Bull. Natl. Mus. Nat. Sci., Ser. B, 38(4), pp. 189–195, December 22, 2012

Flavonoids from Reaumuria soongarica (Tamaricaceae) in Mongolia
Tsukasa Iwashina1,*, Sergey V. Smirnov2, Oyunchimeg Damdinsuren3 andKatsuhiko Kondo4
1

Department of Botany, National Museum of Nature and Science,
Amakubo 4–1–1, Tsukuba, Ibaraki 305–0005, Japan2
Department of Plant Systematics, Altai State University, Barnaul, Altai, 656099, Russia
3
Biology Division, Hovd State University, Hovd, Hovd Province, 213500, Mongolia
4
Laboratory of Plant Genetics and Breeding Science, Department of Agriculture, Faculty of Agriculture,
Tokyo University of Agriculture, Funako 1737, Atsugi, Kanagawa 243–0034, Japan* E-mail: iwashina@kahaku.go.jp(Received 21 August 2012; accepted 26 September 2012)

Abstract Ten ﬂavonoids were isolated from the aerial parts of Reaumuria soongarica which is
growing in the deserts of Mongolia. They were identiﬁed as kaempferol 7-O-diglucoside, quercetin 7-O-arabinoside, quercetin 3-O-glucoside, quercetin 3-O-glucuronide, quercetin 7-O-rhamnoside, quercetin 3-O-rutinoside, quercetin 3-methyl ether, quercetin 3-methyl ether 7-O-glucoside,
quercetin 3-methyl ether 4′-O-glucoside and isorhamnetin 7-O-rhamnoside by UV spectra, acidhydrolysis, LC-MS, and direct TLC and HPLC comparisons with authentic samples. Though theﬂavonoids of the genus Reaumuria have been found in another species, R. mucronata, those of R.
soongarica were reported for the ﬁrst time.
Key words : ﬂavonoids, isorhamnetin, kaempferol, quercetin, quercetin 3-methyl ether, Reaumuria soongarica, Tamaricaceae.

Introduction
The genus Reaumuria consists of 12 species,
belongs to the family Tamaricaceae and is distributed in the deserts of northern Africa, Asiaand southern Europe (Yang and Gaskin, 2006).
Reaumuria soongarica (Pall.) Maxim. is shrubs
and 10–30 cm tall, and growing in the deserts andmargins of lowlands in Mongolia. A ﬂavonoid of
the Reaumuria has been isolated from the leavesof R. mucronata Jaub. & Spach and identiﬁed assulphated ﬂavonol, kaempferol 3,7-disulphate(Nawwar et al., 1977). However, the ﬂavonoidsof other Reaumuria species including R. soongarica
were never reported. The family Tamaricaceae
including Reaumuria was recently incorporated
into the order Caryophyllales by Angiosperm
Phylogeny Group (APG), together with the
Plumbaginaceae, Polygonaceae, Droseraceae and

Nepenthaceae. Eight families of the Carylphyllales, Aizoaceae, Amaranthaceae including Chenopodiaceae, Basellaceae, Cactaceae, Didiereaceae,
Nyctaginaceae, Portulacaceae and Phytolaccaceae, synthesize the betalain pigments, instead of
the anthocyanins (Clement et al., 1994; Piattelliand Minale, 1964). In the Tamaricaceae, anthocyanins have been reported from three Tamarix
species, T. parviﬂora DC., T. sp. and T. tetrandra
Pall. ex Bieb., and characterized as cyanidin
3-O-glycoside, cyanidin and delphinidin glycosides (Forsyth and Simmonds, 1954), and cyanidin 3-O-glucoside and 3,5-di-O-glucoside (Scogin, 1977), respectively. Flavonols, kaempferol
and quercetin, and their glycosides are major ﬂavonoids, and also methylated ﬂavonols, rhamnazin, rhamnetin, rhamnocitrin, kaempferide,tamarixetin, kaempferol 7,4′-dimethyl ether anddillenetin, and their glycosides are found in someTsukasa Iwashina et al.

190

species of the family (e.g., Chumbalov et al.,
1975; La et al., 2011; Chakrabarty et al., 1965;
Nawwar et al., 1975, 1984; El Sissi et al., 1973;
Birkbulatova and Korulʼkina, 2001; Wang et al.,2009; Umbetova et al., 2005). Flavonols frequently occur as sulphates in the Tamaricaceae(Harborne, 1975; Tomás-Barberán et al., 1990;
Saleh et al., 1975; El Ansari et al., 1976). Flavones, chrysoeriol, apigenin 7,4′-dimethyl ether,luteolin 5-methyl ether were found in Myricaria
bracteata (Royle) Franchet. (Zhou et al., 2006)
and three Tamarix species, T. chinensis Lour.
(Wang et al., 2009), T. elongata Redeb. and T.
laxa Willd. (Umbetova et al., 2004, 2005). Polymethylated ﬂavones, gardenins A–C and E,
nevadensin, tamadone and tamaridone were also
isolated from Tamarix dioica Roxb. ex Roth(Parmar et al., 1994). In this paper, we describe
the identiﬁcation of ﬂavonoids and their chemical properties from the aerial parts of Reaumuria
soongarica growing in Mongolia.
Materials and Methods
Plant materials
Reaumuria soongarica (Pall.) Maxim. wascollected between Hovd and Erdeneburen Sum,
2350 m alt., Hovd Prov., Mongolia in 16 Sept.
2007, during the Altai Mountains and adjacentarea Botanical Expedition in September 2007.
Voucher specimen was deposited in the herbarium of National Museum of Nature and Science,
Japan (TNS).
General
UV spectra were recorded on a Shimadzu
MPS-2000 Multi purpose recording spectrophotometer according to Mabry et al. (1970).
LC-MS were measured on a Shimadzu LC-MS
systems using a Inertsil ODS-4 column [I.D.
2.1×100 mm (GL Sciences Inc., Japan)], at a
ﬂow-rate of 0.1 ml min−1 eluting with MeCN/
H2O/HCOOH (20 : 75 : 5), ESI＋ 4.5 kV and ESI−
3.5 kV, 250ºC. HPLC survey of the isolated ﬂavonoids and crude extracts was performed with a
Shimadzu HPLC systems using a Senshu Pak

Pegasil ODS column (I.D. 6.0×150 mm, Senshu
Scientiﬁc Co. Ltd., Japan), at a ﬂow-rate of
1.0 ml min−1. Detection was 350 nm and eluent
was used MeCN/H2O/H3PO4 (20 : 80 : 0.2). Acidhydrolysis of the ﬂavonol glycosides was performed in 12% aq. HCl, 100°C, 30 min. Flavonolaglycones and sugars were identiﬁed with HPLC
and PC, respectively, in comparisons withauthentic specimens. The solvent systems ofTLC (Merck) and preparative PC (Advantec) are
as follows; BAW (n-BuOH/HOAc/H2O＝4 : 1 : 5,
upper phase), 15% HOAc and BEW (n-BuOH/
EtOH/H2O＝4 : 1 : 2.2) in room temperature.
Extraction and separation
Dryed aerial parts (23.3 g) of R. soongarica
were extracted with MeOH. After concentration,
crude extracts were applied to preparative paper
chromatography using solvent systems, BAW,
15% HOAc and then BEW. The obtained ﬂavonoids were puriﬁed with Sephadex LH-20 column chromatography using solvent system, 70%
MeOH.
Identiﬁcation
The ﬂavonoids were identiﬁed by UV spectroscopy, LC-MS, characterization of acid hydrolysates, and direct TLC and HPLC comparisonswith authentic samples. TLC, HPLC, UV and
LC-MS data of the isolated ﬂavonoids are as follows.
Kaempferol 7-O-diglucoside (1). TLC (Rf):
0.83 (BAW), 0.81 (BEW), 0.07 (15%HOAc);
color UV (365 nm)—yellow, UV/NH3—brightyellow. HPLC (tR): 13.89 min. UV λmax (nm):
MeOH 256, 369; ＋NaOMe decomposition;＋AlCl3 267, 306sh, 360, 434; ＋AlCl3/HCl 265,303sh, 360, 422; ＋NaOAc 257, 409; ＋NaOAc/
H3BO3 255, 375. LC-MS: m/z 609 [M−H]−(molecular ion peak, kaempferol＋2 mol glucose), m/z 287 [M−324＋H]＋ (fragment ion
peak, kaempferol).
Quercetin 7-O-arabinoside (2). TLC (Rf): 0.28
(BAW), 0.31 (BEW), 0.07 (15%HOAc); color
UV (365 nm) and UV/NH3—yellow. HPLC (tR):
5.16 min. UV λmax (nm): MeOH 256, 372;

Flavonoids from Reaumuria soongarica＋NaOMe decomposition; ＋AlCl3 271, 457;
＋AlCl3/HCl 265, 299sh, 362, 425; ＋NaOAc
263, 416; ＋NaOAc/H3BO3 260, 390. LC-MS:
m/z 435 [M＋H]＋, 433 [M−H]− (molecular ion
peaks, quercetin＋1 mol arabinose).
Quercetin 3-O-glucoside (isoquercitrin, 3).
TLC (Rf): 0.68 (BAW), 0.77 (BEW), 0.20
(15%HOAc); color UV (365 nm)—dark purple,
UV/NH3—dark yellow. HPLC (tR): 4.82 min.
UV λmax (nm): MeOH 258, 263sh, 360;
＋NaOMe 272, 330, 408 (inc.); ＋AlCl3 275,
436; ＋AlCl3/HCl 269, 296sh, 362, 402;
＋NaOAc 273, 325, 390; ＋NaOAc/H3BO3 262,
381. LC-MS: m/z 465 [M＋H]＋, 463 [M−H]−(molecular ion peaks, quercetin＋1 mol glucose),m/z 303 [M−162＋H]＋ (fragment ion peak,quercetin).
Quercetin 7-O-rhamnoside (vincetoxicoside B,
4). TLC (Rf): 0.67 (BAW), 0.69 (BEW), 0.07
(15%HOAc); color UV (365 nm)—yellow, UV/
NH3—bright yellow. HPLC (tR): 8.53 min. UV
λmax (nm): MeOH 256, 269sh, 374; ＋NaOMe
decomposition; ＋AlCl3 256, 272, 459; ＋AlCl3/
HCl 265, 298sh, 361, 427; ＋NaOAc 263, 413;
＋NaOAc/H3BO3 260, 389. LC-MS: m/z 449[M＋H]＋, 447 [M−H]− (molecular ion peaks,
quercetin＋1 mol rhamnose), m/z 303 [M−146＋H]＋, 301 [M−146−H]− (fragment ion
peaks, quercetin).
Quercetin 3-O-rutinoside (rutin, 5). TLC (Rf):
0.51 (BAW), 0.51 (BEW), 0.58 (15%HOAc);
color UV (365 nm)—dark purple, UV/NH3—
dark yellow. HPLC (tR): 4.53 min. UV λmax(nm): MeOH 257, 264sh, 358; ＋NaOMe 273,
323, 411 (inc.); ＋AlCl3 274, 432; ＋AlCl3/HCl
268, 299, 362, 396; ＋NaOAc 273, 327, 403;
＋NaOAc/H3BO3 262, 378. LC-MS: m/z 611[M＋H]＋, 609 [M−H]− (molecular ion peaks,
quercetin＋each 1 mol glucose and rhamnose),m/z 303 [M−308＋H]＋ (fragment ion peak,quercetin).
Quercetin 3-O-glucuronide (miquelianin, 6).
TLC (Rf): 0.49 (BAW), 0.44 (BEW), 0.30
(15%HOAc); color UV (365 nm)—dark purple,
UV/NH3—dark yellow. HPLC (tR): 5.02 min.
UV λmax (nm): MeOH 257, 266sh, 356;

191

＋NaOMe 275, 323, 405 (inc.); ＋AlCl3 273,
424; ＋AlCl3/HCl 274, 303, 361, 405sh;＋NaOAc 272, 328, 400; ＋NaOAc/H3BO3 264,373. LC-MS: m/z 479 [M＋H]＋, 477 [M−H]−(molecular ion peaks, quercetin＋1 mol glucuronic acid), m/z 303 [M−176＋H]＋ (fragment
ion peak, quercetin).
Quercetin 3-methyl ether (7). TLC (Rf): 0.89
(BAW), 0.89 (BEW), 0.07 (15%HOAc); color
UV (365 nm)—dark purple, UV/NH3—dark yellow. HPLC (tR): 12.17 min. UV λmax (nm):
MeOH 257, 265sh, 358; ＋NaOMe 274, 323,
410 (inc.); ＋AlCl3 275, 435; ＋AlCl3/HCl 264,
301, 359, 396sh; ＋NaOAc 273, 327, 398;
＋NaOAc/H3BO3 262, 379. LC-MS: m/z 317[M＋H]＋, 315 [M−H]− (molecular ion peak,tetrahydroxy-monomethoxyﬂavone).
Quercetin 3-methyl ether 7-O-glucoside(transilin, 8). TLC (Rf): 0.66 (BAW), 0.75
(BEW), 0.29 (15%HOAc); color UV (365 nm)—dark purple, UV/NH3—dark yellow. HPLC (tR):
5.17 min. UV λmax (nm): MeOH 257, 268sh,
360; ＋NaOMe 270, 395 (inc.); ＋AlCl3 276,
440; ＋AlCl3/HCl 270, 298sh, 364, 403;
＋NaOAc 261, 371; ＋NaOAc/H3BO3 261, 370.
LC-MS: m/z 479 [M＋H]＋, 477 [M−H]−(molecular ion peaks, quercetin 3-methyl ether＋
1 mol glucose), m/z 317 [M−162＋H]＋, 315[M−162−H]− (fragment ion peaks, quercetin
3-methyl ether).
Quercetin 3-methyl ether 4′-O-glucoside (neochilenin, 9). TLC (Rf): 0.62 (BAW), 0.59
(BEW), 0.23 (15%HOAc); color UV (365 nm)
and UV/NH3—dark yellow. HPLC (tR):
6.74 min. UV λmax (nm): MeOH 256sh, 269,
349; ＋NaOMe 273, 380 (dec.); ＋AlCl3 268sh,
277, 298sh, 354, 400; ＋AlCl3/HCl 260sh, 278,295sh, 348, 398; ＋NaOAc 275, 377; ＋NaOAc/
H3BO3 257sh, 269, 352. LC-MS: m/z 479[M＋H]＋, 477 [M−H]− (molecular ion peaks,
quercetin 3-methyl ether＋1 mol glucose).
Isorhamnetin 7-O-rhamnoside (10). TLC (Rf):
0.76 (BAW), 0.77 (BEW), 0.07 (15%HOAc);
color UV (365 nm)—yellow, UV/NH3—brightyellow. HPLC (tR): 16.60 min. UV λmax (nm):
MeOH 255, 267sh, 373; ＋NaOMe decomposi-

Tsukasa Iwashina et al.

192

tion; ＋AlCl3 265, 320sh, 364, 429; ＋AlCl3/HCl
264, 319sh, 362, 427; ＋NaOAc 256, 415;
＋NaOAc/H3BO3 255, 374. LC-MS: m/z 463[M＋H]＋, 461 [M−H]− (molecular ion peaks,
isorhamnetin＋1 mol rhamnose), m/z 317[M−146＋H]＋, 315 [M−146−H]− (fragment
ion peaks, isorhamnetin).
Results and Discussion
Ten ﬂavonoids (1–10) were isolated from theaerial parts of Reaumuria soongarica. Flavonoid
1 produced kaempferol and glucose by acidhydrolysis. UV spectral properties in addition tovarious shift reagents (NaOMe, AlCl3, AlCl3/HCl,
NaOAc and NaOAc/H3BO3) according to Mabry
et al. (1970) showed that 1 is 7-substituted
kaempferol. The attachment of 2 mol glucose tokaempferol was shown by LC-MS survey, i.e.,
appearance of the molecular ion peak, m/z 609[M−H]− and fragment ion peak, m/z 287[M−324＋H]＋. From the results describedabove, 1 was characterized as kaempferol
7-O-diglucoside.
Acid hydrolysis of 2 liberated quercetin andarabinose. UV spectral properties showed that
this glycoside is 7-substituted quercetin. Since
molecular ion peak, m/z 435 [M＋H]＋, appearedon LC-MS, it was shown that 1 mol arabinose isattached to quercetin. Thus, 2 was identiﬁed as
quercetin 7-O-arabinoside (Fig. 1).
UV spectral data of 3 and 5 showed that they
are 3-substituted quercetin. Quercetin and glucose, and quercetin, glucose and rhamnose were
produced by acid hydrolysis of 3 and 5, respectively. Finally, 3 and 5 were identiﬁed as quercetin 3-O-glucoside (isoquercitrin, Fig. 2) and

Fig. 1.

Quercetin 7-O-arabinoside (2).

quercetin 3-O-rutinoside (rutin, Fig. 4) by direct
TLC and HPLC comparisons with authentic samples from the leaves of Corylopsis spp. (Hamamelidaceae) (Iwashina et al., 2012).
Flavonoid 4 showed yellow under UV light(365 nm), which shows that the compound is aﬂavonol having free 3- and 4′-hydroxyl groups,
as well as 1 and 2. Quercetin and rhamnose were
liberated by acid hydrolysis of 4. It was shown
by UV spectral survey and LC-MS that 1 molrhamnose is attached to 7-position of quercetin.

Fig. 2.

Quercetin 3-O-glucoside (Isoquercitrin, 3).

Fig. 3. Quercetin 7-O-rhamnoside (Vincetoxicoside B, 4).

Fig. 4.

Quercetin 3-O-rutinoside (Rutin, 5).

Flavonoids from Reaumuria soongarica

Thus, 4 was identiﬁed as quercetin 7-O-rhamnoside (Fig. 3).
Flavonoid 6 produced quercetin and glucuronic acid by acid hydrolysis. LC-MS survey
showed the attachment of 1 mol glucuronic acidto quercetin. UV spectral properties of original
glycoside indicated that 6 is 3-substituted quercetin. Finally, 6 was identiﬁed as quercetin
3-O-glucuronide (miquelianin, Fig. 5) by direct
TLC and HPLC comparison with authentic sample from the fronds of Adiantum capillus-veneris
L. (Adiantaceae) (Iwashina et al., 1995).
LC-MS survey of 7 showed that the compoundis tetrahydroxy-monomethoxyﬂavone. It wasdetermined by UV spectral survey that amethoxyl group is attached to 3-position of ﬂavonol. Finally, Rf values of TLC and retention
time of HPLC of the compound completely
agreed with those of authentic quercetin
3-methyl ether from the ﬂowers of Neoporteria
spp. (Cactaceae) (Iwashina et al., 1984). Thus, 7
was identiﬁed as an aglycone, quercetin 3-methyl
ether (Fig. 6).
It was shown by acid hydrolysis that 8 and 9
are quercetin 3-methyl ether glycosides. Glucose
was liberated as a glycosidic sugar from the bothglycosides. The attachment of 1 mol glucose to

Fig. 5.

Quercetin 3-O-glucuronide (Miquelianin, 6).

Fig. 6.

Quercetin 3-methyl ether (7).

193

7-position and 4′-position of quercetin 3-methyl
ether was determined by UV spectral and LC-MS
survey of 8 and 9, respectively. Finally, 8 and 9
were identiﬁed as quercetin 3-methyl ether
7-O-glucoside (transilin, Fig. 7) and quercetin
3-methyl ether 4′-O-glucoside (neochilenin, Fig.
8) by direct TLC and HPLC comparisons withauthentic samples from the ﬂowers of Parodia
sanguiniﬂora Frič ex Backbg. and Neochilenia
spp. (Cactaceae) (Iwashina et al., 1984).
Isorhamnetin and rhamnose were produced byacid hydrolysis of 10. It was shown by UV spectral and LC-MS survey that 1 mol rhamnose isattached to 7-position of isorhamnetin. From theresults described above, 10 was determined as
isorhamnetin 7-O-rhamnoside (Fig. 9).

Fig. 7. Quercetin 3-methyl ether 7-O-glucoside(Transilin, 8).

Fig. 8. Quercetin 3-methyl ether 4′-O-glucoside(Neochilenin, 9).

Fig. 9.

Isorhamnetin 7-O-rhamnoside (10).

Tsukasa Iwashina et al.

194

Since kaempferol 3,7-disulphate alone wasreported from the genus Reaumuria (Nawwar etal., 1977), ten ﬂavonols, which were isolated
from R. soongarica in this survey, were reported
from the genus for the ﬁrst time. Moreover,though quercetin 3-O-glucuronide (6) and quercetin 3-O-glucoside (3) have been found in otherTamaricaceous species, Myricaria germanica(L.) Desv. (La et al., 2011) and Tamarix nilotica(Ehrenb.) Bunge (Nawwar et al., 1984), andsome Myricaria and Tamarix species (La et al.,2011; Chakrabarty et al., 1965; Ishak et al.,
1972; Umbetova et al., 2005; Nawwar et al.,1984), respectively, other eight ﬂavonols, kaempferol 7-O-diglucoside (1), quercetin 7-O-arabinoside (2), quercetin 7-O-rhamnoside (4), quercetin
3-O-rutinoside (5), quercetin 3-methyl ether (7),quercetin 3-methyl ether 7-O-glucoside (8), quercetin 3-methyl ether 4′-O-glucoside (9) and isorhamnetin 7-O-rhamnoside (10), were found in
the Tamaricaceae for the ﬁrst time. Flavonol sulphates have been reported from some Tamaricaceous species (Harborne, 1975; Tomás-Barberán
et al., 1990). However, they were not recognizedin R. soongarica.
Acknowledgments
The collection of plant materials in Mongolia
in 2007 was supported by a Grant-in-Aid for the
Scientiﬁc Programs (A) (no. 19255004, Representative, Katsuhiko Kondo) from the Ministryof Education, Culture, Sports, Science and Technology, Japan.
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