boeck. Leaves 26 C. michelianus L. Leaves 26 C. rotundus L. Leaves 26 C. schimperianus Leaves 26 Steud. Luteolin 7rutinoside R1 = R3 = R4 = R5 = H 26 C. articulatus L. Leaves R2 = Rham (16) Glc Luteolin 7glucuronide R1 = R3 = R5 = H 4`glucoside R2 = Glucuronic acid C. laevigatus L. Leaves 26 R4 = Glc OH R1

R O O 2

OH O C. bulbosus Vahl Leaves 24 C. bowmanii Benth. Leaves 24 C. compressus L. Leaves 24 C. castaneus (Willd.) Leaves 24 C. cuspidatus H. B. K. Leaves 24 R1 = R2 = R3 = H Apigenin C. enervis R. Br. Leaves 25

C. nervulosus (KÜK.) Leaves 24 C. perangustus T. S. Leaves 24

Blake. 53 C. sulicinux Leaves 24 C.B.Clarke

Page Apigenin 7glucoside R1 = R3 = H, R2 = Glc C. laevigatus L. Leaves 26

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Apigenin R2 = Glucuronic acid C. laevigatus L. Leaves 26 7glucuronide R1 = R3 = H C. alopecuroides Infloresce- Vicenin 2 R1 = R3 = Glc, R2 = H 19 Rottb. nces

Leaves and Tricin R1 = R2 = H, R3 = Me in about 90 species 24,25 inflorescences C. alopecuroides Rottb. Leaves 26 C. difformis L. Leaves 26 R1 = H, R2 = Glc C. digitatus Roxb. Leaves 26 Tricin 5glucoside R3 = Me C. fenzelianus Leaves 26 C. maculatus Leaves 26 Boeck Leaves 26 C. rotundus L. R1 = H Leaves Tricin 5diglucoside C. laevigatus L. 26 R2 = Glc – Glc, R3 = Me C. alopecuroides R1 = Glc, R2 = H Leaves 26 Tricin 7glucoside Rottb. R3 = Me Leaves 26 C. michelianus L. C. conglomeratus Leaves 26 R1 = Glucuronic acid Tricin 7glucuronide Rottb. Leaves 26 R2 = H, R3 = Me C. laevigatus L. C. bulbosus Vahl Leaves 26 C. digitatus Roxb. Leaves 26 R1 = Glc – Glc Tricin 7diglucoside C. fenzelianus Leaves 26 R2 = H, R3 = Me C. laevigatus L. Leaves 26 C. michelianus L. Leaves 26 Tricin 7,4`diglucoside R1 = R3 = Glc, R2 = H C. laevigatus L. Leaves 26 OR3

4 OR

R1O O

2 OR O OH C. aquatilis R. Br. Leaves 24 C. brevifolius Rottb. Leaves 24 C. flaccidus R. Br. Leaves 24 C. haspan L. Leaves 24 C. leavis R. Br. Leaves 24 Quercetin R1 = R2 = R3 = R4 = H C. prolifer Lam. Leaves 24 C. squarrosus L. Leaves 24 C. tenuispica Steud. Leaves 24

C. tenuiculmis Boeck Leaves 24 54 C. rotundus L. Aerial parts 23

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C. cunninghamii Leaves 24 R1 = R3 = R4 = H C. Clarke Leaves 24 Quercetin 3–methyl R2 = Me C. dactylotes Benth. Leaves 24 ether C. rigidellus Benth. Leaves 24 C. tetraphyllus R. Br. Leaves 24 Quercetin 3,7dimethyl R1 = R2 = Me C. dactylotes Benth. Leaves 24 ether R3 = R4 = H C. rigidellus Benth. Leaves 24 Quercetin 3,7,3`tri- R1 = R2 = R3 = Me, R4 = H C. dactylotes Benth. Leaves 24 methyl ether C. rigidellus Benth. Leaves 24 R1 = R4 = H C. alopecuroides Quercetin Infloresc- R2 = R3 = Me Rottb. 19 3,3´dimethyl ether ences

R1 = R3 = H C. alopecuroides Quercetin Infloresc- R2 = R4 = Me Rottb. 19 3,4´dimethyl ether ences

C. alopecuroides Leaves [26] R1 = R3 = R4 = H Quercetin 3rutinoside Rottb. Aerial parts [23] R2 = Rham (16) Glc C. rotundus L. Rhamnetin R1 = Me, R3 = H 3Orhamnosyl (14) C. rotundus L. Mature tubers 28 R2 = rham (14) rham. rhamno-pyranoside

R1O O

OR2

O OH Tubers and 23 Kaempferol R1 = R2 = H C. rotundus L. aerial parts C. dactylotes Benth. Leaves 24 R1 = H, R2 = Me C. cunninghamii Leaves 24 Kaempferol 3methyl C. Clarke Leaves 24 ether C. sexflorus R. Br. Leaves 24 C. tetraphyllus R. Br. Leaves 24 C. dactylotes Benth. Leaves 24 R1 = R2 = Me Kaempferol 3,7dimeth C. cunnirghamii Leaves 24 ylether C. B. Clarke Leaves 24

C. rigidellus Benth. Leaves 24 R1 = H, R2 = O-–D–(2G- C. alopecuroides Aerial parts 19 Kaempferol 3O-–D– glucosylrutinoside) Rottb. (2G-glucosylrutinoside)

Kaempferol 3-O-–D– R1 = H, R2 = -O-–D–(2G- C. alopecuroides Aerial parts 19 (2G-xylosylrutinoside) xylosylrutinoside) Rottb. R5

R6 R1

2 R O 7 R

3 R R4 1 5 7

5,7,4`– R = R = R = H C. conglomeratus Whole 29 55 Trimethoxy6prenyl R2 = R4 = R6 = OMe Rottb. plant 3 flavan R = CH2CH=C(CH3)2 5,7-Dihydroxy–3`,5`- R1 =R6 = H, R2 = R4 = OH C. conglomeratus Tubers 30 Page

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3 5 7 dimethoxy–6– R = CH2CH=C(CH3)2, R = R = OMe Rottb. prenylflavan 7,3`-Dihydroxy-5,5`- C. conglomeratus Whole 31 R1 = CH CH=C(CH ) , R2 = R5 = OH, R3 dimethoxy-8- 2 3 2 Rottb. plant = R6 = H, R4 = R7 = OMe prenylflavan R1 = CH CH=C(CH ) C. conglomeratus Whole 31 5,7,3`-Trihydroxy-5`- 2 3 2 R2 = R4 = R5 = OH, R3 = R6 = H, R7 = Rottb. plant methoxy-8-prenylflavan OMe 5-Hydroxy-7, 3`, 5`- tri- R1 = R3 = R6 = H, R2 = R5 = R7 = OMe, C. conglomeratus Tubers 30 methoxyflavan R4 = OH Rottb. 5,3´-Dihydroxy-6,4´- R1 = R2 = R7 = H, R3 = R6 = OMe 4 5 C. capitatus Vand. dimethoxyflavan R = R = OH OH Rhizomes 32 OH

HO O

5,7,4´,5´-Tetrahydroxy- C. capitatus Vand. Rhizomes 32 OH O 6,3´-diprenylflavanone

Me Me

MeO O C. conglomeratus Tubers 33 Rottb.

MeO

Aureusidin R1 = R2 = R3 = R5 = in about 60 Fruits, leaves and (4,6,3`,4`-Tetrahydroxy 2426 R6 = H, R4 = OH species inflorescences aurone) C. alopecur- Leaves 26 oides Rottb. Leaves 26 Sulphuretin C. capitatus Leaves 26 R1 = R2 = R3 = R4 = (6,3`,4`Trihydroxyauron Vand. Leaves 26 R5 = R6 = H e) C. fuscus L. C. michelia-nus L. Leptosidin6O-D R1 = OMe C. scariosus R. R2 = Glc (14) rham. Leaves 34 glucopyranosylOL Br. rhamnopyranoside R3 = R4 = R5 = R6 = H Mariscetin R1 = R4 = OH in about 19 Inflorescences 24 (7Hydroxyaureusidin) R2 = R3 = R5 = R6 = H species 6,3`,4`Trihydroxy4me R1 = R2 = R5 = R6 = H C. capitatus Rhizomes and roots 35 thoxy5methylaurone R3 = Me, R4 = OMe Vand. 6,3`Dihydroxy4, 4` R1 = R2 = R5 = H 3 6 C. capitatus R = R = Me Rhizomes and roots 36 56 dimethoxy5methylauro Vand. ne R4 = OMe 1 3

4,6,3`,4`Tetramethoxy R = R = H C. capitatus Page Rhizomes and roots 36 R2 = R5 = R6 = Me Vand. aurone

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R4 = OMe 4,6,3`,4`Tetrahydroxy R1 = R2 = R 5 = R 6 = H, R4 = OH, C. capitatus Rhizomes and roots 37 5methylaurone R3 = Me Vand. 4,6,3`,4`Tetrahydroxy7 R1 = Me C. capitatus Rhizomes and roots 37 methylaurone R2 = R3 = R5 = R6 = H, R4 = OH Vand. 6, 3`, 4`Trihydroxy4 R1 = Me C. capitatus R2 = R3 = R5 = R6 = H, Rhizomes and roots 37 methoxy7methyl Vand. aurone R4 = OMe OH OH

HO O

OH (+) Catechin R = -OH C. longus L. Whole plant 27 (-) Epicatechin R = -OH C. longus L. Whole plant 27 2. Coumarins: R1

O O O

R2 R1 = C. alopecuroides O-CH2CH=C(CH3)2 Aerial parts 18 Imperatorin R2 = H Rottb.

C. alopecuroides Bergapten R1 = H, R2 = OMe Aerial parts 18 Rottb. C. alopecuroides Xanthotoxin R1 = OMe, R2 = H Rottb. Aerial parts 18

C. alopecuroides R1 = OH, R2 = H Aerial parts 18 Xanthotoxol Rottb.

R3 O O

R4 C. alopecuroides R1 = R4 = H, R2 = OH Isoscopoletin Rottb. Aerial parts 18 R3 = OMe

R1 = R4 = H C. alopecuroides Esculetin Aerial parts 18 R2 = R3 = OH Rottb. R1 = R2 = R4 = H Umbelliferone C. incompletus - 38 R3 = OH R1 = R4 = H Scopoletin C. incompletus - 38 R2 = OMe, R3 = OH R1 = R3 = OMe 5,7-Dimethoxycoumarin C. incompletus - 38 R2 = R4 = H R1= R2= H 7,8-Dimethoxycoumarin C. incompletus - 38 57 R3= R4 = OMe 5,7,8- R1 = R3 = R4 = OMe

C. incompletus - 38 Page Trimethoxycoumarin R2 = H

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Leptodactylone R1 = R3 = OMe, R2 = H, R4 = OH C. incompletus - 38 R1 = R4 =H, R2 = OH Prenyletin 3 C. incompletus - 38 R = -OCH2CH=C(CH3)2 5,7-Dimethoxy-8- R1 = R3 = OMe, R2 = H (,-Dimethylallyloxy) C. incompletus - 38 R4 = -OC(CH ) CH=CH coumarin 3 2 2 7-Methoxy-8- R1 = R2 = H, R3 = OMe (,-dimethylallyloxy) C. incompletus - 38 R4 = -OC(CH ) CH=CH coumarin 3 2 2 7-(,-Dimethylallyloxy) R4 = OMe, R1 = R2 = H 3 C. incompletus - 38 8-methoxycoumarin R = -OC(CH3)2CH=CH2 OCH3

H3CO

Pimpinellin C. papyrus - 39

O O O

3. Chromones:

C. rotundus L. Aerial parts 23

Khellin R1 = R2 = CH3 C. rotundus L. Aerial parts 11 Visnagin R1 = CH3, = R2 = H C. rotundus L. Aerial parts 11 Ammiol R1 = CH2OH, = R2 = CH3 C. rotundus L. Aerial parts 11 Khellol--D- 11 R = CH O-glu, = R = H C. rotundus L. Aerial parts glucopyranoside 1 2 2 4. Coumarans:

Basal and Remirol C. nipponicus 40 aerial stems

5. Stilbenoids: OH OH

C. longus L. Whole plant 27 Longusone A HO

O HO OH

Longusol A HO OH C. longus L. Whole plant 27

HO O

58 HO OH

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C. longus L. Whole plant 27

Longusol B HO

HO O OH

O C. longus L. Whole plant 27 HO Longusol C

OH O

HO OH OH

3 R2 R 5 R

3,5, 3´,4´- C. capitatus Vand. Rhizomes 31 Tetramethoxystilbene R1 = R2 = R4 = R 5 = OMe, R3 = H

Resveratrol R1 = R2 = R4 = OH, R3 = R5 = H C. longus L. Whole plant 27 Piceatannol R1 = R2 = R4 = R5 = OH, R3 = H C. longus L. Whole plant 27 2-Prenyl-3,4`-dihydroxy- R1 = H, R2 = R4 = OH C.conglomer Tubers 33 3 5 5-methoxy stilbene R = CH2=CHC(CH3)2, R =OMe -atus Rottb.

HO O OH

Trans- Scirpusin A R = H C. longus L. Whole plant 27 59 Trans- Scirpusin B R = OH C. longus L. Whole plant 27

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O HO

OH C. longus L. O Cassigarol E Whole plant 27

OH OH

O HO C. longus L. Whole plant 27 OH Cassigarol G O

HO OH OH

HO H O

OH C. longus L. Whole plant 27 Pallidol

OH OH 6. Phenylpropanoids: p-Coumaric acid COOH C. rotundus L. Tubers 41 HO

COOH C. rotundus L.

HO Ferulic acid Tubers 41

H3CO

C. conglomeratus Tubers 29 4Hydroxyallylbenzene R = H Rottb. 60 C. conglomeratus 3Ethoxy4hydroxyallylbenzene R = OEt Tubers 29

Rottb. Page

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Isoaragoside R1 = H: R2 = caffeoyl; R3 = Ara C. rotundus L. Rhizomes 42 Chionoside A R1 = Feruloyl: R2 = H; R3 = Ara C. rotundus L. Rhizomes 42 Helioside C R1 = Feruloyl: R2 = Xyl; R3 = Ara C. rotundus L. Rhizomes 42

7. Quinones: C. haspan L. Root and 43 rhizomes C. alopecuroides Root and 44 Dihydrocyperaquinone Rottb. rhizomes Roots and 44 C. alternifolius L. rhizomes Roots and C. platystylis R. Br. rhizomes 43

C. aristatus Rottb. Roots and 44 rhizomes C. conicus (R. Br.) Roots and 44 Boeck rhizomes C. decompositus Roots and 44 (R. Br.) F. Muell. rhizomes C. exaltatus Retz. Roots and 44 rhizomes C. eragrostis Lam. Roots and 44 Cyperaquinone rhizomes R = Me, R1 = CH 2 C. haspan L. Roots and 44 rhizomes C. javanicus Houtt. Roots and 44 rhizomes C. nipponicus Basal stems 40 C. pilosus Vahl Roots and 43 rhizomes C. subulatus R. Br. Roots and 44 rhizomes C. vaginatus R. Br. Roots and 44 rhizomes C. aristatus Rottb. Roots and 43 Demethylcyperaquinone rhizome 44 R = H, R1 = CH 2 C. compressus L. Roots and rhizome

C. conicus (R. Br.) Roots and 44 Boeck rhizomes Hydroxycyperaquinone 61 C. cyeroides (L.) Roots and 44 1 R = CH2OH, R = CH2 O. Ktzetl rhizomes

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C. decompositus (R. 44 Root and Br.) rhizomes F. Muell. Roots and 44 C. eragrostis Lam. rhizomes Roots and 44 C. haspan L. rhizomes C. javanicus Houtt. Roots and 44

rhizomes C. stoloniferus Retz. Roots and 44

rhizomes C. subulatus R. Br. Roots and 44

rhizomes C. vaginatus R. Br. Roots and 44

rhizomes C. conicus (R. Br.) Roots and 44 Conicaquinone R = Me, R1 = O Boeck rhizomes

Roots and C. alternifolius L. 44 Tetrahydrocyperaquinone rhizomes

Roots and Scabiquinone C. distans L. 40,44 rhizomes

C. eleusinoides Roots and 44

Künth rhizomes C. scaber (R. Br.) Roots and 44

Boeck rhizomes

Roots and C. distans L. 44 Dihydroscabequinone rhizomes

C. scaber (R. Br.) Roots and 44

Boeck rhizomes

C. dietricheae var. Roots and Breviquinone R = Me brevibracteatus 44

(Domin) kükenth. rhizomes 62

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C. dietricheae var. Hydroxybreviquinone brevibracteatus Roots and 44 R = CH OH 2 (Domin) kükenth. rhizomes

C. aff. dactylotes Roots and 44 Benth. rhizomes C. decompositus (R. Roots and 43 Br.) F. Muell. rhizomes C. dietricheae Boeck Roots and 44 Hydroxydietrichequin- R1= CH – (CH ) – CH=CH – (CH ) rhizomes one 3 2 7 2 7 R2 = OH, R3 = Me, R4 = H C. fulvus R. Br. Roots and 44 rhizomes C. javanicus - 43 C. rutilans (C. B. Roots and clarke) Rhizomes 44 Maiden & Betche. 1 R = C17H35 and increasing C. capitatus Vand. Under- 44-46 Capiquinones A–K by CH2 to C27 H55 ground R2 = R3 = H, R4 = Me organs OH OH O

OH C. alopecuroides Inflorescen- 27 Alopecuquinone HO Rottb. ces

OH OH O 7. Phenolic acids:

P-Hydroxybenzoic acid HO COOH C. rotundus L. Tubers 41

HO COOH Protocatechuic acid C. rotundus L. Tubers 41

HO COOH Vanillic acid C. rotundus L. Tubers 41

H3CO

Aerial C. rotundus L. parts Ellagic acid 12

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8. Iridoides, benzodihydrofurans, and misclleanous:

Rhizomes 42 Rotunduside A C. rotundus L.

C. rotundus L. Rhizomes

Rotunduside B 42

C. rotundus L. Rhizomes 6``-O-p- Coumaroylgenipin 42 gentiobioside

1-[2,3-Dihydro-6- hydroxy-4,7-dimethoxy- Rhizomes 2S-(prop-1-en-2- C. rotundus L. 47 yl)benzofuran-5- yl]ethanone

2S-Isopropenyl-4,8- Rhizomes dimethoxy-5-methyl-2,3- C. rotundus L. 47 dihydrobenzo-[1,2-b;5,4- b`]difuran

2S-Isopropenyl-4,8- dimethoxy-5-hydroxy-6- Rhizomes methyl-2,3- C. rotundus L. 47 dihydrobenzo[1,2-b;5,4- b`]difuran

1α-Methoxy-3β- hydroxy-4α-(3′,4′- dihydroxyphenyl)-1, C. rotundus L. Rhizomes 48 2,3,4- tetrahydronaphthalin

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1α,3β-Dihydroxy-4α- (3′,4′-dihydroxyphenyl)- C. rotundus L. Rhizomes 48 1,2,3,4- tetrahydronaphthalin

C. rotundus L tubers 4,7-Dimethyl tetralone 49

Me O

n-Butyl--D- C. rotundus L. Areal parts 12 fructopyranoside

Ethyl--D- C. rotundus L. Areal parts 12 glucopyranoside

Table 2: Main nitrogenous constituents isolated from different Cyperus species. Compound name Structure Plant source Organ Ref. Rotundine A

C. rotundus L. Rhizomes 50

Rotundine B R = H Rotundine C RO (6epirotundine B)

C. rotundus L. Rhizomes 50

N C. rotundus L. 51,52 Octopamine C. papyrus L. Rhizomes C. esculentus L.

6, 7-Dihydro-2, 3- C. rotundus L. 51,52 dimethyl-5- C. papyrus L. Rhizomes 65 cyclopentapyrazine C. esculentus L.

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Adenosine C. rotundus L. Aerial 12 parts

Uridine C. rotundus L. Aerial 12 parts

Tryptophan -D- fructofuranoside C. rotundus L. Aerial 12 parts

REFERENCES 14. Seo EJ, Lee D, Kwak JH, Lee S, Kim YS, Jung Y. 1. Lawrence GHM. Taxonomy of Vascular Plants. Edn 12, Antiplatelet effects of Cyperus rotundus and its component The Macmillan Company, New York, 1968, 392-394. (+)-nootkatone. J. Ethnopharmacol. 2011; 135: 48-54. 2. Hutchinson J. The Families of Flowering Plants. Edn 3, 15. El-Gohary HMA. Study of essential oil of the tuber of Oxford Univ. Press, Oxford, 1973, 35. Cyperus rotundus L and Cyperus alopecuroides Rottb. 3. Willis JC, Shaw HKA. A dictionary of the Flowering Bull. Fac. Pharm. Cairo Univ. 2004; 42(1): 157-164. Plants and Ferns. Edn 8, Cambridge University Press, 16. Hifnawy MS, Ammar HH, Kenawy SK, Zaki ME, Yossef Cambridge, London, New York, 1973, 330. AK, Awaad AS. Phytochemical and biological studies on 4. Kirtikar KR, Basu BD, Colonel LI. Indian Medicinal alkaloidal content of some allergy producing plants Plants. Edn 2, Vol. IV, Published by M/S Bishen Singh growing in Egypt. Bull. Fac. Pharm. Cairo Univ. 1999; Mahendra Pal Singh, Mahendra, 37(2): 107-117. 1975, 2632-2640. 17. Hifnawy MS, El-Hyatmy YY, Kenawy SA, Yossef AK, 5. Hickey M, King C, Watters SM. 100 Families of Awaad AS. Carbohydrate, liped, protein and amino acid Flowering Plants. Edn 2, Cambridge University Press, contents of Chenopodium murale, Cyperus alopecuroides, 1988, 499-501. Desmostachia bipinnata and Tamaric nilotica as allergic 6. Tackholm V. Student’s Flora of Egypt. Edn 2, Cairo plants. Bull. Fac. Pharm. Cairo Univ. 1999; 37(2): 99-106. University, Beirut, 1974, 780-790. 18. Awaad AS. Zain ME. Cyperus alopecuroides Coumarins 7. Boulos L. Medicinal Plants of North Africa. Reference and antimicrobial activity. Egypt. J. Pharm.Sci. 1999; Publications, Inc., Algonac, 1983, 323-324. 40(2): 107-116. 8. Chevallier A. The Encyclopedia of Medicinal Plants. 19. Sayed HM, Mohamed MH, Farag SF, Mohamed GA, Ebel Dorling Kindersley Ltd., London, 1996, 197. R, Omobuwajo ORM, Proksch P. Phenolics of Cyperus 9. El-Moghazy AM. The study of the Egyptian Cyperus alopecuroides Rottb. inflorescences and their biological rotundus-Pharmacognostical study of the tuber. J. Pharm. activities. Bull. Pharm. Sci., Assiut Univ. 2006; 29(1): 9- Sci. (U.A.R.). 1967; 8(1): 35-48. 32. 10. Watt JM, Breyer-Brandwijke MG. The Medicinal and 20. Zoghbi MGB, Andrade EHA, Oliveira J, Carreira LMM, Poisonous Plants of Southern and Eastern Africa. Edn 2, Guilhon GMSP. Yield and chemical composition of the E. & S. Livingstone Ltd; Edinburgh and London, 1962, essential oil of the stems and rhizomes of Cyperus 373-375. articulatus L. cultivated in the State of Para´, Brazil. J. 11. Sayed HM, Mohamed MH, Farag SF, Mohamed GA, Essent. Oil Res. 2006; 18: 10-12. Proksch P. A new steroid glycoside and furochromones 21. Awaad AS, Soliman GA, El-Sayed DF, El-Gindi OD, from Cyperus rotundus L. Nat. Prod. Res. 2007; 21(4): Alqasoumi SI. Hepatoprotective activity of Cyperus 343-350. alternifolius on carbon tetrachloride–induced 12. Sayed HM, Mohamed MH, Faraga SF, Mohamed GA, hepatotoxicity in rats. Pharm. Biol. 2012; 50: 155-161. Omobuwajoc ORM, Proksch P. Fructose-amino acid 22. Bhawna K, Kumar SS, Lalit S, Sharmistha M, Tanuja S. conjugate and other constituents from Cyperus rotundus L. Cyperus scariosus: A potential medicinal herb. Int. Res. J. Nat. Prod. Res. 2008; 22(17): 1487-1497. Pharm. 2013; 4: 17-20. 13. Maurice MI. Handbook of African Medicinal Plants. CRC 23. Sayed HM, Mohamed MH, Farag SF, Mohamed GA. 66 Press, Boca Raton, Ann Arbor, London, Tokyo, 1993, 351- Phytochemical and biological studies of Cyperus rotundus 354. L. growing in Egypt. Bull. Pharm. Sci. Cairo Univ. 2001; 39: 195-203. Page

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24. Harborne JB, Williams CA, Wilson KL. Flavonoids in 39. Harborne JB. Baxter H. Phytochemical Dictionary; Taylor leaves and inflorescences of Australian Cyperus species.  Francis Ltd., London, 1993; p. 362 Phytochemistry 1982; 21(10): 2491–2507. 40. Morimoto M, Fuji Y, Komai K. Antifeedants in 25. Harborne JB, Williams CA, Wilson KL. Flavonoids in Cyperaceae: coumaran and quinones from Cyperus spp. leaves and inflorescences of Australian Cyperaceae. Phytochemistry 1999; 51(4): 605-608. Phytochemistry 1985; 24(4): 751–766. 41. Koichiro K, Kunikazu U. Secondary metabolic compounds 26. El-Habashy I, Mansour RMA, Zahran MA, El-Hadidi MN, in purple nutsedge (Cyperus rotundus L.) and their plant Saleh NAM. Leaf flavonoids of Cyperus species in Egypt. growth inhibition. Shokubutsu no Kagaku Chosetsu 1981; Biochem. Syst. Ecol. 1989; 17(3): 191-195. 16(1): 32–37. 27. Morikawa T, Xu F, Matsuda H, Yashikawa M. Structures 42. Zhou Z, Zhang H. Phenolic and iridoid glycosides from the and radical scavanging activities of novel nor-stilbene rhizomes of Cyperus rotundus L. Med. Chem. Res. 2013; dimer, longusone A, and new stilbene dimer, longusone A, 22: 4830–4835 B, and C, from Egyptian herbal medicine Cyprus longus. 43. 43- Allan RD, Correll RL, Wells RJ. A new class of Heterocycles 2002; 57(11): 1983-1988. quinones from certain members of the family Cyperaceae. 28. Singh NB, Singh PN. A new flavanol glycoside from Tetrahedron Lett. 1969; 53: 4669-4672. mature leaves of Cyperus rotundus. J. Indian Chem. Soc. 44. 44- Allan RD, Wells RJ, Correll RL, Macleod JK. The 1986; 63: 450-455 presence of quinones in the genus Cyperus as an aid to 29. Nassar MI, Abu-Mustafa EA, Abdel-Razik AF, Dawidar classification. Phytochemistry 1978; 17(2): 263-266. AM. A new flavanan isolated from Cyperus 45. 45- Masanori M, Yoshiyuki S, Ryoko M, Koichiro K. conglomeratus. Pharmazie 1998; 53(11): 806-807. Electron Transport Inhibitor in Cyperus javanicus. Biosci. 30. Abdel- Mogib M, Basaif SA, Ezmirly ST. Two novel Biotechnol. Biochem. 2001; 65(8): 1849–1851. flavans from Cyperus conglomeratus. Pharmazie 2000; 46. 46- Alves AC, Moreira MM, Paul MI, Costa MA. A series 55(9): 693-695. of eleven dialkyl-hydroxybenzoquinones from Cyperus 31. Abdel-Razik AF, Nassar MI, El-khrisy EDA, Dawidar capitatus. Phytochemistry 1992; 31(8): 2825-2827. AAM, Mabry TJ. New prenylflavans from Cyperus 47. Amesty A, Burgueñ-Tapia E, Joseph-Nathan P, Ravelo conglomeratus. Fitoterapia 2005; 76(7-8): 762-764. ÁG, Estĕvez-Braun A. Benzodihydrofurans from Cyperus 32. Abdel-Mogib M, Serag MS. Prenylflavanone from C. teneriffae. J. Nat. Prod. 2011; 74: 1061-1065. capitatus Alex. J. Pharm. Sci. 2001; 15(2); 129-131. 48. Zhou Z, Yin W. Two novel phenolic compounds from the 33. Basaif SA. stilbenes from Cyperus conglomeratus J. Saudi. rhizomes of Cyperus rotundus L. Molecules 2012; 17: Chem. Society 2003; 7(2): 259-262. 12636-12641. 34. Bhatt SK, Saxena VK, Singh KV. A leptosidin glycoside 49. Thebtaranonth C, Thebtaranonth Y, Wanauppathamkul S, from leaves of Cyperus scariosus. Phytochemistry 1981; Yuthavong Y. Antimalarial sesquiterpenes from tubers of 20(11): 2605. Cyperus rotundus: Structure of 10,12-peroxycalamenene, a 35. Seabra RM, Moreira MM., Costa MAC, Paul MI. 6,3',4'- sesquiterpene endoperoxide. Phytochemistry 1995; 40(1): trihydroxy-4-methoxy-5-methylaurone from Cyperus 125-128. capitatus. Phytochemistry 1995; 40(5): 1579–1580. 50. Jeong S, Miyamoto T, Inagaki M, Kim Y, Higuchi R. 36. Seabra RM, Andrade PB, Ferreres F, Moreira MM. Rotundines A-C, three novel sesquiterpene alkaloids from Methoxylated aurones from Cyperus capitatus. Cyperus rotundus. J. Nat. Prod. 2000; 65(5), 673-675. Phytochemistry 1997; 45(4): 839–840. 51. Smith TA. Phenethylamine and related compounds in 37. Seabra RM, Silva AMS, Andrade PB, Moreira MM. plants. Phytochemistry 1977; 16(1): 9-18. Methylaurones from Cyperus capitatus. Phytochemistry 52. Cantalejo MJ. Analysis of volatile components derived 1998; 48(8): 1429–1432. from raw and roasted earth-almond (Cyperus esculentus 38. Antonio D, Eliseo R, Paola S, Antonia S, Ildefonsa S.A. L.). J. Agric. Food Chem. 1997; 45: 1853-1860 Coumarins in Cyperus incompletus. Biochem. Syst. Ecol. 1993; 21(2): 305-312.

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