Brief Review on the Genus Diospyros: a Rich Source of Naphthoquinones

Asian J. Adv. Basic Sci.: 2017, 5(2), 34-53 ISSN (Print): 2454 – 7492 ISSN (Online): 2347 – 4114 www.ajabs.org Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones

Venu Sharma

School of Biotechnology, University of Jammu, Jammu & Kashmir, INDIA * Correspondance: E-mail: [email protected]

(Received 01 Sept, 2017; Accepted 14 Sept, 2017; Published 21 Sept, 2017)

ABSTRACT: Diospyros genus (Ebenaceae) comprises about 500 species. A number of them are used for their multiple pharmacological activities. Ethano-phramacologically various plant parts are formulated and prescribed in the form of extracts and the decoctions for remedy of different diseases in many tribes. These activities are due to presence of bioactive secondary metabolites in the plant. Systematic and detailed investigation on the composition and pharmacological significance of medicinal plants should be conducted to standardize the formulations, based on ingredients. In the present review, naphthoquinone, naphthalene and naphthol derivatives isolated from Diospyros species are documented here with the pharmacologically important species of the genus.

Keywords: Diospyros genus; species; Ebenaceae; pharmacological activities; naphthoquinones.

INTRODUCTION: Diospyros genus belongs to the retic, laxative and stypic. Its dried flowers are reported to family Ebenaceae. The plants of Ebenaceae are wide be used in urinary, skin and blood diseases. A dilute ex- spread in tropics and sub tropics, occasionally into tem- tract is used as an astringent lotion for eyes5. Heartwood perate areas. According to Hegnaeur1 the family consists of D.mollis has been found to be active against hook- of seven genera, namely Diospyros, Euclea, Maba, worms but less active against tapeworms14. Oncothea, Rhaphidanthe, Royena and Tetraclis. However Stem of D.maritima Blume is used to treat rheumatic at present Maba, Rhaphidanthe, Royena and Tetraclis are diseases in Taiwan15. D.morrisiana bark has been shown included under Diospyros and Oncotheca is included as a to exhibit antibiotic activity16, known as "Shan Hung monotypic family2. Thus most of the botanists consider Shih" in herbal medicine of Taiwan. Bark of D.nigra is that it is composed of the three genera Diospyros, Euclea antirheumatic17 and is also used in swellings, the fruits and Lassiocarpa. The genus Diospyros Linn. is by far the are antidysentric and the leaves are laxative, styptic and largest with 500 species3 out of which 50 species are antileucorrhoeic18. Bark of D.peregrina Gurke is used in found in India4, mostly in the evergreen forests of Deccan, the treatment of dysentry and intermittent fevers19. Its Assam and Bengal. A few of them occur in N. India also5. ethanolic extract has been claimed to possess anti Medicinal impotence of the Diospyros Species: protozoal activity against Entamoeba histolitica, antiviral Chemical examination of Ebenaceae generally confined activity against Ranikhet disease virus and hypoglycemic to the genus Diospyros. A number of Diospyros species activity in albino rats8. Leaves of D.quaesita Thw are are reputed for their local herbal medicinal uses6,7. In the used for treatment of asthma20. In bark extract of treatment of asthma, abdominal pains, dysentry, leprosy, D.tomentosa hyposensitive activity was confirmed21. D. whopping cough, menstrual troubles and as antibiotics tricolor is reported to be efficaciuos in leprosy. several parts of the plant have been used since a long A purified extract of persimmon fruits has been shown to time. 50% Ethanol extract of D. montana and exhibit a strong detoxifying activity on various snake D.pereqrina were found to have weak antiprotozoal8, venom but not against bee venom22. The antibacterial, antiviral and hypoglycemic activity. The common antifungal and antiallergic properties of Diospyros have persimmones are the edible fruits of D.kaki and been attributed to the presence of naphthoquinones23. The D.discolar. Naphthoquinones and other related quinonoid most interesting is their biological activity against parasit- compounds are one of the major natural product classes ic protozoa namely Leishmania, Trypnosoma and Plas- with varied biological activities9-11. The medicinal proper- modium. Plumbagin and other related quinones have been ties of some of the Diospyros species are as follow; A active against Leishmania spp., while diospyrin was found decoction of D.candolleana bark is used in rheumatism to be active against Leishmania donovani24. and swellings12. Barks of D.exsculpta and D.malabarica are used as a remedy for dysentry5. The bark extract of The heartwood of this genus has considerable economic D.ferrea Bakh, Willd syn. Mababuxifolia is found to have importance as a source of timbers and also as edible antitumour activity13. Leaves of D.malanoxylon are diu- fruits25,26. The heartwood of D.ebenum (ebony tree) is 34

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones] extremely hard, durable and resistant to seasonal changes5. naphthol. Naphthols being sensitive to oxidation are easily D.quaesita is well known for the quality of timber known converted to black polymeric material. These compounds as calamander or king Ebony. Furniture made from its are supposed to be derived from the oxidative coupling of timber is so highly ranked that this tree was exploited to 3-methyl - naphthalene-1,8-diol or their biogenetic equiv- near extinction during the Dutch occupation of Sri alents arising by the hydroxylations at the 2,4,5 or 7- Lanka20. In a brief study carried on the resistance of vari- positions . ous timbers of Diospyros species, the allelochemicals, Dimerisation may also take place at 2,4,5 or 7-positions22. such as quinones, flavonoids, and terpenoids possess natu- Isodiospyrin, diospyrin and mamagakinone examplify the ral repellant and toxic properties27. three ways in which the two naphthoquionones units link The wood of D.celebica was found to be highly resistant together, namely arene to arene, arene to quinone and to the subterranean termites, Reticuliterms lusi-fungus and quinone to quinone respectively36. On the basis of struc- Reticuliterms flaviceps28. The napthoquinones tural features, it has been suggested that naphthol and isodiospyrin, microphyllone and plumbagin were identi- naphthoquinone derivatives of Diospyros species are fied as major termicidal components, while diospyrin, a formed from acetate -polymelonate units. Four pathways major naphthoquinone of D.montana was not toxic to have been described for the biosynthesis of termites at the concentration tested. 7-Methyljuglone naphthoquiones in higher plants37,38. showed to be toxic at 0.100 g in 24 h while the dimer less toxic to termites29. D.montana Roxb. (Commonly known as bistendu) is a shrub of moderate size, which is distributed throughout the greater part of India. Different parts of this plant have been reported to be used in the treatment of dysentry, hiccups, urinary stones and liver disorders30. Its leaves and seeds extract exhibited antibacterial activity31. Its various parts have been reported to be efficacious in fever, dysu- ria, gravel, neuralgia, pneumonia, puerperal fever and spider bite poison32. Its bark extract has been reported to be used as anti inflammatory, antipyretic and analgesic. Alcoholic extract of its bark inhibited Ehrlich ascites carcinoma in mice32. Its tender twigs and leaves are used as fodder33. Its crushed leaves are used by Mundas of Chhota Nagpur to poison fish34. Meliola diospyri syd. an ascomycetes fungi, is reported on the leaves of this plant. Its fruits are bitter with an unpleasant odour. They are poisonous and applied externally to boils35. Its wood is moderately hard and is used for making small articles of furniture. It is classified as a good fuel wood.

Phytochemical investigation on various parts (viz., bark, Figure 1: Some examples of Diospyros species. heartwood of stem and root, mesocarp) of over forty species of Diospyros have been revealed that these species Table-1 contains a list of naphthalene, naphthol and are rich in naphthoquinones (table-1), naphthols. Flavo- naphthoquinone derivatives isolated from various noid, triterpenoid and steroid derivatives are also occur in Diospyros species. The naphthoquinone isodiospyrin high yields. Triterpenes of the lupane series viz. lupeol, isolated from stem and roots of D. morrisiana showed betulin and betulinic acid in addition to widely distributed cytotoxic activity in HCT-8 and P-388 screens77. A major β- sitosterol have proved to be good taxonomic markers of quinone diospyrin isolated from bark of D. montana ex- this genus20. This genus is however, characterized by the hibited growth inhibitory activity towards Ehrlich ascites ability to produce naphthoquinones, usually in the form of carcinoma in mice13. dimers and triterpenes of the lupane series. The Diospyros species are rich source of naphthols , dimers of 7-methyljuglone ( 5-hydroxy-7-methyl-1 , 4- naphthoquinone ) and plumbagin ( 5-hydroxy- 2-methyl- 1, 4-naphthoquinones ). Diospyrol isolated from fresh berries of D. mollis is the only example of dimeric 35

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones]

Molecular S. formula & Ref. Compound Source Plant part No. Melting point 39 Juglone C10H6O3 D. lycioides * O Orange needles 164-65 1.

O H O 40 Plumbagin(2-Methyljuglone) C11H8O3 D. elliptifolia Bark Orange needles 75 D. gracilipes Root bark & Stem bark41 42 O D. hebecarpa Leaves & Bark Me D. hoyleana Roots & Bark43 2. D. kaki Roots44 45 22 OH O D. maritima Bark , Roots & Fresh D. mespiliformis fruits 46

D. samoensis Bark47 Leaves48 46 Droserone C11H8O4 D. maritima Fresh fruits Yellow needles 181 O

3. M e OH

OH O

43 7-Methyljuglone C11H8O3 D. abloflavescens Bark, Root & Leaves Orange-red needles 124-25 D. chloroxylon Stem44, Stem bark44 & Wood45 D. ebenaster Roots46 O D. greenwayi Root bark & Stem bark47 Me D. hallierii Root bark, Stem bark & D. lotus 48 Fruit 4. D. melanoxylon 49 OH O Roots D. montana Bark, Sapwood & Eb- D. nicaraguensis ony50 D. squarrosa Bark36 D. usambarensis Wood51 Root bark & Stem bark52 Root bark53

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones]

54 3-Methoxyjuglone C11H8O4 D. morrisiana Heartwood

O Me

OH O

55 Shinanolone C11H12O3 D. japonica Roots Colourless needles 108 D. kaki var. Roots & Woods44 sylvestris OH Heartwood54 D. morrisiana 6. Me

OH O 56 7-Methyl--dihydrojuglone C11H10O3 D. hebecarpa Fresh leaves O 112-13 Me 7.

OH O

53 3-Methoxy-7-methyljuglone* C12H10O4 D. usambarensis Root bark 209-10° 57 O D. kaki Roots

8. OMe

OH O

*probably artifact

53 2-Methoxy-7-methyljuglone * C12H10O4 D. usambarensis Root bark

Me 9. OMe

*probably artifact OH O

44 2,6-Dimethoxy-7- C14H12O7 D. montana Stem methoxycarbonyljuglone 194 10. Orange crystals

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones]

125 Plumbagin methyl ether C12H10O3 D. melanoxylon Heartwood Yellow needles 94 O

11. Me

OMe O

58, 59 2-Methylnaphthazarin C11H8O4 D. heterotricha Root bark Bronze-green plates 174-75 D. lycioides spp. Root bark59 sericea

OH O 12. Me

OH O 47 Droserone-5-methyl ether C12H10O4 D. melanoxylon Heartwood Yellow needles 173-74 O

13. Me

OMe O

60 Yerrinquinone C14H12O7 D. montana Fungal infected stem 14. Orange clusters 193

22 Isoshinanolone C11H12O3 D. maritima Roots Colourless crystals 160 (d) D. samoensis Leaves48 OH O D. siamang Stem bark & Wood61 15.

R R Me OH 48 3-Bromoplumbagin (R=Br) C11H7 BrO3 D. maritima Fresh fruits

16. 3-Chloroplumbagin (R=Cl) C11H7 ClO3 Orange-yellow leaflets 125 47 8-Methoxy-3-methyl-1,2- C12H10O3 D. melanoxylon Heartwood naphthoquinone 17. 144 Red crystals

62 Diomelquinone A C12H10O4 D. melanoxylon Heartwood 18. Orange needles 152-53

63,64 Canaliculatin C21H14O6 D. canaliculata Stem bark 19. Yellow plates >300

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones]

65 Ebenone C22H16O5 D. ebenum Stem bark Brown crystals 231-32

M e OH O 20.

OH OH Me O 44 45 Diospyrin C22H14O6 D. chloroxylon Stem, Stem Bark , Wood & Orange-red cubes/prisms 258 D. gilleti Dried roots66 OH O D. hoyleana OH O Roots & Barks43 D. kaki 44 Roots D. mespiliformis 43 Roots & Barks 21. Me 61 D. montana 44 O Me Roots O D. piscatori 40 Bark , 67 68 Leaves , Stem bark &Wood36 Roots69 70 3,3’- Bidiomelquinone A C24H18O8 D. melanoxylon Wood Orange-yellow crystals 292-94 O Me O OMe 22. 3 3' OH HO OMe O Me O

71 Ehretione C22H14O6 D. ehretioides Wood Orange needles 232 (d)

OH O OH O 23.

O Me O

65 Elliptinone C22H14O6 D. ebenum Stem bark Orange needles > 310 D. elliptifolia Bark40 O D. maritima Fresh fruits72 & Roots22 Me 24. OH O D. mollis Dried fruits, Bark & Fresh- roots73 O OH D.samoensis Me Leaves48 O

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones]

47 Habibone C22H14O6 D. greenwayi Root bark Deep red mass 260-61 O M e

25. O

M e OH O

OH O 57 Maritinone C22H14O6 D. kaki Roots Red needles 193-95 D. maritima Roots22 & Fresh fruit72 O H O D. samoensis Leaves48

M e 26. O O M e

O H O

61 Neodiospyrin C22H14O6 D. ismailii Wood & Fruit Red needles OH O 205-10(d) D. kaki Roots57,62 D. rotundifolia Roots74 Me 27. O O O

Me 75 Rotundiquinone C22H14O6 D. batocana Root bark Red needles 320 (d) D. ismailli Wood & Fruits61 OH O D. rotundifolia Roots74,76 28. OH O

O Me O

23 Isodiospyrin C22H14O6 D. bipindensis Stem bark OH O Orange-red prisms 226-28 D. chloroxylon Stem, Wood & Stem bark44,45 D. ebenaster Roots & Bark46 Me D. ferrea 29. Roots22 Me O D. gilleti OH Roots & Bark43 O D. japonica Roots55 D. kaki Roots44 O D.morrisiana D. montana Stem77, Heartwood54,78,79& 40

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones]

D. texana Roots80 D. usambarensis Bark36 D. virginiana Roots & Bark46 D. zombensis Root bark53 Bark & Wood40 Root bark81 Root bark81 77 82 Biramentacenone C22H14O6 D. lolin Heartwood Orange-yellow rods 235 (d) D. maritima77 Bark36 O OH D. melanoxylon D. montana O 77 30. Me D. novoguiensis Me O

OH O

23 Diosindigo A C24H20O6 D. bipindensis Bark Blue needles 317 (d) D. buxifolia Sapwood84 D. cauliflora Wood85 OMe 52 Me D. consolatae Root & Stem bark OH O D. ehretioides Wood85 31. D. greenwayi Root bark & Stem bark47 O OH M e D. heterotricha Root bark58 OMe D. mafiensis Stem bark86 D. melanoxylon Heartwood83 D. squarrosa Root bark & Stem bark52 83 Diosindigo B C24H20O6 D. melanoxylon Heartwood Blue needles 232-34 D. usambarensis Root bark & Stem bark87 OH OMe O 32. Me Me O

OMe OH

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones]

44 Mamegakinone C22H14O6 D. kaki Roots , Orange crystals 253 (d) D. lotus Roots49,80 D. Lycioides Root bark88 OH O O OH D. mollis Dried fruits, Bark & Fresh Roots73 33. D. montana Bark36, M e Me D. usambarensis O O Root bark53, Root & Stem D. zombensis 87 bark 52 Root bark & Stem bark

72 Ethylidene-6,6’-biplumbagin C24H18O6 D. maritima Fresh fruits

M e

C HM e

34. O O H H O

O Me

Diosquinone D. batocana Root bark75 35. 85,86 Orange-red needles C22H14O7 D. mafiensis Root bark 36 OH O 200-00.5 D.montana Bark OH O D. tricolor Bark89 D. verrucosa Root bark & Stem bark90 Me O O Me O

75 -Dihydrodiospyrin C22H16O6 D. batocana Root bark Orange-red crystals 226 (d) D. montana Fresh bark91 OH O OH O 36.

Me O Me O

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones]

92 Tetrahydrodiospyrin C22H18O6 D. montana Fresh bark Red needles 198

O H O 37. OH O

Me O Me OH 93 3’-Methoxydiospyrin C23H16O7 D. mannii Stem bark Yellow-orange needles 220-25

OH O

38. OH O OMe

M e O Me O 36 8’-Hydroxydiospyrin C22H14O7 D. montana Bark 39. Red needles 266-68 75,94 Batocanone C22H14O7 D. batocana Root bark 127-30 O O O HO O 40. HO O Me Me

1 36 2’- Chlorodiospyrin (R=Cl, R =H) C22H13ClO6 D. montana Wood Red crystals 269-71 1 3’- Chlorodiospyrin (R=H, R =Cl) C22H13ClO6 Orange-red needles 266-68 41. OH O OH O R1 Me

O Me R O

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones]

36 3’-Chloro-2’-hydroxydiospyrin C22H13ClO7 D. montana Bark Red crystals 260-63

OH O OH O

42. Cl Me O Me OH O

63,64 8-(5-Hydroxy-7-methyl-1,4- C22H14O7 D. montana Bark naphthoquinon-2-yl)-7-methyl-4- 262-64 oxochromen-5-carboxylic acid

Red crystals (R=H) and its C H O ethyl ester (R=Et) 24 18 7 234-36 43. Orange needles OH O

O Me O Me COOR 83 4,11-Dihydroxy- 5 -methoxy-2,9- C23H16O6 D. melanoxylon Heartwood dimethyldinaphtho[1,2-b:2’,3’- 335-38 d]furan-7,12-quinone Violet crystals OH O Me

44. O

Me Me O

O OH 36 3,5’-O-Cyclodiospyrin C22H12O6 D. montana Wood Orange needles 269-71

OH O

45. O O

M e O M e O

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones]

64 Cyclocanaliculatin C21H12O6 D. canaliculata Bark Yellow plates >300 O

O Me 46.

OH O O O

54,79 2’-Methoxyisodiospyrin C23H16O7 D. morrisiana Heartwood 47. (R=OMe, R1=R2=R3=R4=H)

3’-Methoxyisodiospyrin 1 2 3 4 C H O (R =OMe, R=R =R =R =H) 23 16 7

3,3’-Dimethoxyisodiospyrin 1 3 2 4 (R =R =OMe, R=R =R =H) C24H18O8 2,3’-Dimethoxyisodiospyrin (R1=R2=OMe, R=R3=R4=H) C24H18O8 2,2’-Dimethoxyisodiospyrin 2 1 3 4 (R=R =OMe, R =R =R =H) C H O 3,2’-Dimethoxyisodiospyrin 24 18 8 (R=R3=OMe, R1=R2=R4=H) 2 3 R C24H18O8 R 3 2 R1 O O O 3' HO 2' R

OH 8' O Me Me R4

22 8’-Hydroxyisodiospyrin C22H14O7 D. ferrea var. Root bark buxifolia Dark red needles O H O 275-77 Root bark88 D. lycioides spp.

sericea

48. Me O Me O

OH O HO 86 6’’,8’-Bisdiosquinone C44H26O14 D. mafiensis Root bark Deep brown crystals >315

O O O HO O O O OH 49. HO O O Me Me Me O O

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones]

76 4,9-Dihydroxy-1,2,6,7,11,12- C26H22O4 D. natalensis Roots & Branches hexamethylperylene-3,10-quinone

Brown-red needles O H O Me 50. M e Me M e Me

Me O H O

74,76 Galpinone C33H20O9 D. galpinni Roots & Bark Orange-red needles >335 O O HO O Me 51. OH O

Me O OH Me O

74,76 Isoxylospyrin C33H18O9 D. galpinni Roots Yellow crystals >350 D. hallierii Root bark & Stem bark48 HO Me D. whyteana Roots & Branches74,76 O O 52. Me O O OH O O

HO Me

45 Xylospyrin C33H18O9 D. chloroxylon Wood Bright yellow crystals >400 D. ebenaster Bark46 HO Me D. texana Bark46 O O M e 53. O O

OH O OH O

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones]

95 54. Bis-isodiospyrin C44H26O12 D. austroafricana Fruits Orange prisms >320 var. rubriflora D. japonica Roots55 O O D. lotus Roots49,80 95 HO OH D. lycioides Fruits O O O O OH OH D. morrisiana Roots80 D. piscatoria Roots69 Me Me 87 Me Me D. usambarensis Roots & Stem bark O O 6-{2-(7- D. Bark96 55. Methyljuglone)}isodiospyrin chaemaethamnus 76 Whyteone HO M e C44H24O12 D. galpinni Roots 74,76 O D. whyteana Roots & Branches O M e O O O H O 56. O

HO 6 M e O M e 8'

O O H

95 97 6-Hydroxy-4,5-dimethoxy-2- C13H12O5 D. ebenum * naphthoic acid (R=H)

Methyl-6-hydroxy-4,5-dimethoxy-2- C H O naphthoate (R=Me) 14 14 5

57. C O O R

H O

O M e O M e

44 Naphthalene Derivative C15H18O4 D. chloroxylon Stem & Stem bark 58. 49 98 3-Methylnaphthalene-1,8-diol C11H10O2 D. mollis Berries OH OH 59.

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones]

99 Macassar II (R=H) C13H14O3 D. celebica Heartwood Colourless prisms 107-07.

Macassar III (R=CH3) Pale yellow needles O M e O M e O R 60.

M e

5

C14H16O3 70 100 5-Hydroxy-4-methoxy-2- C12H10O3 D. quiloensis Heartwood naphthaldehyde

(R1=OH, R=OMe, R2=R3=H)

4,5-Dimethoxy-2-naphthaldehyde C13H12O3 (R=R1=OMe, R2=R3=H)

6-Hydroxy-4,5-dimethoxy-2-

naphthaldehyde 101 2 1 3 C H O D. ebenum Heartwood (R =OH, R=R =OMe, R =H) 13 12 4 165 Pale yellow needles

4,5,6-Trimethoxy-2-naphthaldehyde 1 2 3 101 (R=R =R =OMe, R =H) C14H14O4 D. ebenum Heartwood Pale yellow plates 125 61. 4,5,8-Trimethoxy-2-naphthaldehyde 1 3 2 (R=R =R =OMe, R =H) C14H14O4 D. mollis Dried fruits, Bark & Fresh 5-Hydroxy-4,6,8-trimethoxy-2- fruits73

naphthaldehyde

1 2 3 (R =OH, R=R =R =OMe) C H O 4,5,6,8-Tetramethoxy-2- 14 14 5 naphthaldehyde (R=R1=R2=R3=OMe)

1 C15H16O5 R R 4 5 2 6 R 2

O H C 8 R 3

[(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones]

98 99 Diospyrol C22H18O4 D. mollis Berries , Fruits , 251-57 Dried ripe fruits102 OH OH OH OH & Fresh fruits73 62.

MeMe

CONCLUSION: Phytochemical investigation on vari- and Eastern Africa being an Account of their ous plant parts (viz., bark, heartwood of stem and root, Medicinal and other Uses, Chemical Composi- mesocarp) of over forty species of Diospyros have been tion, Pharmacological Effects and Toxicology in revealed that these species are rich in naphthoquinones, Man and Animal., Edn 2: 369 naphthols. These phytochemicals have proved to be good 7. Kokwaro, J. O. (1976) Medicinal Plants of East taxonomic markers of this genus. This genus is however, Africa, East African Literatute Bureau, Kampala, characterized by the ability to produce naphthoquinones, Nairobi and Dares Salaam usually in the form of dimers and triterpenes of the lupane 8. Dhar, M. L., Dhar, M. M., Dhawan, B. N., series. Herein, we documented the different Mehrotra, B. N., Ray, C. (1968) ‘Screening of naphthoquinones present in the genus. Various Indian plants for biological activity’, Indian Diospyros species have the potential multiple pharma- journal of experimental biology, 6(4): 232-247 cological and therapeutic activities which can be ex- 9. Fournet, A., Barrios, A. A., Munoz, V., plained by the presence of various bioactive metabo- Hocquemiller, R., Cave, A. (1992) ‘Effect of lites in the species. Different parts of the plants are natural naphthoquinones in BALB/c mice infect- employed as folk prescription and the related health ed with Leishmania amazonensis and L. products are unpersuasive, so conduction of detailed venezuelensis’, Tropical medicine and parasitol- investigations on the composition and pharmacologi- ogy, 43(4):219-222 cal significance of medicinal plants is an inevitable 10. Sepúlveda-Boza, S., Cassels, B. K. (1996) ‘Plant need to standardize the formulations, based on ingre- metabolites active against Trypanosoma cruzi’, dients. Planta Medica, 62(02): 98-105 11. Akendengue, B., Ngou-Milama, E., Laurens, A., ACKNOWLEDGEMENT: Author is thankful to Hocquemiller, R. (1999) ‘Recent advances in the Prof. Pahup Singh (Emeritus Scientist), Department of fight against leishmaniasis with natural prod- Chemistry, University of Rajasthan, Jaipur for his ucts’, Parasite, 6(1):3-8. kind guidance. 12. Kirtikar, Basu, (2001) Indian Medicinal Plants with illustrations. 2001, 7: 2084-2086. REFERENCES: 13. Hazra, B., Sur, P., Roy, D. K., Sur, B., Banerjee, 1. Hegnauer, R. (1973) In Chemotaxonomie der A. (1984) ‘Biological activity of diospyrin to- Pflanzen, Birkhäuser Basel, 130-174 wards Ehrlich ascites carcinoma in Swiss A 2. Willis, J. C. (1973) A Dictionary of the Flowering mice’, Planta medica, 50(04), 295-297. Plants and Ferns (revised by H. K. Airy Shaw), 14. Bringmann, G., Günther, C., Ochse, M., Schupp, Cambridge University Press, London, 8th edn, 397 O., Tasler, S. (2001) Biaryls in nature: a multi- 3. Willis, J. C. (1966) A Dictionary of the Flowering facetted class of stereochemically, biosynthetical- Plants and Ferns (revised by H. K. Airy Shaw), ly, and pharmacologically intriguing secondary Cambridge University Press, London, 7th edn, 360 metabolites, Springer Vienna, 1-249. 4. Pearson, R. S., Brown, H. P. (1932). Commercial 15. Kuo, Y. H., Huang, S. L., & Chang, C. I. (1998) timbers of India: their distribution, supplies, ‘A phenolic and an aliphatic lactone from anatomical structure, physical and mechanical Diospyros maritima’, Phytochemistry, 49(8), properties and uses (Vol. 2). Government of In- 2505-2507. dia central publication branch. 16. Xiu-Zhen, Y., Yao-Haur, K., Tsong-Jyh, L., To- 5. The Wealth of India, A Dictionary of Indian Raw Shii, S., Chung-Hsiung, C., Mcphail, D. R., & Materials and Industrial Products. (1952) Vol. III, Mcphail, A. T. (1989) ‘Cytotoxic components of CSIR, New Delhi, 76 Diospyros morrisiana’, Phytochemistry, 28(5), 6. Watt, J. M., Breyer-Brandwijk, M. G. (1962) 1541-1543. The Medicinal and Poisonous Plants of Southern 17. Deb D. B. The Flora of Tripura State, Today and Tomorrow’s Publishers, New Delhi, 1981, 1: 426. 49

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