Secondary metabolites isolated from H. plantaginea.

No.	Secondary metabolites	Part	Ref.
Steroids
1	Gitogenin	Flowers	16, 29 and 30
2	(25R)-2α,3β,17β,24β-Tetrahydroxy-5α-spirostanane	Flowers	31
3	Gitogenin-3-O-β-d-galactopyranoside	Flowers	30
4	Gitogenin-3-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside	Flowers, leaves	24, 30 and 32
5	Gitogenin-3-O-α-l-rhamanopyranosyl(1→2)-β-d-galactopyranoside	Flowers, leaves	24 and 30
6	12-Hydroxy-gitogenin-3-O-α-l-rhamnopyranosyl-(1→2)-β-d-galactopyranoside	Leaves	24 and 32
7	Gitogenin-3-O-β-d-glucopyranosyl-(1→4)-O-[α-l-rhamnopyranosyl(1→2)]-β-d-galactopyranoside	Flowers	30
8	Gitogenin-3-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside	Flowers, underground	11, 16, 29, 30 and 33
9	Gitogenin-3-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside	Flowers, underground	11, 16, 29, 30 and 33
10	Gitogenin-3-O-β-d-glucopyranosyl-(1→2)-O-[O-α-l-rhamnopyranosyl-(1→4)-β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galsctopyranoside	Flowers, underground	11, 16, 29, 30 and 33
11	Gitogenin-3-O-β-d-xylopyranosyl-(1→4)-β-d-glucopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside	Flowers	30
12	Tigogenin-3-O-β-d-glucopyranosyl(1→4)-O-[α-l-rhamnopyranosyl-(1→2)]-β-d-galactopyranoside	Flowers, leaves	24 and 30
13	Hostaside IV	Leaves	24
14	Manogenin	Flowers	16
15	9-Dehydromanogenin	Flowers, leaves	31 and 32
16	(25R)-2α,3β,24β-Trihydroxy-5α-spirost-9(11)-en-12-one	Flowers	31
17	Hostasaponin A	Rhizomes	34
18	Hostasaponin B	Rhizomes	34
19	9,11-Dehydromanogenie-3-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside	Leaves	24 and 32
20	β-Sitosterol	Flowers, leaves	32 and 33
21	β-Stigmasterol	Leaves	32
22	β-Sitosterol-3-O-β-d-glucopyranoside	Flowers, leaves	16, 29, 32, 33 and 35
23	Stigmasterol-3-O-β-d-glucoside	Flowers	35
24	(2α,3β,5α,25R)-2,3-Dihydroxy-22-methoxyfurostan-26-yl-β-d-glucopyranoside	Underground	11
25	16,22-Oxido-26-hydroxycholest-4-en-3-one	Flowers	31
26	(2α,3β,5α,16β)-Pregn-20-ene-20-carboxylic acid-2,16-dihydroxy-γ-lactone-3-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranosyl	Underground	11
27	2α,3β-Dihydroxy-2α-pregn-16-en-20-one	Rhizomes	34
28	Hostaside III	Leaves	24
29	Hostaside I	Leaves	24
30	Hostaside II	Leaves	24
Flavonoids
31	Kaempferol	Flowers	29, 36 and 37
32	Astragalin	Flowers	37
33	Kaempferol-7-O-β-d-glucoside	Flowers	29 and 35–37
34	Kaempferol-3,7-di-O-β-d-glucoside	Flowers	37
35	Kaempferol-3-O-β-d-sophoroside	Flowers	37
36	Plantanone A	Flowers	37
37	Kaempferol-3-O-rutinoside	Flowers	29, 36 and 37
38	Kaempferol-3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside-7-O-β-d-glucopyranoside	Flowers	39
39	Hostaflavone A	Flowers	39
40	Kaempferol-3-O-rutinoside-7-O-glucoside	Flowers, leaves	32 and 37
41	Kaempferol-3-O-(2′′-O-β-d-glucopyranosyl)-β-d-rutinoside	Leaves	32
42	Kaempferol-3-O-β-d-glucopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranoside	Flowers	37
43	Plantanone B	Flowers	37
44	Kaempferol-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside	Flowers	37
45	Kaempferol-3-O-{β-d-glucopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranosyl}-7-O-β-d-glucopyranoside	Flowers	37
46	Plantanone C	Flowers	41
47	Quercetin	Flowers	36
48	Hostaflavanone A	Flowers	38
49	5,7-Dimethoxy-4′-hydroxyflavan	Flowers	40
50	5,7-Dimethoxy-8-methyl-4′-hydroxyflavan	Flowers	40
51	Epicatechin	Flowers	40
52	Catechin	Flowers	40
53	Epigallocatechin	Flowers	40
54	Gallocatechin	Flowers	40
Alkaloids
55	Hostasinine A	Whole plants	42
56	Hostasine	Whole plants	43
57	8-Demethoxyhostasine	Whole plants	43
58	8-Demethoxy-10-O-methylhostasine	Whole plants	43
59	10-O-Methylhostasine	Whole plants	43
60	(+)-Haemanthamine	Whole plants	43
61	O-Demethylhaemanthamine	Whole plants	43
62	Haemanthidine	Whole plants	43
63	Yemenine C	Whole plants	43
64	Lycorine	Whole plants	43
65	Pseudolycorine	Whole plants	43
66	O-Methylcorenine	Whole plants	43
67	9-O-Demethyl-7-O-methyllycorenine	Whole plants	43
68	Albomaculine	Whole plants	43
69	7-Deoxy-trans-dihydronarciclasine	Whole plants	43
70	8-O-Demethylmaritidine	Whole plants	43
71	Ungermine	Whole plants	43
72	Norsanguinine	Whole plants	43
73	(1S,3S)-1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid	Flowers	38
74	(1R,3S)-1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid	Flowers	38
Phenylethanols and acetophenones
75	Phenethyl-O-β-d-glucopyranoside	Flowers	38 and 40
76	Phenethanol-β-d-gentiobioside	Flowers	34
77	Phenethyl-O-rutinoside	Flowers	34
78	4-Hydroxylacetophenone	Flowers	40
79	Acetophenone-4-O-β-d-glucoside	Flowers	40
80	2-Hydroxyl-6-methoxyacetophenone-4-O-β-d-glucoside	Flowers	40
Phenylpropanoids
81	anti-1-Phenylpropane-1,2-diol	Flowers	38
82	anti-1-Phenylpropane-1,2-diol-2-O-β-d-glucopyranoside	Flowers	38
83	Coumaric acid	Flowers	40
84	3-(4-Hydroxy-3-methoxyphenyl) acrylic acid methyl ester	Flowers	40
85	3,4-Dihydroxycinnamyl alcohol-3-O-glucoside	Flowers	40
Terpenoids
86	Hoplanoside A	Flowers	44
87	Lomacarinoside A	Flowers	44
88	(4S)-4-Hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one,4-[3-(β-d-glucopyranosyloxy)butyl]	Flowers	45
89	Roseoside	Flowers	45
90	Plantaginoside	Flowers	45
Aliphatics
91	Docosanol	Leaves	32
92	Arachic acid	Flowers	29 and 36
93	Hexadecanoic acid	Flowers	29 and 36
94	Hostacerebroside A	Flowers	46
91	Docosanol	Leaves	32
92	Arachic acid	Flowers	29 and 36
93	Hexadecanoic acid	Flowers	29 and 36
94	Hostacerebroside A	Flowers	46
95	1-O-β-d-Glucopyranosyl-(2S,3R,4E,8Z)-2-[(2-hydroxytetradecanoyl)amido]-4,8-octadecadienyl-1,3-diol	Flowers	31
96	(2S)-1-O-Linenoyl-3-O-β-d-galactopyranosylglycerol	Flowers	31
97	(2S)-1-O-(10,13)-Octadecenoyl-3-O-β-d-galactopyranosyl glycerol	Flowers	31
Others
98	4-Hydroxybenzaldehyde	Flowers	40
99	4-Hydroxy-3-methoxybenzene	Flowers	31
100	(2-Methyl) heptyl phthalate	Flowers	31
101	(2-Methylphenyl) (4-hydroxy-3-methoxyphenyl)-1,4-diene-3-pentanone	Flowers	31