ISOFLAVONOIDS OF THE TRIBE DALBERGIEAE: A CHEMOSYSTEMATIC CONTRIBUTION TO THE SUBFAMILY PAPILIONOIDEAE

Carvalho, Adonias A.; Santos, Lucivania R. dos; Freitas, Jurema S. de; Chaves, Mariana H.

doi:10.21577/0100-4042.20170588

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Revisão • Quím. Nova 43 (9) • Sept 2020 • https://doi.org/10.21577/0100-4042.20170588 copy

ISOFLAVONOIDS OF THE TRIBE DALBERGIEAE: A CHEMOSYSTEMATIC CONTRIBUTION TO THE SUBFAMILY PAPILIONOIDEAE

Authorship SCIMAGO INSTITUTIONS RANKINGS

Plants from Fabaceae family have several secondary metabolites and high biological potential. The subfamily Papilionoideae (Fabaceae) has 28 tribes, of which Dalbergieae comprises 49 genera and 1325 species. Isoflavonoids are chemotaxonomic markers of Papilionoideae and have important biological properties. This review describes the isoflavonoids and biological activities from the tribe Dalbergieae (Fabaceae-Papilionoideae) species, in the period of 1945 to 2019. A total of 240 isoflavonoids were found in 69 species and in 15 genera. Formononetin, biochanin A and medicarpin were the most frequent isoflavonoids in this tribe. Dalbergia, Machaerium, Andira and Pterocarpus genera had a high number of species with occurrence of isoflavonoids. A total of 81 isoflavanoids and 46 species showed biological activities. This suggests that more works are necessary to evaluate the potential of this tribe. The present study contributes to the taxonomic classification of genus or species in the family, subfamily or tribe, once the correlation between secondary metabolites and morphological data is an important tool for the classification, phylogeny and evolution of species. This compilation also contributes to extend and update the researched period on the occurrence of isoflavonoids in species of the tribe Dalbergieae, described in the literature in other bibliographic reviews.

Keywords:
isoflavonoids; isoflavones; Dalbergieae; Papilionoideae; Fabaceae

Gênero	Espécie	Parte da planta	Compostos	Ref.
Aeschynomene	A. fascicularis	casca das raízes	Isoflavana: 217	24
	A. fascicularis	casca das raízes	Pterocarpanos: 168 e 182	25
	A. fluminensis	folhas e galhos	Isoflavona: 1	26
	A. sensitiva	partes aéreas e sementes	Isoflavona: 47; Rotenoide: 183	27
Andira	A. anthelmia	raízes	Isoflavonas: 16, 17, 22, 27 e 28	28
	A. fraxinifolia	raízes	Isoflavonas: 17 e 50	29
	A. humilis	raízes	Isoflavonas: 16, 17, 22, 25, 26, 27 e 50; Isoflavanona: 126	30
	A. inermis	folhas	Isoflavonas: 2, 10, 18 e 32; 2-Arilbenzofurano-3-carbaldeídos: 236, 237 e 238	31
		casca do caule e sementes	Isoflavonas: 2, 10, 16, 17, 18 e 50	32
		raízes	Isoflavonas: 21, 26 e 27	33
	A. parviflora	cerne	Isoflavonas: 16 e 17; Isoflavana: 202	34
	A. surinamensis	casca dos galhos	Isoflavonas: 10, 17, 18 e 50	35
Arachis	A. hypogaea	sementes	Pterocarpanos: 174 e 178	36
Brya	B. ebenus	madeira de cocus	Isoflavanas: 203, 204, 205 e 212; Pterocarpenos: 228, 229, 230, 231 e 232	37
Centrolobium	C. sclerophyllum	cerne	Isoflavona: 10	38
Centrolobium	C. sclerophyllum; C. paraense; C. tomentosum e C. robustum	cerne	Isoflavonas: 2 e 10; Isoflavanona: 139; Pterocarpano: 156; Isoflavanas: 195, 198 e 200; Isoflaveno: 226	39
Dalbergia	D. boehmii	cerne	Isoflavonas: 14, 16, 17 e 44; Pterocarpanos: 156, 157 e 158; Coumestano: 233; Coumaronocromona: 239;	40
	D. candenatensis	cerne	Isoflavonas: 2 e 107; Isoflavanas: 195 e 200; Isoflavanquinona: 222	41
	D. candenatensis	cerne	Pterocarpanos: 179 e 180; Isoflavana: 199	42
	D. cochinchinensis	sementes	Rotenoides: 184, 186 e 187	43
	D. congesta	raízes	Isoflavonas: 85	44
	D. coromandeliana	folhas	Isoflavona: 20	45
	D. ecastaphyllum	casca do caule	^a a Compostos identificados por CLAE-EM; Isoflavonas: 1, 2 e 17	21
		cerne	Isoflavonas: 2, 13 e 17; Pterocarpanos: 156, 157, 160, 162, 163 e 165; Isoflavanas: 195, 196, 197 e 200	46
		cerne	Isoflavona: 2; Isoflavanas: 200 e 205	47
	D. frutescens	casca do caule	Isoflavonas: 1, 2, 7, 16, 17, 32, 33, 34, 35 e 69	48
	D. horrida	raízes	Isoflavonas: 85 e 95; Isoflavanonas: 140 e 152	49
	D. lanceolaria	casca das raízes	Isoflavona: 26	50
	D. melanoxylon	casca do caule	Isoflavona: 2; Isoflavononas: 151 e 153	51
	D. monetaria	casca do caule	Isoflavonas: 49, 103, 106, 111, 112, 116 e 121	52
	D. monetaria	sementes	Isoflavonas: 45 e 46; Rotenoides: 184, 187, 188, 189, 190, 191 e 192	53
	D. nigra	folhas secas	Isoflavona: 67	54
	D. nitidula	cerne	Isoflavona: 42	55
	D. nitidula	cerne	Pterocarpanos: 164, 171 e 172	56
	D. odorifera	folhas	Isoflavonas: 16, 17, 18 e 64	57
		cerne	Isoflavononas: 128, 129 e 141; Isoflavana: 195	58
		cerne	Isoflavonas: 1, 2, 49, 91 e 106; Isoflavononas: 85, 129, 132, 133, 136 e 141; Pterocarpano: 156	59
		folhas	Isoflavonas: 16 e 17	60
		cerne	^a a Compostos identificados por CLAE-EM; Isoflavonas: 2, 13, 15, 70 e 95; Isoflavanonas: 128, 129, 133, 135 e 141; Pterocarpanos: 156 e 166; Isoflavanquinona: 222	22
		cerne	Isoflavonas: 2 e 64; Pterocarpano: 156; Isoflavanas: 200 e 201; Isoflavanquinona: 222	61
		cerne	Isoflavona: 2; Pterocarpano: 156; Isoflavanquinona: 222	62
		cerne	Isoflavonas: 2, 9, 15, 18, 44 e 70; Isoflavononas: 128, 129, 133, 135 e 141; Pterocarpano: 156	63
		cerne	Isoflavona: 2; Pterocarpanos: 156, 166, 175, 176 e 177; Isoflavanas: 195, 200, 208 e 209; Isoflavena: 227	64
		cerne	Isoflavonas: 2 e 11; Isoflavanas: 195 e 201; Isoflavanquinona: 222	65
		cerne	Isoflavonas: 2, 11 e 48; Isoflavanona: 141; Pterocarpano: 156; Isoflavanas: 195, 201 e 206; Isoflavanquinona: 222	66
		cerne	Isoflavona: 2; Isoflavonona: 133; Pterocarpano: 156	67
Dalbergia	D. odorifera	cerne	Isoflavona: 60; Isoflavonona: 133; Isoflavanas: 200	68
		casca do caule	Isoflavonas: 2, 16, 17, 75 e 91	69
		cerne	Isoflavanona: 133; Pterocarpano: 156; Isoflavana: 200; Coumestonas: 234 e 235	70
		casca	Pterocarpano: 160; Isoflavana: 210; Isoflavanquinona: 223	71
	D. paniculata	casca	Isoflavonas: 6, 17 e 77	72
		casca	Isoflavonas: 2, 17, 88, 110, 111 e 122; Rotenoide: 194	73
		casca do caule	Isoflavonas: 2, 17 e 111	74
		sementes	Isoflavonas: 87 e 122; Rotenoide: 193	75
		raízes	Isoflavonas: 17, 75 e 76; Rotenoide: 185	76
	D. parviflora	cerne	Isoflavonas: 2, 10, 16, 17, 51, 57, 98 e 99; Isoflavanonas: 129, 131, 133, 134, 135 e 142; Isoflavanas: 195, 200 e 205	77
		galhos e cerne	Isoflavonas: 49, 55, 107 e 108; Isoflavononas: 135 e 142; Pterocarpanos: 160 e 179	78
		cerne	Isoflavonas: 2, 10, 11, 14, 16, 17, 43, 48, 50, 54, 56, 60, 64, 89, 92, 98 e 99; Isoflavononas: 127, 128, 129, 131, 133, 134, 135, 142 e 143; Isoflavanas: 195, 200 e 210	20
		galhos	Isoflavonas: 2, 17 e 94; Isoflavononas: 129 e 133; Isoflavanas: 200 e 208	23
		cerne	Isoflavona: 57; Isoflavononas: 130, 137, 138, 144 e 145	20
		cerne	Isoflavonas: 2, 14, 16, 17, 10, 43, 48, 50, 54, 60, 64, 89, 92, 98, 99 e 102	79
	D. riparia	madeira	Isoflavonas: 32, 34, 64 e 122	80
	D. rubiginosa	raízes	Isoflavona: 81; Pterocarpano: 181	81
	D. sissoo	folhas	Isoflavonas: 7, 16, 17, 26, 27, 50, 74, 122, 123 e 124	82
		casca das raízes	Isoflavonas: 17 e 24; Rotenoide: 184	83
		folhas e casca do caule	Isoflavonas: 11, 20, 26, 30, 66, 67 e 74	84
		partes aéreas	Isoflavonas: 16, 17, 18, 22, 29, 61, 63 e 64	85
	D. sissoides	flores	Isoflavona: 17	86
	D. spinosa	sementes	Isoflavonas: 85 e 95	87
		folhas e casca do caule	Isoflavonas: 29 e 68	88
		raízes	Isoflavonas: 85, 86, 95 e 122	89
	D. spruceana	cerne	Isoflavonas: 2, 7, 17 e 122; Pterocarpanos: 156 e 177	90
	D. sympathetica	folhas	Isoflavonas: 18 e 31	91
	D. tonkinensis	folhas e raízes	Isoflavonas: 1, 5, 9, 21, 26, 49, 64, 124, 125; Pterocarpanos: 156 e 175; Isoflavana: 195	92
	D. tonkinensis	cerne	Isoflavona: 17	93
	D. vacciniifolia	cerne	Isoflavonas: 58, 59, 104 e 105	94
	D. variabilis	casca e madeira	Isoflavonas: 2 e 38; Pterocarpanos: 156 e 169; Isoflavanas: 195 e 200;	95
	D. velutina	caule	Isoflavonas: 2, 7, 11, 17, 32, 38, 41, 51, 71, 72, 89 e 91	96
		raízes	Isoflavanos: 207, 213, 214, 215 e 216	97
		raízes	Isoflavonas: 74, 90, 91, 93, 109, 110 e 124	98
	D. vietnamensis	caule	Isoflavonas: 88, 96, 122 e 124	99
	D. volubilis	flores	Isoflavonas: 17 e 39	100
	D. cearensis, D. ecastophyllum e D. variabilis	cerne	Isoflavanas: 195, 197 e 200	101
	D. retusa	cerne	Isoflavonas: 36 e 38	102
Diphysa	D. robinioides	cerne	Isoflavanas: 210 e 211	103
Geoffroea	G. decorticans	casca do caule	Isoflavanonas: 146, 154 e 155	104
Kotschya	K. strigosa	frutos	Isoflavanol: 232	105
Machaerium	M. aristulatum	caule	Isoflavona: 2; Pterocarpanos: 156 e 177	106
	M. aristulatum	casca do caule	Isoflavonas: 2 e 10	107
	M. acutifolium	folhas	^b b Compostos identificados por IT-ESI-MS. Isoflavonas: 16 e 24	108
	M. kuhlmannii e M. nictitans	tronco	Isoflavona: 2; Pterocarpano: 156	109
	M. mucronulatum	cerne	Isoflavona: 10; Pterocarpano: 173; Isoflavanas: 200 e 208; Isoflavanquinona: 221	110
Machaerium	M. opacum	cerne	Isoflavanas: 200 e 208	111
	M. pedicellatum	cerne	Isoflavanas: 218 e 219	112
	M. vestitum	cerne	Isoflavona: 2; Pterocarpanos: 156 e 165; Isoflavanas: 195 e 200	113
	M. villosum	madeira	Isoflavonas: 1, 3, 9 e 10; Isoflavanas: 200 e 208; Pterocarpanos: 157 e 173	110
Ormocarpum	O. kirkii	casca do caule e raízes	Isoflavonas: 84 e 120	114
		raízes	Isoflavanonas: 147, 148 e 149	115
		raízes	Isoflavanona: 147	116
Platymiscium	P. floribundum		Pterocarpano: 156	117
		cerne	Pterocarpanos: 156, 157, 163165 e 170	118
		tronco	Pterocarpanos: 156, 157, 163, 165, 170	119
		tronco	Isoflavona: 100; Pterocarpanos: 156, 157, 163, 165 e 170	120
	P. gracile	serragem	Isoflavona: 10; Pterocarpano: 157	121
	P. yucatanum	tronco	Pterocarpanos: 156 e 157	122
Pterocarpus	P. erinaceus	casca dos galhos	Isoflavonas: 10; Isoflavonoide benzofurano: 240	123
	P. erinaceus	casca dos galhos	Pterocarpano: 157	124
	P. indicus	raízes	Isoflavonas: 2, 10, 17, 19, 32 e 38; Pterocarpano: 156 e 160	125
	P. indicus	cerne	Isoflavona: 2; Pterocarpano: 159	126
	P. macrocarpus	cerne	Isoflavanona: 150	127
		planta	Isoflavona: 23	128
		cerne	Isoflavonas: 8, 40 e 62	129
		cerne	Isoflavona: 73	130
	P. santalinus	cerne	Isoflavona: 53	131
		cerne	Isoflavona: 97	132
		cerne	Isoflavona: 52	133
	P. soyauxii	cerne	Isoflavanas: 200, 201, 218 e 220; Isoflavanquinona: 222	134
	P. soyauxii	cerne	Isoflavonas: 10, 12, 13, 37, 43, 78, 98, 99, 101, 102, 113, 114 e 115; Pterocarpanos: 157, 159, 160, 161 e 167	135
Vatairea	V. guianensis	folhas	Isoflavonas: 11, 79 e 118	136
		alburno	Isoflavona: 2; Isoflavonol: 233	137
		folhas	Isoflavonas: 80, 82, 83 e 117	138
Zornia	Z. brasiliensis	partes aérias	Isoflavonas: 4 e 5; Pterocarpano: 156	139

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Nº	R₈	R₇	R₆	R₅	R_2’	R_3’	R_4’	R_5’	Nome
1	H	OH	H	H	H	H	OH	H	daidzeína
2	H	OH	H	H	H	H	OCH₃	H	formononetina
3	H	OCH₃	H	H	H	H	OH	H	isoformononetina
4	H	OCH₃	H	H	H	H	OCH₃	H	7,4’-dimetoxi-isoflavona
5	H	O-β-D-glc	H	H	H	H	OCH₃	H	ononina
6	H	O-β-L-rha-(1 →6)-β-D-glc	H	H	H	H	OCH₃	H	formononetina 7-rutinosídeo
7	H	OH	H	H	H	O-CH₂-O		H	pseudobaptigenina
8	H	O-α-L-rha	OCH₃	OH	H	H	H	H	5,7-dihidroxi-6-metoxi-isoflavona 7-rha
9	H	OH	H	H	H	OH	OH	H	3’-hidroxidaidzeína
10	H	OH	H	H	H	OH	OCH₃	H	calicosina
11	H	OH	H	H	H	OCH₃	OH	H	3’-metoxidaidzeína
12	H	OCH₃	H	H	H	OCH₃	OH	H	saianedina
13	H	OH	H	H	H	OH	H	OCH₃	pterosonina E
14	H	OH	H	H	OCH₃	H	OCH₃	H	2’-metoxiformononetina
15	H	OH	H	H	OH	H	OCH₃	H	2’-hidroxiformononetina
16	H	OH	H	OH	H	H	OH	H	genisteína
17	H	OH	H	OH	H	H	OCH₃	H	biochanina A
18	H	OCH₃	H	OH	H	H	OH	H	prunetina
19	H	OH	H	OCH₃	H	H	OCH₃	H	5-O-metilbiochanina A
20	H	OCH₃	H	OH	H	H	O-β-D-apio-(1→6)-β-D-glc	H	coromandelina;
21	H	O-β-D-apio-(1→6)-β-D-glc	H	OH	H	H	OH	H	ambocina
22	H	O-β-D-glc	H	OH	H	H	OCH₃	H	biochanina A 7-O-β-D- glc
23	H	O-α-L-rha	H	OH	H	H	OCH₃	H	7-O-α-L-rha-4-metoxi-5-hidroxi-isoflavona
24	H	γ,γ-dimetilalliloxi	H	OH	H	H	OCH₃	H	7-γ,γ-dimetilalliloxi-5-hidroxi-4’-metoxi-isoflavona
25	H	O-xil(1→6)-glc	H	OH	H	H	OCH₃	H	biochanina A 7-O-β-D-xil-(1→6)-β-D-glc
26	H	O-β-D-apio-(1→6)-β-D-glc	H	OH	H	H	OCH₃	H	lanceolarina
27	H	O-β-D-apio-(1→5)-β-D-apio-(1→6)-β-D-glc	H	OH	H	H	OCH₃	H	biochanina A 7-O-β-D-apio-(1→5)-β-D-apio-(1→6)-β-D-glc
28	H	O-α-L-rha-(1→6)-β-D-glc	H	OH	H	H	OCH₃	H	biochanina A 7-O-α-L-rha-(1→6)-β-D-glc
29	H	OCH₃	H	OH	H	H	O-β-D-gal	H	prunetina 4’-O-β-D-gal
30	H	OCH₃	H	OH	H	H	O-β-D-glc	H	prunetina 4’-O-β-D-glc
31	H	OCH₃	H	OH	H	H	O-β-D-gen	H	dalsimpatetina
32	H	OH	OCH₃	H	H	H	OCH₃	H	afrormosina
33	H	OH	OCH₃	H	H	H	OH	H	gliciteina
34	H	OH	OCH₃	H	H	O-CH₂-O		H	fujikinetina
36	OH	OH	H	H	H	H	OCH₃	H	retusina
37	OH	OCH₃	H	H	H	H	OCH₃	H	8-hidroxi-4’,7-dimetoxi-isoflavona
38	OCH₃	OH	H	H	H	H	OCH₃	H	8-O-metilretusina
39	rha	OCH₃	H	H	H	H	OCH₃	H	volubilina
40	OH	O-β-D-glc	H	H	H	H	OCH₃	H	retusina 7-O-β-D-glc
41	H	OH	H	OH	H	O-CH₂-O		H	3’,4’-metilenodioxi orobol
42	H	OH	H	H	OCH₃	H	OH	OH	4’,5’,7-trihidroxi-2’-metoxi-isoflavona
43	H	OH	H	H	OH	H	OCH₃	OH	khrinona A
44	H	OH	H	H	OH	H	OCH₃	OCH3	2’,7-dihidroxi-4’,5’-dimetoxi-isoflavona
45	H	OH	H	H	OCH₃	H	OCH₃	OCH3	7-hidroxi-2’,4’,5’-trimetoxi-isoflavona
46	H	O-β-D-glc	H	H	OCH₃	H	OCH₃	OCH3	7-β-D-glc-2’,4’,5’-trimetoxi-isoflavona
47	H	O-β-D-glc	H	H	OH	H	OCH₃	OCH3	daidzeína 7-O-β-D-glc
49	H	OH	H	OH	H	OH	OH	H	orobol
50	H	OH	H	OH	H	OH	OCH₃	H	pratenseína
51	H	OH	H	OH	H	OCH₃	OH	H	3’-O-metilorobol
52	H	OCH₃	H	OH	H	O-β-D-glc	OH	H	4’,5-dihidroxi-7-O-metilisoflavona 3’-O-β-D-glc
53	H	OCH₃	H	OH	H	O-β-D- (3”-E-cinamoil)-glc	OH	H	4’,5-dihidroxi-7-O-metilisoflavona 3’-O-β-D- (3”-E-cinamoil)-glc
54	H	OH	H	OH	OCH₃	H	OH	H	teralina
55	H	OH	H	OH	OH	H	OCH3	H	2’-hidroxibiochanina A
56	H	OH	H	OH	OCH₃	H	OCH3	H	2’-metoxibiochanina A
57	H	OCH3	H	OH	OH	H	OH	H	cajanina
58	H	OH	OCH₃	H	OCH₃	H	OH	H	6,2’-dimetoxi-7,4’-dihidroxi-isoflavona
59	H	OH	OCH₃	H	OCH₃	H	OCH3	H	6,2’,4’-trimetoxi-7-hidroxi-isoflavona
60	H	OH	H	H	OCH₃	OH	OCH3	H	khrinona E
61	H	OH	OCH₃	H	H	H	OCH3	H	irisolidona
62	H	O-α-L-rha	OCH₃	OH	H	H	OCH3	H	irisolidona 7-O-α-L-rha
63	H	OCH3	OH	OCH₃	H	H	OH	H	muningina
64	H	OH	OCH₃	OH	H	H	OH	H	tectorigenina
65	H	OCH3	OCH₃	OH	H	H	OH	H	7-O-metiltectorigenina
66	H	O-β-D-apio-(1→6)-β-D-glc	OCH₃	OH	H	H	OH	H	tectorigenina 7-O-β-D-apio-(1→6)-β-D-glc
67	H	OCH₃	OCH₃	OH	H	H	O-6-O-β-D-apio-β-D-glc	H	5-hidroxi-6,7-dimetoxi-4’-O-6-O-β-D-apio-β-D-glc isoflavona
68	H	OCH₃	OCH₃	OH	H	H	O-β-D-gal	H	7-metiltectorigenina 4’-O-β-D-galactosídeo
69	H	OH	OCH₃	H	H	OH	OCH₃	H	odoratina
70	H	OH	H	H	OH	OH	OCH₃	H	koparina
71	H	OH	H	H	H	OCH₃	OH	OCH₃	veluisoflavona A
72	OCH₃	OH	H	H	H	H	OH	OCH₃	veluisoflavona B
73	CH₃	O-α-L-rha	H	OCH₃	H	H	OCH₃	H	5,4’-dimetoxi-8-metilisoflavona 7-O-α-L-rha
74	β-D-glc	OH	H	OH	H	H	OH	H	genisteína-8-C-β-D-glc
75	geranila	OH	H	OH	H	H	OCH₃	H	olibergina B
76	geranila	OCH₃	H	OH	H	H	OCH₃	H	8-C-geranil-7-O-metilbiochanina A
77	glc	OCH₃	H	OH	H	H	OH	H	prunetina 8-C-glc
78	OH	OCH₃	H	H	H	OH	H	OCH₃	pterosonina D
79	prenila	OH	H	OH	H	H	OH	H	lupiwighteona
80	prenila	OH	H	OH	H	O-CH₂-O		H	5,7-dihidroxi-3’,4’-metilenodioxi-8-prenilisoflavona
81	H	OCH₃	OCH₃	OH	H	O-CH₂-O		H	5-didroxi-6,7-dimetoxi-3’,4’-metilodioxi-isoflavona
82	2”,2”-dimetilpirano-(5”,6”:8,7)		H	OH	H	H	OCH₃	H	5,3’-dihidroxi-4’-metoxi-2”,2”-dimetilpirano-(5”,6”:8,7)-isoflavona
83	2”,2”-dimetilpirano-(5”,6”:8,7)		H	OH	H	H	OH	H	derrona
84	2’,2’-dimetilpirano-(5”,6”:8,7)		prenila	OH	H	H	OH	H	osajina
85	H	OH	OCH₃	OH	H	O-CH₂-O		H	dalspinina
86	H	O-β-D-apio- (1 →6)-glc	OCH₃	OH	H	O-CH₂-O		H	dalspinina-7-O-β-D-apio-(1→6)-glc
87	H	OH	OCH₃	H	OCH₃	O-CH₂-O			dalpatiena
88	H	O-β-D-glc	OCH₃	H	OCH₃	H	O-CH₂-O		dalpatina
89	H	OH	H	OH	OCH₃	H	O-CH₂-O		khrinona D
90	H	O-β-D-glc	H	OH	OCH₃	H	OH	OCH₃	dalvelutinosídeo
91	H	OH	H	OH	OCH₃	H	OH	OCH₃	olibergina A
92	H	OH	H	OH	OCH₃	H	OCH₃	OCH₃	7-demetilrobustigenina
93	H	O-β-D-apio-(1”’→6”)-O-β-D-glc	H	OH	OCH₃	H	OH	OCH₃	2’,5’-dimetoxi-genisteína-7-O-β-D-apio-(1’”→6”)-O-β-D-glc
94	H	OH	H	OH	OCH₃	H	OCH₃	OH	5,7,5’-trihidroxi-2’,4’-dimetoxi-isoflavona
95	H	OH	OCH₃	OH	H	OCH₃	OCH₃	H	dalspinosina
96	H	O-β-D-apio-(1→6)-β-D-glc	OCH₃	OH	H	OCH₃	OCH₃	H	dalspinosina 7-O-β-D-apio-(1→6)-β-D-glc
97	H	OCH₃	OH	H	OCH₃	H	OCH₃	OCH₃	6-hidroxi-7,2’,4’,5’-tetrametoxi-isoflavona
98	H	OH	H	OH	OCH₃	OH	OCH₃	H	khrinona C
99	H	OH	H	OH	OH	H	OCH₃	OH	khrinona B
101	H	OH	OCH₃	H	OCH₃	OH	OCH₃	H	pterosonina C
102	H	OH	OH	H	OCH₃	OH	OCH₃	H	2’,4’-dimetoxi-3’,6,7-trihidroxi-isoflavona
103	H	OH	O-acetil-β-D-glc	OH	H	OH	OH	H	6-(O-acetil-β-D-glc)orobol
104	H	OH	OCH₃	H	OCH₃	H	OCH₃	OCH₃	6,2’,4’,5’-tetrametoxi-7-hidroxi-isoflavona
105	H	O-β-D-apio-(1→6)-β-D-glc	OCH₃	H	OCH₃	H	OCH₃	OCH₃	6,2’,4’,5’-tetrametoxi-7-O-β-D-apio-(1→6)-β-D-glc isoflavona
106	H	OH	β-D-glc	OH	H	OH	OH	H	6-(β-D-glc) orobol
108	H	OH	H	OH	OCH₃	H	OH	OH	dalparvona B
109	β-D-glc	OH	H	OH	H	H	OH	OH	orobol-8-C-β-D-glc
110	β-D-glc	OH	H	OH	H	H	OH	OCH₃	dalpanitina
111	β-D-glc	OH	β-D-glc	OH	H	H	OH	H	paniculatina
112	β-D-glc	OH	H	OH	H	OH	OH	H	mono-C-glc 8-(β-D-glc)orobol
113	OCH₃	OH	H	H	OCH₃	OH	OCH₃	H	7,3’-dihidroxi-8,2’,4’-trimetoxi-isoflavona
114	OH	OH	H	H	OCH₃	OH	OCH₃	H	pterosonina A
115	OH	OCH₃	H	H	OCH₃	OH	OCH₃	H	pterosonina B
116	6”-O-acetil-β-D-glc	OH	H	OH	H	OH	OH	H	8-(6”-O-acetil-β-D-glc)orobol
117	prenila	O-β-D-glc	H	OH	H	OH	OCH₃	H	5,3’-dihidroxi-4’-metoxi-7-O-β-glc-8-prenilisoflavona
118	prenila	OH	H	OH	H	OCH₃	OH	H	5,7,4’-trihidroxi-3’-metoxi-8-prenilisoflavona
119	prenila	OH	H	OH	H	OH	OCH₃	H	5,7,3’-trihidroxi-4’-metoxi-8-prenilisoflavona
120	prenila	OH	prenila	OH	H	H	OCH₃	H	5,7-dihidroxi-4’-metoxi-6,8-diprenilisoflavona
121	β-D-glc	OH	O-β-D-glc	OH	H	OH	OH	H	di-C-glicosidena-6,8-bis(β-D-glc)orobol
122	H	OH	OCH₃	OH	OCH₃	H	OCH₃	OCH₃	caviunina
123	H	O-β-D-glc	OCH₃	OH	OCH₃	H	OCH₃	OCH₃	caviunina 7-O-β-D-glicopiranosídeo
124	H	O-β-D-apio-(1”’→6”)-O-β-D-glc	OCH₃	OH	OCH₃	H	OCH₃	OCH₃	dalsissoosídeo
125	OCH₃	O-β-D-apio-(1→6)-β-D-glc	H	OH	OCH₃	H	OCH₃	OCH₃	isocaviunina-7-O-β-D-apio-(1→6)-β-D-glicopiranosídeo


Nº	R₇	R₆	R₅	R₃	R_2’	R_3’	R_4’	R_5’	Nome
126	OH	H	OH	H	H	H	OH	H	dihidrogenisteína
127	OH	H	H	H	H	OH	OCH₃	H	7,3’-dihidroxi-4’-metoxi-isoflavanona
128	OH	H	H	H	OH	H	OCH₃	H	vestitona
129	OH	H	H	H	OCH₃	H	OCH₃	H	sativanona
130	OH	H	H	H	OH	H	O-CH₂-O		soforol
131	OH	H	H	H	OCH₃	H	O-CH₂-O		onogenina
132	OH	H	H	OH	OCH₃	H	OCH₃	H	2’,4’-dimetoxi-3,7-dihidroxi-isoflavanona
133	OH	H	H	H	OCH₃	OH	OCH₃	H	violanona
134	OH	H	H	H	OCH₃	H	OCH₃	OH	dalparvina
135	OH	H	H	H	OCH₃	OCH₃	OCH₃	H	3’-O-metilviolanona
136	OH	H	H	H	OCH₃	H	OCH₃	OCH₃	2’,4’,5’-trimetoxi-7-hidroxi-isoflavanona
137	OH	H	H	H	OH	OCH₃	OCH₃	H	dalparvina B
138	OH	H	OH	H	H	OH	OCH₃	H	kenusanona G
139	OH	H	H	H	H	OCH₃	OH	OCH₃	7,4’-dihidroxi-3’,5’-dimetoxi-isoflavanona
141	OCH₃	H	OH	OH	OH	H	OCH₃	H	2’,3’,7-trihidroxi-4’-metoxi-isoflavanona
142	OH	H	OH	H	OCH₃	OH	OCH₃	H	secundiflorol H
143	OH	H	H	OH	OH	OH	OCH₃	H	isodarparvinol B
144	OH	H	OH	H	OCH₃	H	OH	OH	dalparvina A
145	OH	H	H	OH	OH	OCH₃	OCH₃	H	dalparvina C
146	OH	H	H	H	OH	OH	OCH₃	prenila	7,2’,3’-trihidroxi-4’-metoxi-5’- prenilisoindanona
147	OH	4”-hidroxiprenila	OH	H	OH	H	OH	H	4”-hidroxidifisolona
148	O-glc	prenila	OH	H	OH	H	OH	H	7-O-glicosildifisolona
149	O-glc	prenila	OH	H	OH	H	O-glc	H	7,4’-di-O-glicosildifisolona
150	OH	C-glc	OH	H	OH	H	OH	H	macrocarposídeo
151	OCH₃	H	OH	OH	OCH₃	2”,2”-dimetilpirano [5”,6”:3’,4’]		H	3,5-dihidroxi-2’,7-dimetoxi-2”,2”-dimetilpirano [5”,6”:3’,4’] isoflavanona
153	OCH₃	H	OH	OH	OCH₃	prenila	OH	H	3,4’,5-trihidroxi-2’,7-dimetoxi -3’-prenilisoflavanona

154	OH	H	OH	H	OH	OH	OCH₃	prenila	5,7,2’, 3’-tetrahidroxi-4’- metoxi-5’-prenilisoflavanona
155	OH	H	H	OH	OH	OH	OCH₃	prenila	3,7,2’,3’-tetrahidroxi-4’-metoxi-5’- prenilisoflavanona


Nº	R₄	R₃	R₂	R₇	R₈	R₉	R₁₀	Nome
156	H	OH	H	H	H	OCH₃	H	medicarpina
157	H	OCH₃	H	H	H	OCH₃	H	homopterocarpina
158	H	OH	H	H	O-CH₂-O		H	macckiaina
159	H	OCH₃	H	H	O-CH₂-O		H	pterocarpina
160	H	OH	H	H	OH	OCH₃	H	3,8-dihidroxi-9-metoxipterocarpano
161	H	OH	H	H	OCH₃	OH	H	kushenina
162	H	OH	H	H	OCH₃	OCH₃	H	3-hidroxi-8,9-dimetoxipterocarpano
163	OH	OH	H	H	H	OCH₃	H	3,4-dihidroxi-9-metoxipterocarpano
165	H	OH	H	H	H	OCH₃	OH	vesticarpano
166	H	OH	H	H	H	OCH₃	OCH₃	metilnissolina
167	H	OCH₃	H	H	H	OH	OH	8,9-dihidroxi-3-metoxipterocarpano
168	H	OH	OCH₃	H	H	OCH₃	H	2-metoximedicarpina
170	H	OCH₃	OCH₃	H	H	OCH₃	H	2,3,9-trimetoxipterocarpano
173	H	OCH₃	OH	H	H	OCH₃	OH	mucronucarpano
174	OH	OH	H	H	H	OCH₃	OH	aracarpeno 1
175	OH	OCH₃	H	H	H	OCH₃	OH	melilotocarpano D
176	OH	OCH₃	H	H	H	OCH₃	OCH₃	melilotocarpano C
177	OCH₃	OCH₃	H	H	H	OCH₃	OH	odoricarpana
178	OH	OH	H	OH	H	OCH₃	H	aracarpeno 2
179	OH	OCH₃	H	H	O-CH₂-O		H	4-hidroxi-3-metoxi-8,9-metilenodioxipterocarpano
180	geranila	OCH₃	H	H	O-CH₂-O		H	nutiducol


Nº	R₈	R₇	R₆	R_2’	R_3’	R_4’	R_5’	Nome
195	H	OH	H	OH	H	OCH₃	H	vestitol
196	H	OH	H	OCH₃	H	OH	H	neovestitol
197	H	OCH₃	H	OH	H	OCH₃	H	7-O-metilvestitol
198	H	OH	H	OCH₃	H	OCH₃	H	sativano
199	geranila	OH	H	H	H	OCH₃	H	candenatenina F
200	H	OH	H	OH	OCH₃	OCH₃	H	mucronulatol
201	H	OH	H	OH	H	OCH₃	OCH₃	5’-metoxivestitol
202	H	OH	H	OH	OH	OCH₃	H	7,2’,3’-trihidroxi-4’-metoxi-isoflavana
203	OH	OH	H	OCH₃	H	OCH₃	OCH₃	7,8-dihidroxi-2’,4’,5’-trimetoxi-isoflavana
204	OH	OH	H	OH	OCH₃	OCH₃	H	7,8,2’-trihidroxi-3’,4’-dimetoxi-isoflavana
205	OH	OH	H	OCH₃	OH	OCH₃	H	8-demetilduartina
206	OH	OH	H	OH	OH	OCH₃	H	3’,8-dihidroxivestitol
207	OCH₃	OH	H	OH	OH	OCH₃	H	3’-hidroxi-8-metoxivestitol
208	OCH₃	OH	H	OCH3	OH	OCH₃	H	duartina
209	OCH₃	OH	H	OH	OCH₃	OCH₃	H	isoduartina
210	prenila	OH	H	OH	H	OCH₃	H	4’-O-metilpreglabridina
212	H	OH	OH	OCH₃	OH	OCH₃	H	6,7,3’-trihidroxi-2’,4’-dimetoxi-isoflavana
217	H	OH	H	OH	OH	OCH₃	2-metilbut-3-en-2-ila	secundiflorol G
218	OCH₃	OCH₃	OH	OH	OCH₃	OCH₃	H	machaerol B
219	OH	OCH₃	OH	OH	OCH₃	OCH₃	H	machaerol C