Chapter VI

The Ultraviolet Spectra of

Isoflavones, Flavanones and Dihydroflavonols
VI-1. The UV Spectra of Isoflavones, Flavanones and Dihydroflavonols in
Methanol. . . . . . . . . . . . . . . . . . . . . . . . . . . . 165
VI-2. The UV Spectra of Isoflavones, Flavanones and Dihydroflavonols in the
Presence of NaOMe . . . . . . . . . . . . . . . . . . . . . . . 167
2a. The Detection of 3',4'-Dihydroxyl Groups in Isoflavones by the Effect of
NaOMe on the UV Spectrum . . . . . . . . . . . . . . . . . . . 167
2 b. The UV Spectra of Flavanones and Dihydroflavonols in the Presence of
NaOMe . . . . . . . . . . . . . . . . . . . . . . . . . . . . 168
VI-3. The UV Spectra of Isoflavones, Flavanones and Dihydroflavonols in the
Presence of NaOAc. . . . . . . . . . . . . . . . . . . . . . . . 169
3a. The Detection of7-Hydroxyl Groups in Isoflavones by the Effect ofNaOAc
on the UV Spectrum . . . . . . . . . . . . . . . . . . . . . . . 169
3 b. The Detection of 7-Hydroxyl Groups in Flavanones and Dihydroflavonols
by the Effect ofNaOAc on the UV Spectrum . . . . . . . . . . . . . 170
VI-4. The Detection of A-Ring Ortho-dihydroxyl Groups in Isoflavones,
Flavanones and Dihydroflavonols by the Effect of NaOAc/H 3 B0 3 on
the UV Spectrum. . . . . . . . . . . . . . . . . . . . . . . . . 170
VI-5. The UV Spectra of Isoflavones, Flavanones and Dihydroflavonols in the
Presence of AIC1 3 and AICl 3 /HCI. . . . . . . . . . . . . . . . . . 171
5a. The Detection of A-Ring Ortho-dihydroxyl Groups in Isoflavones,
Flavanones and Dihydroflavonols by the Effect of AIC1 3 and AICI 3 /HCI
on the UV Spectrum . . . . . . . . . . . . . . . . . . . . . . . 171
5b. The Detection of 5-Hydroxyl Groups in lsoflavones, Flavanones and
Dihydroflavonols by the Effect of AICI 3 /HCI on the UV Spectrum. . . . 171
VI-6. Index of Ultraviolet Absorption Spectra of Isoflavones, Flavanones and
Dihydroflavonols 172
References. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 174

VI-I. The UV Spectra of Isoflavones (I), Flavanones (11)

and Dihydroflavonols (111) in Methanol
Isoflavones, flavanones and dihydroflavonols all give similar uv spectra as a result
of their having litde or no conjugation between the A- and B-rings. They are all readily
distinguished from flavones and flavonols by their UV spectra, which typically exhibit
an intense Band II absorption with only a shoulder or low intensity peak representing
Band I.

T. J. Mabry et al., The Systematic Identification of Flavonoids

© Springer-Verlag New York Inc. 1970
166 The Ultraviolet Spectra of Isoflavones, Flavanones and Dihydroflavonols

Wö
• 0

o I' S' o
I. Isoflavone skeleton 11. Flavanone skeleton 1II. Dihydroflavonol skeleton

The UV Spectra of Isoflavones in MeOH

The Band 11 absorption of isoflavones usually occurs in the region 245 - 270 nm,
and is relatively unaffected by increased hydroxylation of the B-ring, cf. the Band 11
position in: 5,7-dihydroxyisoflavone (259 nm); 5,7,4'-trihydroxyisoflavone (261 nm) and
5,7,3',4'-tetrahydroxyisoflavone (262 nm). Band 11 is, however, shifted bathochromically
by increased oxygenation in the A-ring (Table VI-1).
Table VI-I. Band II in the UV spectra of isoflavones differing in their A-ring oxidation pattern

Spectrum Isoflavone Oxidation pattern Band 11

No. (nm)
A-ring B-ring

108 Daidzein 7 4' 249

113 Genistein 5,7 4' 261
129 6-H ydroxygenistein 5,6,7 4' 270

Some specific effects of isoflavone oxidation and substitution pattern on the UV

spectra are:
(1) Simple polyoxygenated isoflavones which have their Band 11 absorption in the
265 - 270 nm range are usually trioxygenated in the A-ring (cf. spectra 129, 130, 131, 132,
138 and 139).
(2) The UV spectra of 6,7-dioxygenated isoflavones, such as texasin and afrormosin
(spectra 121 and 124) are unusual [1,2] in that Band I is abnormally intense; thus the
spectra appear similar to those observed for flavones (however, paper chromatography
or NMR spectroscopy c1early identifies them as isoflavones).
(3) Methylation or glycosylation of either 7- or 4'-hydroxyl groups in isoflavones
has litde or no effect on the UV spectrum (e. g. spectra pairs: 108, 109; 108, 120; 110, 111;
113,114; 113,115; 113,116; 113,118; 126,127; 130,131 and 133,134) while substitution
of the 5-hydroxyl groups causes a 5 -10 nm hypsochromic shift of Band 11 (e. g. spectra
pairs: 105, 106 and 113, 117).
(4) Loss of a 5-hydroxyl group causes a 7 -17 nm hypsochromic shift in Band 11
(see spectra pairs: 104,105; 108,113; 109,114; 110,119; 111,120; 121,129; 124,132;
125,133; 126, 133 and 127,135).
The UV Spectra of Flavanones and Dihydroflavonols in MeOH
The UV spectra of dihydroflavonols are alm ost identical with those obtained for
the equivalent flavanones (cf. spectra 141, 148 and 146, 153); thus the presence or absence
of the C-3 hydroxyl group in flavonoids which do not have a C 2 - C 3 double bond
makes little difference to the UV spectra. Both flavanones and dihydroflavonols have
their major absorption peak (Band 11) in the range 270 - 295 nm and are therefore
c1early distinguished from the spectra of isoflavones (which have their Band 11 peaks
between 245 and 270 nm). Removal of the 5-hydroxyl group from a flavanone or di-
hydroflavonol causes a 10 -15 nm hypsochromic shift of the major absorption band,
i.e., Band 11 (cf. spectra pairs 148, 151; 149,153 and 141,144). Increasing oxygenation in
the B-ring of flavanones and dihydroflavonols has no noticeable effect on their UV
spectra (cf. spectra 141, 149 and 155).
 The UV Spectra ofIsoflavones, Flavanones and Dihydroflavonols in the Presence ofNaOMe 167

VI-2. The UV Spectra of Isoflavones,

Flavanones and Dihydroflavonols in the Presence of NaOMe
2a. The Detection of 3', 4'-Dihydroxyl Groups in Isoflavones by the Effect
of NaOMe on the UV Spectrum
The spectra of isoflavones containing A-ring hydroxyl groups usually show batho-
chromic shifts of both Band I and Band 11 in the presence of NaOMe. In addition, the
peaks in the UV spectrum of a 3',4'-dihydroxyisoflavone show reduced intensity within
a few minutes with added NaOMe (see spectra 125, 128, 133, 134, 135 and 137).

OROBOl 7·0·GlUCOSIDE GENISTEIN 7.Q.RHAMNOGlUCOSIDE

MeOH MeOH
2 NaOMe immediately 2 NaOMe immediately
3 NaOMe after 5 min. " (unchanged after 20 min.)
I ,"I
I
I 4 NaOMe after 10 min. , I
I
I I
I I
I I
I I

,,
I I
I

,,
I
I 2
I
,, I
I
,, I I
I
,
I
I I
I I
I I
\ I
\ I

,,,
\ I
\ I
\ I
\
\"
I
I, \
\
\
\
\
\
\
\
\
--,,, _-
....
200 500 200 500
A,nm A,nm
Fig. VI-l. The different effects of NaOMe on the spectra of isoflavones having a 3',4' -dihydroxyl grouping
(orobol 7-0-g1ucoside) and a 4'-hydroxyl group (genistein 7-0-rhamnoglucoside)
168 The Ultraviolet Spectra of Isoflavones, Flavanones and Dihydroflavonols

A comparison of the decomposition rates of a 4'-monohydroxyisoflavone and a 3',4'-

dihydroxyisoflavone (Fig. VI-I) suggests that the rapid decomposition of the latter may
be diagnostic for the 3',4'-dihydroxyl system in isoflavones. The only other isoflavone
showing signs of decomposition in NaOMe was 6-hydroxygenistein (4',5,6,7-tetra-
hydroxyisoflavone), which contains the alkali sensitive 5,6,7-hydroxylation pattern.
Other methods for detecting ortho-dihydroxyl groups in flavonoids (e.g. AICl 3 and
NaOAc/H 3 B0 3 ) do not distinguish the ortho-dihydroxyl system in the B-ring of iso-
flavones.

2 b. The UV Spectra of Flavanones and Dihydroflavonols

. in the Presence of NaOMe
The UV spectra of all flavanones and dihydroflavonols with A-ring hydroxylation
show bathochromic shifts ofBand II with NaOMe. For dihydroflavonols, the magnitude

NaOMe
1. Immediately
OH
2. After 3 min.
3. After 8 min.

NaOMe I
I
I
I
I
"\
\
\
,,
\

,,
I
I 1\
I I'
I I I
1

'I\/ \
I I ,
I

\
\
\
\
\
~
\
\
\

,
\
\

' .....

200 500
X.,nm
Fig. VI-2. The UV spectrum of sakuranin in the presence of NaOMe; the spectra illustrate the conversion of
sakuranin to the equivalent ionized chalcone
 The UV Spectra of Isoflavones, Flavanones and Dihydroflavonols in the Presence of NaOAc 169

of the bathochromic shift depends upon the presence or absence of a free 5-hydroxyl
group. Spectra of 5,7-dihydroxy-dihydroflavonols (spectra 151, 152, 153 and 154) exhibit
a consistent 34 - 40 nm shift of the major absorption peak, whereas spectra of the 7-
hydroxy-dihydroflavonols lacking a free 5-hydroxyl group (spectra 148, 149, 150 and 155)
show a 55 - 60 nm shift. In both cases, an increase in the Band II peak intensity is ob-
served.
The UV spectra of flavanones in the presence of NaOMe also exhibit bathochromic
shifts ofthe main absorption band (Band II) of about 35 nm for 5,7-dihydroxyflavanones
and 60 nm far 7-hydroxyflavanones. Again, the shifts are accompanied by an increase
in the intensity of Band Ir. Under alkaline conditions, however, some flavanones (in
particular those lacking a free 5-hydroxyl group [3,4] will isomerize to chalcones, which
have an entirely different UV spectrum (see Fig. VI-2).
Flavanones with 5,6,7 or 6,7,8 hydroxylation patterns decompose in the presence of
NaOMe and, as a consequence, their UV spectra degenerate (e.g. spectrum 142). Haro-
witz and Jurd [3] have reported that 3',4'-dihydroxyflavanones decompose rapidly in
the presence of NaOH; however, this effect was not noticed with NaOMe in the present
compilation.

VI-3. Tbe UV Spectra of Isoflavones,

Flavanones and Dibydroflavonols in tbe Presence of NaOAc
3a. The Detection of 7-Hydroxyl Groups in Isoflavones by the Effect
of N aOAc on the UV Spectrum
NaOAc specifically ionizes the 7-hydroxyl group in isoflavones [3]. Unlike many
flavones and flavonols, isoflavones do not contain ionizable 3- or 4' -hydroxyl groups,
and therefore the interpretation ofthe spectral shifts is simplified. NaOAc causes Band II
of the UV spectrum of a 7-hydroxyisoflavone to shift 6 - 20 nm bathochromically (see
Table VI-2. The shift oj Band II in the UV spectra oj7-hydroxyisoj7avones with Na04c

Spectrum Isoflavone Bathochromic

No. shift (nm)
104 7-Hydroxyisoflavone 21
105 5,7-Dihydroxyisoflavone 14
107 2-Carboxy-5,7-dihydroxyisoflavone 14
108 Daidzein 4
110 Formononetin 6
113 Genistein 10
116 Sophoricoside 11
117 Genistein 5-methyl ether 8
119 Biochanin A 11
121 Texasin -2
123 2-Carboxy-6,7-dihydroxy-4'-methoxyisoflavone 13
124 Afrormosin -2
125 3',4',7-Trihydroxyisoflavone 8
126 Pseudobaptigenin 8
128 Baptigenin 8
129 6-Hydroxygenistein dec
130 Tectorigenin 6
132 Irisolidone 8
133 Orobol 8
136 Pratensein 9
138 Irigenin 5
170 The Ultraviolet Spectra of Isoflavones, Flavanones and Dihydroflavonols

Table VI-2); however, as was previously observed for flavones little or no shift occurs
when there is an oxygen substituent at position 6 (e.g. spectra 121 and 124). Degenera-
tion of the UV spectrum with time was observed for 6-hydroxygenistein (4',5,6,7-tetra-
hydroxyisoflavone, spectrum 129).

3b. The Detection of 7-Hydroxyl Groups

in Flavanones and Dihydrotlavonols by the Effect of NaOAc
on the UV Spectrum
The presence or absence of a free 7-hydroxyl group in flavanones and dihydro-
flavonols may readily be determined from their UV spectra by comparing the positions
of the major absorption peak (Band II) in the methanol spectrum with that of the same
peak in the NaOAc spectrum. The shift is about 34- 37 nm for the 5,7-dihydroxyflava-
nones and 5,7-dihydroxy-dihydroflavonols and 51- 58 nm for their 5-deoxy-equivalents
(see Table VI-3). Degeneration ofthe UV spectrum with time was observed for 5,6,7-tri-
hydroxyflavanone (spectrum 142).

Table VI-3. 7he shift of Band II in the UV spectra of 7-hydroxyj7avanones and 7-hydroxydihydroj7avonols in the
presence of NaOAc

Spectrum Flavonoid Bathochromic

No. shift (nm)
ofBand n a

Flavanones
140 Pinocebrin 34
141 Liquiritigenin 51
142 5,6,7-Trihydroxyflavanone dec
144 Naringenin 34
146 Eriodictyol 36
Dihydroflavonols
148 Garbanzol 58
149 Dihydrofisetin 57
150 (+ )-Fustin 3-0-g1ucoside 58
151 Dihydrokaempferol 36
152 Engeietin 36
153 Taxifolin 37
154 Astilbin 37
155 Dihydrorobinetin 58

a Major absorption band.

VI-4. The Detection of A-Ring Ortho-dihydroxyl Groups in

Isoflavones, Flavanones and Diltydroflavonols by the Effect of
NaOAc/H 3 B0 3 on the UV Spectrum
B-Ring ortho-dihydroxyl groups are not detectable by the effect of NaOAc/H 3 B0 3
on the UV spectra of isoflavones, flavanones and dihydroflavonols because the B-rings
in these flavonoids lack effective conjugation with the major chromophore. However,
there is evidence (spectra 121 and 123) that 6,7-dihydroxyl groups in the A-ring of iso-
flavones and flavanones (and presumably dihydroflavonols) are detectable by a 10 to
15 nm bathochromic shift of Band I on the addition of NaOAc/H 3 B0 3 .
 The UV Spectra of Isoflavones, Flavanones and Dihydroflavonols 171

VI-5. The UV Spectra of Isoflavones, Flavanones and

Dihydroflavonols in the Presence of AlCl 3 and AlCI 3 /HCl
5a. The Detection of A-Ring Ortho-dihydroxyl Groups in Isoflavones, Flavanones
and Dihydroflavonols by the Effect of AICI 3 and AICI 3 /HCI on the UV Spectrum
The presence of a 3',4'-dihydroxyl group in isoflavones, flavanones and dihydro-
flavonols is not detectable by means of the AICl 3 UV spectrum, because the B-ring has
little or no conjugation with the major chromophore. In contrast, from limited data
(spectra 121, 129, and 142) it appears that A-ring ortho-dihydroxyl groups which do not
involve the C-5 hydrogen-bonded hydroxyl group are detectable in flavanones and iso-
flavones (and presumably also in dihydroflavonols, although no examples were avail-
able). When these compounds contain ortho-dihydroxyl groups at positions 6, 7 or 7, 8
the AICl 3 spectrum exhibits bathochromic shifts (usually for both Band I and Band II)
with respect to the AICI 3 /HCI spectrum (cf., for example, spectra 121 and 142 with 122
and 143, respectively).

5 b. The Detection of 5-Hydroxyl Groups in Isoflavones, Flavanones and

Dihydroflavonols by the Effect of AICI 3 /HCI on the UV Spectrum
Band II in the UV spectra of all 5-hydroxyisoflavones examined in the present
investigation, with the exception of 2-carboxy-5,7-dihydroxyisoflavone (see Table VI-4,
spectrum 107), undergoes a consistent 10-14 nm bathochromic shift (relative to the
spectrum in methanol) in the presence of AICI 3 /HCI (Table VI-4). The spectra of iso-
flavones lacking a free 5-hydroxyl group are unaffected by this reagent.
With 5-hydroxyflavanones and 5-hydroxydihydroflavonols the AICI 3 /HCI reagent
also causes a consistent bathochromic shift (20 - 26 nm) of Band II (Table VI-4).

Table VI-4. The shift of Band II in the UV spectra of 5-hydroxyisoj7avones, 5-hydroxyj7avanones,

and 5-hydroxydihydroj7avonols in the presence of A1CI 3 /HCl

Spec- Flavonoid Bathochromic Spec- Flavonoid Batochromic

trum shift trum shift
No. ofBand Ir No. ofBand Ir
(nm) (nm)

Isoj7avones 136 Pratensein 11

105 5,7 -Dihydroxyisofla vone 14 137 Pomiferin 11
107 2-Carboxy-5,7-dihydroxy- 10 138 Irigenin 10
isoflavone 139 Iridin 10
113 Genistein 21
Genistin 12
Flavanones
114
115 Sphaerobioside 11 140 Pinocebrin 20
116 Sophoricoside 10 142 5,6,7-Trihydroxyflavanone 22
118 Prunetin 12 143 5,6,7 -Trihydroxyflavanone 26
119 Biochanin A 12 7-O-gl ucuronide
120 Lanceolarin 12 144 Naringenin 22
129 6-H ydroxygenistein 11 146 Eriodictyol 20
130 Tectorigenin 11 147 Hesperidin 23
131 Tectoridin 10
132 Irisolidone 12 Dihydroj7avonols
133 Orobol 12 151 Dihydrokaempferol 21
134 Orobol7-0-glucoside 11 152 Engeietin 21
135 Orobol7-0-rhamno 10 153 Taxifolin 22
glucoside 154 Astilbin 22
 - .l
VI-6. Index a of Ultraviolet Absorption Spectra of Isoflavones, N

Flavanones and Dihydroflavonols

-
Spectrum Oxidation pattern
No.
2 3 5 6 7 8 2' 3' 4' 5'
>-l
::s-
o
I soflavones
104 7-Hydroxyisoflavone OH
c:::
::;:'
'1
105 5,7-Dihydroxyisoflavone OH OH <
106 5,7 -Dimethoxyisoflavone OCH 3 OCH 3 'ö·"
107 2-Carboxy-5, 7-dihydroxyisoflavone COOH OH OH Ö
108 Daidzein OH OH tZl
'0
109 Daidzein 7-0-glucoside (Daidzin) O-glu OH
-
0
0
110 Formononetin OH OCH 3 ::;
111 Formononetin 7-0-glucoside O-glu OCH 3 0
....,
'"
112 F ormononetin 7-O-glucoside tetraacetate OCH 3
0 gIU '0"
- ]
(AC)4
113 Genistein OH
1 H OH
-
::::.
<
0
114 Genistin OH O-glu OH
'0"
0
115 Sphaerobioside OH O-rut OH Y'
116 Sophoricoside OH OH O-glu :!1
117 Genistein 5-methyl ether OCH 3 OH OH <
OH
118 Prunetin OH OCH 3
'0"
0
OH
119 BiochaninA OH OCH 3
'0"
0
120 Lanceolarin OH ~o-aPiO-] OCH 3 '"
syl-glu '0"
Q.
121 Texasin OH H OCH 3
122 Texasin 7-0-glucoside OH O-glu OCH 3 0
2-Carboxy-6, 7-dihydroxy-4' -methoxyisofla vone COOH OH OH
s:
'<
123 OCH 3 Q.
'1
124 Afrormosin OCH 3 OH OCH 3 0
3' ,4',7-Trihydroxyisofla vone OH OH OH ::::.
125
126 Pseudobaptigenin OH -O-CH 2 -O- <
0
'0"
127 Pseudobaptisin O-rut -O-CH 2 -O- e..
128 Baptigenin OH OH OH OH '"
129 6-Hydroxygenistein OH OH OH OH
130 Tectorigenin OH OCH 3 OH OH
131 Tectoridin OH OCH 3 O-glu OH
132 Irisolidone OH OCH 3 OH OCH 3
133 Orobol OH OH OH OH
134 Orobol 7-0-glucoside OH O-glu OH OH
 ......
::s
0-
(1)
~
Spectrum Oxidation pattern 0
....
No.
2 3 5 6 7 8 2' 3' 4' 5' g
....
I»
135 OroboI7-0-rhamnoglucoside OH OH OH <
[O-rh-] ö·
glu i'D
136 Pratensein OH OH OH OCH 3
137 Pomiferin OH CsH g O-CsH s OH OH >
-
r::r
Oll
138 Irigenin OH OCH 3 OH OCH 3 OCH 3 OH 0
....
Iridin O-glu OH '0
139 OH OCH 3 OCH 3 OCH 3 g.
Flavanones ::s
CIl
140 Pinocembrin OH OH '"g
0
141 Liquiritigenin OH OH .;
I»
142 5,6,7-Trihydroxyflavanone OH OH OH ..........0
143 5,6,7-Trihydroxyflavanone 7-0-g1ucuronide OH OH O-gluc Oll
144 Naringenin OH OH OH 0
Q
145 Sakuranin O-glu OCH 3 OH I»
<
0
146 Eriodictyol OH OH OH OH ::s
(1)
147 Hesperidin OH O-rut OH OCH 3 Y'
Dih ydroj1avonols ~
<
I»
148 Garbanzol OH OH OH ::s
0
149 Dihydrofisetin OH OH OH OH ::s
(1)
(+ )-Fustin 3-0-g1ucoside Oll
150 O-glu OH OH OH
151 Dihydrokaempferol OH OH OH OH §
0-
152 Engeietin O-rh OH OH OH
153 Taxifolin 0
OH OH OH OH OH 5'
154 Astilbin O-rh OH OH OH OH '<
0-
155 Dihydrorobinetin ....
OH OH OH OH OH 0
Q
I»
a Abbreviations: glu = glucosyl; gluc = glucuronosyl; gly = glycosyl; rh-glu = rhamnoglucosyl; rut= rutinosyl. <
0
::s
0
<;;"

.....
-.I
w
174 The Ultraviolet Spectra of Isoflavones, Flavanones and Dihydroflavonols

References
1. Dyke, S.F., W.D. Ollis, M. Sainsbury, and J.S.P. Schwarz: Tetrahedron 20,1331 (1964).
2. Markham, K.R., W. T. Swift III, and T.J. Mabry: J. Org. ehern. 33,462 (1968).
3. Jurd, L., and R.M. Horowitz: 1. Org. ehern. 26, 2561 (1961).
4. Narasimhachari, N., and T.R. Seshadri: Proc. Indian Acad. Sei. 27 A, 223 (1948); 30 A, 271 (1959); ehern.
Abstr. 44, 1493 (1950).
 104
7 -HYDROXY1SOFLAVONE
MeOH
MeOH + NaOMe
HO

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) invisible
(UV/NH a) fluorescent light
blue
R f Values: 0.90 (TBA), 0.38 (HOAc)
UV SPECTRAL DATA (Amaz,nm)
MeOH 242, 299, 305sh
NaOMe 264, 336
AICl a 243, 299, 305sh
AICla/HCI 243,299,305sh
I
,-,
\
NaOAc 263, 311sh, 336 I \
I \
NaOAc/HaBOa 252sh, 301 \
(Proc. I) \
\
\
\
\

200 500
A,nm

MeOH + AICl 3 Belh MeOH + NaOAc

MeOH + AICl 3 + Hel MeOH + NaOAc + H3 B0 3 - - - - -

I
I
I
I
I
I
\

\
\
I
I
I
\
\
I
I
I
I
I
I
I
I
I
I
I
\
\

200 500 200 500

k,nm A,nm
 105
5,7-DIHYDROXYISOFLAVONE
MeOH
MeOH + NoOMe

""II
,
,
, I
CHROMATOGRAPHIC DATA , I
I
Spot Appearance: (UV) deep purpIe I
(UV/NH a) deep purpIe
I '
Rf Values: 0.93 O(TBA), 0.33 (HOAc) I '

,, '
I '
I '

':'
UV SPECTRAL DATA (Amllz,nm)
MeOH 259, 303sh, 315sh
,,
NaOMe 274, 329 \
, I
I

AICl 3 272, 311, 367 ,,,,/

AICVHCI 273, 313sh, 367
NaOAc 273,327
NaOAc/HaBO a 260,317sh I
".,
,

,,
I ,
(Proc. I) I ,

,,
, ,,
200 500
A,nm

MeOH + AICI 3 - - MeOH + NoOAc

MeOH + AICl 3 + HCI ----- MeOH + NoOAc + H3 ß0 3 - - - - -

,, ,f,,
,, ,,",, r,
,, , ,
,, ,, I
,
I
I

,, ,, I
I , \,
,, ,, I
I ,,
,, ,, I
I ,,
,, ,, I
I ,,
,, ,, I
I ,,
,, ,, I
I ,,
,, I
I ,,
\.!
I
I
I
I
,,
I
I
\ ,
'"
\

, ..... '" ... -,,

\
\

200 500 200 500

A,nm A,nm
 106
5,7-DIMETHOXYISOFLAVONE
MeOH SOlh
MeOH .. NoOMe

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) light blue
(UV /NH a ) light hlue
Rf Values: 0.90 (TBA), indef. (HOAc)
UV SPECTRAL DATA (AmlU/!,nm)
MeOH 251,308sh
NaOMe 251,309sh
AlCl" 250,305sh
AlCla/HCl 250,305sh
NaOAc 252sh, 306sh
NaOAc/HaBO a 252sh, 306sh
(Proc. I)

200 500
>-,nm

MeOH .. AICl 3 Solh MeOH .. NoOAc Solh

MeOH .. Alel 3 .. HCI MeOH .. NoOAc .. H3 S0 3

200 500 200 500

>-,nm >-,nm
 107
2-CARBOXY-
5,7 -DIHYDROXYISOFLAVONE MeOH
MeOH + NoOMe

,.
HO
1" ,
1
1
1
otI

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) deep purple
(UV/NH:i ) deep purpJe

RrValues: 0.75 (TBA), 0.74 (HOAc)

UV SPECTRAL DAT A (A-mux,nm)
MeOH 257, 298sh, 323sh
NaOMe 272,332
AlCl:i 243sh. 281. 324 ,..,
I \
AlCLJHCl 278, 317sh I \
I \
NaOAc 271. 331 I \
I I \
NaOAc/HßO:i 258,309sh \.1 \
\
(Proc. I) \
\
\
\

200 500
>-,nm

MeOH + AICl 3 MeOH + NoOAc

MeOH + AICl 3 + Hel MeOH + NoOAc + H3 B0 3 - - - - -

,
I

I
I
I
I
I
I ;'
I,
,,
I, ,
"l ,

,,
I
I
I
I
I
I
I
I
I
I

,
I
I
\

200 500 200 500

>-,nm >-,nm
 108
DAIDZEIN
MeOH
MeOH + NoOMe
HO

OH

,,
,\

,,,",,,
CHROMATOGRAPHIC DATA ,,
Spot Appearance: (UV) invisible ,
,,
(UV/NH 3 ) Iluorescent light
blue \,
,,
Rf Values: 0.87 (TBA) , 0.36 (HOAc) ,
\,,
,
UV SPECTRAL DAT A (Ama",nm)
MeOH 238sh, 249, 259sh, 303sh
NaOMe 259, 289sh, 3'28
\
...'-\\\
AICl a 24Osh, 249, 260sh, 300sh \
\
AICla/HCI 24Osh, 249, 262sh, 302sh \
\
NaOAc 253, 272sh, 310, 330sh \
\
NaOAc/HaBO a 261sh, 303 \
(Proc. I) \
\
\
\
\
\

200
>-,nm

MeOH + AICI 3 80th MeOH + NoOAc

MeOH + AICI 3 + HCI MeOH + NoOAc + H3 803 - - - - -

200 500 200 500

>-,nm >-,nm
 109
DAIDZEIN 7 -O-GLUCOSIDE
(DAIDZIN) MeOH
MeOH + NoOMe

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) invisible
(UV/NH 3 ) fluorescent light
blue
Re Values: 0.63 (TBA) , 0.65 (HOAc)
UV SPECTRAL DATA (Amaz,nm)
MeOH 256,313sh
NaOMe 256, '272sh, 320sh
AICl a 258, 304sh
AICI 3/HCI 257, 303sh, 262sh
NaOAc 256,322sh
NaOAc/H3BOa 254,318sh
(Proc. I)

200 500

MeOH + NoOAc - -
MeOH + AICl 3 MeOH + NoOAc + H3 B0 3 - - - - -
MeOH + AICI 3 + HCI

,,
\
~

\
\
\ \
I \
\ \
\ \
\
, -- .........
\
,
--
\ \

" .... ..... _-

200 500 200 500
>-,nm >-,nm
 110
FORMONONETIN
MeOH
MeOH + NaOMe
HO

o
ri'\
CHROMATOGRAPHIC DATA ,r, \ \
\
\
Spot Appearance: (UV) invisihle \
\
(UV /NH a) fluor-escent light \
I
hlue I
I
I
Rf Values: 0.88 (TBA), 0.38 (HOAc) \
\
UV SPECTRAL DATA (A.n<I.r,nm) I
I
I
MeOH 240sh, 248, 259sh, 311 I
I
NaOMe 255,273sh, 335 I
AICI:l 239sh, 248, 261sh, 301
\
\
I
,
....
\
AICl:/HCI 240sh, 249, 261sh, 301 I
I \
NaOAc 254, 312sh, 334 i, I \
\
\
NaOAc/HaBO" 264sh. 303 \-
\
(Proc. I) \
\
\
\
\
\
' ....

200
~,nm

MeOH + AICI 3 Both MeOH + NaOAc

MeOH + AICI 3 + HCI
,
MeOH + NaOAc + H3 B0 3
I
I
I
I
\
I
\
\
\
\
\
\
\
\
\
\
\
\
\
\
\
\
\

200 500 200 500

~,nm ~,nm
111
FORMONONETIN 7 -O-GLUCOS1DE
MeOH - -
MeOH + NaOMe
IIUCDlJl-O

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) fluorescent light
blue
(UV/NH a) fluorescent light
blue
Re Values: 0.66 (TBA), 0.74 (HOAc)
UV SPECTRAL DATA (Am.u;nm)
MeOH 251sh,258,301sh
NaOMe 250sh,258, 301sh
AICl a 251sh, 259, 300sh
AICla/HCI 250sh, 257, 301sh
NaOAc 257,304sh
NaOAc/HaBO a 255, 302sh
(Proc. I)

200 300
)..,nm

MeOH + AICI 3 - - MeOH + NaOAc 80th __

MeOH + AICI 3 + HCI ----- MeOH + NaOAc + H3 803

I I
200 300 500
)..,nm
 112
FORMONONETIN 7-0-GLUCOSIDE
TET RAACETATE MeOH
MeOH + NoOMe

1tllllCII,l-llucos,l-O

OCHS

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) fluorescent light
blue
(UV/NH a) fluorescent light
I
blue I
I
I
Rf Values: 0.93 (TBA), 0.01 (HOAc) I
I
I
UV SPECTRAL DAT A (A.,na ..,nm) I

,,
\
\
MeOH 250sh, 258, 302sh
NaOMe 251sh, 259, 302sh \
\
AICLj 251sh, 259, 302sh \
AICl,,/HCl 251sh, 260, 304sh I
I
NaOAc 259, 305sh I
\
NaOAc/RjBO" 259, 302sh
,,
\
\
(Proc. I)
'-
200 500
>",nm

MeOH + AICl 3 MeOH + NoOAc Both

MeOH + NoOAc + H3 B0 3
MeOH + AICI 3 + HCI

I I
200 500 200 300 400 500
>",nm
113
GENISTEIN
MeOH
MeOH + NaOMe
HO

,,..,,
CHROMATOGRAPHIC DATA
11

.,, ,,,
Spot Appearance: (UV) deep purple
(UV/NHa) deep purpIe
Rf Values: 0.85 (TBA) , 0.30 (HOAc) ,,
,,
UV SPECTRAL DATA (A"""",nm)
,,
MeOH 261,328sh ,,
NaOMe
AICl a
276,327sh
272, 307sh, 372 \
,
AICI,/HCI 273, 309sh, 372 \
\
NaOAc 271,325 \"\
NaOAc/HßOa 262,336sh
\
(Proc. I) \
\
\
\
\
\
\
\

200 500
~,nm

MeOH + AICI 3 Both MeOH + NaOAc

MeOH + AICI 3 + HCI MeOH + NaOAc + H3 B0 3 - - - __

500 200 500

~,nm ~,nm
 114
GENISTIN
MeOH
MeOH + NoOMe

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) deep purple
(UV /NHJ deep purpIe
{\
Hf Values: 0.55 (TBA), 0.63 (HOAc)
,
UV SPECTRAL DAT A (AmttJ.,nm) I I
I I
I
I I
MeOH Z61,330sh I I I
I
I I
NaOMe Z71,356sh I I
I
AlCl:, zn, 308sh, 375 I
\ I
I I
I
\
AlCL/HCI Z72, 307sh, 374 \ /
\
NaOAc Z61,331sh \
\
NaOAc/HßOa 261,328sh \
\
(Proc. I) \
\
\
\

,
\
\
"-
"- ,
I I
200 300 400 500
A,nm

MeOH + AICl 3 MeOH + NoOAc

Both
MeOH + AICl 3 + Hel MeOH + NoOAc + H3 B0 3 - - - __

200 500 200 500

A,nm A,nm
 115
SPHAEROBIOSIDE
MeOH
MeOH + NoOMe
rh....,ucllJl-O

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) deep purple I
(UVjNHa ) deep purpie
,
, I
, I

R{ Values: 0.57 (TBA), 0.74 (HOAc) ,

I

UV SPECTRAL DATA (Ama;c,nm)

, I
I

MeOH 262,327sh ,, I

NaOMe 270, 307sh, 351sh ,,

AICl 3
AICla/HCI
271, 30Ssh, 378
272, 307sh, 378
, \
\
NaOAc 262, 289sh, 325sh \
NaOAc/HaBO a 262, 289sh, 325sh \

(Proc. I) \\
,,
- ""
\
.\

....

200
).,nm

MeOH + AICI 3 80th MeOH + NoOAc 80th

MeOH + AICI 3 + HCI MeOH + NoOAc + H3 80 3

1\

I
200 500 200 300 500
 116
SOPHOR1COSI DE
MeOH
MeOH + NoOMe

O-IIIC.,/

,'I

, ,',
11 ," '
,,
,,, ,,,
CHROMATOGRAPHIC DATA
Spot Appearance: (UV) deep purpie
,,
,, ,,, ,,,
(UV/NH a) deep purpie
Re Values: 0.60 (TBA), 0.58 (HOAc)
,, ,, ,,
UV SPECTRAL DAT A (Xma.-,nm)
, , ,,
MeOH 261,324sh
\\} : ,,
,
NaOMe
AICl a
248sh, 274, 326
273, 311sh, 371 0f ,,,
AICl:/HCl 273, 312sh, 371 ,,
NaOAc 272, 326 ,
NaOAc/HaBO a 262, 327sh
\ ,,-,,
(Proc. I) ~
,,
,,
,,
\,
/ I
200 300 soo
}",nm

MeOH + AICI 3 Both MeOH + NoOAc

MeOH + AICI 3 + HCI MeOH + NoOAc + H3 B0 3 - - - - -

,",
1
1

:'
I' '
" I
,I '
,,
v \
I

,,
,

200 300 200 soo

,,",nm ,,",nm
 117
GENISTEIN 5-METHYL ETHER
MeOH
MeOH + NaOMe
HO

{\,
CHROMATOGRAPHIC DATA I
I
I I
Spot Appearance: (UV) invisible I I
I I
(UV/NH) nuorescent light I I
I I
blue I I
I I
I I
Rf Values: 0.79 (TBA), 0.41 (HOAc) I \
I \
UV SPECTRAL DAT A (Am,t;l,nm)
I
I
I " \
\
MeOH 256, 283sh, 317 sh I \
I \
NaOMe 266, 295sh \

"
I
\
AICL, 256, 286sh, 317sh \

AIClx/HCl 256. 284sh, 316sh " \

\
\
NaOAc 264,315 \
\
NaOAc/H 3 B0 3 256, 321sh \
\
(Proc.1) \
\

,,
\
\

,
200 500
>-,nm

MeOH + AICI J 60th MeOH + NaOAc

MeOH + AICI J + HCI MeOH + NaOAc + HJ 60 J - - - - -

200 500 200 500

>-,nm >-,nm
 118
PRUNETIN
MeOH
MeOH + NoOMe

ON

11

CHROMATOGRAPHIC DATA
'\1
, 1
1
Spot Appearance: (UV) deep purpie
(UV /NHa) deep purpie , I 11
I 1
I 11
Rf Values: 0.86 (TBA), 0.35 (HOAc) ,
,,
I 1
1
UV SPECTRAL DAT A (Ama ..,nmJ 1
I 1
I 1
MeOH 262, 327sh 1 I 1
\
NaOMe 272, 353sh 1 I 1
AlCl a 273, 309sh, 374 1,,1 1
1
AICla/HCI 274, 31Osh, 370 \
\
NaOAc 262, 330sh \
\
NaOAc/HßOa 262,332sh \
\
(Proc. I) \
\

,
\
\

",,
,
I " I
200 300 400 500
A,nm

MeOH + AIC/ 3 MeOH + NoOAc Bolh

MeOH + AIC/ 3 + Hel ----- MeOH + NoOAc + H3 B0 3

i
1
1
1
11
11
11
I 1
I 1
1 1
I 1
I 1
I 1
I 1

\~! \
\
\
\
I
I
I
1
1
1
\ I 1
~, 1
\1 \
\
\
\
\\
,,- ....
_
\
\"'.. ...... / "-
1 1
200 300 400 500 200 500
)",nm )",nm
 119
BIOCHANIN A
MeOH
MeOH + NaOMe
lfO

CHROMATOGRAPHIC DATA '\

I,
Spot Appearance: (UV) deep purpie
I,
,,
(UV jNH'j) deep purpie
I I

Rr Values: 0.89 (TBA), 0.30 (HOAc) I '

II 'I
UV SPECTRAL DATA (l\ma",nm) II 'I
I I
I I
MeOH 261,330sh I I
NaOMe 249sh, 273, 327 I I
I I
273, 310sh, 375 I ,
AICI'j I ,
AICI,/HCI 273, 310sh, 373 / \
NaOAc
NaOAc/H"BO"
272, 327
262. 330sh
,
I
\
(Proc. I)
,,-,,,
,,
,,
,
,,
200 500
>-,nm

MeOH + AICl 3 Both MeOH + NaOAc

MeOH + AICI 3 + HCI MeOH + NaOAc + H3 B0 3 - - - - -

200 500 200 500

>-,nm >-,nm
 120
LANCEOLARIN
MeOH
MeOH + NoOMe
IpIozIUCOl,I- 0

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) deep purple
(UV/NH a) deep purpIe
Re Values: 0.68 (TBA), 0.67 (HOAc) I
I

I ,
UV SPECTRAL DATA U'mu:t,nm) , I
I I
I I
MeOH 262,325sh I I
NaOMe 244sh. 267.368 / I
I
AlCl" 273, 305sh, 382 I
I
AlCl,/HCl 273, 304sh, 380 I
261,321sh I
NaOAc
NaOAc/HßO" 261, 320sh
(Proc. I)

200 500
>-,nm

MeOH + AICl 3 Solh MeOH + NoOAc Soth

MeOH + AICI 3 + HCI MeOH + NoOAc + H3 S0 3

I I
200 300 500 200 50(\
>-,nm >-,nm
121
TEXASIN
I MeOH
I
I MeOH + NoOMe
I
HO I
I
I
I
I
I "
o I / \
I I
~,

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) fI uorescent light
blue
(UV/NH a) fluorescent pale
yellow

Re Values: 0.80 (TBA), 0.31 (HOAc)

UV SPECTRAL DAT A (Ama;c,nm)

MeOH 255, 325
NaOMe 254, 351
AICI.~ 237sh, 251, 3#
AICljHCl 257, 325
NaOAc 25.3sh, 339
NaOAc/HaBO:! 253sh. 338
(Proc. I)

200 500
"-,nm

MeOH + AICl 3 MeOH + NoOAc

MeOH + AICl 3 + HCI MeOH + NoOAc + H3 B0 3 - - - __

I
I
I
I
I
I

500 200 500

"-,nm "-,nm
 122
TEXASIN 7-0-GLUCOSIDE
MeOH - -
MeOH + NaOMe

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) fluorescent light
\
blue \
(UVjNHa) fluorescent pale \
\
yellow \
\
I
Re Values: 0.56 (TBA) , 0.66 (HOAc) I
\
I
UV SPECTRAL DATA (Amaz,nm) I
I
\
MeOH 259, 326 I
I
NaOMe 255, 278sh, 368 I
AICI 3 260, 325 I
I
AICI,/HCI 259, 325 I
\
NaOAc 257,333, 366sh \
NaOAc/HaB03 259, 328
(Proc. I)

200 500
>-,nm

MeOH + AICl 3 80th --- MeOH + NaOAc

MeOH + AICI 3 + HCI MeOH + NaOAc + H3 803 - - - - -

200 500 200

>-,nm
 123
2-CARBOXY -6,7 -DIHY DROXY-
4'-METHOXYISOFLAVONE MeOH
MeOH + NoOMe

HO

HO OCH,

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) fluorescent pale
yellow
(UV/NH 3 ) fluorescent yellow
Re Values: 0.63 (TBA), 0.71 (HOAc)
UV SPECTRAL DATA ("maz,nm) I
I'
\
I \
MeOH 238, 254sh, 323 I \
I \
NaOMe 249, 349 I \
I \
AICl a 246sh, 289sh, 363 I \
I \
AICVHCl 238, 276sh, 336 I \
NaOAc 251sh, 343 \ I \
\ I \
NaOAc/HaB0a 335 ..../ \
\
(Proc. I) \
\
\

200 500
>",nm

MeOH + AICl 3 MeOH + NoOAc

MeOH + AICI 3 + HCI MeOH + NoOAc + H3 B0 3

.
I
I
I
I
I
I
I
I
I"
\j \
\
\
I
\
\
\
\
\
\
\
\
1

200 500 200 500

>",nm >",nm
 124
AFRORMOSIN
MeOH
MeOH + NoOMe

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) Iluorescent light
bIue
(UV/NH:) brigbter
Iluorescent blut'
,...
I •
Rf VaIues: 0.86 (TBA), 0.39 (HOAc) I \
I \
I \
UV SPECTRAL DAT A U'mtU,nm) I \
I \
I \
MeOH 258, 320 I \
\
NaOMe 258, 349 \
\
AICI" 255,319 \
AICljHCl 255,318 \
\
NaOAc 256, 347 \
\
NaOAc/HßO" 256, 325 \
\
(Proc. I) \
\
\

200 500
A,nm

MeOH + AICI 3 Both MeOH + NoOAc

MeOH + AICl 3 + HCI MeOH + NaOAc + H3 B0 3
I
I
I
I
I
I
I
I
I

-'\
\
\
I
I

,\
\

,
\
\
\
\
\
\
\
\

200 5UO 200 500

A,nm A,nm
 125
3',4',7-TRIHYDROXYISOFLAVONE
MeOH
MeOH + NoOMe
HO

CHROMATOGRAPHIe DATA

Spot Appearance: (UV) invisible I

(UV/NH:l ) nuorescent light
I
I
/\
I I
I I I
blue I I I
I I \
Rr Values: 0.89 (TBA), 0.29 (HOAc) I I I
I I I
I I I
UV SPECTRAL DATA (X,nar,nm) I I
,
\
I
I
I
,_/
\
MeOH 240,249,260sh,293,308sh , I

NaOMe 257,336 (dec.)

AICl~ 246sh,275, 296, 364sh
AICL/HCl 241,249,261sh,292,309sh
NaOAc 257, 291sh, 331
NaOAc/H~BOa 271,297, 351sh
(Proc.lI)

200 500
}",nm

MeOH + NoOAc
MeOH + AICl 3 MeOH + NoOAc + H3 B0 3 - - - -
MeOH + AICl 3 + HCI

I
I
I
I
I
I
I
I ~ I
I I I
\/ I ~
I I ' 1\
I, ....' \
,,
,,
I
I

,
I
I
I ('.
111 I
" I I

,,
I I
I
I
I
\
I
, \
I
I I
I \

,
\
,
I \
I
\ ",,
\
,
\
"
\,
-',
200 . 500 200
}",nm }",nm
126
PSEUDOBAPT1GEN1N
MeOH
MeOH + NoOMe
HO

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) invisible
(UV/NH a) fluorescent light
blue
R f Values: 0.85 (TBA), 0.39 (HOAc)
UV SPECTRAL DATA (Amaz,nm)
MeOH 241sh,250,262sh,295,345sh
NaOMe 259, 293sh, 335 (dec.) .......
/ \
AICl 3 242sh, 249, 264sh, 296 \
\
AICl:/HCl 242sh, 249, 262sh, 295 \
\
NaOAc 258, 297 sh, 333 \
\
NaOAc/HaBO a 251, 262sh, 296 \
\
(Proc. I1) \
\
\
\
\
\

200 500
>-,nm

MeOH + NoOAc
MeOH + NoOAc + H3 B0 3 - - - - -
MeOH + AICl 3 Both
MeOH + AICI 3 + HCI

,,
I
I

I
, \
\

, \
\

\
\
\
\
\
\
\
\
,
\
\
\ I
\/
,
\

,,
\

\
\
\
\
\
\

,
\
\

", .... -
500 200 300 400 500
>-,nm >-,nm
 127
PSEUDOBAPTlS1N
MeOH
80th ---
MeOH + NoOMe

rhamnOllucasyl - 0

CHROMATOGRAPHIe DAT A
Spot Appearance: (UV) fluorescent light
blue
(UV/NH a) fluorescent light
blue
R f Values: 0.55 (TBA), 0.75 (HOAc)
UV SPECTRAL DATA (l\ma;r"nm)
MeOH 249, 261, 292
NaOMe 249, 261, 292
AlCl a 250, 262, 291
AlCla/HCI 249,261,291
NaOAc 261, 291
NaOAc/H aB0 3 261,291
(Proc. I)

200 500

MeOH + AICl 3 80th --- MeOH + NaOAc 80th

MeOH + AICl 3 + Hel MeOH + NaOAc + H3 80 3

200 500 200 500

A,nm A,nm
 128
BAPTIGENIN
MeOH
MeOH + NoOMe
HO

I
I
I
I
I
I
CHROMATOGRAPHIC DATA I
I ,..,
Spot Appearance: (UV) Ouorescent light
I
I I
I \,
I
blue I I \
I I \
(UV/NH 3 ) brighter Ouores- I
I ,
cent light blue I I \
I I I
I \
Re Values: 0.87 (TBA) , 0.34 (HOAc) \r" ,
, , I
I
,,
,
,

UV SPECTRAL DATA (X",,,,,,nm) ,

\./'
,, I
~eOH
NaO~e
239,247,265,304sh
245, 255sh, 286sh, 335 (dec.) , \
AICI 3 238, 246sh, 283, 302sh
AICla/HCI 238,246, 266, 302sh
NaOAc 255, 285sh, 330
NaOAc/HaBO a 247sh, 258sh, 304sh
(Proc.lI)

500

MeOH + Alel 3
I
MeOH + Alel 3 + Hel I
I
I
I
I
I
\
I

,
I
I

"
,,
\
\

,,
,,
,,
\
,
\
\

\,
\
, \
\
\
,,
\

MeOH + NoOAc
MeOH + NoOAc + H3 B0 3 - - - - -

200 500 200 500

>..,nm
129
6-HYDROXYGEN1STE1N MeOH
MeOH + NoOMe

HO

HO

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) deep purpIe
(UV/NH a) deep purple
Re Values: 0.79 (TBA), 0.36 (HOAc)
UV SPECTRAL DATA (AtnIIZ,nm) i\
I \
, I \
MeOH 245sh, 270, 350sh
-
\ I \
\ I \
NaOMe 259. 307, 330sh (dec.)
AICl 3 239, 248sh, 275, 295sh, 356
\\ ,"' ...... ,
\J '
AICla/HCl 281, 329 \\
NaOAc 250sh, 303, 338sh, 418 (dec.) \
\
NaOAc/H:,BO a 275, 320 \
\
(Proe. 11) \
\
\
'---

200
)",nm

MeOH + AICl 3 MeOH + NoOAc

MeOH + AICl 3 + Hel MeOH + NoOAc + H3 B03

500 200 500

 130
TECTORIGENIN
MeOH
MeOH + NoOMe
110

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) deep purple n,
(UV/NH 3 ) deep purpie I'

,,
I
Rf Values: 0.83 (TBA), 0.38 (HOAc) I

UV SPECTRAL DATA (Ama:t,nm)

,,
I
,,
MeOH
NaOMe
267, 330sh
278, 328 ,,
AICl a 276,311,378 ,
AICla/HCl 277, 309sh. 366 '--,\
NaOAc 273,339 \
\
NaOAc/HaBO a 268, 335sh \
\
(Proc. I) \
\
\
\
\
,
\
\

200 500
"-,nm

MeOH + AICl 3 MeOH + NoOAc

MeOH + AICI 3 + HCI MeOH + NoOAc + H3 B0 3 - - - - -

,.
1\
I,
I ,
I ,

, ,
I ,
I I
I I
, I
, I

, ,
, I
I I

" I
"\J
,,
, I

... ,
\
\
\
\
'-".--,

200 500 200 500

"-,nm
 131
TECTORIDIN
MeOH
MeOH + NoOMe

CHROMATOGRAPHIC DAT A
,,
,,, ,,,
Spot Appearance: (UV) deep purple
(UV/NH a) deep purple
,,
Re Values: 0.59 (TBA), 0.74 (HOAc)
,,, ,,,
UV SPECTRAL DAT A (A.na ..,nm) , ,
MeOH 266,331 I '
,,
,,
I '
NaOMe 274,365
AICl 3 277, 315sh, 380
278, 322sh, 381 \
AlCI 3 /HCI \
NaOAc 266, 331sh \
\
NaOAc/H 3 BOa 266,330sh \
\
(Proc. I) \
\
\

',,----,
"
200 500
A,nm

MeOH + AICl 3 Both MeOH + NoOAc Both

MeOH + AICl 3 + Hel MeOH + NoOAc + H3 B0 3

200 500 200 500

A,nm A,nm
132
IR/SOL/DONE
MeOH
MeOH + NoOMe
HO

,
,,,,,
;\

,,
,,, ,,,
CHROMATOGRAPHIe DATA
Spot Appearance: (UV) deep purple
,,
,,, ,,,
(UV jNH a) deep purpIe

,, ,,
R f Values: 0.88 (TBA). 0.34 (HOAc)

UV SPECTRAL DATA (Amo%.nm) J ,

,,
MeOH 265, 335sh ,,
NaOMe 248,273,339
,,
AICl a 276. 316, 378
,,
AICla/HCI
NaOAc
277, 312sh. 373
273,339 ,, r I
I \
\
NaOAcjH 3 BO a 271. 333 I \
I \
(Proc. I) \
\
\
\
,
\

200 500
>--,nm

MeOH + AICl 3 Both MeOH + NoOAc

MeOH + AICl 3 + HCI MeOH + NoOAc + H3 B0 3 - - - - -

r,
,,, ,,,

200 500
>--,nm >--,nm
 133
OROBOL
MeOH
MeOH + NaOMe

HO

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) deep purpie
(UVjNHa) deep purpie
Re Values: 0.80 (TBA), 0.24 (HOAc)
UV SPECTRAL DATA (>-maz,nm)
MeOH 262, 294sh, 338sh
NaOMe 269, 334 (dec.)
AlCl a 270, 298sh, 365 ~-,
I \
AICla/HCI 273,371 I \
I \
NaOAc 270,322 \
NaOAc/HaBO a 266,294sh \
\
(Proe. 11) \
\
\

,,
\
\

200 SOG
~,nm

MeOH + AICl 3 MeOH + NaOAc

MeOH + AICI 3 + HCI MeOH + NaOAc + H3 B0 3 - - - - -

I
I
I
I
I
I
I
I
I
I
I
I
I
I
I
I
I I
I I
IJ

200 500 200 300 400 500

~,nm ~,nm
134
OROBOL 7-O-GLUCOSIDE
MeOH
MeOH + NoOMe

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) -deep purpIe
(UV/NH:1) deep purpIe
Rf Values: 0.39 (TBA), 0.54 (HOAc)
UV SPECTRAL DAT A (Ama,.,nm)
MeOH 262, 290sh, 343sh
NaOMe 294sh, 337 (dec.) \
\
AICI" 269, 297sh, 372 \
\
AICIa/HCI 272, 297sh, 376 \
NaOAc 261, 331sh \
\ ,/" \
NaOAc/HßO" 258, 269sh, 293sh, 322sh \ ......... .., / \
\
(Proc.lI) \
\
\
\
\
\

200 500
>-,nm

MeOH + AICl 3 MeOH + NaOAc

MeOH + AICI 3 + HCI MeOH + NaOAc + H3 B0 3 - - - - -

500 200 500

>-,nm >-,nm
 135
OROBOL 7-0-RHAMNOGLUCOSIDE
MeOH
MeOH + NaOMe
rhamnOilucosyl-O

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) deep puq>le
(UV /NHJ deep puq>le
Re Values: 0.33 (TBA), 0.65 (HOAc)
UV SPECTRAL DATA (Ama:r,nm)

MeOH 262, 290sh, 343sh

NaOMe 294sh, 337 (dec.)
AlCl" 269, 297sh, 372
'AlCI 3 /HCl 272, 297sh, 376
NaOAc 261,331sh
NaOAc/HaB°:l 258, 269sh, 293sh, 322sh
(Proc. II)

200 500

MeOH + NaOAc
MeOH + AICI 3 MeOH + NaOAc + H3 B0 3
MeOH + AICl 3 + HCI ,
I
I
I
I
I
I
I
I
I
I
I
I
I
I
I

200 500 200 500

)",nm )",nm
 136
PRATENSEIN
MeOH
MeOH + NaOMe
111

CHROMATOGRAPHIC DAT A
Spot Appearance: (UV) deep purple
(UV/NH:i ) deep purple
Rr Values: 0.81 (TBA), 0.31 (HOAc)
'I
I
I
I
UV SPECTRAL DATA (~ma.r,nm) I
I
MeOH 262, 292sh, 330sh I
I
NaOMe 270, 321 I
I
AICl a 272, 311sh, 371 I

,,
I
AICla/HCI 273, 314sh, 371 I
NaOAc 271,325sh
,... _-
NaOAc/HaBO a 263, 295sh, 335sh ......
,,
(Proc. I) ,,
,
,,
,
200 500
>-,nm

MeOH + AICI 3 Both MeOH + NaOAc

MeOH + AICl 3 + HCI MeOH + NaOAc + H3 B0 3 - - - - -

200 500 200 500

)",nm >-,nm
 137
POM1FERIN
MeOH
MeOH + NoOMe

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) deep purpie
(UV/NH a) deep purpie
Rr Values: 0.93 (TBA),O.02 (HOAc)
UV SPECTRAL DAT A (X",gz,nm)
MeOH 274, 353sh
NaOMe 271 (dec.)
AICl a 284 \
\
AICIa/HCl 285 \
NaOAc 274, 352sh \
\
NaOAc/HaBOa 276, 352sh \
\
(Proc.II)
,
\
\

"" ...... .....

200 300 400 soo

"-,nm

MeOH + AICI 3 MeOH + NoOAc

MeOH + AICI 3 + HCI MeOH + NoOAc + H3 B0 3 - - - - -

I
\ I
\ I
I
I
I
I
I
I
I
\
\
\
\
" ....
'--
200 soo 200 500
 138
IRlGENIN
MeOH
MeOH + NoOMe

,
I
I
CHROMATOGRAPHIC DATA I
I \
Spot Appearance: (UV) deep purple
(UV/NH 3 ) deep purple , ,.
I
I
"
'\

\ ,\
I , •

Rr Values: 0.85 (TBA), 0.48 (HOAc) I : I

UV SPECTRAL DAT A (l\mu,nm) I, \
I I I

,,
J I
MeOH 268, 336sh I
NaOMe 273,336 ,,
AICl a
AICI 3 /HCI
275, 316, 371
278, 315sh, 374 \
, ,,r, \
NaOAc 273,338 \,." \\
NaOAc/Hß0 3 268,339sh
\
(Proc. I) \
\
\
\
\
\

"
200 soo
>-,nm

MeOH + AICI 3 - - - MeOH + NoOAc

MeOH + AICl 3 + HCI MeOH + NoOAc + H3 B0 3 - - - - -

I
I
I
I
I
I
I I
I
I

,
I
I I
I I
I
I ,, I
I

,, ,
I I
I I
I
,
, ,, ,
I
I
I
I

, ,,
I
I

,,
I
I I
I I
I
1

200 soo 200 300 .wo soo

>-,nm >-,nm
 1.39
lRIDIN
MeOH
MeOH + NoOMe

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) deep purple
(UV/NH a) deep purplt'
Rf Values: 0.61 (TBA), 0.78 (HOAr)
UV SPECTRAL DAT A (Amaz,nm) I
I
I
MeOH 268,331sh I
I
NaOMe 270, 356 I
I
MGl a 277, 319sh, 382 I
\
AIGla/HCl 278, 379 I
NaOAc 268, 335sh I
I
NaOAc/H:1BO" 268, 335sh \
\
(Proc. I) \
\ ,
\,
....... -- .....
",
200 500
>--,nm

MeOH + AICl 3 MeOH + NoOAc Both

MeOH + AICl 3 + HCI MeOH + NoOAc + H3 B0 3

I
I
I
I
I
I
I
I
I
I
I
I
I
I

v
I
I
I
I
I

,,
I
I ,
\
\
"

I
200 500 200 300 500
>--,nm >--,nm
 140
PINOCEMBRIN MeOH
MeOH + NoOMe

HO

"" ,
I"
I
,
I I
I I
I ,
, I
CHROMATOGRAPHIC DATA , I
I I
, I
Spot Appearance: (UV) deep purple I I
I ,
(UV/NH a) deep purple I I
I I
Re Values: 0.92 (TBA), 0.29 (HOAc) I I
I I
I I
UV SPECTRAL DAT A (Amaz,nm) I I
I I
I I
MeOH 289, 325sh I ,
NaOMe 245,324 I I
I I
AICI:< 311, 375 I
I
AICI~/HCI 309, 373 I
I
NaOAc 253sh, 323 I
I
NaOAc/HßO" 291,326sh I
(Proc. I) I
I

,
I
I
I
\

200
>-,nm

MeOH + AICl 3 MeOH + NoOAc

MeOH + AICl 3 + Hel Solh MeOH + NoOAc + H3 S0 3 - - - - -

I
I
I

,,
I
I

\
\
\
',\
\
\ ,

200 500 200 500

>-,nm >-,nm
 1',
11
, 1
, I
1 1

141 r-----------;, I----------------~

1
LlQUIRITIGENIN MeOH
MeOH + NoOMe
I
1
1
I
Oll
"
11
11
1
1
1
11 1
11 1
, 1
, 1 1
1

,
1 1
1 1
I
,
I 1

,,,
CHROMATOGRAPHIC DAT A 1 1
1
1
,
Spot Appearance: (UV) fluorescent light 1 1

,,
blue 11
11
(UV/NH a) fluorescentyellow 1,

,
11 I
11

,,,
R[ Values: 0.87(TBA), 0.39 (HOAc) I
"\I
UV SPECTRAL DATA (Am"""nm)
MeOH
NaOMe
276,312
250, 298sh, 327sh, 335 ,
AICI.~
AICl:/HCI
276, 311
276,311
,'
1
1 '
'

NaOAc 255sh, 282, 327sh, 335 1 '

I'
J
NaOAc/HaBO:1 278,312
(Proc. I)

200 500
>",nm

MeOH + NoOAc
MeOH + AICl 3 Solh
MeOH + NoOAc + H3 S03
MeOH + AICI 3 + HCI

,"
, 1
, 1
I 1
I 1
I 1

~\
,
'\1
1 1
, 1
, 1
I 1

1 ,
I
- /'
\
\
1
I, 1
I, 1
" \
1
1
1
\
\

I 1
200 300 400 500 200 300 400 500
>",nm >",nm
 142
5,6,7 -TRIHYDROXYFLA V ANONE
MeOH
MeOH + NaOMe

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) deep purple
(UV/NH a) deep purple
Re Values: 0.83 (TBA) , 0.47 (HOAc)
UV SPECTRAL DATA ().mII.It,nm) ,.\
\
MeOH 2~h, 295, 362.sh \
NaOMe 2+5,300,377 (dec.) \
\
AICl a 251sh,328,381sh \
\
AICla/HCI 251sh, 317, 373sh \
\
NaOAc 248sh, 299, 385, (dec.) \
\
NaOAc/HaBO a 249sh, 30+, 371 \
(Proc.lI) \
,,
\

~,nm

MeOH + NaOAc
MeOH + NaOAc + H3 B03 - - - - -

MeOH +AICI 3
MeOH + AICI 3 + HCI
I
I
I
I
I
I
I
I
\
I I
, I
I I ,
I I ,
I I ,
I I ,
I I ,
I I ,
I I ,
I I ,
I I ,
I I ,
I I ,
I I ,
I I ,
I I ,
I I ,
I I
I , I
I I , I
I I ,
I I
I , I
I I , I
I
\j
,-,'-- ,
I I
I
I \ ......
\
\
....

200 500 200 300 400 500

)",nm )",nm
 143
5,6,7-TRIHYDROXYFLAVANONE MeOH
7 -O-GLUCU RONI DE MeOH + NoOMe

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) deep purple I
,
\
I \
(UV/NH:i ) greenish purple \
\
I \
R f Values: 0.60 (TBA), 0.76 (HOAc) I \
I \

,,I
\
UV SPECTRAL DATA ("maz,nm) \
\
MeOH 239, 288, 362 \ ,
NaOMe 253sh, 295, 345sh (dec.)
,,
............
AICl 3 237sh, 316, 432 ,,
AICI 3 /HCI 237sh, 314, 427 ,,
NaOAc 287, 353 (dec.) ,,
NaOAc/Hß 0 3 284,377 ,
(Proc.lI) \ ,,
.... ....

200 SOG
~.nm

MeOH + AICI 3 --- MeOH + NoOAc

MeOH + AICl 3 + HCI MeOH + NoOAc + H3 B0 3 - - - - -

I
I
I

n
I
t' I
I \ I
I I I I
I I I I
I I I I
I I I I
I I I I
I I I I
I I I
I
I
I
I
I
I
I
I
I
I
I
V

, , , . /0.

" ,
,,"" ,~
\ ,,
200 200 SOG
~.nm ~.n~
 144
NA RINGENIN
MeOH
MeOH + NaOMe
HO
DM

, r\\
,,,
CHROMATOGRAPHIC DATA
\

,
\
Spot Appearance: (UV) deep purpie

,,,
\
\
(UV /NH 3 ) greenish purple \

,
\

,,,
\
R f Values: 0.88 (TBA), 0.33 (HOAc) \

,
\ \
\,..

,\
\
,
UV SPECTRAL DATA (l\muz,nm) \

,,,
\
\
MeOH 289,326sh \ \

,
\ \
NaOMe 245,323 \ \
\ \
AlCI~ 312,375 \ \
AICI,/HCI 311,371 \ \
\ \
NaOAc 284sh,323 \ \
\ \
NaOAc/H"BO" 290, 332sh \ \
(Proc. I) \ \
\ \
\
\
\
I

200 500

MeOH + AICI 3
MeOH + AICI 3 + HCI ----- MeOH + NaOAc
MeOH + NaOAc + H3 80 3 - - - - -

\
\
\
\
\
\

,,,.r
,
,,, \

,
\

,,,
\
\
\

,
\

,,, , ,,
\
\

IV) ,
\

,
\

\ I
,,
\
\
\
\
, I \ \ ,,
, I
,,
, ,,
, I I
\ l

I~ -"" ,,,
~
\
.... ~

I I
200 300 AOO 500 200 500
>-,nm >-,nm
 145
SAKURANIN
MeOH
MeOH + NoOMe

DM

CHROMATOGRAPHIC DATA
Spot Appearance: (UV) fluorescent blue-
green
(UVjNR3) fluorescent green
Rf Values: 0.70 (TBA), 0.77 (ROAc) I "'-',\
I \
UV SPECTRAL DATA (hfll<J$,nm) I \
I \
I \
MeOR 280, 317sh I \
I \
NaOMe 315, 393 I \
I \
AlC1 3 280,312sh I \
I \
AIC1 3 /HCl 280, 310sh I \
,I \
NaOAc 279,314sh '_,-, I \
\
NaOAc!H3B03 279,313sh
.....

\
(Proc. I) \
\
\
\
\ ,
200
,,",nm

MeOH + AICl 3 Both MeOH + NoOAc Solh - -

MeOH + AICI 3 + HCI MeOH + NoOAc + H3 S0 3

f\
f\
v
v
I I J I
200 300 500 200 300 500
>--,nm
 146
ERIODICTYOL MeOH
MeOH + NoOMe

HO
Oll
,
f\I
, I
I I
I I

,
I I
, I
I I
I I
I I
I I
CHROMATOGRAPHIC DATA I I I

Spot Appearance: (UV) deep purple

(UV /NH 3 ) deep purple
I
I
I n I
I
I
i'
I
I
I
I I
I I
R r Values: 0.84 (TBA), 0.39 (HOAc) "\ ,I II

UV SPECTRAL DATA (Amaz,nm)

\
\ ,
I I
I
I I

, , '
MeOH 289, 324sh , I
NaOMe 246,324

u'j\\,
\ I '
AICI 3
AlCIa/HCI
310, 378
309,373
", '\
II
NaOAc 289sh,325
NaOAc/H:iBO a 289, 333sh
(Proc. I)

, J
200 300 400 500
>-',nm

MeOH + NoOAc
MeOH + AICl 3 MeOH + NoOAc + H3 B0 3 - - - - -
MeOH + AICl 3 + Hel

•,
I
I ,..
,1
I

,, ,,
,I
I I1
I II
,,
,,, ,,,
, 1
I
I

,,
1 ' I

,,
1 ' I
I ' I
1
I
I,
'
I'
'
,,
I I 1

\1 ' 1
\
\

1/ ' \
\
\
\
\
\
\
\
\
"" ......
200 500 200 500
>-',nm >-',nm
 147
HESPERIDIN
MeOH
MeOH + NoOMe
rhamnllllucOSJI- 0 OCHS

CHROMATOGRAPHIC DATA
'1\
Spot Appearance: (UV) deep purpie " I
I
(UV/NH a ) light blue I
I
I

I ~
R[ Values: 0.51 (TBA), 0.78 (HOAc)
I
UV SPECTRAL DATA (>-'m,,,,,,nm) I I
I I I
MeOH 283,326 I I
I I
NaOMe 242,286,356 I I
I I
AICl a 308,383 \ I
AICIa/HCI 306,379 I
I
284,328
,
NaOAc I
I
NaOAc/HaBO a
(Proc. I)
284,326
,,-,

v
I ,
,
\ /
I \
,\
\.'
,,
I I
200 300 400
~,nm

MeOH + NoOAc
MeOH + NoOAc + H3 B0 3 - - - - -
MeOH + AICI 3 - -
MeOH + AICI 3 + HCI -----

,.
I
I
I
I
" ,
I
I
I I ,
I
I I I
I I I
I I I
I I I
I I I
I I
I
I
I
\
\
"'''-,,
"
200 soo 200
~,nm ~,nm
 148
GARBANZOL r'I
,
I I
I I
I I
I I
HO I 1
OH I 1
j\ I I
I I
I' , 1
I I I I
I I
I I MeOH
I MeOH + NoOMe

,, ,
I r
I I

CHROMATOGRAPHIC DATA I ,,I

,
I

,,,
Spot Appearance: (UV) pale yellow I

(UVjNH a) lightyeHow-
purple J
I
I
Rf Values: 0.87 (TBA) , 0.52 (HOAc) I
I
I
UV SPECTRAL DATA ().mlJtl,nm)
MeOH 276,311
I '
NaOMe 250, 297sh, 334- II I'
AlCl a 309, 347m , I
J
AlCIa/HCI 276, 309, +08sh
NaOAc 25+,282, 334
NaOAc/HaBOs 277, 312
(Proc. I)

200 500

MeOH + Alel 3 MeOH + NoOAc

MeOH + Alel 3 + Hel MeOH + NoOAc + H3 BO:; -----

,,
I
1
I

;1
"
I" 1
I I
I I
, 1
I 1

,
, I

,,,
I

,I
1
\/',-,
I I

,,
I
I

,,
,,
\
\
.... _-,
200 300 AOO 500 200 500
>-,nm >-,nm
 149
DIHYDROFlSETlN
MP.OH
MeOH + NaOMe

HO

,l', , I

,,
, I
CHROMATOGRAPHIC DAT A , I
, I
Spot Appearance: (UV) pale yellow , I
, , I

,,,
(UV/NH a) light yellow-
purple I
I
,
,,,
Rr Values: 0.75 (TBA) , 0.63 (HOAc) I
I
UV SPECTRAL DAT A (Amaz,nm) I t'
11\
~eOH 277,310 ,I, ,, , I
I
I

NaOMe 252, 297sh, 334 (dec.) I

AICl a 235, 308, 349sh
AlCIR/HCl 234,278,308
NaOAc 256sh, 285, 334
NaOAc/HaBOa 281,314sh
(Proc.lI)

200 soo
A,nm

MeOH + NaOAc
MeOH + AICl 3 MeOH + NaOAc + H3 80 3 - - - - -
MeOH + AICl 3 + Hel

I
I
I
I
I
I
I
I
I
1"\I
I
I
,,
"
,,",,
I

,,
,,, ,
,
,,, ,,,
I

I
\
\ ,\
, ,,
,, ,,, -'"
\
\ \
\
,,
,, ,,
\
\
'J
,,
, ,
\
\

\
\

200 soo 200 500

A,nm
 150
(+ )-FUSTIN 3-0-GLUCOSIDE
MeOH
MeOH + NoOMe

CHROMATOGRAPHIC DATA
1"1
I 1
Spot Appearance: (UV) pale yellow
(UV/NH 3 ) light yellow.
I
I I
I
1
1
1 I ,

,,
purpie I I ,
I I ,
I ,
R[ Values: 0.57 (TBA) , 0.78 (HOAc) \ I ,
I ,
UV SPECTRAL DATA (Ama."nm) I I
I ,

,,
I I
MeOH 234sh, 280, 311 sh I
NaOMe 252, 296sh, 337 ,,
AICI~ 237,281, 318sh ,,
AICIR/HCI 234sh, 280, 311sh, 394sh
,,
NaOAc 254sh, 288,338
,,
NaOAc/H"BO" 284, 315sb
(Proc. I) ,
' .......

200 500
"-,nm

MeOH + AICI 3 MeOH + NoOAc

MeOH + AICI 3 + HCI MeOH + NoOAc + H3 B0 3 - - - - -

1
1
1
1
1
1
1
1
1
I

,,
j'
I'

,
I I

,,
, I
, I
1
1 I I
1 I I

,
1 I '
1
1
1
I
I
'\
, \
1 I \
I \
I' \
\ \
\
\
\
\
\

200 500 200 300 400 500

"-,nm "-,nm
 151
DIHYDROKAEMPFEROL
MeOH + AICI 3
MeOH + AICI 3 + HCI
HO Oll

CHROMATOGRAPHIC DATA
\
Spot Appearance: (UV) deep purpie 1
1
(UV/NH a) deep purpie I
I
\
Rf Values: 0.86 (TBA), 0.48 (HOAc) 1 1
1
1
UV SPECTRAL DATA (X,naz,nm) 1
1
1
MeOH 291, 329sh 1
NaOMe 246,325 1
1
AIClg 274sh, 316, 382 1
1
AIClg/HCI 280sh, 312, 378
,,,
1
1
NaOAc 254sh, 284sh, 327
,
,,
NaOAc/HgBO g 296, 336sh
(Proe. I) "
11 I
It I
11 I
11 I
1 I
I I
1 I
1
1
1 200 500
I ~,nm
1

:-------.,
I

1
MeOH
MeOH + NoOAc
MeOH + NoOMe
MeOH + NoOAc + H3 B0 3 - - - - -

~
11
1
1
1
1
1
1\

I
1 I
1 I
1 I
1 1 I
1 I I
1 I I
1 1 I
1 I I
1 I I
1 I
1 I
I I
1 \
1 I
I \
1 \
I 1 \
I 1 \
I 1 \

l)J
\ \
1 \
\ \
\ \
\
\
1 1
200 300 400 500 200 500
>-,nm ~,nm
 152
ENGELETIN
,l'I
, I

,'
, 1

IIOWI
· "::~......,. )-IN ,'
, 1
, 1
, 1
, 1
~ lMeOH
,I MeOH
Oll + NoOMe
,
,,,
I' 1
I
, I 1
CHROMATOGRAPHIC DATA "
, I
, 1

,,, ,
, 1 1
, I

,,
1
Spot Appearance: (UV) deep purpIe , 1 1
(UV/NH a) deep purple

Re Values: 0.76 (TBA), 0.74 (HOAc)

,, 1
1
1
" 1
1
UV SPECTRAL DATA (A,,,,,",,,nm)
, 1

,,,
1
I
MeOH 293, 332sh 1
, I

,,,
NaOMe 248, 327 1
AlCl a 277sh, 329, 383sh I
1
AICla/HCI 269sh, 314, 379
, 1

,,,
1
NaOAc 283, 329 1
1
NaOAc/HaBOa 294,338sh 1
1 ,
.../
(Proc. I) I
I
\ ,,
,

200 500
~.nm

MeOH + AICl 3 MeOH + NoOAc

MeOH + AICl 3 + Hel MeOH + NoOAc + H3 B0 3 - - - - -

I
I
I
1
1
1
1
1
1
1 ,'11
1 , 1
1 , 1
, 1
, 1
, 1
, 1

,
,
,
, I
1
I
1
,,
\

, 1 \
, 1 \
, 1 \
, I \
, 1 \

,
I I
I
\
\
\
I I \
I I \
l 1 \
1 \
\
,_...... " ,
,-, \
\

"
200 500 200 500
~.nm
 153
TAX1FOL1N MeOH

ON nON
MeOH + NoOMe
{'I

HOWI. .~_
,
, I
, I
ON , I
, ··N I I
, I
ON , I
, I
ON , I
, I
, I
, I
fI' I
CHROMATOGRAPHIC DATA 1\', II
I , I
Spot Appearance: (UV) deep purple 1 , I
1 , I

:
(UV/NH a) deep purple I

Re Values: 0.72 (TBA), 0.59 (HOAc)

1
I
I
, , 1

I
1,\ 1

''
UV SPECTRAL DATA (Am"""nm) I
\ 1
\ 1

:''
MeOH 290, 327sh 1
\
' 1
1
NaOMe 246sh, 326 (dec.) \
\
1
1
AICl 3 280sh, 312, 375 \ I 1
312,375 '/ I
AICla/HCl 1
NaOAc 289sh,327
NaOAc/H aB0 3 292, 337sh

u
(Proc.II)

I I
200 300 500
>-,nm

MeOH + NoOAc
MeOH + AICl 3 MeOH + NoOAc + H3 B0 3 - - - - -
MeOH + AICI 3 + HCI

,
I
I
1
1
I
1
I
1
I
1
1

r,
I
1

,,,
I
1
I
I
,
,,,
I
1
1
I 1
1 I
1
I
1
\
1
\
\ ,,
\
\
\
\
\
\
\
\

200 500 200 500

>-,nm >-,nm
 154
ASTILBIN
MeOH
MeOH + NoOMe

,.
,,, ,,, 11

CHROMATOGRAPHIC DATA ,,
, ,
I ,

,,, ,,,
I ,
Spot Appearance: (UV) deep purpie
(UV/NH a) deep purpie
Re Values: 0.66 (TBA), 0.71 (HOAc) ,, ,, ,,,
,
,,
,, ,, ,,,
UV SPECTRAL DATA (Amaz,nm) I ,

MeOH 292, 327sh

/\, ,,
,, ,,
\
NaOMe 2<Ki,328
AICl a 238, 316, 375sh
,, ,,
AICla/HCI 287sh, 314, 378
,, ,,
NaOAc 290sh,329
,, ,,
,,
NaOAc/H3 BO a 294, 335sh
(Proc. I) ,,
, \
\ ,

200 300 500

A,nm

MeOH + AICI 3 MeOH + NoOAc

MeOH + AICI 3 + HCI MeOH + NoOAc + H3 B0 3 - - - - -

,,
, \
\
\
\
\
\
\
\
\
\
\
\
\
\

200 500 200 300 500

A,nm A,nm
 155
Dl HYDROROBlNETlN
MeOH
MeOH + NaOMe
HO

,I
"
, 1
, 1
, 1
o , 1
, 1
, 1
, 1
, 1
CHROMATOGRAPHIC DATA ,
, 1

,,,
1
1
Spot Appearance: (UV) pale yellow
,
1

,,,
1
(UV/NH 3 ) light yellow- 1
purpie 1

,
1

,,,
1
R f Values: 0.36 (TBA), 0.58 (HOAc) 1
\

,
\
UV SPECTRAL DAT A (l\..,a ..,nm)
,,,
\,
1
1
MeOH 275,308
,
1
\
NaOMe 251,334 (dec.) \
AIC1 3 280, 307, 345sh 1
\
AICl 3 /HCl 275,307 1
1
NaOAc 257sh, 280, 333 \
1
NaOAc/H 3 B0 3 278,312sh 1
(Proe. II) \
\
\
\

200 500
)",nm

MeOH + AICl 3 MeOH + NaOAc

1 MeOH + NaOAc + H3 B0 3 - - - - -
1 MeOH ~ AICI 3 + HCI
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1
1

,
1
1 ,

\,
1 , \
\
\
\
\
\
\
\
\
\
\
\ ,...
200 300 400 500 200 300 400 500
)",nm )",nm