Table 1.

Structures of terpenes (1–65) and cyclopeptides (66–109) isolated 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	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{22}+4$$ [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	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{27}+26$$ [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	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{25}+10.0$$ [19]	R. yunnanensis[19,21]
41	Rubianol-b	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{25}+16.8$$ [19]	R. yunnanensis[19,21]
42	Rubianol-c	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{25}+36.4$$ [19]	R. yunnanensis[19,21,22]
43	Rubianol-d	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{25}+63.6$$ [19]	R. yunnanensis[19,21,22]
44	Rubianol-e	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{25}+18.1$$ [19]	R. yunnanensis[19,21,22]
45	Rubianol-g	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{25}+206.1$$ [21]	R. yunnanensis[21]
46	Rubianoside I	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{25}+10.9$$ [19]	R. yunnanensis[19,21,22]
47	Rubianoside II	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{25}+2.2$$ [21]	R. yunnanensis[21]
48	Rubianoside III	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{25}+3.5$$ [21]	R. yunnanensis[21]
49	Rubianoside IV	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{25}+90.5$$ [21]	R. yunnanensis[21]
50	3β,6α-dihydroxy-urs-14-en-12-one	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{20}–10.7$$ [20]	R. schumanniana[20]
51	3β-hydroxy-urs-30-p-Z-hydroxycinnamoyl-12-en-28-oic-acid	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{16}+6.5$$ [20]	R. schumanniana[20]
52	3β-hydroxy-olean-30-p-E-hydroxycinnamoyl-12-en-28-oic-acid	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{16}+13.1$$ [20]	R. schumanniana[20]
53	Rubiarbonol A 7-acetate	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{23}+1.7$$ [22]	R. yunnanensis[22]
54	Rubiyunnanol A	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{16}+23.2$$ [22]	R. yunnanensis[22]
55	Rubiyunnanol B	$$247-248/{\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{16}+25.8$$ [22]	R. yunnanensis[22]
56	19,28-Didehydroxyrubiarbonol A	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{16}+39.7$$ [22]	R. yunnanensis[22]
57	Rubiyunnanol C	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{18}–28.9$$ [22]	R. yunnanensis[22]
58	Rubiarbonone E 19-acetate	$$259-260/{\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{23}–4.6$$ [22]	R. yunnanensis[22]
59	2-Hydroxyrubiarbonone E	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{23}+19.7$$ [22]	R. yunnanensis[22]
60	Rubianol-e3-O-(6’-O-acetyl)-β-D-Gluc	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{25}–25.2$$ [22]	R. yunnanensis[22]
61	2α-Acetoxy-28-acetylrubiarboside G	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{16}–27.9$$ [22]	R. yunnanensis[22]
62	Rubiarboside G 28-acetate	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{16}–21.7$$ [22]	R. yunnanensis[22]
63	3-β-friedelinol	281-283 [23]	R. cordifolia[23]
64	Rubiarboside G 28-al	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{16}–41.7$$ [22]	R. yunnanensis[22]
65	Rubiarbonol A 3-O-β-D-glucopyranosyl- (1–2)- β-D-Gluc	$${\left[\mathrm{\alpha }\right]}_{\mathrm{D}}^{16}–9.0$$ –9.0 [22]	R. yunnanensis[22]