Bull. Natl. Mus. Nat. Sci., Ser. B, 36(4), pp. 141–154, November 22, 2010

Saussurea Species from the Altai Mountains and Adjacent Area,
and Their Flavonoid Diversity
Tsukasa Iwashina1, *, Sergey V. Smirnov2, Oyunchimeg Damdinsuren3and Katsuhiko Kondo4
1

Department of Botany, National Museum of Nature and Science, Amakubo 4–1–1, Tsukuba, 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 15 Aug. 2010; accepted 22 Sept. 2010)

Abstract Seven Saussurea species, i.e., S. alpina, S. daurica, S. laciniata, S. pricei, S. pseudoalpina, S. salicifolia and S. salsa, were collected in the Altai Mountains in Russia and Mongolia.
They were surveyed for flavonoid characters. Thirteen flavonoids belonging to flavones andflavonols, i.e., apigenin 7-O-glucuronide, apigenin 7-O-glucoside, luteolin 7-O-glucuronide, luteolin 7-O-glucoside, chrysoeriol 7-O-glucuronide, chrysoeriol 7-O-glucoside, chrysoeriol 7-Orhamnoside, jaceosidin, nepetin, hispidulin (flavones), quercetin 3-O-rutinoside, quercetin 3-Oglucoside and isorhamnetin 3-O-rutinoside (flavonols), were found in various combination fromtheir species. Of their species, S. daurica, S. laciniata and S. salsa synthesized flavone glycosides
alone. On the other hand, S. pricei, S. pseudo-alpina and S. alpina were occurred flavonol glycosides. The former species was accompanied with free flavones. S. salicifolia synthesized only one
flavone aglycone, hispidulin. Thus, it was clear that the genus Saussurea is not only morphologically and geographically but also chemically diversified.
Key words : Altai Mountains, flavones, flavonoid diversity, flavonols, Saussurea.

Introduction
The genus Saussurea DC. (Asteraceae) consists of some 300 species, which are mainly distributed in east Asia and widely adapted fromlowlands to high alpine zones (Mabberley, 1997).
Some of the plants occur in the Himalayas, theTien Shan Mountains and the Altai Mountains. S.
medusa Maxim. is characterized by highly pubescent bracts of its inflorescences, which areconsidered to be an adaptive morphological trait,
allowing the plant to flowers at low temperatures.
Therefore, the plant is also named ‘sweater
plant’ (Tsukaya et al., 2002). Another Saussurea
species, S. involucrata Karel. & Kir. with largetranslucent cream-colored bracts concealing thehuge inflorescence, are named ‘glasshouse plant’(Ohba, 1988).
Flavonoids have been reported from some
Saussurea species which are mainly native to
China. Flavones, apigenin and its 7-O-glucosideand 7-O-neohesperidoside, chrysoeriol 7-O-glucoside and a flavonol, quercetin were isolated
from S. gossypiphora D. Don (Lin-gang andMin, 1989; Zheng et al., 1991). Quercetin andquercetin 3-O-rutinoside, and hispidulin and pectolinarigenin were found in S. controversa DC.
(Syrchyna et al., 1993) and in S. elegans Ledeb.
(Sham’yanov et al., 1983), respectively. Two
flavonol glycosides, quercetin 3-O-rutinoside and3-O-rhamnoside, and two free flavones, jaceosidin and hispidulin were isolated from S. involu-

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crata (Jia et al., 1983, 1988; Yi et al., 2005).
Apigenin and its 7-O-neohesperidoside, luteolin
and its 7-O-neohesperidoside, and quercetin andits 3-O-glucoside were reported from S. medusa(Jia et al., 1989; Fan and Yue, 2003). From
S. pulchella Fisch. ex Colla (Basargin and Tsiklauri, 1990) and S. tridactyla Sch.Bip. ex Hook.f.
(Zhang et al., 2003), common flavonoids, apigenin, luteolin, kaempferol and quercetin andtheir glycosides were reported. A flavone glycoside, acacetin 7-O-rutinoside was also isolated
from S. tridactyla (Ren et al., 2001). An anthocyanin, cyanidin 3-O-glucoside, which was foundin Saussurea species for the first time, was isolated from S. pulchella (Basargin and Tsiklauri,1990). Comparatively rare polymethoxyflavonol,
penduletin was reported from the whole plantsof S. parviflora DC. (Yang et al., 2003). New
two crotonylated flavonoids, kaempferol andquercetin 3-O-(6-crotonyl)-glucosides were
found in S. japonica (Thunb.) DC. in China (Shiet al., 1991). Dihydrochalcone, asebogenin 2-Oglucoside was first reported from S. mongolica
Franchet, together with flavonol glycosides,
rhamnocitrin 3-O-rhamnoside, and kaempferol
and quercetin 3-O-glucosides and 3-O-rhamnosides (Jiang et al., 2004). Rare flavonol glycosides, quercetin and tamarixetin 5-O-glucosides,and 6-hydroxykaempferol 3-methyl ether 6-Oglucoside were isolated from S. stella Maxim.,
together with apigenin and acacetin and their
7-O-glucosides, luteolin, chrysoeriol 7-O-glucoside, and kaempferol and quercetin 3-O-rhamnosides (Shen et al., 2004; Zheng et al., 1997).
Recently, we surveyed nine Saussurea species,
S. alberti Regel & Winkler, S. elegans, S.
gnaphalodes Ostenf., S. involucrata, S. konuroba
Saposchn., S. kuschakewiczii C. Winkl., S. leucophylla Schrenk, S. schanginiana Fisch. & Herd.,
and S. sordida Kar. & Kir. from the Tien Shan
Mountains in Kazakhstan and Kirgyz for
flavonoid compounds (Kusano et al., 2007). Tenflavonol glycosides, kaempferol 3-O-rutinoside,
5-O-glucoside and 7-O-glucoside, quercetin 3-Orutinoside, 3-O-glucoside, 3-O-galactoside, 5-Oglucoside and 7-O-glucoside, and isorhamnetin

3-O-rutinoside and 5-O-glucoside, eight flavone
aglycones, luteolin, luteolin 7-methyl ether,hispidulin, nepetin, selagin, selagin 7-methyl
ether, velutin and jaceosidin, and thirteen flavone
glycosides, apigenin 7-O-rutinoside and 7-O-glucoside, luteolin 7-O-rutinoside, 7-O-glucoside, 7O-galactoside, 7-O-glucuronide and 5-O-glucoside, hispidulin and nepetin 7-O-glucosides, isovitexin, isoorientin, apigenin 6,8-C-glycoside andluteolin 8-C-glycoside, were reported (Kusano etal., 2007). Their Saussurea species variously differed in their flavonoid composition. It has beenshown that Saussurea species is not only morphologically but also chemically diversified.
In this paper, as a series of flavonoid survey inthe genus Saussurea, flavonoid compounds of thespecies from the Altai Mountains were investigated.

Materials and Methods
Plant materials
Seven Saussurea species were collected in
Russia and Mongolia during the Altai Mountains
and adjacent area Botanical Expedition in September 2007. Voucher specimens have been deposited in the herbarium of National Museum of
Nature and Science, Japan (TNS). Collection
sites and dates of plant materials are as follows.
Saussurea alpina DC. High mountain meadow,
Bayan Gol, 2450 m alt., Erdeneburen Sum, Hovd
Prov., Mongolia. 48°3869N, 091°0774E, 16
Sept. 2007 (TNS9531921).
Saussurea daurica Adams. (Fig. 1). Lake sideof Eli-Hur, 2070 m alt., Bayan-Ulgii-Aimak,
Bayan-Ulgii Prov., Mongolia. 48°3552N,
090°0024E, 14 Sept. 2007 (TNS9531904).
Modon Ovou, 1555 m alt., South of Hovd
City, Hovd Prov., Mongolia. 47°5688N,
091°4667E, 15 Sept. 2007.
Saussurea laciniata Ledeb. River side,
Ongostnii Ulaan Mountain. Northeast of Hovd
City, Hovd Prov., Mongolia. 48°1639N,
091°5308E, 15 Sept. 2007.
Saussurea pricei N.D. Simpson (Fig. 2). Dry
steppe of Bayan Gol, 2018 m alt., Tsambagarav

Flavonoids from Saussurea in Altai

Fig. 1.

143

Saussurea daurica.

Fig. 3.

Fig. 2.

Saussurea pricei.

Mountain, Erdeneburen Sum, Hovd Prov., Mongolia. 48°3888N, 091°1162E, 16 Sept. 2007
(TNS9531920).
Saussurea pseudo-alpina N.D. Simpson. High
mountain meadow, 2450 m alt., Bayan Gol,
Erdeneburen Sum, Hovd Prov., Mongolia.
48°3869N, 091°0774E, 16 Sept. 2007.
Saussurea salicifolia DC. The place which
Chuya River joins with Katum River, 780 m alt.,
Onguday District, Altai Republic, Russia.
50°2377N, 086°4041E, 21 Sept. 2007
(TNS9531929).
Saussurea salsa Spreng. (Fig. 3). Chavtsaliin
Gol, 1260 m alt., Erdeneburen Sum, Hovd Prov.,
Mongolia. 48°4023N, 091°19Å94E, 17 Sept.
2007.
General
UV spectra were recorded on a Shimadzu

Saussurea salsa.

MPS-2000 Multi purpose recording spectrophotometer according to Mabry et al. (1970). LCMS were measured using a Inertsil ODS-4 column [I.D. 2.1100 mm (GL Sciences Inc.)],at a flow-rate of 0.1 ml min1, eluting with
MeCN/H2O/HCOOH (20 : 75 : 5) or (30 : 65 : 5),
ESI 4.5 kV and ESI 3.5 kV, 250°C. 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.), ata flowe-rate of 1.0 ml min1. Detection was
350 nm and eluents were MeCN/H2O/H3PO4(20 : 80 : 0.2) for glycosides and (35 : 65 : 0.2) for
aglycones.
Extraction and separation
Dryed leaves of S. alpina (0.4 g), S. daurica(62.6 g), S. pricei (16.5 g), S. pseudo-alpina (0.5g) and S. salsa (27.1 g), and dryed aerial parts of
S. laciniata (15.4 g) and S. salicifolia (9.1 g) wereextracted with MeOH, respectively. After concentration, the extracts were separated by preparative paper chromatography using solvent systems: BAW (n-BuOH/HOAc/H2O4 : 1 : 5, upper
phase), 15% HOAc and then BEW (nBuOH/EtOH/H2O4 : 1 : 2.2). Isolated flavonoids

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Tsukasa Iwashina et al.

were purified by Sephadex LH-20 column chromatography using solvent system: 70% MeOH.
Identification
The flavonoids were identified by UV spectroscopy, LC-MS and direct TLC and HPLC
comparisons with authentic samples. TLC, UV
and LC-MS data of the isolated flavonoids wereas follows.
Apigenin 7-O-glucuronide (1). TLC: Rf 0.61
(BAW), 0.23 (BEW), 0.15 (15%HOAc); UV –dark purple, UV/NH3 – dark greenish yellow. UV:l max (nm) MeOH 268, 333; NaOMe 273, 379(inc.); AlCl3 275, 298, 347, 376; AlCl3/HCl
275, 299, 340, 373; NaOAc 256sh, 267, 388;NaOAc/H3BO3 268, 340. LC-MS: m/z 447[MH], 445 [MH](apigenin1 mol glucuronic acid); m/z 271 [M176H], 269[M176H] (apigenin).
Apigenin 7-O-glucoside (cosmosiin, 2). TLC:
Rf 0.66 (BAW), 0.66 (BEW), 0.13 (15%HOAc);
UV – dark purple, UV/NH3 – dark greenish yellow. UV: l max (nm) MeOH 268, 333; NaOMe
273, 379 (inc.); AlCl3 276, 299, 347, 377;
AlCl3/HCl 276, 298, 339, 376; NaOAc 257,
267, 389; NaOAc/H3BO3 268, 341. LC-MS:
m/z 433 [MH], 431 [MH] (apigenin1
mol glucose); m/z 271 [M162H] (apigenin).
Luteolin 7-O-glucuronide (3). TLC: Rf 0.34
(BAW), 0.19 (BEW), 0.08 (15%HOAc); UV –dark purple, UV/NH3 – yellow. UV: l max (nm)
MeOH 256, 268, 348; NaOMe 269, 392 (inc.);
AlCl3 273, 422; AlCl3/HCl 267, 273sh, 294,
358, 378sh; NaOAc 260, 402; NaOAc/
H3BO3 260, 369. LC-MS: m/z 463 [MH], 461[MH] (luteolin1 mol glucuronic acid); m/z
287 [M176H], 285 [M176H] (luteolin).
Luteolin 7-O-glucoside (4). TLC: Rf 0.36
(BAW), 0.38 (BEW), 0.06 (15%HOAc); UV –dark purple, UV/NH3 – yellow. UV: l max (nm)
MeOH 255, 266sh, 348; NaOMe 267, 391(inc.); AlCl3 273, 427; AlCl3/HCl 264sh,
273, 295, 359, 383; NaOAc 260, 405;NaOAc/H3BO3 259, 373. LC-MS: m/z 449[MH], 447 [MH] (luteolin1 mol glu-cose); m/z 287 [M162H], 285 [M162
H] (luteolin).
Chrysoeriol 7-O-glucuronide (5). TLC: Rf
0.41 (BAW), 0.19 (BEW), 0.08 (15%HOAc);
UV – dark purple, UV/NH3 – yellow. UV: l max(nm) MeOH 253, 268, 345; NaOMe 266, 391(inc.); AlCl3 264sh, 273, 296sh, 364sh, 387;
AlCl3/HCl 262, 273sh, 294sh, 357, 384sh;
NaOAc 259, 406; NaOAc/H3BO3 255sh,
265sh, 354. LC-MS: m/z 477 [MH], 475[MH] (chrysoeriol1 mol glucuronic acid).
Chrysoeriol 7-O-glucoside (6). TLC: Rf 0.49
(BAW), 0.44 (BEW), 0.08 (15%HOAc); UV –dark purple, UV/NH3 – yellow. UV: l max (nm)
MeOH 253, 268, 345; NaOMe 266, 391 (inc.);
AlCl3 264sh, 273, 296sh, 364sh, 387;
AlCl3/HCl 262, 273sh, 294sh, 357, 384sh;
NaOAc 259, 406; NaOAc/H3BO3 255,
265sh, 354. LC-MS: m/z 463 [MH], 461[MH] (chrysoeriol  1 mol glucose), m/z 301[M162H] (chrysoeriol).
Chrysoeriol 7-O-rhamnoside (7). LC-MS: m/z
447 [MH] (chrysoeriol1 mol rhamnose),m/z 299 [M146H] (chrysoeriol).
Quercetin 3-O-rutinoside (rutin, 8). TLC: Rf
0.49 (BAW), 0.52 (BEW), 0.46 (15%HOAc);
UV – dark purple, UV/NH3 – yellow. UV: l max(nm) MeOH 257, 266sh, 356; 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 611[MH], 609 [MH] (quercetineach 1 mol
glucose and rhamnose); m/z 303 [M308H]
(quercetin).
Isorhamnetin 3-O-rutinoside (narcissin, 9).
TLC: Rf 0.55 (BAW), 0.61 (BEW), 0.48
(15%HOAc); UV – dark purple, UV/NH3 – yellow. UV: l max (nm) MeOH 255, 265sh, 357;
NaOMe 273, 330, 411 (inc.); AlCl3 269, 303,
367sh, 403; AlCl3/HCl 268, 300, 359, 395;NaOAc 272, 325, 408; NaOAc/H3BO3 256,267sh, 361. LC-MS: m/z 625 [MH], 623[MH] (isorhamnetineach 1 mol glucose andrhamnose); m/z 479 [M146H] (isorhamnetin1 mol glucose); m/z 317 [M308H],315 [M308H](isorhamnetin).

Flavonoids from Saussurea in Altai

Hispidulin (5,7,4-Trihydroxy-6-methoxyflavone, 11). UV: l max (nm) MeOH 275, 335;
NaOMe 276, 324, 393 (inc.); AlCl3 263sh,
282sh, 302, 360, 387sh; AlCl3/HCl 287sh,
300, 354, 387sh; NaOAc 275, 312, 330,
391; NaOAc/H3BO3 277, 340. LC-MS: m/z
301 [MH], 299 [MH] (trihydroxymonomethoxyflavone).
Nepetin (5,7,3,4-Tetrahydroxy-6-methoxyflavone, 12). UV: l max (nm) MeOH 256, 272,
345; NaOMe 272, 336, 405 (inc.); AlCl3
274, 303sh, 422; AlCl3/HCl 259, 283, 294sh,
363, 393sh; NaOAc 273, 326sh, 397;NaOAc/H3BO3 266, 376, 427sh. LC-MS: m/z
317 [MH], 315 [MH] (tetrahydroxymonomethoxyflavone).
Jaceosidin (5,7,4-Trihydroxy-6,3-dimethoxyflavone, 13). UV: l max (nm) MeOH 274, 343;
NaOMe 274, 330, 405 (inc.); AlCl3 256sh,
273sh, 282sh, 366, 387sh; AlCl3/HCl 275sh,
285sh, 359, 387sh; NaOAc 266sh, 275, 323sh,
402; NaOAc/H3BO3 275, 348. LC-MS: m/z
331 [MH], 329 [MH] (trihydroxydimethoxyflavone).
Results and Discussion
Identification of flavonoids
Flavonoid 1 was obtained as pale yellow powder (ca. 5 mg) from S. daurica and S. laciniata.
UV spectral properties of the compound showed
the presence of free 5- and 4-hydroxyl and substituted 7-hydroxyl groups of flavone nucleus. Itsacid hydrolysis liberated apigenin and glucuronic
acid. The attachment of 1 mol glucuronic acid toapigenin was shown by LC-MS, i.e., appearanceof a molecular ion peak, m/z 447 [MH]. Original glycoside was finally identified as apigenin
7-O-glucuronide (Fig. 4) by direct TLC andHPLC comparison with authentic sample fromthe leaves of Uncarina grandidieri (Baill.) Stapf.
(Pedaliaceae) (Yamazaki et al., 2007).
UV spectral properties of flavonoid 2 was essentially the same with those of apigenin 7-Oglucuronide, showing that the compound is apigenin 7-O-glycoside. LC-MS survey indicated145

Fig. 4.

Apigenin 7-O-glucuronide (1).

Fig. 5.

Apigenin 7-O-glucoside (2).

Fig. 6.

Luteolin 7-O-glucuronide (3).

that 1 mol hexose is attached to apigenin. Direct
TLC and HPLC comparison of flavonoid 2 withauthentic cosmosiin from the leaves of Helwingia
japonica (Thunb.) F.G. Dietrich (Cornaceae)(Iwashina et al., 1997) showed that the flavonoid
is apigenin 7-O-glucoside (Fig. 5).
Flavonoids 3 and 4 (ca. 10 mg and 5 mg) wereobtained as pale yellow powders from S. daurica
and S. salsa, respectively, and shown by UV
spectral survey to be flavones having free hydroxyl groups to 5-, 3- and 4-positions and aglycosyl group to 7-position. Luteolin and glucuronic acid (3) and luteolin and glucose (4)were liberated by their acid hydrolysis. Molecular ion peaks, m/z 463 [MH] (3) and m/z 449[MH] (4) appeared on the chromatograms of
LC-MS, showing the attachment of 1 mol glucuronic acid and glucose to luteolin, respectively.
Finally, flavonoids 3 and 4 were identified as luteolin 7-O-glucuronide (Fig. 6) and luteolin 7-O-

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Tsukasa Iwashina et al.

glucoside (Fig. 7) by direct TLC and HPLC
comparisons with authentic samples from Uncarina grandidieri (Yamazaki et al., 2007) andSchmalhausenia nidulans Petrak (Asteraceae)(Iwashina and Kadota, 1999).
Flavonoid 5 produced chrysoeriol and glucuronic acid by acid hydrolysis. The attachmentof 1 mol glucuronic acid to chrysoeriol was
shown by UV spectral and LC-MS survey. Original glycoside was compared its Rf values and retention time with those of authentic chrysoeriol
7-O-glucuronide (Fig. 8) from the leavesof Chrysanthemum japonense Nakai var.
ashizuriense Kitam. (Uehara et al., unpublisheddata), by TLC and HPLC, and they completely
agreed with each other. Flavonoids 6 and 7 werealso characterized as chrysoeriol 7-O-glucoside(Fig. 9) and chrysoeriol 7-O-rhamnoside (Fig.
10) by UV spectral and LC-MS survey.
UV spectral properties of flavonoid 8 were

Fig. 7.

those of flavonol having free 5-, 7-, 3- and 4hydroxyl and 3-O-glycosyl groups. By acid hydrolysis, quercetin, glucose and rhamnose were
liberated. The presence of each 1 mol glucose
and rhamnose was shown by LC-MS survey. Finally, flavonoid 8 was identified as quercetin 3O-rutinoside (Fig. 11) by TLC and HPLC comparison with authentic rutin from the leavesof Saruma henryi Oliver (Aristolochiaceae)(Iwashina et al., 2002).
Flavonoid 9 was obtained as pale yellow powder (ca. 15 mg) from S. pricei and was flavonolhaving 5-, 7- and 4-hydroxyl, and 3- and 3-substituted hydroxyl groups, which was shown by
UV spectral survey. Since isorhamnetin (3,5,7,4tetrahydroxy-3-methoxyflavone) was liberated
by acid hydrolysis, it was shown that 3-hydroxyl
group was glycosylated. As glycosidic sugars,
glucose and rhamnose were produced. Rf valuesof TLC and retention time of HPLC of flavonoid
9 agreed with those of authentic isorhamnetin 3O-rutinoside (Fig. 12) from the leaves ofAsarum caulescens Maxim. (Aristolochiaceae)

Luteolin 7-O-glucoside (4).

Fig. 8.

Chrysoeriol 7-O-glucuronide (5).

Fig. 9.

Chrysoeriol 7-O-glucoside (5).

Fig. 10.

Chrysoeriol 7-O-rhamnoside (7).

Fig. 11.

Quercetin 3-O-rutinoside (rutin, 8).

Flavonoids from Saussurea in Altai(Iwashina et al., 2005).
LC-MS of three flavone aglycones, 11, 12 and13 indicated molecular ion peaks, m/z 301[MH] (trihydroxy-monomethoxyflavone), 317[MH] (tetrahydroxy-monomethoxyflavone)and 331 [MH] (trihydroxy-dimethoxyflavone),respectively. By UV spectral survey, they wereshown to be 5,7,4-trihydroxy-6 or 8-substituted
flavone, 5,7,3,4-tetrahydroxy-6 or 8-substituted
flavone and 5,7,4-trihydroxy-6,3 or 8,3-substituted flavone. Finally, they were identified as
hispidulin (11, Fig. 13), nepetin (12, Fig. 14)
and jaceosidin (13, Fig. 15) by direct HPLC
comparisons with authentic standards from theleaves of Cirsium oligophyllum (Franch. &Savat.) Matsum. as hydrolysates of 4-O-glucosides (hispidulin and nepetin) (Iwashina et al.,1999) and the leaves of Chrysanthemum japonense var. ashizuriense (jaceosidin) (Uehara etal., unpublished data).
Though flavonoid 10 could not be isolated, it
was characterized as quercetin 3-O-glucoside(Fig. 16) by HPLC comparison of peak retention
time of crude extract from S. pseudo-alpina andFig. 12.
9).

147

authentic isoquercitrin from the leaves of Phytolacca americana L. (Phytolaccaceae) (Iwashina
and Kitajima, 2009).
Flavonoid composition of seven Saussurea
species in the Altai Mountains
Seven flavone glycosides, apigenin 7-O-glucuronide (1), apigenin 7-O-glucoside (2), luteolin
7-O-glucuronide (3), luteolin 7-O-glucoside (4),chrysoeriol 7-O-glucuronide (5), chrysoeriol 7O-glucoside (6) and chrysoeriol 7-O-rhamnoside(7), three flavonol glycosides, quercetin 3-O-rutinoside (8), isorhamnetin 3-O-rutinoside (9) and
quercetin 3-O-glucoside (10), and three flavone
aglycones, hispidulin (11), nepetin (12) andjaceosidin (13) were found in seven Saussurea
species used as plant materials. Of flavone glycosides found in this experiment, 2 has been reported from S. involucrata (Kusano et al., 2007), S.
gossypiphora (Lin-gang and Min, 1989; Zheng etal., 1991), S. tridactyla (Zheng et al., 2003) andS. stella (Shen et al., 2004; Zheng et al., 1997), 3
from S. gnaphalodes (Kusano et al., 2007), 4
from S. involucrata, S. gnaphalodes (Kusano etal., 2007) and S. tridactyla (Zhang et al. 2003),
and 6 from S. gossypiphora (Zheng et al., 1991)
and S. stella (Zheng et al., 1997; Shen et al.,2004) (Table 1). However, 1, 5 and 7 were foundFig. 14.

Nepetin (12).

Fig. 15.

Jaceosidin (13).

Isorhamnetin 3-O-rutinoside (narsissin,

Fig. 13.

Hispidulin (11).

S. parviflora

Acacetin 7-rutinoside
Apigenin 7-glucoside
Apigenin 7-rutinoside
Luteolin 7-glucoside

S. tridactyla

Luteolin

Apigenin
7-glucorhamnoside
Luteolin
7-glucorhamnoside

S. pulchella

Quercetin
Penduletin

Quercetin

Apigenin
Luteolin

S. medusa

Apigenin7-neohesperidoside
Apigenin 7-rutinoside
Luteolin
7-neohesperidoside

Quercetin

Hispidulin
Jaceosidin
Luteolin
Nepetin

S. involucrata

Apigenin 7-glucoside
Hispidulin 7-glucoside
Luteolin 7-glucoside
Nepetin 7-glucoside

Quercetin

Hispidulin
Pectolinarigenin

S. elegans

Flavonolaglycones

Apigenin 7-glucoside
Quercetin
Apigenin7-neohesperidoside
Chrysoeriol 7-glucoside

Flavoneglycosides

Kaempferol 3-glucoside
Quercetin 3-rutinoside

Quercetin 3-rhamnoside
Quercetin 3-rutinoside

Quercetin 3-glucoside

Quercetin 3-rhamnoside
Quercetin 3-rutinoside

Quercetin 3-rutinoside

Kaempferol 3-rutinoside
Isorhamnetin 3-rutinoside
Quercetin 3-rutinoside

Flavonolglycosides

Reports of flavonoids from Saussurea species

S. controversa

Apigenin

Flavoneaglycones

S. gossypiphoraSpecies

Table 1.

Jia et al. (1989)
Fan and Yue (2003)

Jia et al. (1983)
Jia et al. (1988)
Yi et al. (2005)
Kusano et al. (2007)

Syrchina et al. (1993)

Sham’yanov et al. (1983)
Kusano et al. (2007)

Lin-gang and Min (1989)
Zheng et al. (1991)

References

Yang et al. (2003)

Ren et al. (2001)
Zhang et al. (2003)

Cyanidin 3-glucoside Basargin and Tsiklauri (1990)(Anthocyanin)

Others148
Tsukasa Iwashina et al.

Isorhamnetin 3-rutinoside
Quercetin 3-rutinoside

Isorhamnetin 5-glucoside
Kaempferol 5-glucoside
Kaempferol 7-glucoside
Quercetin 5-glucoside
Quercetin 7-glucoside

S. sordida

Hispidulin
Luteolin
7-methyl ether
Nepetin
VelutinQuercetin 3-glucoside
Quercetin 3-rutinoside

S. kuschakewiczii

S. leucophylla

Quercetin 3-rutinoside

S. konuloba

Luteolin 5-glucoside

Quercetin 3-rutinoside

S. alberti

Isorhamnetin 5-glucoside
Kaempferol 3-rhamnoside
Quercetin 5-glucoside
Quercetin 3-rhamnoside
6-Hydroxykaempferol 3methyl ether 6-glucoside

S. stella

Acacetin 7-glucoside
Kaempferol
Apigenin 7-glucoside
Chrysoeriol 7-glucoside

Kaempferol 3-glucoside
Acebogenin
Kaempferol 3-rhamnoside2-glucoside
Quercetin 3-glucoside(Dihydrochalcone)
Quercetin 3-rhamnosideRhamnocitrin 3-rhamnoside

S. mongolica

Acacetin
Apigenin
Luteolin

Kaempferol 3-(6-crotonyl)glucoside
Kaempferol 3-glucoside
Quercetin 3-(6-crotonyl)glucoside
Quercetin 3-glucoside

S. japonica

Kusano et al. (2007)

Kusano et al. (2007)

Kusano et al. (2007)

Kusano et al. (2007)

Kusano et al. (2007)

Zheng et al. (1997)
Shen et al. (2004)

Jiang et al. (2004)

Shi et al. (1991)

Flavonoids from Saussurea in Altai
149

Kusano et al. (2007)
Quercetin 3-galactoside
Quercetin 3-glucoside
Quercetin 3-rutinoside

Flavonolglycosides

Apigenin 6,8-C-glycoside
Isoorientin
Isovitexin
Luteolin 7-galactoside
Luteolin 8-C-glycoside
S. schanginiana

S. gnaphalodes

Luteolin
SelaginSelagin7-methyl ether

Apigenin 7-rutinoside
Luteolin 7-glucoside
Luteolin 7-glucuronide
Luteolin 7-rutinoside

Flavonolaglycones
Flavoneglycosides
Flavoneaglycones
Species

Table 1.

(Continued)

OthersKusano et al. (2007)

Tsukasa Iwashina et al.

References

150

Fig. 16. Quercetin 3-O-glucoside (isoquercitrin,10).

in Saussurea species for the first time.
Of three flavonol glycosides, quercetin 3-Orutinoside (8) has been reported from somespecies, i.e., S. alberti, S. konuloba, S.
kuschakewiczii, S. elegans, S. leucophylla, S. involucrata, S. schanginiana (Kusano et al., 2007),
S. controversa (Syrchina et al., 1993), S. pulchella (Basargin and Tsiklauri, 1990) and S. tridactyla (Zhang et al., 2003). Isorhamnetin 3-O-rutinoside (9) and quercetin 3-O-glucoside (10) havebeen found in S. elegans and S. leucophylla(Kusano et al., 2007), and S. kuschakewiczii, S.
schanginiana (Kusano et al., 2007), S. medusa(Jia et al., 1989), S. japonica (Shi et al., 1991)
and S. mongolica (Jiang et al., 2004).
Of three flavone aglycones found in this experiment, hispidulin (11) has been reported from S.
elegans, S. leucophylla and S. involucrata,
nepetin (12) from S. gnaphalodes and S. involucrata, and jaceosidin (13) from S. involucrata(Kusano et al., 2007).
Flavonoid patterns of the species used as plantmaterials in this experiment were apparently different with each other (Table 2). Their species
were roughly divided into four types, i.e., 1)
flavone glycoside alone in S. daurica (Fig. 17),
S. laciniata (Fig. 18) and S. salsa (Fig. 19), 2)
flavonol glycosides alone in S. alpina (Fig. 20)
and S. pseudo-alpina (Fig. 21), 3) coexistence offlavonol glycosides and flavone aglycones in S.
pricei (Fig. 22), and 4) flavone aglycone alone in
S. salicifolia (Fig. 23). We have already surveyed nine Saussurea species native to the Tien
Shan Mountains for flavonoids (Kusano et al.,2007). We have shown that flavonoid diversity ofFlavonoids from Saussurea in Altai
Table 2.

151

Flavonoid composition of seven Saussurea species in the Altai Mountains and adjacent area
Flavone glycosides

Flavonol glycosides

Flavone aglycones

SpeciesS. daurica
S. laciniata
S. salsa
S. pricei
S. pseudo-alpina
S. alpina
S. salicifolia

1

2

3

4

5




















6

7

8

9

10











11

12

13












1apigenin 7-glucuronide, 2apigenin 7-glucoside, 3luteolin 7-glucuronide, 4luteolin 7-glucoside, 5chrysoeriol
7-glucuronide, 6chrysoeriol 7-glucoside, 7chrysoeriol 7-rhamnoside, 8quercetin 3-rutinoside, 9isorhamnetin
3-rutinoside, 10quercetin 3-glucoside, 11hispidulin, 12nepetin and 13jaceosidin.

Fig. 17. HPLC chromatogram of flavonoid glycosides from Saussurea daurica. 1apigenin 7-glucuronide,2apigenin 7-glucoside, 3luteolin 7-glucuronide, 4luteolin 7-glucoside, 5chrysoeriol 7-glucuronide
and 7chrysoeriol 7-rhamnoside. Other peaks were organic acids and so on.

Fig. 18. HPLC chromatogram of flavonoid glycosides from Saussurea laciniata. 1apigenin 7-glucuronide,2apigenin 7-glucoside, 3luteolin 7-glucuronide and 5chrysoeriol 7-glucuronide. Other peaks wereorganic acids and so on.

152

Tsukasa Iwashina et al.

Fig. 19. HPLC chromatogram of flavonoid glycosides from Saussurea salsa. 2apigenin 7-glucoside, 3luteolin 7-glucuronide, 4luteolin 7-glucoside, 5chrysoeriol 7-glucuronide and 6chrysoeriol 7-glucoside.
Other peaks were organic acids and so on.

Fig. 20. HPLC chromatogram of flavonoid glycosides from Saussurea alpina. 8quercetin 3-rutinoside and9isorhamnetin 3-rutinoside. Other peaks were organic acids and so on.

Fig. 21. HPLC chromatogram of flavonoid glycosides from Saussurea pseudo-alpina. 8quercetin 3-rutinoside,9isorhamnetin 3-rutinoside and 10quercetin 3-glucoside. Other peaks were organic acids and so on.

Flavonoids from Saussurea in Altai

153

Fig. 22. HPLC chromatogram of flavonoid glycosides from Saussurea pricei. 8quercetin 3-rutinoside and9isorhamnetin 3-rutinoside. Other peaks were organic acids and so on.

Fig. 23. HPLC chromatogram of flavonoid glycosides from Saussurea salicifolia. Peak of flavonoid glycoside isabsent on the chromatogram.

Saussurea species is also comparatively high in
the Altai Mountains, and various flavonoid patterns appeared. Thus, it was shown that the genus
Saussurea is not only morphologically and geographically but also chemically diversified.
Acknowledgements
The collections of plant materials from theAltai Mountains and adjacent area in 2007 were
supported by a Grant-in-Aid for the Scientific
Programs (A) (no. 19255004; Representative,
Katsuhiko Kondo) from the Ministry of Educa-

tion, Culture, Sports, Science and Technology,
Japan.

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