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Literature Review
Journal of Chinese Integrative Medicine: Volume 4, 2006   Issue 4
A survey of chemical and pharmacological studies on Solidago
1. Tao JIANG (Department of Pharmacognosy, School of Pharmacy, Second Military Medical University, Shanghai 200433, China )
2. Bao-Kang HUANG (Department of Pharmacognosy, School of Pharmacy, Second Military Medical University, Shanghai 200433, China )
3. Lu-Ping QIN (Department of Pharmacognosy, School of Pharmacy, Second Military Medical University, Shanghai 200433, China E-mail: lpqin@smmu.edu.cn)

Zhong Xi Yi Jie He Xue Bao/J Chin Integr Med, 2006, 4(4): 430-435   www.jcimjournal.com

Correspondence to: Prof. Lu-Ping QIN. E-mail: lpqin@smmu.edu.cn

  
     Herbal medicine has been used for treating different diseases in China for thousands of years. The genus Solidago L., commonly known as goldenrod, is one of the largest genera of the Asteraceae family, with 120 species, most of them growing wildly in North America. It is reported that Solidago plants have been shown to have good diuretic, choleretic, antiseptic and wound-healing activity. All species are herbaceous perennials ranging from 5 cm to 3 m tall. These usually have small heads with yellow pistillate ray and perfect disc florets aggregated into flat-topped, wand-shaped or pyramidal inflorescences. The phyllaries are generally lanceolate to ovate, present in 2-4 graduated series, and have a translucent midrib.
     There are four species of Solidago in China, including Solidago decurrens, Solidago virgaurea, Solidago pacifica and Solidago canadensis. They are widely distributed in Shanghai, Zhejiang, Jiangxi, Shaanxi and Taiwan provinces of China. In addition, one vars. Solidago virgaurea L. var. dahurica kitag is regarded as a traditional Chinese medicine in Xinjiang province and Northeast China. Solidago canadensis, a perennial plant originating from North America, was introduced into China as a horticultural plant in the 1970s. It has become an invasive weed and caused damage to crops in dry fields, impeded the recovery of vegetation in abandoned fields in recent years in China.
     In order to understand and make good use of Solidago plants, we surveyed the research documents about chemical principles and pharmacological activities of these plants.
 
  

1 CHEMICAL PRINCIPLES
    Many scholars found and isolated some chemical principles from the plants of genus Solidago L., such as flavonoids, leiocarposide, saponins, carotenoids, sesquiterpenes and diterpenes. The structures of new compounds isolated from plants of genus Solidago L. and the chemical principles of genus Solidago L. are shown below (Table 1 and Figure 1).

Table 1 Chemical principles of genus Solidago L.(to be continued)

No.

Chemical principle

Source

Reference No.

1

Leiocarposide

a ,b

1-3

2

2-Methoxybenzy-2,3,6-trimethoxybenzoate

a

2

3

Β-sitosterol

a

2

4

3,5-Dimethoxy-4-acetoxycinnamyl angelate

a

2

5

3-Methoxy-4-acetoxycinnamyl angelate

a

2

6

2-Methoxybenzyl-2,6-dimethoxybenzoate

a

2

7

Benzyl-2-hydroxy-6-methoxybenzoate

a

2

8

Methyl(2E,8Z)-decadien-4,6-diynoate

a

2

9

Benzyl-2,6-dimethoxybenzoate

a

2

10

Methyl(2Z,8Z)-decadien-4,6-diynoate

a

2

11

Caffeic acid

a

4

12

Chlorogenic acid

a,h

4,21

13

A-pinene

b,c,f,h

4,7,11,17

14

B-myrcene

b,c,f,h

4,7,11,17

15*

Virgaureasaponin 3

b

5

16

Quercetin-D-glucoside

b

6

17

Kaempferol-D-glucoside

b

6

18

Kaempferol-3-O-rutinoside

b,g

6,20

19

Limonene

b,c,j

7,11,22

20

B-elemene

b,c

7,11

21

δ-elemene

b,c

7,11

22

Germacrene B

b,c

7,11

23

Germacrene D

b,c

7,11

24

δ-cadinene

a,b

7,11

25

Oleanolic acid

b

8

26

Bayogenin

b

8

27*

Virgaureoside A

b

9

28*

Solidagosaponins 21

b

10

29*

Solidagosaponins 22

b

10

30*

Solidagosaponins 23

b

10

31*

Solidagosaponins 24

b

10

32*

Solidagosaponins 25

b

10

33*

Solidagosaponins 26

b

10

34*

Solidagosaponins 27

b

10

35*

Solidagosaponins 28

b

10

36*

Solidagosaponins 29

b

10

37*

Solidagosaponins 30

b

10

38*

Canadensissaponin 1

c

12

39*

Canadensissaponin 2

c

12

40*

Canadensissaponin 3

c

12

41*

Canadensissaponin 4

c

12

42

Bayogeninsaponin 1

c

13

43

Bayogeninsaponin 2

c

13

44

Bayogeninsaponin 3

c

13

45

Bayogeninsaponin 4

c

13

46

3-Epi-α-cubebene

c

14

47

3-Epi-β-cubebene

c

14

48

3β-(3R-acetoxyhexadecanoyloxy)-lup-20(29)-ene

c

15

49

3β-(3-ketohexadecanoyloxy)-lu-20(29)- ene

c

15

50

3β-(3R-acetoxyhexadecanoyloxy)-29-nor-luan-20-one

c

15

51

3β-(3-hetohexadecanoyloxy)-29-nor-lupan-20-one

c

15

52*

Elongatolide A

d

16

53*

Elongatolide B

d

16

54*

Elongatolide C

d

16

55*

Elongatolide D

d

16

56*

Elongatolide E

d

16

57*

Trans-clerodane 5

e

17


Table 1 (continuation) Chemical principles of genus Solidago L.

No.

Chemical principle

Source

Reference No.

58*

Trans-clerodane 6

e

17

59*

Trans-clerodane 7

e

17

60

Erythrodiol-3-acetate

g

18

61

α-tocopherol-quinone

g

18

62

Trans-phytol.

g

18,19

63

Ent-germacra-4(15),5,10(14)-trien- 1α-ol

g

19

64

B-amyrin acetate

g

19

65

Methyl-3,5-di-O-caffeoyl quinate

g

19

66

Ent-germacra-4(15),5,10(14)-trien-1β-ol

g

19

67

B-dictyopterol

g

19

68

3,5-Di-O-caffeoyl quinic acid

g

19

69

Kaempferol

g

20

70

Epi-torilenol

h

20

71

(5αH,6βH,7αH,8βH,10α-6,8-cycloeudesm-4(15)-en-1a-ol),
1,10-seco-eudesma-4(15), 5(10)-dien-1-al

h

20

72

Cis-eudesm-4(10)-en-1-one

h

20

73

Quercetin-3-O-β-D-rutinoside(rutin)

b

21

74

Isoschaftoside

i

21

75*

(+)-18-Tigloyxymannol

k

23

76*

18-Hydroyabieta-7,13(14)-diene

k

23

77*

18-Tigloyoxyabieta-7,13(14)-diene

k

23

78*

7-Hydroy-13,15-dihydroxyabieta-8 (14)- ene-18-oic acid

k

23

79*

15- Hydroydehydroabietic acid

k

23

*New compound; a: Solidago decurrens Lour.; b: Solidago virgaurea L.; c: Solidago canadensis; d: Solidago elongate Nutt.; e: Solidago arguta; f: Solidago odora Ait.; g:Solidago virga-aurea var gigantean; h:Solidago gigantea Ait.; i: Solidago graminifolia; j: Solidago chilensis; k: Solidago rugosa.


Figure 1 (A) Structures of new compounds isolated from plants of genus Solidago L.


Figure 1 (B) Structures of new compounds isolated from plants of genus Solidago L.

  
2 PHARMACOLOGICAL ACTIVITIES
2.1 Diuretic activity

    The aerial parts of Solidago virgaurea L. is used as a diuretic. In the experiment, Guo24 found the quantity of urine was low with high dosage of the extracts from the aerial parts of Solidago virgaurea L..
2.2 Anti-inflammatory activity
    Solidago virgaurea L. has been traditionally used as an anti-inflammatory herbal medicine for many years. Inflammatory model of ear edema was induced by dimethyl benzene in mice. The extract of Solidago virgaurea L. was tested on anti-inflammation activity in mice. The result showed that the ear edema induced by dimethyl benzene could be obviously reduced when given 105 mg/kg (i.g.) in mice25 .  

2.3 Antifungal activity
    Essential oils and ethanol extracts from the leaves and roots of 35 medicinal plants commonly used in Brazil were screened for anti-Candida albicans activity. The oils were obtained by water-distillation using a Clevenger-type system. Essential oils from 13 plants showed anti-Candida activity, including Solidago chilensis26 .
    Roser et al27 identified and analyzed thirty-six different compounds of the essential oils from leaves and inflorescences of Solidago chilensis Meyen by GC-FID (gas chromatography and flame-ionization-detector), GC-MS (gas chromatography and mass spectrum) and 13C-NMR(13C and nuclear magnetic resonance spectroscopy). In addition, the antifungal activity of the leaf oil was assayed against five different strains of filamentous fungi and one yeast. The result showed that the human pathogenic dermatophyte was the most sensitive.
2.4 Anticancer activity
    Gross et al28 found that the extract of S. virgaurea exhibits strong cytotoxic activities on various tumor cell lines. The active component mostly resides in the leaves of the plant and is soluble in water. When the extract was fractionated by a Sephadex G-100 column, the active fraction corresponded to a molecular weight of approximately 40 000. This cytotoxic activity is effective on various tumor cell lines, including human prostate carcinoma, breast carcinoma, melanoma, and small cell lung carcinoma. To examine the effect of the cytotoxic activity on tumor cells in vivo, the rat prostate carcinoma cell line (AT6.1) and an SCID (severe combined immunodeficiency) mouse model. AT6.1 cells were injected into the flank of SCID mice, and then the G-100 fraction of S. virgaurea was injected intraperitoneally or subcutaneously every 3 days. The size of the tumor was measured for up to 25 days. The growth of the tumor was significantly suppressed by the G-100 fraction at 5 mg/kg without any apparent side effects. Therefore, S. virgaurea is considered to be promising as an antineoplastic medicine with minimal toxicities.
2.5 Antioxidant activity
    Thirty-five plant species were selected from the published literature as traditionally used by the indigenous peoples of the boreal forest in Canada for three or more symptoms of diabetes or its complications. Antioxidant activities in methanol extracts support the contribution of these traditional medicines in a lifestyle historically low in the incidence of diabetes. It is reported that antioxidant activity of Solidago canadensis extract was greater than green tea, ascorbic acid and Trolox29 .

  
3 PERSPECTIVE
    The genus Solidago L. comprises a large group of medicinal plants with recognized therapeutic applications, especially S. virgaurea, S. gigantea and S. canadensis, the aerial parts of which are used in folk medicine in many countries.
    Furthermore, S. canadensis has caused serious harm to crop production, orchards, lawns, natural environments and biodiversity in China30 . Studies on the physical and ecological characteristics of newly introduced exotic weeds are of practical significance in the predication of their potential distribution areas and their habitats. It is urgent for us to make good use of this plant.
    Although great progress has been made over the past decades in study of chemical active components and pharmacological activities of genus Solidago, the results are still unsatisfactory. It is necessary for us to make good use of Solidago plants and find out which plant shows high activity and low toxicity.
  
References
1. Hiller K, Gil-Rjong R, Franke P. A saponin from Solidago decurrens[J]. Pharmazie, 1979, 34(5-6) : 360-361.
2. Bohlmann F, Chen ZL, Schuster A. Aromatic esters from Solidago drcurrens[J]. Phytochemistry, 1981, 20(11) : 2601-2602.
  
3. Bader G, Janka M, Hannig HJ, et al. Quantitative determination of leiocarposide in Solidago virgaurea L[J]. Pharmazie, 1990, 45(5) : 380-381.
4. Liu QH, Dai JZ, Yang PM, et al. Adipose injection and preparation method of Solidago decurrens Loure. CN: 02136369, 2003-02-12.
5. Bader G, Wray V, Hiller K. Virgaureasaponin 3, a 3, 28-bisdesmosidic triterpenoid saponin from Solidago virgaurea[J]. Phytochemistry, 1992, 31(2) : 621-623.
    
6. Hiller K, Gil-Rjong R, Otto A. Flavonoids of Solidago virgaurea L.var.leicarpa(Benth)A.Gray[J]. Pharmazie, 1979, 34(9) : 571-572.
7. Fijita, Shinichi. Components of the essential oils of Solidago virgaurea Linn.ssp[J]. Nippon Nogei Kagaku Kaishi, 1990, 64(11) : 1729-1732.
8. Tamas M, Rosea M. Saponins from species of Solidago growing in Romania[J]. Farmacia, 1988, 36(3) : 167-171.
9. Hiller K, Dube G, Zeigan D. Virgaureosid A-a new bisdesmoside phenol glycoside from Solidago virgaurea L[J]. Pharmazie, 1985, 40(11) : 795-796.
10. Miyase T, Inose Y, Ueno A. Studies on the Constituents of Solidago virgaurea L. Ⅲ. Structures of Solidago saponins XXI-XXIX[J]. Chem Pharm Bull, 1994, 42(3) : 617-624.
  
11. Xia WX, He W, Wen GY. The constituents of the essential oil from Solidago canadensis[J]. Chin Bull Bot, 1999, 16(2) : 178-180.
12. Reznicek G, Jurenitsch J, Plasun M. Four major saponins from Solidago canadensis[J]. Phytochemistry, 1991, 30(5) : 1629-1633.
    
13. Reznicek G, Jurenitsch J, Freiler M, et al. Isolation and structure elucidation of further saponins from Solidago canadensis[J]. Planta Med, 1992, 58(1) : 94-98.
  
14. Kasali AA, Ekundayo O, Paul C, et al. Epi-Cubebanes from Solidago canadensis[J]. Phytochemistry, 2002, 59(8) : 805-810.
    
15. Chaturvedula VS, Zhou BN, Gao Z, et al. New lupane triterpenoids from Solidago canadensis that inhibit the lyase activity of DNA polymerase-beta[J]. Bioorg Med Chem, 2004, 12(23) : 6271-6275.
    
16. Anthonsen T, Mclrindle R. The constitution of diterpenoids from solidago elongata Nutt[J]. Acta Chem Scand, 1969, 23(3) : 1068-1070.
  
17. Michael J. Constituents of the essential oil of Solidago odora Ait[J]. Economic Botany, 1999, 53(3) : 281-283.
18. Sung JH, Lee JO, Son JK, et al. Cytotoxic constituents from Solidago virga-aurea var. gigantea MIQ[J]. Arch Pharmacal Res, 1999, 22(6) : 633-637.
  
19. Choi SZ, Choi SU, Lee KR. Phytochemical constituents of the aerial parts from Solidago virga-aurea var. gigantea[J]. Arch Pharm Res, 2004, 27(2) : 164-168.
  
20. Kalemba, Danuta, Marschall, et al. Constituents of the essential oil of Solidago gigantea Ait. (giantgoldenrod)[J]. Flavour Fragrance J, 2001, 16(1) : 19-26.
  
21. Thiem B, Wesolowska M. Phenolic compounds in two Solidago L. species from in vitro culture[J]. Acta Poloniae Pharmaceutica, 2001, 58(4) : 277-281.
  
22. Vila R, Mundina M, Tomi F, et al. Composition and antifungal activity of the essential oil of Solidago chilensis[J]. Planta Med, 2002, 68(2) : 164-167.
    
23. Lu T, Vargas D, Franzblau SG, et al. Diterpenes from Solidago rugosa[J]. Phytochemistry, 1995, 38(2) : 451-456.
    
24. Guo XZ. Dictionary of Toxic Chinese Materia Medica. Tianjin: Tianjin Science and Technology Translation and Publishing Co., 1992. 3.
25. EL-Ghazaly M. Anti-inflammatory activity of Solidago virgaurea L[J]. Arzneimittelforschung, 1992, 42(3) : 333-335.
26. Duarte MC, Figueira GM, Sartoratto A, et al. Anti-Candida activity of Brazilian medicinal plants[J]. J Ethnopharmacol, 2005, 97(2) : 305-311.
    
27. Vila R, Mundina M, Tomi F, et al. Composition and antifungal activity of the essential oil of Solidago chilensis[J]. Planta Med, 2002, 68(2) : 164-167.
    
28. Gross SC, Goodarzi G, Watabe M, et al. Antineoplastic activity of Solidago virgaurea on prostatic tumor cells in an SCID mouse model[J]. Nutr Cancer, 2002, 43(1) : 76-81.
    
29. McCune LM, Johns T. Antioxidant activity in medicinal plants associated with the symptoms of diabetes mellitus used by the indigenous peoples of the North American boreal forest[J]. J Ethnopharmacol, 2002, 82(2-3) : 197-205.
    
30. Huang H, Guo SHL. Analysis of population genetic differences of the invasive plant Solidago Canadensis[J]. Bulletin of Botanical Research, 2005, 25(2) : 197-204.
  
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