Xanthones as Potential Antioxidants

Send Orders for Reprints to [email protected] Current Medicinal Chemistry, 2013, 20, 4481-4507

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Xanthones as Potential Antioxidants S.S. Pandaa, M. Chanda, R. Sakhujab and S.C. Jain*,a a

Department of Chemistry, University of Delhi, Delhi 110007, India; bDepartment of Chemistry, Birla Institute of Technology and Science, Pilani 333031, Rajasthan, India Abstract: Xanthones (dibenzo- -pyrones) constitutes an important class of oxygenated heterocycles and occur as secondary metabolites in plants and microorganisms. They are known for various biological activities such as antioxidant, monoamine oxidase inhibitor, antihypertensive, hepatoprotective, antithrombotic, antifungal and anticancer. The tricyclic scaffold as well as the nature and/or position of the substituents present on it play an important role in displaying various biological activities. The unique structural scaffold and medicinal importance of xanthones have therefore attracted many Scientists in the past, to isolate or synthesize xanthones or their analogs as potential drug candidates. It would not be wrong to call them as close cousins to the polyphenol family that are known to possess strong antioxidant effects on the nervous system. The main two sources of xanthones are: Isolation from natural resources or synthesis. Though few reviews have been published in the past, mainly focusing on the anticancer activities of xanthone derivatives, but there is not a single review which is based on their antioxidant activities. We therefore have made efforts to briefly summarize natural and synthetic xanthones possessing antioxidant activity in this review.

Keywords: Xanthone, antioxidant, natural product, synthesis. INTRODUCTION In spite of various modern techniques, such as biochemical engineering and fermentation, for exploring microorganisms and marine natural products, medicinally useful plants are still an important source for discovering new drug candidates. More than 70% of the current small bioactive molecules used in pharmacy are derived from various traditional medicinal plants. The term xanthone (from the Greek word, meaning yellow) designates the chemical compound dibenzo- -pyrone (1), which does not occur as such in nature. However, a large number of xanthone analogs have been isolated from natural sources such as fungi, lichens and also from a few higher plants that mainly belongs to Guttiferae (Gluciaceae) and Gentianaceae families, during the last decade [1-5]. All these oxygenated heterocyclic derivatives bear a structural relationship to -pyrone natural products such as flavonoids and chromones, which have attracted medicinal chemist’s interest, due to their diverse pharmacological properties [6]. Numerous reports have appeared in the past concerning their antioxidant [7, 8], antithrombotic [9], cardiotonic, vasorelaxant [10], antiulcer, choleretic, anti-inflammatory [11, 12], antiallergic, diuretic and MAO inhibitory activity [13]. Xanthone derivatives, on the other hand, are known for their potent cytotoxic [14, 15], antimicrobial [16-18], antiviral [19, 20] and antifungal activities [21, 22]. They are used as nutritional supplements which improve conditions in chronic inflammatory diseases and are known to prevent premature aging [3], because of their antioxidant property. Due to these diverse properties, this class of compounds can be utili*Address correspondence to this author at the Department of Chemistry, University of Delhi, Delhi 110007, India; Tel:/Fax: 91-11-27667725-1387; E-mail: [email protected] 0929-8673/13 $58.00+.00

zed as promising chemical scaffold for the development of new pharmacophores. Xanthone structure is described as the “privileged structure” by Lesch and Bräse [23] due to their interaction with different types of drug targets. The carbons are often numbered according to a biosynthetic convention, because of its biogenetic origin in higher plants and due to the symmetrical structure,. Thus, carbons 1-4 are assigned to the ring A (acetate-derived) and carbons 5–8 to the ring B (shikimate- derived) [2]. O B

A O 1

Recent review on xanthones covers the literature that concerned with their structural elucidation along with their biological activities [24, 25]. Biological and medicinal properties of xanthones have also been mentioned from time to time regardless their distribution among organisms [6, 26]. Some other reports deal only with xanthones isolated from natural source with specific genus [27], family [2] or belonging to a certain class of xanthones [3, 4]. We have made efforts to summarize synthetic and naturally occurring xanthones possessing antioxidant activity in this communication. Antioxidants are the compounds that inhibit oxidation of other molecules in a biological system at low concentration and thus play diverse physiological role in the body. Numbers of antioxidants have been reported earlier from various plants, which converts reactive radicals to less reactive species. Plants possess their own antioxidant system (defense strategies) to cope up with oxidative stress. This antioxidative system comprises both non-enzymatic and enzymatic © 2013 Bentham Science Publishers

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                                                           

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           

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                                             

                                        

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

 



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 

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

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



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



                                                                          

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 

 

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

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 

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

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

 

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

 

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

       





                                                                                 

 

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 

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

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

  

  



                                       

        O

R OH

OH

O  R = H  R = OH

OH

                                          

                                                                                                                                                                                                                                                                                                                                                         

4484 Current Medicinal Chemistry, 2013, Vol. 20, No. 36

Table 1.

Panda et al.

Naturally Occurring Xanthones Along with their Origin

S.No.

Structures O

1

Ref.

Garcinia subelliptica (Woods)

[30]

Garcinia subelliptica (Woods)

[30]

Garcinia subelliptica (Woods)

[30]

Garcinia subelliptica (Woods) Calophyllum thorelii (Bark)

[30] [74]

Garcinia subelliptica (Woods)

[30]

Cratoxylum cochinchinense (Stems)

[42]

Garcinia polyantha (Stem Bark)

[43]

OH

O OH

Plant Origin (Part)

OH

28

1,4,5-Trihydroxy-3,6-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one O

2

OH

O OH

OH

29

1,4,5-Trihydroxy-6-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-9H-xanthen-9-one O

OH

O

3

O

OH

30

8,11-Dihydroxy-2,2-dimethyl-9-(2-methylbut-3-en-2-yl) pyrano[3,2-c]xanthen-7(2H)-one O

OH OH

4

O 31

OH

1,2,5-Trihydroxy-4-(2-methylbut-3-en-2-yl)-9H-xanthen-9-one R5

R1

O

R2 R4

5

O R3

32 R1 = R 2 = R3 = OH; R4 =R5 = H 33 R1 = OCH3; R 2 = OH; R3 = OCH3; R4 = OH; R5 = H 34 R1= R2 = OH; R 3 = R4 = OCH3; R5 = H 35 R1 = OH; R 2 = R3 = H; R4 = OCH3; R 5 = OH 36 R1 = OH; R 2 = H; R3 = OCH3; R4 = OH; R 5 = H 37 R1 = OH; R 2 = H; R3 = OH; R4 = R 5 = H

OH O

6

OH

HO HO

OMe

O 38

Cratoxylumxanthones C OH

O

OH

O

7

O

OH 39

1,5,8-Trihydroxy-6 -methyl-6 -(4-methylpent-3-enyl)-pyrano[2 ,3 :3,4]xanthen-9-one (Bangangxanthone A)

Xanthones as Potential Antioxidants

Current Medicinal Chemistry, 2013, Vol. 20, No. 36 4485 (Table 1) contd….

S.No.

Structures OH

8

O

Plant Origin (Part)

Ref.

Garcinia polyantha (Stem Bark)

[43]

Garcinia vieillardii (Stem Bark)

[43]

Garcinia vieillardii (Stem Bark)

[43]

Garcinia vieillardii (Stem Bark)

[43]

Garcinia vieillardii (Stem Bark)

[43]

Garcinia vieillardii (Stem Bark)

[43]

Garcinia vieillardii (Stem Bark)

[43]

OH

O OH

40

1,4,8-Trihydroxy-2-(3-methyl-2-buten-1-yl)-9H-xanthen-9-one (Bangangxanthone B) O

9

O

OH

O

O

O 41

1,2-Dihydro-5-hydroxy-9,10-dimethoxy-1,1,2-trimethyl-6H-furo[2,3-c]xanthen-6-one

OH HO

O

O

10 O

OH

17

Vieillardixanthone O

11

HO

OH

O 42

1,6-Dihydroxy-9H-xanthene-9-one O

OH

O

12 OH

OH

43

4-(1,1-Dimethyl-2-propen-1-yl)-1,3,5-trihydroxy-9H-xanthen-9-one (Pancixanthone A) O

OH

O

13

O

OH 44 1,2-Dihydro-5,10-dihydroxy-1,1,2-trimethyl-6H-furo[2,3-c] xanthen-6-one (Pancixanthone B) O

14

O

O OH

OH

O

45

1,2-Dihydro-5,10-dihydroxy-9-methoxy-1,1,2-trimethyl-6H-furo[2,3-c]xanthen-6-one(6-O-Methyl-2deprenylrheedia xanthone B)

4486 Current Medicinal Chemistry, 2013, Vol. 20, No. 36

Panda et al.

(Table 1) contd….

S.No.

Structures OH

15

O

Plant Origin (Part)

Ref.

Garcinia smeathmannii (Stem Bark)

[43]

Garcinia smeathmannii (Stem Bark)

[43]

Garcinia xanthoschymu (Bark)

[43]

Garcinia xanthoschymu (Bark)

[43]

Garcinia xanthoschymu (Bark)

[43]

OH

O

OH

OH

46

2-[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]-1,3,5,8-tetrahydroxy-9H-xanthen-9-one (Smeathxanthone A) OH

16

O

OH

O

O

OH

47

5,7,10-Trihydroxy-2-methyl-2-(4-methyl-3-penten-1-yl)- 2H,6H-pyrano[3,2-b]xanthen-6-one (Smeathxanthone B) O

OH OH

17

O

O OH

48

1,2,5-Trihydroxy-6-methoxy-9H-xanthene-9-one O

18

HO

OH

O O

OH

49

1,4,6-Trihydroxy-5-methoxy-9H-xanthene-9-one O

OH

HO

OH O

19

50

1,2,7-Trihydroxy-4-(1,1-dimethylallyl)-9H-xanthene-9-one O

OH O

20

O O

Garcinia dulcis

O

(Flowers)

O

51

[43]

1-Hydroxy-2,3,4,5-tetramethoxy-9H-xanthen-9-one (Dulcisxanthones C) OH

O O

O

21

O

OH

52

5,13-Dihydroxy-3,3,10,10-tetramethyl-6-(3-methyl-2-buten-1-yl)-10H-dipyrano[3,2-a:2',3'i]xanthen-14(3H)-one (Dulcisxanthones D)

Garcinia dulcis (Flowers)

[43]

Xanthones as Potential Antioxidants

Current Medicinal Chemistry, 2013, Vol. 20, No. 36 4487 (Table 1) contd….

S.No.

Structures O

Plant Origin (Part)

Ref.

Garcinia dulcis (Flowers)

[43]

Garcinia dulcis (Flowers)

[43]

Garcinia mangostana (Fruits)

[43]

Garcinia mangostana (Fruits)

[43]

Garcinia mangostana (Fruits)

[43]

Garcinia mangostana (Fruits)

[43]

OH

HO HO

O

OH 53

22

2-[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]-1,3,6,7-tetrahydroxy-5-(3-methyl-2-buten-1-yl)-9Hxanthen-9-one (Dulcisxanthones E) OH

O O

23

O

O 54

OH

5,11-Dihydroxy-9-methoxy-3,3-dimethyl-10-(3-methyl-2-buten-1-yl)-pyrano[3,2-a]xanthen-12(3H)one (Dulcisxanthones F) OH

O O

24

O

O 55

13-Hydroxy-3,3,10,10-tetramethyl-10H-dipyrano[3,2-a:2',3'-i]xanthen-14(3H)-one (Thwaitesixanthon) O

25

OH

O

OH 56

OH

2-[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]-1,3,5-trihydroxy-9H-xanthen-9-one (Mangostinone) OH

O O

26

HO

O

OH

57

2,3-Dihydro-5,9,11-trihydroxy-3,3-dimethyl-10-(3-methyl-2-buten-1-yl)-pyrano[3,2-a]xanthen12(1H)-one (Mangostenone D) OH

OH

O

OH O

27 HO

O

OH

58

1-(2,3-Dihydroxy-3-methylbutyl)-3,6,8-trihydroxy-2-methoxy-7-(3-methyl-2-buten-1-yl)-9Hxanthen-9-one (Mangostenone E)

4488 Current Medicinal Chemistry, 2013, Vol. 20, No. 36

Panda et al.

(Table 1) contd….

S.No.

Structures

O

28

Ref.

Garcinia mangostana (Fruits)

[43]

Garcinia mangostana (Fruits)

[43]

Garcinia mangostana (Fruits)

[43]

Garcinia mangostana (Fruits)

[43]

Garcinia mangostana (Fruits)

[43]

Garcinia mangostana (Fruits)

[43]

OH

R3O R2O

Plant Origin (Part)

OR1

O

18 R1=R2=H; R3=CH3 19 R1=R2=R 3=H OH HO OH

O O

29

HO

O 59

1,2-Dihydro-1,8,10-trihydroxy-2-(2-hydroxy-propan-2-yl)-9-(3-methylbut-2-enyl)furo [3,2a]xanthen-11-one

O

OH

HO

30 O

OH 60

1,3,7-Trihydroxy-2,8-bis(3-methylbut-2-enyl)-9H-xanthene-9-one OH

O O

31

HO

O 61

OH

1,3,6,7-Tetrahydroxy-8-(3-hydroxy-3-methylbutyl)-2-(3-methyl-2-buten-1-yl)-9H-xanthen-9-one (Garcinone C)

OH

O OH

32

HO

O

OH

62

2,3,6,8-Tetrahydroxy-1,4,7-tris(3-methyl-2-buten-1-yl)-9H-xanthen-9-one (Garcinone E) OH

33

O

OH

O OH

OH 63

1,3,5,8-Tetrahydroxy-2,4-bis(3-methyl-2-buten-1-yl)-9H-xanthen-9-one (Gartanin)

Xanthones as Potential Antioxidants

Current Medicinal Chemistry, 2013, Vol. 20, No. 36 4489 (Table 1) contd….

S.No.

Structures OH

Plant Origin (Part)

Ref.

Artocarpus kemando (Stem bark)

[44]

Aspergillus sydowii (Fungus)

[45]

Aspergillus sydowii (Fungus)

[45]

Garcinia mangostana (Mangosteen) (Pericarp)

[46]

Garcinia xanthochymus (Bark)

[47]

Garcinia xanthochymus (Bark)

[47]

O

O O

O

34

OH 64

OH

5a,6-Dihydro-2,3,8-trihydroxy-5,5,11,11-tetramethyl-5H,7H,11H-benzofuro[3,4-bc]pyrano[3,2h]xanthen-7-one (Artomandin)

OH

O

O

O OH

35 O 65

Methyl-2,8-dihydroxy-6-methyl-9-oxo-2,9-dihydro-1H-xanthene-1-carboxylate (Aspergillusone A) OH

36

O

HO

O

O OH

OH

O 66

Methyl 1,2,8-trihydroxy-6-(hydroxymethyl)-9-oxo-2,3,4,9-tetrahydro-1H-xanthene-1-carboxylate (Aspergillusone B) OH

37

O

OH

O OH

O 67

1,5,8-Trihydroxy-3-methoxy-2-(3-methyl-2-buten-1-yl)-9H-xanthen-9-one

O

OH

O OH

38

OH

O O 68

OH

HO

O

OH

3,4a,5,14b-Tetrahydro-9,14-dihydroxy-2,4,4-trimethyl-5-(3,4,6,8-tetrahydroxy-9-oxo-9H-xanthen-1yl)-4H,13H-benzo[4,5]pyrano[3,2-b]xanthen-13-one (Bigarcinenone B) O

OH

O

O

39 HO

O 69

OH OH

1-(2,5-Dihydro-4-methyl-5-oxo-2-furanyl)-3,4,6,8-tetrahydroxy-9H-xanthen-9-one (Garcinexanthone F)

4490 Current Medicinal Chemistry, 2013, Vol. 20, No. 36

Panda et al.

(Table 1) contd….

S.No.

Structures OH

O

Plant Origin (Part)

Ref.

Swertia mussotii Franch

[48]

Swertia mussotii Franch

[48]

Mangifera indica various parts and Swertia chirayita (whole plant)

[49] [72]

Garcinia mangostana (Fruits)

[50]

Garcinia mangostana (Fruits)

[50]

Garcinia mangostana (Fruits)

[50]

Garcinia mangostana (Fruits)

[50]

OH O

40

O

O 9

Methylswertianin O

O

OH

HO

O

41

O 70

O

1,7-Dihydroxy-2,3,8-trimethoxy-9H-xanthen-9-one OH O

HO HO

OH

O OH

OH

42

HO

O

OH

23

Mangiferin O

OH

O

43

OH

OH 71

1,3,5-Trihydroxy-2,4-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one OH

O O

44

O

O 72

OH

5,13-Dihydroxy-3,3,10,10-tetramethyl-2,3,11,12-tetrahydro-1H-dipyrano[3,2-a:2',3'-i]xanthen14(10H)-one OH

45

O

OH

O OH

OH 63

1,3,5,8-Tetrahydroxy-2,4-bis(3-methyl-2-buten-1-yl)-9H-xanthen-9-one (Gartanin) O

46

OH

O OH

O 73

1,5-Dihydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one

Xanthones as Potential Antioxidants

Current Medicinal Chemistry, 2013, Vol. 20, No. 36 4491 (Table 1) contd….

S.No.

Structures OH

O

Plant Origin (Part)

Ref.

Garcinia xanthochymus (Bark)

[51]

Garcinia xanthochymus (Bark)

[51]

Garcinia xanthochymus (Bark)

[51]

Garcinia xanthochymus (Bark)

[51]

Garcinia xanthochymus (Bark)

[51]

Garcinia xanthochymus (Bark)

[51]

OH

HO OH O

O 74 OH

47

3,6,7,11-Tetrahydroxy-2-(2-hydroxypropan-2-yl)-9-(2-methylbut-3-en-2-yl)-2H-furo[3,2-b]xanthen5(3H)-one O

48

HO

OH

O OH

OH

75

7-(3,7-dimethylocta-2,6-dien-1-yl)-1,3,5,6-tetrahydroxy-9H-xanthen-9-one OH

O

O

49

OH

O 76

8,11-Dihydroxy-2,2-dimethylpyrano[3,2-c]xanthen-7(2H)-one OH

O

50

HO

OH

O

O

OH 77 OH

5,9,10-Trihydroxy-7-(3-hydroxy-3-methylbutyl)-2-(2-hydroxypropan-2-yl)-8-(3-methylbut-2-en-1yl)-1H-furo[2,3-c]xanthen-6(2H)-one OH

O

51

HO

OH

O

O

OH 78

6,10,11-Trihydroxy-8-(3-hydroxy-3-methylbutyl)-3,3-dimethyl-9-(3-methylbut-2-en-1yl)pyrano[2,3-c]xanthen-7(3H)-one OH

O

52

HO

O

OH

O

OH 79

5,9,10-Trihydroxy-7-(3-hydroxy-3-methylbutyl)-8-(3-methylbut-2-en-1-yl)-6H-furo[2,3-c]xanthen-6one

4492 Current Medicinal Chemistry, 2013, Vol. 20, No. 36

Panda et al.

(Table 1) contd….

S.No.

Structures

Plant Origin (Part)

Ref.

Swertia punicea Hemsl

[52]

Calophyllum thwaitesii (Roots)

[53]

Calophyllum thwaitesii (Roots)

[53]

Garcinia cowa (Twigs)

[54]

Garcinia mangostana (Fruits) and Garcinia cowa (Twigs)

[50] [54]

Garcinia cowa (Twigs)

[54]

HO HO

O

OH

O OH

HO OH HO O OH

OH

53 HO

O

OH

O 80

OH

1,1',3',4,6,6',7',8-Octahydroxy-2'-((2S,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2Hpyran-2-yl)-9H,9'H-[2,4'-bixanthene]-9,9'-dione OH

O O

54

HO

O 81

9,11-Dihydroxy-3,3-dimethyl-10-(3-methylbut-2-en-1-yl) pyrano[3,2-a]xanthen-12(3H)-one (Calothwaitesixanthone) OH

O O

55

O

O 82

13-Hydroxy-3,3,10,10-tetramethyl-3H-dipyrano[3,2-a:2',3'-i]xanthen-14(10H)-one (Thwaitesixanthone)

O

OH

O

56

OH HO

O

O 83

4,8-Dihydroxy-2-(2-hydroxypropan-2-yl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2H-furo[3,2b]xanthen-5(3H)-one (Mangostanin)

O

OH

H3CO

57 HO

O

OH

18

-Mangostin O

58

HO

OH

O O

O 84

1,6-Dihydroxy-3,5-dimethoxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one (Cowaxanthone A)

Xanthones as Potential Antioxidants

Current Medicinal Chemistry, 2013, Vol. 20, No. 36 4493 (Table 1) contd….

S.No.

Structures

O

Ref.

Garcinia cowa (Twigs)

[54]

Garcinia cowa (Twigs)

[54]

Cratoxylum sumatranum (Root bark)

[55]

Polygala hongkongensis (Herbs)

[56]

Polygala hongkongensis (Herbs)

[56]

Polygala hongkongensis (Herbs)

[56]

OH

O

59 O

Plant Origin (Part)

O 85

OH

1,3-Dihydroxy-6,7-dimethoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one (Cowaxanthone B)

O

OH

O HO

60

O

O 86

5,9-Dihydroxy-8-methoxy-2,2-dimethyl-7,10-bis(3-methylbut-2-en-1-yl)pyrano[3,2-b]xanthen6(2H)-one (Cowaxanthone C) OH

O OH O 87

61

O

5,8-Dihydroxy-3,3-dimethylpyrano[2,3-c]xanthen-7(3H)-one OH

OH

O OH

O

O

62

O

O

OH OH OH

88 H

O

OH

6-[[2-O-(6-Deoxy- -L-mannopyranosyl)- -D-glucopyrano- syl]oxy]-1,7-dihydroxy-3-methoxy-9Hxanthen-9-one (Polyhongkongenoside A) OH

OH

O O

63

O

O

O

O

OH

89

1-( -D-Glucopyranosyloxy)-8-hydroxy-2,6-dimethoxy-9H-xanthen-9-one (Polyhongkongenoside B) OH

HO

O

HO O

64

O

OH

O

O HO

OH OH

O

OH 90

2-(6-O-D-Apio- -D-furanosyl- -D-glucopyranosyl)-1,3,6-trihydroxy-7-methoxy-9H-xanthen-9one(Polygalaxanthone III)

4494 Current Medicinal Chemistry, 2013, Vol. 20, No. 36

Panda et al.

(Table 1) contd….

S.No.

Structures

Polygala hongkongensis(Herbs)

[56]

Garcinia xanthochymus (Bark)

[57]

Artocarpus nobilis (Root Bark)

[58]

Artocarpus nobilis (Root Bark)

[58]

Cratoxylum cochinchinense (Roots)

[59]

OH

O HO

OH OH

O

65 HO

Ref.

OH

O

H

Plant Origin (Part)

O

O

O

OH

91

OH

6-[[2-O-(6-Deoxy- -L-mannopyranosyl)- -D-glucopyrano-syl]oxy]-1,3-dihydroxy-7-methoxy-9Hxanthen-9-one (Polygalaxanthone V)

O

HO

OH

O

OH

OH

OH

OH HO

66

O

O

O

OH 92

(1S,2S)-1-(7-((E)-3,7-Dimethylocta-2,6-dien-1-yl)-1,3,5,6-tetrahydroxy-8-(3-methylbut-2-en-1-yl)-9oxo-9H-xanthen-4-yl)-5,9,10-trihydroxy-2-(2-hydroxypropan-2-yl)-7,8-bis(3-methylbut-2-en-1-yl)1H-furo[2,3-c]xanthen-6(2H)-one O

HO

67

OH

O

HO

OH

O 93

6,10,11,13-Tetrahydroxy-3,3-dimethyl-9-(prop-1-en-2-yl)-8,9-dihydrobenzo[c]pyrano[3,2h]xanthen-7(3H)-one (Artobiloxanthone) OH

O

O O

68

O 94

HO

OH

1,3,8-Trihydroxy-5,5,11,11-tetramethyl-5a,6-dihydro-5H-benzofuro[3,4-bc]pyrano[3,2-h]xanthen7(11H)-one (Cycloartobiloxanthone) O

HO

69

O OH

OH

O

95

5,9,10-Trihydroxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)pyrano[3,2-b]xanthen-6(2H)-one (Macrulaxanthone)

Xanthones as Potential Antioxidants

Current Medicinal Chemistry, 2013, Vol. 20, No. 36 4495 (Table 1) contd….

S.No.

Structures

OH

Plant Origin (Part)

Ref.

Cratoxylum cochinchinense (Roots)

[59]

Garcinia mangostana (Fruits) Cratoxylum cochinchinense (Roots)

[43] [59]

Garcinia mangostana (Fruits) Cratoxylum cochinchinense (Roots)

[43] [59]

Cratoxylum cochinchinense (Roots)

[59]

Symphonia globulifera (Seeds)

[60]

Symphonia globulifera (Seeds)

[60]

O O

70 O 96

OH OH

3,4,8-Trihydroxy-2-methoxy-1-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one (Celebixanthone) OH

O O

71

HO

O 97

OH

5,9,11-Trihydroxy-3,3-dimethyl-10-(3-methyl-2-buten-1-yl)- pyrano[3,2-a]xanthen-12(3H)-one (Garcinone B) OH

O

OH

O

72 HO

O 98

OH

1,3,6-Trihydroxy-8-(3-hydroxy-3-methylbutyl)-7-methoxy-2-(3-methyl-2-buten-1-yl)-9H-xanthen-9one (Garcinone D)

O

73

OH

H3CO HO

O 99

OCH3

1,6-Dihydroxy-3,7-dimethoxy-2,8-bis(3-methyl-2-buten-1-yl)-9H-xanthen-9-one ( -Mangostin) O

OH

O

74

O

O OH

OH

100

1,3,5-Trihydroxy-6,7-dimethoxy-2,4-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one (Globuliferin) O

OH

O

75

O OH

O 101

O

6,11-Dihydroxy-9,10-dimethoxy-3,3-dimethyl-5-(3-methylbut-2-en-1-yl)pyrano[2,3-c]xanthen7(3H)-one (Symphonin)

4496 Current Medicinal Chemistry, 2013, Vol. 20, No. 36

Panda et al.

(Table 1) contd….

S.No.

Structures O

Plant Origin (Part)

Ref.

Symphonia globulifera (Seeds)

[60]

Cratoxylum cochinchinense (Stems)

[61]

Cratoxylum cochinchinense (Stems)

[61]

Garcinia mangostana (Pericarp)

[62]

Garcinia mangostana (Pericarp)

[62]

Garcinia afzelii-(Stem bark)

[63]

OH

O O

O 102

OH

76

O

5,10-Dihydroxy-8,9-dimethoxy-2,2-dimethyl-12-(3-methylbut-2-en-1-yl)pyrano[3,2-b]xanthen6(2H)-one (Gaboxanthone) O

OH

HO O

OH 103

77

2-[(2E)-3,6-Dimethyl-2,5-heptadien-1-yl]-1,3,7-trihydroxy-4-(3-methyl-2-buten-1-yl)- 9H-xanthen9-one

O

78

OH

HO HO

O 104

O

1,6,7-Trihydroxy-3-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one (Dulcisxanthone B)

O

O

OH

O

79 O 105

OH

OH

1,3,5-Trihydroxy-7-methoxy-8-(3-methyl-2-oxobut-3-en-1-yl)-2-(3-methylbut-2-en-1-yl)-9Hxanthen-9-one (Mangostingone) OH

O

OH

O OH

80

O

106

1,5,8-Trihydroxy-3-methoxy-2,4-bis(3-methylbut-2-en-1-yl)-9H-xanthen-9-one (8Hydroxycudraxanthone G) OH

81

HO

O

O 107

O

OH

4,6,8-Trihydroxy-1-methoxy-2-(3-methylbut-2-en-1-yl)-9H-xanthen-9-one (Afzeliixanthone A)

Xanthones as Potential Antioxidants

Current Medicinal Chemistry, 2013, Vol. 20, No. 36 4497 (Table 1) contd….

S.No.

Structures O

Plant Origin (Part)

Ref.

Garcinia afzelii-(Stem bark)

[63]

Swertia decussate-(Whole plant)

[64]

Swertia decussate (Whole plant) Swertia chirayita (Whole plant)

[64] [72]

Swertia decussate (Whole plant) Swertia minor (Whole plant)

[64] [73]

Swertia decussate (Whole plant)

[64]

Swertia speciosa (Rhizomes)

[65]

O

O O 108

82

OH

OH

(Z)-4-hydroxy-2-(3-hydroxy-3-methylbut-1-en-1-yl)-1,7-dimethoxy-9H-xanthen-9-one (Afzeliixanthone B) OH

O

O OH

83

O

O 109

2,8-Dihydroxy-1,6-dimethoxy-9H-xanthen-9-one (Gentiacaulene) OH

O

O O

84

O

O 110

1-Hydroxy-3,7,8-trimethoxy-9H-xanthen-9-one (Decussatin) OH

O

OH OH

85

O

O 111

1,2,8-Trihydroxy-6-methoxy-9H-xanthen-9-one (Swertianin) OH

O

OH O

86

O

O 112

1,8-Dihydroxy-2,6-dimethoxy-9H-xanthen-9-one (Swertiaperennin) OH OH O

OH

HO

87

O

HO

O OH

HO O

O 113

O

O

6-Hydroxy-3,5-dimethoxy-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(2-((2S,3R,4S,5R)-3,4,5trihydroxytetrahydro-2H-pyran-2-yl)ethyl)tetrahydro-2H-pyran-2-yl)oxy)-9H-xanthen-9-one

4498 Current Medicinal Chemistry, 2013, Vol. 20, No. 36

Panda et al.

(Table 1) contd….

S.No.

Plant Origin (Part)

Structures

OH

Ref.

O O

88

HO

O

OH 114

Cudrania tricuspidata (Root bark)

[66]

3,6,8-Trihydroxy-2-methoxy-1-(3-methylbut-2-en-1-yl)-5-(2-methylbut-3-en-2-yl)-9H-xanthen-9one (Cudraxanthone C)

OH

O OH

89

O

O

OH 115

Cudrania tricuspidata (Root bark)

[66]

Cudrania tricuspidata (Root bark)

[66]

Cudrania tricuspidata (Root bark)

[66]

Cudrania tricuspidata (Root bark)

[66]

2,3,8-Trihydroxy-6-methoxy-1-(3-methylbut-2-en-1-yl)-5-(2-methylbut-3-en-2-yl)-9H-xanthen-9one (Cudraxanthone D) O

OH

HO HO

O

OH

116

90

1,3,6,7-Tetrahydroxy-5-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-9H-xanthen-9-one (Cudraxanthone L) O

OH

HO HO

O

O 117

91

4,7,8-Trihydroxy-2,3,3-trimethyl-9-(3-methylbut-2-en-1-yl)-2H-furo[3,2-b]xanthen-5(3H)-one (Cudraxanthone M)

O

92

HO

O OH

OH

O

118

1,5,6-Trihydroxy-3-methoxy-4-(2-methylbut-3-en-2-yl)-9H-xanthen-9-one (Isocudraniaxanthone B)

Xanthones as Potential Antioxidants

Current Medicinal Chemistry, 2013, Vol. 20, No. 36 4499 (Table 1) contd….

S.No.

Structures O

Plant Origin (Part)

Ref.

Cudrania tricuspidata (Root bark)

[66]

Cudrania tricuspidata (Root bark)

[66]

Garcinia virgata(Stem bark)

[67]

Garcinia virgata (Stem bark)

[67]

Hypericum styphelioide (Leaves)

[68]

OH

HO HO

O 119

93

OH

1,3,6,7-Tetrahydroxy-4-(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-9H-xanthen-9-one (Macluraxanthone B)

OH

O OH

94 HO

O 120

OH

2,3,6,8-Tetrahydroxy-1-(3-methylbut-2-en-1-yl)-5-(2-methylbut-3-en-2-yl)-9H-xanthen-9-one

O

HO

OH

O

OH

OH

95

121

(E)-4-(3,7-Dimethylocta-2,6-dien-1-yl)-1,3,5,6-tetrahydroxy-8-(3-methylbut-2-en-1-yl)-9H-xanthen9-one (Virgataxanthone A) OH

O O

HO

O

OH

122

96

(E)-8-(3,7-Dimethylocta-2,6-dien-1-yl)-5,9,11-trihydroxy-3,3-dimethylpyrano[3,2-a]xanthen12(3H)-one (Virgataxanthone B) O

97 OH

O 123

OH

OH

2-((1S,4S)-2,2-Dimethyl-4-(prop-1-en-2-yl)cyclopentyl)-1,3,5-trihydroxy-9H-xanthen-9-one

4500 Current Medicinal Chemistry, 2013, Vol. 20, No. 36

Panda et al.

(Table 1) contd….

S.No.

Structures

O

98

O

N

Ref.

Hypericum styphelioide (Leaves)

[68]

Garcinia vieillardii (Bark)

[35]

Arrabidaea samydoides (Stems)

[69]

Garcinia multiflora (Stems)

[70]

Garcinia multiflora (Stems)

[70]

OH

O 124

OH

Plant Origin (Part)

OH

2-((1R,4R)-2,2-dimethyl-4-(prop-1-en-2-yl)cyclopentyl)-1,3,5-trihydroxy-6-nitroso-9H-xanthen-9one O

99

O

OH

O OH

O

125

5,10-Dihydroxy-9-methoxy-1,1,2-trimethyl-1H-furo[2,3-c]xanthen-6(2H)-one OH O

OH

OH

O

HO

OH

HO

O OH

O

100

O

126

OH

(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-(1,3,6,7-tetrahydroxy-9-oxo-9H-xanthen-2yl)tetrahydro-2H-pyran-3-yl 4-hydroxybenzoate

OH

101

O O

HO

O 127

OH

(E)-1-(3,7-Dimethylocta-2,6-dien-1-yl)-3,6,8-trihydroxy-1-(3-methylbut-2-en-1-yl)-1H-xanthene2,9-dione (Garcinianone A)

OH

O O

102 HO

O 128

OH

(Z)-1-(3,7-Dimethylocta-2,6-dien-1-yl)-3,6,8-trihydroxy-1-(3-methylbut-2-en-1-yl)-1H-xanthene-2,9dione (Garcinianone B)

Xanthones as Potential Antioxidants

Current Medicinal Chemistry, 2013, Vol. 20, No. 36 4501 (Table 1) contd….

S.No.

Structures

OH

Plant Origin (Part)

Ref.

Wardomyces anomalus (Fungus)

[32]

Wardomyces anomalus (Fungus)

[32]

Garcinia cantleyana var. (Twigs)

[71]

Garcinia cantleyana var. (Twigs)

[71]

Swertia chirayita (Whole plant)

[72]

Swertia chirayita (Whole plant)

[72]

O OH

103

HO

O 129

OH

2,3,6,8-Tetrahydroxy-1-methyl-9H-xanthen-9-one

OH

O OH

104

HO

O 130

OH OH

2,3,4,6,8-Pentahydroxy-1-methyl-9H-xanthen-9-one

R7

R1

O

R6

R2 R3

O R5

105

131 R1 =

R3 =

R4

R5 =

OH, R 2 =

R4 =

O

OH

R6

= R7

=H 132 R1 = R 3 = R 7 = OH, R 2 = R 4 = R 5 = R6 = H 133 R1 = R 3 = R 5 = R 7 = OH, R 2 = R 4 = R6 = H 134 R1 = R 3 = R 5 = R 6 = OH, R 2 = R 4 = R7 = H O

106

HO

O O

OH

135

1,3,6-Trihydroxy-5-methoxy-7-(3-methyl-2-oxo-but-3-enyl)-9H-xanthen-9-one

OH

O

OH

HO 107

O

O

10 1,7,8-Trihydroxy-3-methoxy-9H-xanthen-9-one (Swertianin)

OH

108

O

O OH

OH

O

11

1,5,8-Trihydroxy-3-methoxy-9H-xanthen-9-one (Bellidifolin)

4502 Current Medicinal Chemistry, 2013, Vol. 20, No. 36

Panda et al.

(Table 1) contd….

S.No.

Structures

OH

O

109

Ref.

Swertia chirayita (Whole plant)

[72]

Swertia chirayita (Whole plant)

[72]

Swertia minor (Whole plant)

[73]

Swertia minor (Whole plant)

[73]

Swertia minor (Whole plant)

[73]

Swertia minor (Whole plant)

[73]

OH

O O

Plant Origin (Part)

OH

136

1,3,8-Trihydroxy-5-methoxy-9H-xanthen-9-one (Isobellidifolin)

OH HO

O

HO

O

OH

O

OH

110

O OH

O

137

1,5-Dihydroxy-3-methoxy-8-(3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)9H-xanthen-9-one (Swertianolin)

OH

111

O

O

OH

O 138 O

1,8-Dihydroxy-4,6-dimethoxy-9H-xanthen-9-one

OH

O

OH O

112

O

O 9

1,8-Dihydroxy-2,6-dimethoxy-9H-xanthen-9-one (Methylswertianin)

OH

113

O

O

OH

O

O

139 1,8-Dihydroxy-3,6-dimethoxy-9H-xanthen-9-one

OH

O

O O

114

O

O 140

8-Hydroxy-1,2,6-trimethoxy-9H-xanthen-9-one

Xanthones as Potential Antioxidants

Current Medicinal Chemistry, 2013, Vol. 20, No. 36 4503 (Table 1) contd….

S.No.

Structures

O

Ref.

Calophyllum thorelii (Bark)

[74]

Calophyllum thorelii (Bark)

[74]

Calophyllum thorelii (Bark)

[74]

Artocarpus obtusus FM Jarrett (Bark)

[75]

Artocarpus obtusus FM Jarrett (Bark)

[75]

Artocarpus obtusus FM Jarrett (Bark)

[75]

OH

O

O

115

Plant Origin (Part)

OH 141

1,5-Dihydroxy-2,3,3-trimethyl-4-(3-methylbut-2-en-1-yl)-2H-furo[2,3-b]-9H-xanthen-9-one

OH

O

OH

HO

H

116

O

O 142

(S)-4,6,7-Trihydroxy-2,3,3-trimethyl-2H-furo[3,2-b]xanthen-5(3H)-one (Calothorexanthone)

OH

117

O

OH

O OH

O

143

5,7,10-trihydroxy-1,1,2-trimethyl-1H-furo[2,3-c]xanthen-6(2H)-oneb (Garboginol) OH

O OH

O

O

O

118

HO

OH

144

1,3,5,9-Tetrahydroxy-6,12,12-trimethyl-5,6,6a,7-tetrahydrochromeno[4,5-bc]pyrano[3,2-h]xanthen8(12H)-one (Pyranocycloartobiloxanthone A)

OH

119

O

O

O OH 145 O

6,10-Dihydroxy-9-isopropyl-3,3,10-trimethyl-10,11-dihydro-3H-cyclopenta[c]pyrano[3,2h]xanthene-7,12-dione (Dihydroartoindonesianin C) OH

O

OH OH

O 120

O HO

O OH

146 1,3,5,6,9-Pentahydroxy-5,12,12-trimethyl-5,6,6a,7-tetrahydrochromeno[4,5-bc]pyrano[3,2h]xanthen-8(12H)-one (Pyranocycloartobiloxanthone B)

 

 

 









  











 

 



 







 

 



 



   

 

 



 





 

 











          

            

  

 





  









 











 



 

  

  





 











 































 

  











 





  





 















 



 

























        





  







          

 





                                                                                                                                                                 

 



          

                                                                                                                                                                                                                                                                          

 

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                                                                                                                                                                                                                                                                                                                                                           

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                                                                                                                                                                                                                                                                                                                                                         



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

                                                                                                     







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                                                                                                                                 