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Table 8.1 Compounds isolated from B. monnieri.

No. Compound Reference

[A] Dammarane type triterpenoid saponins

[A1] Psuedojujubogenin derivatives

1. Bacopaside I (3-O-a-L-arabinofuranosyl-(1-2)-[6-O-sulphonyl-b-

D-glucopyranosyl-

(1-3)]-a-

L-arabinopyranosyl pseudojujubogenin)

59, 60–64

2. Bacopaside II (3-O-a-

L-arabinofuranosyl-(1-2)-[b-D-glucopyranosyl-(1-3)]-b-D-

glucopyranosyl pseudojujubogenin)

59, 60–68

3. Bacopaside III (3-O-[6-O-sulfonyl-b-

D-glucopyranosyl (1-3)]-a-L arabinopyranosyl

pseudojujubogenin)

(Zhou et al., 2007

reported this molecule as bacopaside VI and claimed as a new

molecule).

(Chakravarty et al., 2003

reported 3-O-a-L-arabinofuranosyl-(1-2)-b-D-glucopyranosyl

jujubogenin (a jujubogenin derivative) as bacopaside III).

4. Bacopaside V (3-O-b-

D-glucopyranosyl-(1-3)-a-L-arabinopyranosyl psuedojujubogenin) 70, 61, 65, 67, 71

5. Bacopaside XI (3-O-[a-L-arabinofuranosyl-(1-3)]-6-O-sulfonyl-b-D-glucopyranosyl

pseudojujubogenin)

(Zhou et al., 2009

reported 3-O-[b-D-glucopyranosyl-(1-3)]-b-D-glucopyranosyl

psuedojujubogenin as bacopaside XI).

6. Bacopaside N2 (3-O-[b-

D-glucopyranosyl-(1-3)-b-D-glucopyranosyl]

psuedojujubogenin)

(Zhou et al., 2009

isolated the same molecule and reported it as a new molecule,

bacopaside XI).

(Bhandari et al., 2009

reported 3-O-[a-L-arabinofuranosyl-(1-3)]-6-O-sulfonyl-b-D-

glucopyranosyl pseudojujubogenin as bacopaside XI).

61, 67, 72

7. Bacopaside XII (3-O-[b-

D-glucopyranosyl(1-3){-a-L-arabinofuranosyl(1-2)}-b-D-

glucopyranosyl]-20-O-a-L arabinopyranosyl psuedojujubogenin)

8. Bacopasaponin B (3-O-[a-

L-arabinofuranosyl(1-2)-a-L-arabinopyranosyl]

psuedojujubogenin)

73,74

9. Bacopasaponin C (3-O-[b-

D-glucopyranosyl-(1-3){-a-L-arabinofuranosyl-(1-2)}-a-L-

arabinopyranosyl] psuedojujubogenin)

73, 61–68, 74, 75

10. Bacopasaponin D (3-O-[a-

L-arabinofuranosyl(1-2)-b-D-glucopyranosyl]

psuedojujubogenin)

76,64

182 Chapter 8

https://t.me/med1917

11. Bacopasaponin H (3-O-[a-L-arabinopyranosyl] psuedojujubogenin) 74

12. 3-O-b-

D-Glucopyranosyl pseudojujubogenin 67

13. Bacoside A

(3-O-[a-L-arabinofuranosyl-(1-6)-O-{a-L-arabinopyranosyl-(1-5)}-O-a-D-

glucofuranosyl] oxypseudojujubogenin)

14. Bacopasaponin G (3-O-[b-

D-glucopyranosyl(1-3)-b-D-glucopyranosyl]-20-

deoxypseudojujubogenin)

(Hou et al., 2002

reported 3-O-[a-L-arabinofuranosyl-(1-2)]-a-L-arabinopyranosyl

jujubogenin as bacopasaponin G).

15. Bacopasaponin I (3-O-[b-

D-glucopyranosyl-(1-3)-O-{a-L-arabinofuranosyl-(1-2)}-O-b-D-

glucopyranosyl]-20-deoxypseudojujubogenin)

[A2] Jujubogenin derivatives

16. Bacopaside III (3-O-a-

L-arabinofuranosyl-(1-2)-b-D-glucopyranosyl-jujubogenin)

(Hou et al., 2002

reported 3-O-[6-O-sulfonyl-b-D-glucopyranosyl(1-3)]-a-L-

arabinopyranosyl pseudojujubogenin (a pseudojujubogenin derivative) as

bacopaside III).

17. Bacopaside IV (3-O-b-

D-glucopyranosyl-(1-3)-a-L-arabinopyranosyl jujubogenin) 70, 61, 65, 67, 71

18. Bacopaside VIII (3-O-[b-

D-glucopyranosyl-(1-3){-a-L-arabinofuranosyl(1-2)}-b-D-

glucopyranosyl]-20-O-a-

L-arabinopyranosyl jujubogenin)

19. Bacopaside IX (3-O-[b-

D-glucopyranosyl-(1-4){-a-L-arabinofuranosyl(1-2)}-b-D-

glucopyranosyl]-20-O-a-

L-arabinopyranosyl jujubogenin)

78, 64

20. Bacopaside X (3-O-[a-

L-arabinofuranosyl-(1-2){-b-D-glucopyranosyl-(1-3)}-a-L-

arabinopyranosyl] jujubogenin) (jujubogenin isomer of bacopasaponin C, bacopaside

VII)

(Zhou et al., 2009

isolated 3-O-[b-D-glucopyranosyl(1-2)]-a-L-arabinopyranosyl

jujubogenin and named it as bacopaside X).

61, 63, 66, 68

21. Bacopaside X (3-O-[b-

D-glucopyranosyl(1-2)]-a-L-arabinopyranosyl jujubogenin)

(Sivaramakrishna et al., 2005

isolated the known molecule 3-O-[a-L-arabinofuranosyl-

(1-2){-b-

D-glucopyranosyl-(1-3)}-a-L-arabinopyranosyl] jujubogenin and gave the

trivial name bacopaside X).

22. Bacopaside N1 (3-O-[b-

D-glucopyranosyl-(1-3)-b-D-glucopyranosyl] jujubogenin) 61, 79, 72

23. Bacopasaponin A (3-O-a-

L-arabinopyranosyl-20-O-a-L-arabinopyranosyl jujubogenin) 73

24. Bacopasaponin E (3-O-[b-

D-glucopyranosyl(1-3){-a-L-arabinofuranosyl(1-2)}-a-L-

arabinopyranosyl]-20-O-(a-

L-arabinopyranosyl) jujubogenin)

80,61

Bacopa monnieri (Brahmi) 183

https://t.me/med1917

Table 8.1 (Continued)

No. Compound Reference

25. Bacopasaponin F (3-O-[b-D-glucopyranosyl(1-3){-a-L-arabinofuranosyl(1-2)}-b-D-

glucopyranosyl]-20-O-(a-L arabinopyranosyl) jujubogenin)

80,61

26. Bacopasaponin G (3-O-[a-

L-arabinofuranosyl-(1-2)]-a-L-arabinopyranosyl jujubogenin)

(Pawar et al., 2007

reported 3-O-[b-D-glucopyranosyl(1-3)-b-D-glucopyranosyl]-20-

deoxypseudojujubogenin as bacopasaponin G).

27. 3-O-a-

L-arabinopyranosyl jujubogenin 69

28. Bacoside A

(3-O-[a-L-arabinofuranosyl-(1-3)-a-L-arabinopyranosyl] jujubogenin) 81

29. Bacoside A

(3-O-[b-D-glucopyranosyl-(1-3)-O-{a-L-arabinofuranosyl-(1-2)}-O-b-D-

glucopyranosyl] oxyjujubogenin)

82, 61, 65–69, 75

30. Bacoside A

(3-O-a-L-arabinopyranosyl jujubogenin)

(Mourya et. al., 1995

reported this compound as zizyotin from Zizyphus oenoplea).

83, 84

31. Bacoside A

(20-O-a-L-arabinopyranosyl jujubogenin) 83

32. Bacoside A

(3-O-[b-D-glucopyranosyl-(1-3)-O-{a-L-arabinofuranosyl-(1-2)}-O-b-D-

glucopyranosyl]-20-deoxyjujubogenin)

33. Bacomosaponin A (3-O-[b-

D-glucopyranosyl(1-3){a-L-arabinofuranosyl(1-2)}-b-D-

glucopyranosyl]-20-O-(3,4-diacetyl-a-

L-arabinopyranosyl) jujubogenin)

34. Bacomosaponin B (3-O-[b-

D-glucopyranosyl(1-3){a-L-arabinofuranosyl(1-2)}-a-L-

arabinopyranosyl]-20-O-(3,4-diacetyl-a-

L-arabinopyranosyl) jujubogenin)

[B] Pentacyclic triterpenes

35. Ursolic acid 84

36. Betulinic acid 72, 86, 87

37. Lupeol 84

38. 28-Hydroxy lupeol 84

39. Bacosine 88, 62, 89

40. Ampelozigenin 84

[C] Phenylethyl glycosides

41. Bacopaside A ((3R)-1-octan-3-yl-(6-O-sulfonyl)-b-

D-glucopyranoside) 69

42. Bacopaside B (3,4-dihydroxy phenylethyl alcohol (2-O-feruloyl)-b-

D-glucopyranoside) 69

43. Bacopaside C (Phenylethyl alcohol [5-O-p-hydroxybenzoyl-b-

D-apiofuranosyl-(1-2)]-b-D-

glucopyranoside)

184 Chapter 8

https://t.me/med1917

44. Monnieraside I (a-O-[2-O-(4-hydroxybenzoyl)-b-D-glucopyranosyl]-4-hydroxyphenyl

ethanol)

90, 72, 91

45. Monnieraside II (a-O-[2-O-(3-methoxy-4-hydroxycinnamoyl)-b-

D-glucopyranosyl]-3,4-

dihydroxyphenyl ethanol)

46. Monnieraside III (a-O-[2-O-(4-hydroxybenzoyl)-b-

D-glucopyranosyl]-3,4-dihydroxyphenyl

ethanol)

90, 68, 91

47. Plantainoside A 69

48. Plantainoside B (plantioside B) 68, 69, 90, 91

49. Bacomoside A 68

50. Bacomoside B

51. Bacomoside B

52. Calcerorioside B 69

[D] Phenylpropanoid glycosides

53. Martynoside 69

54. Acetoside 69

[E] Cucurbitacins

55. Bacobitacin A (2,7b,16a,20R-tetrahydroxy-25-acetoxy-cucurbita-1,5,23E-triene-3,11,22-

trione)

56. Bacobitacin B (2,20R-dihydroxy-16a,25-diacetoxy-cucurbita-1,5,23E-triene-3,11,22-

trione)

57. Bacobitacin C (2-O-[{a-

L-rhamnopyranosyl-(1-2)-a-L-arabinofuranosyl-(1-4)}-{a-L-

rhamnopyranosyl-(1-2)-a-

L-arabinopyranosyl}] cucurbitacin E)

58. Bacobitacin D (2-O-[{a-

L-rhamnopyranosyl-(1-2)-a-L-arabinofuranosyl-(1-4)}-{a-L-

rhamnopyranosyl-(1-2)-a-

L-arabinopyranosyl}]-7b,16a,20R-trihydroxy-25-acetoxy-

cucurbita-1,15,23E-triene-3,11,22-trione)

59. Cucurbitacin E 68, 91

60. Cucurbitacin I 68

61. Cucurbitacin E-2-O-b-

D-glucopyranoside 68

[F] Steroids

62. Bacosterol 88,62

63. Stigmasterol 92

Bacopa monnieri (Brahmi) 185

https://t.me/med1917

Table 8.1 (Continued)

No. Compound Reference

64. b-Sitosterol 92

65. Stigmastanol 92

66. Bacosterol-3-O-b-

D-glucopyranoside 62

67. Stigmasterol-3-O-b-glucopyranoside 84

68. n

5,24

-Ergostadien-3b-ol 84

69. b-Daucosterin 84

[G] Flavonoids

70. Luteolin 56, 69, 72, 84

71. Luteolin-7-O-b-glucopyranoside 56, 62

72. Luteolin-7-glucuronide 93

73. Apigenin-7-glucuronide 93

74. Quercetin 84

75. Apigenin 69, 71, 84

[H] Alkaloids

76. Brahmine

77. Herpestine

78. Nicotine

[I] Others

79. 2,4,6-Trihydroxy-5-(3,3-dimethyl propenyl)-3-(4-hydroxy phenyl) propiophenone 94

80. 3-O-b-

D-Glucopyranosyl (3R)-1-octen-3-ol 72

81. p-Hydroxybenzoic acid 84, 72

82. p-Hydroxybenzenemethanol 84

83. 3,4-Dimethoxy cinnamic acid 84

84. Hersaponin

85. D-Mannitol 55, 92

86. Feruloyl glucoside 84

87. Rosavin 84

88. Loliolide 84

186 Chapter 8

https://t.me/med1917

89. Monnierin

95, 96

90. Heptacosane 92

91. Octacosane 92

92. Nonacosane 92

93. Triacontane 92

94. Hentriacontane 92

95. Dotriacontane 92

96. 3-Formyl-4-hydroxy-2H-pyran 56

97. 1-Linolenyl-3-O-b-

D-galactopyranosyl-sn-glycerol 69

98. b-(3,4-dihydroxyphenyl)ethyl-O-b-

D-glucose 69

Bacoside A, first isolated by Chatterji et al., 1965,

was later identified as a mixture of four saponins (bacoside A

(29), bacopaside II (2), bacopasaponin C (9)

and bacopaside X (20) (jujubogenin isomer of bacopasaponin C).

Bacoside B was reported as a mixture of four saponins (bacopaside N1 (22), bacopaside

N2 (6), bacopaside IV (17) and bacopaside V (4)) (Sivaramakrishna et al., 2005).

Deepak and Amit (2013)

mentioned that the details given by Sivar-

amakrishna and co-workers (2005)

are contradicting the original reports (Basu et al., 1967;

Singh et al., 1988

) describing bacoside B.

References reporting new molecules are highlighted in bold.

Ohta et al., 2016

reported two molecules bacomoside B

and B

(50, 51) with optical rotation [a]

þ5.1 and [a]

þ22.0, respectively, but their structures

are the same.

Alkaloids, brahmine (76),

herpestine (77)

and nicotine (78)

reported in the early studies (1931-1972) were not isolated by other authors from B.

monnieri.

Hersaponin (84)

and monnierin (89)

95,96

were reported with doubtful structural details and not isolated by other authors.

Bacopa monnieri (Brahmi) 187

https://t.me/med1917

extract.

Again the same authors isolated three new saponins [bacopaside

III (16), IV (17) and V (4)] from its aerial parts in 2003.

Bhandari and co-workers reported a new sterol glycoside, bacosterol-3-O-

D-glucopyranoside (66) along with known compounds bacopaside I (1),

bacopaside II (2), bacopasaponin C (9), bacosine (39 ), bacosterol (62) and

luteolin-7-O-b-glucopyranoside (71)fromB. monnieri aerial parts in 2006.

Again, in 2007, the same group isolated cucurbitacins, bacobitacin A-D (55–58)

and cucurbitacin E (59), along with three known phenylethyl glycosides

[monnieraside I (44), II (45), III (46)] and plantinoside B (48).

Zhou and co-

workersisolated three new triterpene glycosides, bacopaside VI (3), VII (20)and

VIII (18), along with known molecules, bacopaside I (1), bacopaside II (2)and

bacopasaponin C (9), from B. monnieri whole plant

(Table 8.1).

Pawar and co-workers reported two dammarane glycosides, bacopasaponin

G(14) and bacoside A

(32), together with 10 known compounds from B.

monnieri.

Thereafter, bacopaside IX (19), X (21)andXI(6) along with known

compounds bacopaside I (1), bacopaside II (2), bacopasaponin C (9)andba-

copasaponin D (10)wereisolatedfromB. monnieri whole plant.

Achalcone-

typecompound 2,4,6-trihydroxy-5-(3,3-dimethylpropenyl)-3-(4-hydroxyphenyl)

propiophenone (79) was reported by Suresh et al.

Ohta and co-workers re-

portedbacomosaponinA (33)andB(34)(dammarane-typeoligoglycosides)and

bacomoside A (49), B

(50)andB

(51) (phenylethyl glycosides) as new mol-

ecules from B. monnieri whole plant in 2016.

Dang and co-workers isolated a

new saponin, bacopasaponin I (15), along with a few known molecules from

B. monnieriin 2018

(Tables8.1 and 8.2). There are severalcontradictorynames

in the compounds reported from B.monnieri, and these issues are addressed in

this review [Table 8.1; examples, compounds (3), (5), (6), (14)].

A total of 98 secondary metabolites viz., dammarane-type triterpenoid

saponins (34, 1–34), pentacyclic triterpenes (6, 35–40), phenylethyl glyco-

sides (12, 41–52), phenylpropanoid glycosides (2, 53–54), cucurbitacins

(7, 55–61), steroids (8, 62–69), flavonoids (6, 70–75), alkaloids (3, 76–78) and

other misc ellaneous compounds (20, 79–98) were isolated from B. monnieri

(Table 8.1). Of these 98 compounds, 46 were reported as new molecules

(Table 8.2).

The pharmacological eﬀects of dammarane-type triterpenoid saponins

(mainly bacosides) have been investigated and reviewed by various

authors.

13,15,21,29–35,99,100

Other chemical entities (Table 8.1) in B. monnieri are

relativelyless explored.

In the context of this review, the chemical profilesand

molecular entities of B. monnieri in Ayurvedic formulations are least investi-

gated so far;and thisis one of the priority areas towardjustifying their eﬃcacy.

8.4 Standardization of Brahmi-based and Other

Ayurvedic Formulations

Phytochemical studies revealed dammarane-type triterpenoid saponins

(1–34) as the major secondary metabolites in B. monnieri, of which bacosides

188 Chapter 8

https://t.me/med1917

Table 8.2 Structures of new molecules reported from B. monnieri.

Pseudojujubogenin derivatives

No. Compound Substitution (R)

1. Bacopaside I a-

L-araf-(1-2)-[6-O-sulfonyl-b-D-glc-(1-3)]-a-L-ara

2. Bacopaside II a-

L-araf-(1-2)-[b-D-glc-(1-3)]-b-D-glc

3. Bacopaside III [6-O-Sulfonyl-b-

D-glc-(1-3)]-a-L-ara

4. Bacopaside V b-

D-glc-(1-3)-a-L-ara

5. Bacopaside XI [a-

L-araf-(1-3)]-6-O-sulfonyl-b-D-glc

6. Bacopaside N2 [b-

D-glc-(1-3)-b-D-glc]

8. Bacopasaponin B [a-

L-araf-(1-2)-a-L-ara]

9. Bacopasaponin C [b-

D-glc-(1-3)-{a-L-araf-(1-2)}-a-L-ara]

10. Bacopasaponin D [a-

L-araf-(1-2)-b-D-glc]

11. Bacopasaponin H [a-

L-ara]

13. Bacoside A

[a-L-araf-(1-6)-O-{a-L-ara-(1-5)}-O-a-D-glcf]

7. Bacopaside XII [b-D-glc-(1-3)-{a-L-araf (1-2)}-b-D-glc] a-L-ara

Bacopa monnieri (Brahmi) 189

https://t.me/med1917

Table 8.2 (Continued)

14. Bacopasaponin G [b-

D-glc-(1-3)-b-D-glc]

15. Bacopasaponin I [b-D-glc-(1-3)-O-{a-L-araf-(1-2)}-O-b-D-glc]

Jujubogenin derivatives

16. Bacopaside III a-L-araf-(1-2)-b-D-glc H

17. Bacopaside IV b-

D-glc-(1-3)-a-L-ara H

18. Bacopaside VIII [b-

D-glc-(1-3)-{a-L-araf-(1-2)}-b-D-glc] a-L-ara

19. Bacopaside IX [b-

D-glc-(1-4)-{a-L-araf-(1-2)}-b-D-glc] a-L-ara

21. Bacopaside X [b-

D-glc-(1-2)]-a-L-ara H

22. Bacopaside N1 [b-

D-glc-(1-3)-b-D-glc] H

23. Bacopasaponin A a-

L-ara a-L-ara

24. Bacopasaponin E [b-

D-glc-(1-3)-{a-L-araf-(1-2)}-a-L-ara] a-L-ara

25. Bacopasaponin F [b-

D-glc-(1-3)-{a-L-araf-(1-2)}-b-D-glc] a-L-ara

26. Bacopasaponin G [a-

L-araf-(1-2)]-a-L-ara H

28. Bacoside A

[a-L-araf-(1-3)-a-L-ara] H

29. Bacoside A

[b-D-glc-(1-3)-O-{a-L-araf-(1-2)}-

O-b-

D-glc]

31. Bacoside A

H a-L-ara

33. Bacomosaponin A [b-D-glc-(1-3)-{a-L-araf-(1-2)}-b-D-glc] 3,4-Diacetyl-a-L-ara

34. Bacomosaponin B [b-

D-glc-(1-3)-{a-L-araf-(1-2)}-a-L-ara] 3,4-diacetyl-a-L-ara

32. Bacoside A

(R ¼[b-D-glc-(1-3)-O-{a-L-araf-(1-2)}-O-b-D-glc])

Pentacyclic triterpene

190 Chapter 8

https://t.me/med1917

39. Bacosine

Phenylethyl glycosides

41. Bacopaside A H SO

42. Bacopaside B

43. Bacopaside C p-Hydroxybenzoyl-b-

D-

apiofuranosyl

44. Monnieraside I

45. Monnieraside II

46. Monnieraside III

49. Bacomoside A

Bacopa monnieri (Brahmi) 191

https://t.me/med1917

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