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Table 1 Structures of terpenes (1–65) and cyclopeptides (66–109) isolated from the Genus Rubia

From: Structural and bioactive studies of terpenes and cyclopeptides from the Genus Rubia

NO.

Structures’ name

Mp/°C or [α]/°

Resources & References

1

6-methoxygeniposidic acid

—

R. cordifolia[7]

2

Asperuloside

173-175 [8]

R. tinctorum[8]

130–132 [33]

R. peregrina[9]

3

Asperulosidic acid

[α]D +21 [33]

R. peregrina[9]

4

Deacetylasperulosidic acid

[α]D +21 [33]

R. peregrina[9]

5

3R,3aS,4R,6aR-3,4,6-tris (hydroxymethyl)-3,3a,4,6a-tetrahydro-2H-cyclopenta[b] furan-2-one

α D 22 + 4 [25]

R. cordifolia[25]

6

Rubiacoumaric acid

215/ [α]D +24.5 [10]

R. cordifolia[10]

7

Rubiafolic acid

286-287/ [α]D +58.8 [10]

R. cordifolia[10]

   

R. schumanniana[20]

8

Zamanic acid

α D 27 + 26 [35]

R. schumanniana[20]

9

Maslinic acid

269-271 [31]

R. schumanniana[20]

   

R. yunnanensis[22]

10

Spathodic acid

280 [37]

R. yunnanensis[22]

11

Ursolic acid

272-273 [32]

R. schumanniana[20]

   

R. yunnanensis[22]

12

Oleanolic acid

277.6-280.1 [31]

R. schumanniana[20]

  

281–282 [32]

R. cordifolia[26]

  

280–282 [34]

R. ustulata[27]

13

Karachic acid

260-261/ [α]D +79 [29]

R. schumanniana[20]

14

3-O-acetyloleanolic acid

265-266 [34]

R. ustulata[27]

15

Oleanolic aldehyde acetate

216-218 [36]

R. cordifolia[7]

16

Rubiarbonol A

260-263/ [α]D +36.5 [11]

R. cordifolia[11, 24]

  

260–262 [13]

R. yunnanensis[13, 15, 16, 18, 21, 22]

  

289–290 [16, 18]

 

17

Rubiarbonol B

272-273/ [α]D +30.3 [11]

R. oncotricha[11]

   

R. yunnanensis[15]

   

R. cordifolia[24]

   

R. ustulata[27]

18

Rubiarbonol C

211-213/ [α]D –4.3 [11]

R. oncotricha[11]

19

Rubiarbonol D

218-220/ [α]D +6.1 [11]

R. oncotricha[11]

   

R. akane[28]

20

Rubiarbonol E

290/ [α]D +15.4 [11]

R. oncotricha[11]

21

Rubiarbonol F

280/ [α]D +33.3 [11]

R. oncotricha[11]

   

R. yunnanensis[15]

   

R. yunnanensis[21, 22]

22

Rubiarbonol G

170-173 [13]

R. yunnanensis[13, 15, 16, 18, 22, 30]

  

174–176 [16, 18]

 

23

Rubiarbonol K

—

R. schumanniana[20]

   

R. yunnanensis[22, 30]

24

Rubiarbonol L

—

R. yunnanensis[22, 30]

25

Rubiarbonone A

153-155 [13]

R. yunnanensis[13, 15, 16, 18, 22, 30]

  

160–162 [16, 18]

 

26

Rubiarbonone B

155-157 [14]

R. yunnanensis[14]–[16, 18, 21, 22]

  

255–256 [16, 18]

 

27

Rubiarbonone C

98-100 [14]

R. yunnanensis[14, 21, 22]

28

Rubiarbonone D

231-232/ [α]D +94.4 [15]

R. yunnanensis[15]

29

Rubiarbonone E

258-259/ [α]D +233.4[15]

R. yunnanensis[15, 22]

30

Rubiarbonone F

253-254/ [α]D +26.4 [15]

R. yunnanensis[15]

31

Rubiarboside A

—

R. yunnanensis[15, 21, 22, 30]

32

Rubiarboside B

—

R. yunnanensis[21, 30]

33

Rubiarboside C

—

R. yunnanensis[21, 22, 30]

34

Rubiarboside F

294-295/ [α]D +98.1 [15]

R. yunnanensis[15]

35

Rubiarboside G

>290/ [α]D +56.4 [15]

R. yunnanensis[15, 22]

36

Rubiprasin A

>300/ [α]D +12.8 [12]

R. cordifolia[12]

   

R. ustulata[27]

   

R. akane[28]

37

Rubiprasin B

277-280 [12]

R. cordifolia[12]

   

R. ustulata[27]

   

R. akane[28]

38

Rubiprasin C

171-173 [12]

R. cordifolia[12]

39

Rubiatriol

252-256 [17]

R. cordifolia[17]

40

Rubianol-a

α D 25 + 10.0 [19]

R. yunnanensis[19, 21]

41

Rubianol-b

α D 25 + 16.8 [19]

R. yunnanensis[19, 21]

42

Rubianol-c

α D 25 + 36.4 [19]

R. yunnanensis[19, 21, 22]

43

Rubianol-d

α D 25 + 63.6 [19]

R. yunnanensis[19, 21, 22]

44

Rubianol-e

α D 25 + 18.1 [19]

R. yunnanensis[19, 21, 22]

45

Rubianol-g

α D 25 + 206.1 [21]

R. yunnanensis[21]

46

Rubianoside I

α D 25 + 10.9 [19]

R. yunnanensis[19, 21, 22]

47

Rubianoside II

α D 25 + 2.2 [21]

R. yunnanensis[21]

48

Rubianoside III

α D 25 + 3.5 [21]

R. yunnanensis[21]

49

Rubianoside IV

α D 25 + 90.5 [21]

R. yunnanensis[21]

50

3β,6α-dihydroxy-urs-14-en-12-one

α D 20 – 10.7 [20]

R. schumanniana[20]

51

3β-hydroxy-urs-30-p-Z-hydroxycinnamoyl-12-en-28-oic-acid

α D 16 + 6.5 [20]

R. schumanniana[20]

52

3β-hydroxy-olean-30-p-E-hydroxycinnamoyl-12-en-28-oic-acid

α D 16 + 13.1 [20]

R. schumanniana[20]

53

Rubiarbonol A 7-acetate

α D 23 + 1.7 [22]

R. yunnanensis[22]

54

Rubiyunnanol A

α D 16 + 23.2 [22]

R. yunnanensis[22]

55

Rubiyunnanol B

247 − 248 / α D 16 + 25.8 [22]

R. yunnanensis[22]

56

19,28-Didehydroxyrubiarbonol A

α D 16 + 39.7 [22]

R. yunnanensis[22]

57

Rubiyunnanol C

α D 18 – 28.9 [22]

R. yunnanensis[22]

58

Rubiarbonone E 19-acetate

259 − 260 / α D 23 – 4.6 [22]

R. yunnanensis[22]

59

2-Hydroxyrubiarbonone E

α D 23 + 19.7 [22]

R. yunnanensis[22]

60

Rubianol-e3-O-(6’-O-acetyl)-β-D-Gluc

α D 25 – 25.2 [22]

R. yunnanensis[22]

61

2α-Acetoxy-28-acetylrubiarboside G

α D 16 – 27.9 [22]

R. yunnanensis[22]

62

Rubiarboside G 28-acetate

α D 16 – 21.7 [22]

R. yunnanensis[22]

63

3-β-friedelinol

281-283 [23]

R. cordifolia[23]

64

Rubiarboside G 28-al

α D 16 – 41.7 [22]

R. yunnanensis[22]

65

Rubiarbonol A 3-O-β-D-glucopyranosyl- (1–2)- β-D-Gluc

α D 16 – 9.0 –9.0 [22]

R. yunnanensis[22]