Chemical Constituents of Plants from the Genus Dracocephalum

Steroids. Five steroids were isolated from the genus Dracocephalum [6 – 8][13] [14] [17]. Compounds 23 – 27 from D. tanguticum, 26 from D. rupestre, and 23 from D. moldavica were isolated.

Diterpenoids. Eight diterpenoids, dracocequinones A and B (28 and 29, resp.), dracocephalone A ( 30), komarovispirone (31), cyclocoulterone ( 32), komaroviqui- none (33), and komarovinone A ( 34) were isolated from D. komarovi. Retinal (35) was identified from D. heterophyllum by GC/MS [15][18 – 20].

Sesquiterpenes. Thirty-seven sesquiterpenes were distributed in two species D. heterophyllum and D. kotschyi [20 – 25]. Three norsesquiterpenes, 39, 40, and 41, were isolated from D. heterophyllum [24]. Further derivatives were identified from D. kotschyi and D. heterophyllum by GC/MS [20 – 23] [25].

Monoterpenoids. Monoterpenoids are the major constituents of essential oil. Seventy-two monoterpenoids, 73 – 144, were distribued in D. heterophyllum, D. moldavica, D. forrestii, and D. kotschyi [11] [20 – 28].

Flavonoids. Flavonoids 145 – 201 have been reported to date [6] [7] [10]

[13][24] [29 – 41]. Some of them were reported to have biological activities. Four novel stereoisomeric flavanones, dracorupesins 177 – 180, were isolated from D. rupestre [38].

3. 
   Alkaloids. Sixteen flavonoidal alkaloids, 202 – 217, dracocephins A– D, each of them including four stereoiosmers, were isolated from D. rupestre [42]. Four spermidine alkaloid glycosides, dracotanosides A– D (218 – 221, resp.), were isolated from whole plant of D. tanguticum [43].
   

Table. Chemical Constituents from the Genus Dracocephalum

No. Compound class and name Source Ref.

1	Oleanolic acid	D. tanguticum	[7–9]
		D. moldavica	[10]
		D. kotschyi	[11]
		D. forrestii	[12]
2	3-Oxoolean-12-en-28-oic acid	D. tanguticum	[8] [13]
3	3b-Hydroxy-11a,12a-epoxyolean-13,28b-olide	D. forrestii	[12]
4	3b-Hydroxyurs-11-en-13b,28-olide	D. forrestii	[12]
5	Ursolic acid	D. rupestre	[6]
		D. tanguticum	[7] [9]
		D. kotschyi	[11]
		D. moldavica	[14]
		D. komarovi	[15]
6	Uvaol	D. moldavica	[14]
7	Colosolic acid	D. kotschyi	[11]
8	Ursonic acid	D. komarovi	[15]
9	3b-Hydroxyurs-12-en-28-al	D. forrestii	[12]
10	28-Norurs-12-en-3b-ol	D. forrestii	[12]
11 12 13 14	2a-Hydroxyursolic acid ( ¼(2a,3b)-2,3-dihydroxyurs-12-en-28-oic acid) (3b,18b)-20,28-Epoxy-3-hydroxyurs-21-en-28-one (3b)-Ursane-3,20,28-triol	D. tanguticum D. tanguticum D. forrestii D. forrestii	[8] [13] [8] [13] [12] [12]
15 16 17 18 19	(3b,18a,19a)-Ursane-3,20,28-triol (3b,20a)-3,20-Dihydroxyurs-21-en-28-oic acid 3,13-Dihydroxyursan-13,28-olide ( ¼(3b)-3-hydroxy-13,28- 12,13-Epoxy-28-norursane-3b,17b-diol Betulin	D. forrestii D. tanguticum D. rupestre D. forrestii D. rupestre	[12] [9] [16] [12] [6]
20	Betulinic acid	D. tanguticum D. forrestii D. rupestre D. tanguticum	[8] [9][13] [12] [6] [8] [13]
21	28-Norlup-20( 29)-ene-3b,7b-diol	D. komarovi D. forrestii	[15] [12]
22	Lup-20(29)-en-28-oic acid ethyl ester	D. moldavica	[6]
Steroids
23 Stigmasterol		D. tanguticum	[8]
		D. moldavica	[14]
24 Stigmastan-3-one		D. tanguticum	[8] [13]
25 Sitoindoside I ( ¼ 6-O-palmitoyldaucosterol)		D. tanguticum D. rupestre	[8] [6][17]
27 Ergosta-6,22-diene-3b,5a,8a-triol		D. tanguticum D. tanguticum	[7] [13] [13]
Diterpenoids
28 Dracocequinone A		D. komarovi	[15]
29 Dracocequinone B		D. komarovi	[15]
30 Dracocephalone A		D. komarovi	[18]

Triterpenoids

3b,24-Dihydroxyurs-12-en-28-oic acid

epoxyursan-28-one)
D. forrestii [12]
26 Daucosterol
No. Compound class and name Source Ref.

31. 
    Komarovispirone D. komarovi [19]
    
32. 
    Cyclocoulterone D. komarovi [18]
    
33. 
    Komaroviquinone D. komarovi [18]
    
34. 
    Komarovinone A D. komarovi [15]
    
35. 
    Retinal D. heterophyllum [20]
    

Sesquiterpenes

31. 
    Caryophyllene D. heterophyllum [20][21]
    

D. kotschyi [22]

31. 
    Sesquiphellandrene D. heterophyllum [21]
    
32. 
    a-Bisabolol D. heterophyllum [23]
    
33. 
    Blumenol C glucoside D. heterophyllum [24]
    
34. 
    Byzantionosid B D. heterophyllum [24]
    
35. 
    Icariside B₂ D. heterophyllum [24]
    
36. 
    2,6-Dimethyl-6-( 4-methylpent-3-enyl)bicyclo[3.1.1]hept-2-ene D. heterophyllum [20]
    
37. 
    a-Bourbonene D. heterophyllum [25]
    
38. 
    b-Bourbonene D. kotschyi [22]
    
39. 
    d-Elemene D. heterophyllum [25]
    
40. 
    Elixene D. heterophyllum [20]
    
41. 
    b-Elemene D. kotschyi [22]
    
42. 
    Spathulenol D. kotschyi [22]
    

D. heterophyllum [20][25]

31. 
    allo-Aromadendrene D. kotschyi [22]
    
32. 
    1a,2,3,4,4a,5,6,7b-Octahydro-1,1,4,7-tetramethyl-1H-cyclopropa[e]azulene D. heterophyllum [20]
    
33. 
    Decahydro-1,1,4,7-tetramethyl-4aH-cyclopropa[e]azulen-4a-ol D. heterophyllum [20]
    
34. 
    Decahydro-1,4a,7,7-tetramethylcyclopropa[7,8]azuleno[3a,4-b]oxirene D. heterophyllum [20]
    
35. 
    Viridiflorol D. heterophyllum [20]
    
36. 
    Cubenol D. heterophyllum [20][23]
    
37. 
    t-Muurolol D. heterophyllum [20]
    
38. 
    g-Muurolene D. heterophyllum [20]
    
39. 
    d-Cadinene D. heterophyllum [20]
    

D. kotschyi [22]

31. 
    a-Amorphene D. heterophyllum [20]
    

31. 
    (3R,4aS,8aS )-1,2,3,4,4a,5,6,8a-Octahydro-8a-methyl-5-methylidene-3- (propan-2-yl)naphthalene
    

D. heterophyllum [20]

31. 
    10-Epi-g-eudesmol D. kotschyi [22]
    
32. 
    Copaene D. heterophyllum [20]
    
33. 
    ( E,E )-Farnesol D. kotschyi [22]
    
34. 
    trans-Nerolidol D. heterophyllum [20]
    
35. 
    b-Farnesene D. heterophyllum [25]
    
36. 
    a-Humulene D. heterophyllum [20]
    

D. kotschyi [22]

31. 
    Humulene epoxide II D. heterophyllum [20]
    

D. kotschyi [22]

31. 
    Germacrene D D. heterophyllum [20]
    

D. kotschyi [22]

31. 
    Germacrene A D. kotschyi [22]
    
32. 
    Bicyclogermacrene D. kotschyi [22]
    
33. 
    Caryophyllene oxide D. heterophyllum [20]
    

D. kotschyi [22]

31. 
    Cubeb-4(15)-ene D. heterophyllum [20]
    
32. 
    Octahydro-2,2,7a,trimethyl-4-methylidene-1,3a-ethanoinden-5-ol D. heterophyllum [20]
    

Monoterpenoids

31. 
    d-Limonene D. heterophyllum [20][21]
    

D. kotschyi [22]
D. moldavica [26]

31. 
    
    ¼
    Limonen-10-al ( 2-(4-methylcyclohex-3-en-1-yl)prop-2-enal) D. kotschyi [11]
    
32. 
    trans-Carveol D. heterophyllum [20]
    

D. kotschyi [22]

31. 
    Perilla alcohol D. kotschyi [22]
    
32. 
    Limonen-10-ol 10-O-b-d-glucopyranoside D. kotschyi [11]
    

D. heteropyhllum [24]

31. 
    
    !
    Limonen-10-ol 10-O-b-d-glucopyranosyl-(1 2)-b-d-glucopyranoside D. kotschyi [11]
    

D. heterophyllum [24]

31. 
    Terpinen-4-ol D. heterophyllum [20][23]
    

D. kotschyi [22]

31. 
    p-Menth-1-en-4-ol acetate D. heterophyllum [20]
    
32. 
    a-Terpineol D. kotschyi [22]
    
33. 
    p-Menth-1-en-9-ol D. kotschyi [22]
    
34. 
    p-Mentha-8-ene-1,2-diol D. kotschyi [11]
    
35. 
    b-Phellandrene D. kotschyi [22]
    
36. 
    Carvone D. heterophyllum [23]
    
37. 
    Isopiperitenone D. heterophyllum [23]
    
38. 
    p-Mentha-1(7),8-diene D. kotschyi [22]
    
39. 
    p-Cymene D. kotschyi [22]
    
40. 
    p-Cymen-8-ol D. heterophyllum [20]
    
41. 
    Terpinolene D. heterophyllum [20]
    

D. kotschyi [22]

31. 
    5-Methyl-3-(propan-2-ylidene)cyclohexene D. heterophyllum [20]
    
32. 
    trans-p-Menth-2-en-1-ol D. kotschyi [22]
    
33. 
    cis-p-Mentha-2,8-dien-1-ol D. kotschyi [22]
    
34. 
    g-Terpinene D. heterophyllum [20]
    

D. kotschyi [22]

31. 
    Cuminaldehyde D. kotschyi [22]
    
32. 
    a-Terpinene D. kotschyi [22]
    
33. 
    a-Phellandrene D. heterophyllum [20]
    
34. 
    Eucalyptol D. heterophyllum [20][21][23]
    
35. 
    Linalool D. heterophyllum [21][23][25]
    

D. kotschyi [22]

31. 
    Linalool acetate D. heterophyllum [20]
    
32. 
    Citronellal D. heterophyllum [21][25]
    
33. 
    Citronellol D. moldavica [27]
    

D. heterophyllum [21][25]

31. 
    Citronellyl formate D. heterophyllum [21][25]
    
32. 
    Citronellyl isobutyrate D. heterophyllum [25]
    
33. 
    Citronellyl acetate D. heterophyllum [25]
    
34. 
    Nerol D. heterophyllum [25]
    

D. moldavica [27]

31. 
    Neral D. kotschyi [11][22]
    

D. heterophyllum [21]

31. 
    Neryl acetate D. heterophyllum [25]
    
32. 
    Geraniol D. kotschyi [22]