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Table 1 Structures of terpenes (165) and cyclopeptides (66109) 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]