Bull. Natl. Mus. Nat. Sci., Ser. B, 42(1), pp. 41–47, February 22, 2016

Flavonoid Properties in the Leaves ofBarringtonia asiatica (Lecythidaceae)
Tsukasa Iwashina* and Goro Kokubugata
Department of Botany, National Museum of Nature and Science,
Amakubo 4–1–1, Tsukuba, Ibaraki 305–0005, Japan*E-mail: iwashina@kahaku.go.jp(Received 8 November 2015; accepted 22 December 2015)

Abstract Six C-glycosylﬂavones and four ﬂavonol O-glycosides were isolated from the leavesof Barringtonia asiatica. Of their ﬂavonoids, four ﬂavones and four ﬂavonols were identiﬁed as
isovitexin, vitexin, isoorientin and orientin, and kaempferol 3-O-glucoside, kaempferol 3-O-rutinoside, quercetin 3-O-glucoside and quercetin 3-O-rutinoside, respectively. Other two were unidentiﬁed C-glycosylﬂavones. Though ellagitannins were also present in the leaves, they were not characterized. The ﬂavonoids of B. asiatica were reported for the ﬁrst time. In this survey, it waspresumed that major ﬂavonoids of the Lecythidaceae were not only ﬂavonols such as kaempferol
and quercetin but also C-glycosylﬂavones such as isovitexin, vitexin, isoorientin and orientin.
Key words : Barringtonia asiatica, ﬂavonoids, ﬂavonols, C-glycosylﬂavones, Lecythidaceae.

Introduction
As a series of ﬂavonoid survey of endemic
and/or endangered plants in Japan, we have isolated and identiﬁed the ﬂavonoids from theleaves and/or ﬂowers of Japonolirion osense
Nakai (Petrosaviaceae) (Iwashina et al., 2005a),
Asarum spp. (Aristolochiaceae) (Iwashina et al.,2005b), Cassytha spp. (Lauraceae) (Murai et al.,2008), Cladopus japonicus Imamura and Hydrobryum japonicum Imamura (Podostemaceae)(Murai et al., 2009), Ranzania japonica (T.Ito)
T.Ito (Berberidaceae) (Iwashina and Kitajima,
2009a), Pothos chinensis (Raf.) Merr. (Araceae)(Iwashina et al., 2010), Callianthemum hondoense Nakai & Hara (Ranunculaceae)(Asakawa et al., 2010), Myoporum bontioides(Sieb. et Zucc.) A.Gray (Myoporaceae) (Iwashina and Kokubugata, 2010), Petrosavia sakuraii(Makino) J.J.Sm. (Petrosaviaceae) (Iwashina etal., 2011a), Nipponanthemum nipponicum(Franch ex Maxim.) Kitam. (Asteraceae) (Uehara
and Iwashina, 2012), Iris rossii Baker (Iridaceae)(Mizuno et al., 2012), Crossostephium chinense(L.) Makino (Asteraceae) (Uehara et al., 2014),
Torenia concolor Lindl. var. formosana
Yamazaki (Scrophulariaceae) (Iwashina andKokubugata, 2014), Primula sieboldii E.Morr.
(Primulaceae) (Hashimoto et al., 2015), Asplenium ruta-muraria L. (Aspleniaceae) (Iwashina
et al., 2015a), Iris gracilipes A.Gray (Iridaceae)(Mizuno et al., 2015) and so on.
The genus Barringtonia belongs to the family
Lecythidaceae and consists of ca. 40 species(Hatusima, 1989). In Japan, B. asiatica (L.)
Kurz. and B. racemosa (L.) Spreng. are growing.
B. asiatica is evergreen trees to 15 m tall, andgrowing in Ishigaki and Iriomote Islands in
Ryukyus and Ogasawara Islands, and also Taiwan, Southern China, the Philippines, Indochina,
Malaysia, New Guinea, northern Australia, Melanesia and Micronesia (Setoguchi, 1999). The
species is designated to endangered plant by
Red-data book in Japan.
The ﬂavonoid compounds of Barringtonia
species have been reported by a few authors. A

42

Tsukasa Iwashina and Goro Kokubugata

ﬂavanone, one ﬂavone and two ﬂavonols wereisolated from the leaves of B. racemosa andidentiﬁed as naringenin, luteolin, and kaempferol
and quercetin 3-O-rutinoside, together with twoorganic acids, gallic acid and ferulic acid, as antifungal activity substances (Hussin et al., 2009).
Three ﬂavonols, kaempferol, quercetin and its
3-O-rutinoside, were also found in the leaves andstems of the same species with three organic
acids, gallic acid, ellagic acid and protocatechuicacid (Kong et al., 2014). Two anthocyanins,
cyanidin and delphinidin 3-O-sambubiosides
were isolated from the ﬂowers of B. racemosa
and B. macrostachya Kurz. (Lowry, 1976). Threeﬂavan 3-ols, (＋)-epigallocatechin, (＋)-gallocatechin 4′-methyl ether and (＋)-gallocatechin
4′-methyl ether 5-O-glucoside, were isolated
from the barks of B. acutangula (L.) Gaertn.
(Nguyen et al., 2014).
In B. asiatica, four saponins were isolated
from the seeds (Errington and White, 1967; Itô etal., 1967; Herlt et al., 2002). Eleven triterpenes
were also found in the leaves (Ragasa et al.,2011). However, ﬂavonoids were not reported.
In this paper, we describe the isolation andidentiﬁcation of the ﬂavonoids from the leaves ofBarringtonia asiatica for the ﬁrst time.
Materials and Methods
Plant materials
Barringtonia asiatica (L.) Kurz. was collectedin Nakama-zaki, Iriomote Island, Okinawa Pref.,Japan, 4 July 2012. Voucher specimen was
deposited in the Herbarium of National Museumof Nature and Science, Japan (TNS).
GeneralHigh performance liquid chromatography(HPLC) was performed with Shimadzu HPLC
systems using L-column2 ODS (I.D. 6.0×150 mm,
Chemicals Evaluation and Research Institute,Japan) at a ﬂow-rate of 1.0 ml min−1. Detection
was 350 nm. Eluents were MeCN/H2O/H3PO4(20 : 80 : 0.2 for ﬂavonoid glycosides, 40 : 60 : 0.2
for ﬂavonoid aglycones and 18 : 82 : 0.2 for ella-gitannins). Liquid chromatograph-mass spectra(LC-MS) was performed with Shimadzu LC-MS
systems using L-column2 ODS (I.D. 2.1×100 mm,
Chemicals Evaluation and Research Institute) ata ﬂow-rate of 0.2 ml min−1. ESI＋ 4.5 kV and
ESI− 3.5 kV, 250°C. Eluent was MeCN/H2O/
HCOOH (15 : 85 : 5). Acid hydrolysis was performed in 12% HCl, 100°C, 30 min. After shaking with diethyl ether, aglycones migrated to theorganic layer, and sugars and C-glycosylﬂavoneswere left in aqueous layer. Thin layer chromatography (TLC) was performed with Cellulose F
plastic plate (Merck, Germany) using solvent
systems, BAW (n-BuOH/HOAc/H2O＝4 : 1 : 5,
upper phase), BEW (n-BuOH/EtOH/H2O＝
4 : 1 : 2.2) and 15% HOAc. Paper chromatography (PC) for sugar identiﬁcation was performed
using solvent systems, BBPW (n-BuOH/benzene/pyridine/H2O＝5 : 1 : 3 : 3)andBTPW(n-BuOH/toluene/pyridine/H2O＝5 : 1 : 3 : 3). The
sugar spots were visualized by spraying 1%
methanolic aniline hydrochloride on the paper
chromatograms and heating.
Extraction and separation
Fresh leaves (154.8 g) were extracted with
MeOH. The concentrated extracts were applied
to preparative PC using solvent systems, BAW,
15%HOAc, re-BAW and then re-15% HOAc.
The isolated compounds were puriﬁed by Sephadex LH-20 column chromatography using solvent system, 70% MeOH.
Identiﬁcation of the ﬂavonoids
Flavonoids were identiﬁed by UV spectral survey according to Mabry et al. (1970), LC-MS,
characterization of acid hydrolysates, and TLC
and HPLC comparisons with authentic samples.
Origins of the authentic samples which wereused in this survey were as follows: isovitexinfrom the inﬂorescence of Amorphophallus titanum (Becc.) Becc. ex Arcangeli (Araceae)(Iwashina et al., 2015b), vitexin from the frondsof Adiantum venustum Don (Parkeriaceae)(Iwashina et al., 1995), isoorientin from theleaves of Vitex rotundifolia L.ﬁl. (Verbenaceae)

Flavonoids of Barringtonia asiatica

43

Isovitexin (1).

Fig. 3.

Isoorienin (3).

Fig. 2. Vitexin (2).

Fig. 4.

Orientin (4).

Fig. 1.

(Iwashina et al., 2011b), orientin from the leavesof Acer palmatum Thunb. (Sapindaceae) (Iwashina and Murai, 2008), kaempferol 3-O-glucoside from the leaves of Calystegia japonica
Choisy (Convolvulaceae) (Murai et al., 2015),
kaempferol 3-O-rutinoside from the leaves of
Glycine max (L.) Merr. (Leguminosae) (Murai etal., 2013), quercetin 3-O-glucoside from theleaves of Phytolacca americana L. (Phytolaccaceae) (Iwashina and Kitajima, 2009b) and quercetin 3-O-rutinoside from the leaves of Saruma
henryi Oliver (Aristolochiaceae) (Iwashina et al.,2002). TLC, HPLC, UV and LC-MS data of theisolated ﬂavonoids were as follows.
Isovitexin (1). TLC: Rf 0.69 (BAW), 0.63
(BEW), 0.40 (15%HOAc); color UV (365 nm)
dark purple, UV/NH3 dark greenish yellow.
HPLC: retention time (tR) (min) 14.93. UV:
λmax (nm) MeOH 271, 333; ＋NaOMe 278,
330, 399 (inc.); ＋AlCl3 278, 303, 348, 378sh;＋AlCl3/HCl 279, 301, 344, 377sh; ＋NaOAc
278, 394; ＋NaOAc/H3BO3 272, 347. LC-MS:
m/z 433 [M＋H]＋, 431 [M−H]− (molecular ion
peaks, apigenin＋1 mol glucose).
Vitexin (2). TLC: Rf 0.46 (BAW), 0.44
(BEW), 0.17 (15%HOAc); color UV (365 nm)
dark purple, UV/NH3 dark greenish yellow.
HPLC: tR (min) 14.38. UV: λmax (nm) MeOH

270, 332; ＋NaOMe 279, 330, 394 (inc.);＋AlCl3 276, 303, 346, 382; ＋AlCl3/HCl 277,
302, 340, 379sh; ＋NaOAc 279, 389; ＋NaOAc/
H3BO3 271, 345. LC-MS: m/z 433 [M＋H]＋,
431 [M−H]− (molecular ion peaks, apigenin＋
1 mol glucose).
Isoorientin (3). TLC: Rf 0.45 (BAW), 0.43
(BEW), 0.27 (15%HOAc); color UV (365 nm)
dark purple, UV/NH3 dark yellow. HPLC: tR(min) 14.01. UV: λmax (nm) MeOH 257, 268sh,
351; ＋NaOMe 275, 412 (inc.); ＋AlCl3 274,
422; ＋AlCl3/HCl 261, 276sh, 360, 377sh;＋NaOAc 276, 333, 400; ＋NaOAc/H3BO3 265,
380, 427sh. LC-MS: m/z 449 [M＋H]＋, 447[M−H]− (molecular ion peaks, luteolin＋1 mol
glucose).
Orientin (4). TLC: Rf 0.30 (BAW), 0.30
(BEW), 0.09 (15%HOAc); color UV (365 nm)
dark purple, UV/NH3 dark yellow. HPLC: tR(min) 10.47. UV: λmax (nm) MeOH 256, 268sh,
348; ＋NaOMe 276, 332, 407 (inc.); ＋AlCl3
273, 422; ＋AlCl3/HCl 261, 275sh, 297sh, 357,
386sh; ＋NaOAc 278, 330, 398; ＋NaOAc/
H3BO3 264, 375, 427sh. LC-MS: m/z 447[M−H]− (molecular ion peak, luteolin＋1 mol
glucose).
Kaempferol 3-O-glucoside (astragalin, 5).
TLC: Rf 0.79 (BAW), 0.87 (BEW), 0.39

44

Tsukasa Iwashina and Goro Kokubugata

Fig. 5.

Kaempferol 3-O-glucoside (astragalin, 5).

Fig. 6. Kaempferol 3-O-rutinoside (nicotiﬂorin, 6).

(15%HOAc); color UV (365 nm) dark purple,
UV/NH3 dark greenish yellow. HPLC: tR (min)25.45. UV: λmax (nm) MeOH 266, 346;
＋NaOMe 275, 324, 398 (inc.); ＋AlCl3 273,
303, 351, 392; ＋AlCl3/HCl 275, 302, 345, 391;
＋NaOAc 275, 313, 392; ＋NaOAc/H3BO3 266,
353. LC-MS: m/z 447 [M−H]− (molecular ion
peak, kaempferol＋1 mol glucose).
Kaempferol 3-O-rutinoside (nicotiﬂorin, 6).
TLC: Rf 0.64 (BAW), 0.73 (BEW), 0.59
(15%HOAc); color UV (365 nm) dark purple,
UV/NH3 dark greenish yellow. HPLC: tR (min)20.51. UV: λmax (nm) MeOH 266, 347;
＋NaOMe 275, 324, 400 (inc.); ＋AlCl3 274,
304, 350, 393; ＋AlCl3/HCl 275, 302, 347, 392;
＋NaOAc 275, 316, 395; ＋NaOAc/H3BO3 267,
354. LC-MS: m/z 593 [M−H]− (molecular ion
peak, kaempferol＋each 1 mol glucose and rhamnose), m/z 287 [M−308＋H]＋ (fragment ion
peak, kaempferol).
Quercetin 3-O-glucoside (isoquercitrin, 7).
TLC: Rf 0.65 (BAW), 0.73 (BEW), 0.31
(15%HOAc); color UV (365 nm) dark purple,
UV/NH3 dark yellow. HPLC: tR (min) 16.97.

Fig. 7.

Quercetin 3-O-glucoside (isoquercitrin, 7).

Fig. 8.

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

UV: λmax (nm) MeOH 258, 265sh, 352;
＋NaOMe 274, 331, 403 (inc.); ＋AlCl3 275,
417; ＋AlCl3/HCl 270, 299sh, 354, 393sh;＋NaOAc 274, 323, 395; ＋NaOAc/H3BO3 263,
297, 376. LC-MS: m/z 463 [M−H]− (molecularion peak, quercetin＋1 mol glucose), m/z 303[M−162＋H]＋ (fragment ion peak, quercetin).
Quercetin 3-O-rutinoside (rutin, 8). TLC: Rf
0.54 (BAW), 0.55 (BEW), 0.55 (15%HOAc);
color UV (365 nm) dark purple, UV/NH3 dark
yellow. HPLC: tR (min) 13.69. UV: λmax (nm)
MeOH 257, 264sh, 358; ＋NaOMe 273, 328,
412 (inc.); ＋AlCl3 274, 428; ＋AlCl3/HCl 269,
298sh, 362, 396; ＋NaOAc 273, 326, 402;
＋NaOAc/H3BO3 262, 294, 379. LC-MS: m/z
610 [M−H]− (molecular ion peak, quercetin＋
each 1 mol glucose and rhamnose), m/z 303[M−308＋H]＋ (fragment ion peak, quercetin).
Unknown C-glycosylﬂavone (9). TLC: Rf 0.76
(BAW), 0.76 (BEW), 0.50 (15%HOAc); color
UV (365 nm) dark purple, UV/NH3 dark greenish
yellow. HPLC: tR (min) 24.08. UV: λmax (nm)
MeOH 270, 332; ＋NaOMe 280, 329, 399 (inc.);＋AlCl3 277, 303, 335, 377sh; ＋AlCl3/HCl 277,

Flavonoids of Barringtonia asiatica

302sh, 345, 376sh; ＋NaOAc 279, 316, 395;
＋NaOAc/H3BO3 274, 284sh, 302, 344sh, 406sh.
LC-MS: m/z 585 [M＋H]＋, 583 [M−H]−(molecular ion peaks).
Unknown C-glycosylﬂavone (10). TLC: Rf
0.70 (BAW), 0.76 (BEW), 0.45 (15%HOAc);
color UV (365 nm) dark purple, UV/NH3 darkgreenish yellow. HPLC: tR (min) 21.82. UV:
λmax (nm) MeOH 271, 334; ＋NaOMe 279,
330, 396 (inc.); ＋AlCl3 278, 303, 341, 379;
＋AlCl3/HCl 277, 299sh, 345, 377sh; ＋NaOAc
279, 320, 393; ＋NaOAc/H3BO3 273, 285sh,
303, 348sh, 400sh. LC-MS: m/z 585 [M＋H]＋,
583 [M−H]− (molecular ion peaks).
Results and Discussion
In this survey, ten ﬂavonoids (1–10) were isolated from the leaves of Barringtonia asiatica. It
was shown by UV spectral survey that 1 and 2
were ﬂavones having free 5-, 7- and 4′-hydroxyl
groups (Mabry et al., 1970). They were unhydrolyzable by hot acid treatment, showing that they
are C-glycosylﬂavones. Their LC-MS survey
showed the attachment of 1 mol hexose to trihydroxyﬂavone. Finally, they were identiﬁed as isovitexin (5,7,4′-trihydroxyﬂavone 6-C-glucoside,
1, Fig. 1) and vitexin (5,7,4′-trihydroxyﬂavone
8-C-glucoside, 2, Fig. 2) by TLC and HPLC
comparisons with authentic samples.
Similarly, 3 and 4 were shown to be ﬂavoneswith free 5-, 7-, 3′- and 4′-hydroxyl groups by
UV spectra, and C-glycosylﬂavones by hot acidtreatment. LC-MS survey showed that both ﬂavones are luteolin which attached each 1 mol
hexose. Thus, 3 and 4 were identiﬁed as isoorientin (5,7,3′,4′-tetrahydroxyﬂavone 6-C-glucoside,
3, Fig. 3) and orientin (5,7,3′,4′-tetrahydroxyﬂavone 8-C-glucoside, 4, Fig. 4).
Kaempferol was liberated by acid hydrolysisof 5 and 6. As sugar portions, glucose, and glucose and rhamnose were found in the aqueous
layer. It was shown by UV spectral properties
that they are ﬂavonols having free 5-, 7-,4′-hydroxyl and a substituted 3-hydroxyl groups.
Finally, 5 and 6 were identiﬁed as kaempferol

45

3-O-glucoside (Fig. 5) and kaempferol 3-O-rutinoside (Fig. 6) by direct TLC and HPLC comparisons with authentic astragalin and nicotiﬂorin.
Flavonoids 7 and 8 were shown to be
5,7,3′,4′-tetrahydroxy-3-substituted ﬂavones by
UV spectral survey (Mabry et al., 1970). By acidhydrolysis, quercetin and glucose, and quercetin,
glucose and rhamnose were liberated from them,
respectively. LC-MS survey of 7 and 8 showed
the attachment of 1 mol glucose, and each 1 mol
glucose and rhamnose to quercetin. Thus, they
were identiﬁed as quercetin 3-O-glucoside (isoquercitrin, 7, Fig. 7) and quercetin 3-O-rutinoside (rutin, 8, Fig. 8) by TLC and HPLC comparisons with authentic specimens.
UV spectral survey of 9 and 10 showed thatthey are ﬂavones having free 5-, 7- and4′-hydroxyl groups. Since 9 and 10 were unhydrolyzable by hot acid treatment, they are C-glycosylﬂavones. Their molecular weights were 584(see Experimental), presuming that they are new
C-glycosylﬂavones. However, their further characterization could not performe for a small
amounts of the compounds. As other compounds,
some ellagitannins, which were shown by UV
spectral properties and characterization of acidhydrolysates (ellagic acid), were found.
In this survey, four C-glycosylﬂavones (1–4)
and four ﬂavonol O-glycosides (5–8) were identiﬁed. Of their ﬂavonoids, though quercetin
3-O-rutinoside (8) has been reported from theleaves of B. racemosa (Hussin et al., 2009; Konget al., 2014), other compounds were found in thegenus Barringtonia for the ﬁrst time. The ﬂavonoids of the family Lecythidaceae were hardly
surveyed. However, it has been reported thatmajor ﬂavonoids of the family are quercetin and/or kaempferol, together with another compound,ellagic acid (Giannasi, 1988). Practically, quercetin and its 3-O-rutinoside and kaempferol were
found in another Lecythidaceous species, Napoleona imperialis P.Beavr. (Ukachukwu et al.,2013). Quercetin was also isolated from Bertholletia excelsa Humb. & Borpl., together with gallic acid, gallocatechin, protcatechuic acid, myricetin, ellagic acid etc. (John and Shahidi, 2010).

46

Tsukasa Iwashina and Goro Kokubugata

In another Lecythidaceous species, Planchonia
grandis Ridley and P. careya (F.Muell.) R.
Knuth, three kaempferol p-coumaroylglycosides,
and kaempferol 3-O-gentiobioside, 3-O-glucoside and two acylated 3-O-glycosides werereported from the leaves, respectively (Crublet etal., 2003; McRae et al., 2008). Kaempferol andquercetin glycosides were isolated from Barringtonia asiatica in this survey. However,C-glycosylﬂavones, isovitexin (1), vitexin (2),isoorientin (3) and orientin (4), were also foundas major ﬂavonoids.
References
Asakawa, M., Iwashina, T. and Kitajima, J. 2010. Flavonol glycosides from Callianthemum hondoense andCallianthemum alatavicum in Japan and Tien Shan
Mountains. Biochemical Systematics and Ecology 38:
250–252.
Crublet, M.-L., Long, C., Sévenet, T., Hadi, H. A. and
Lavaud, C. 2003. Acylated ﬂavonol glycosides fromleaves of Planchonia grandis. Phytochemistry 64: 589–
594.
Errington, S. G. and White, D. E. 1967. The structures ofA1-barrigenol and R1-barrigenol. Tetrahedron Letters
14: 1289–1294.
Giannasi, D. E. 1988. Flavonoids and evolution in the
dicotyledons. In: Harborne, J. B. (ed.), The Flavonoids.
Advances in Research since 1980, pp. 479–504, Chapman and Hall, London.
Hashimoto, N., Ohsawa, R., Kitajima, J. and Iwashina, T.
2015. New ﬂavonol glycosides from the leaves andﬂowers of Primula sieboldii. Natural Product Communications 10: 421–423.
Hatusima, S. 1989. Lecythidaceae. In: Satake, Y., Hara,
H., Watari, S. and Tominari, T. (eds.), Wild Flowers ofJapan. Woody Plants, pp. 100, Heibonsha, Tokyo.
Herlt, A. J., Mander, L. N., Pongoh, E., Rumampuk, R. J.
and Tarigan, P. 2002. Two major saponins from seedsof Barringtonia asiatica; Putative antifeedants toward
Epilachna sp. larvae. Journal of Natural Products 65:
115–120.
Hussin, N. M., Muse, R., Ahmad, S., Ramli, J., Mahmood, M., Sulaiman, M. R., Shukor, M. Y. A., Rahman,
M. F. A. and Aziz, K. N. K. 2009. Antifungal activity of
extracts and phenolic compounds from Barringtonia
racemosa L. (Lecythidaceae). African Journal of Biotechnology 8: 2835–2842.
Itô, S., Ogino, T., Sugiyama, H. and Kodama, M. 1967.
Structures of A1-barrigenol and R1-barrigenol. Tetrahedron Letters 24: 2289–2294.
Iwashina, T., Matsumoto, S. and Nakaike, T. 1995. Flavo-

noid characters of ﬁve Adiantum species in Pakistan.
In: Watanabe, M. and Hagiwara, H. (eds.), Cryptogamsof the Himalayas, Vol. 3. Nepal and Pakistan, pp. 179–
191. National Science Museum, Tsukuba.
Iwashina, T., Marubashi, W. and Suzuki, T. 2002. Chalcones and ﬂavonols from the Chinese species, Saruma
henryi (Aristolochiaceae). Biochemical Systematics
and Ecology 30: 1101–1103.
Iwashina, T., Kitajima, J., Kato, T. and Tobe, H. 2005a.
An analysis of ﬂavonoid compounds in leaves ofJaponolirion (Petrosaviaceae). Journal of Plant
Research 118: 31–36.
Iwashina, T., Kitajima, J., Shiuchi, T. and Itou, Y. 2005b.
Chalcones and other ﬂavonoids from Asarum sensu
lato (Aristolochiaceae). Biochemical Systematics andEcology 33: 571–584.
Iwashina, T. and Murai, Y. 2008. Quantitative variation ofanthocyanins and other ﬂavonoids in autumn leaves ofAcer palmatum. Bulletin of the National Museum of
Nature and Science, Series B 34: 53–62.
Iwashina, T. and Kitajima, J. 2009a. Flavonol glycosides
from the monotypic genus Ranzania endemic to Japan.
Biochemical Systematics and Ecology 37: 122–123.
Iwashina, T. and Kitajima, J. 2009b. Flavonoids from theleaves of betalain-containing species, Phytolacca americana (Phytolaccaceae). Bulletin of the National
Museum of Nature and Science, Series B 35: 99–104.
Iwashina, T. and Kokubugata, G. 2010. Flavonoids in theleaves and ﬂowers of Myoporum bontioides native tonorthernmost region in the Myoporaceae. Bulletin of
the National Museum of Nature and Science, Series B
36: 117–125.
Iwashina, T., Peng, C.-I and Kokubugata, G. 2010. Flavone O- and C-glycosides from Pothos chinensis (Araceae). Bulletin of the National Museum of Nature andScience, Series B 36: 27–32.
Iwashina, T., Tobe, H., Takahashi, H. and Yukawa, T.
2011a. Flavonoids from achlorophyllous plant, Petrosavia sakuraii (Petrosaviaceae). Biochemical Systematics and Ecology 39: 883–884.
Iwashina, T., Setoguchi, H. and Kitajima, J. 2011b. Flavonoids from the leaves of Vitex rotundifolia (Verbenaceae), and their qualitative and quantitative comparison
between coastal and inland population. Bulletin of the
National Museum of Nature and Science, Series B 37:
87–94.
Iwashina, T. and Kokubugata, G. 2014. Flavonoids fromthe ﬂowers and aerial parts of Torenia concolor var.
formosana. Bulletin of the National Museum of Natureand Science, Series B 40: 55–59.
Iwashina, T., Kitajima, J., Mizuno, T., Smirnov, S. V.,
Damdinsuren, O. and Kondo, K. 2015a. New kaempferol 3,7-diglycosides from Asplenium ruta-muraria
and Asplenium altajense. Natural Product Communications 10: 417–419.

Flavonoids of Barringtonia asiatica
Iwashina, T., Uehara, A., Kitajima, J. and Yukawa, T.
2015b. Anthocyanins and other ﬂavonoids from Amorphophallus titanum having largest inﬂorescence inplant kingdom, and other two species. Bulletin of the
National Museum of Nature and Science, Series B
33–44.
John, J. A. and Shahidi, F. 2010. Phenolic compounds andantioxidant activity of Brazil nut (Bertholletia excelsa).
Journal of Functional Foods 2: 196–209.
Kong, K. W., Mat-Junit, S., Ismail, A., Aminudin, N. andAbdul-Aziz, A. 2014. Polyphenols in Barringtonia racemosa and their protection against oxidation of LDL,
serum and haemoglobin. Food Chemistry 146: 85–93.
Lowry, 1976. Anthocyanins of the Melastomataceae,
Myrtaceae and some allied families. Phytochemistry
15: 513–516.
Mabry, T. J., Markham, K. R. and Thomas, M. B. 1970.
The Systematic Identiﬁcation of Flavonoids. Springer,
Berlin.
McRae, J. M., Yang, Q., Crawford, R. J. and Ralombo, E.
A. 2008. Acylated ﬂavonoid tetraglycosides from Planchona careya leaves. Phytochemistry Letters 1:
99–102.
Mizuno, T., Okuyama, Y. and Iwashina, T. 2012. Phenolic
compounds from Iris rossii, and their chemotaxonomic
and systematic signiﬁcance. Biochemical Systematics
and Ecology 44: 157–160.
Mizuno, T., Kamo, T., Sasaki, N., Yada, H., Murai, Y. andIwashina, T. 2015. Novel C-xylosylﬂavones from theleaves and ﬂowers of Iris gracilipes. Natural ProductCommunications 10: 441–444.
Murai, Y., Kokubugata, G., Yokota, M., Kitajima, J. andIwashina, T. 2008. Flavonoids and anthocyanins fromsix Cassytha taxa (Lauraceae) as taxonomic markers.
Biochemical Systematics and Ecology 36: 745–748.

47

Murai, Y., Fujinami, R., Imaichi, R. and Iwashina, T.
2009. Flavonoids from riverweeds, Cladopus japonicus
and Hydrobryum japonicum (Podostemaceae). Biochemical Systematics and Ecology 37: 538–540.
Murai, Y., Takahashi, R., Rodas, F. R., Kitajima, J. andIwashina, T. 2013. New ﬂavonol triglycosides from theleaves of soybean cultivars. Natural Product Communications 8: 453–456.
Murai, Y., Setoguchi, H., Ono, E. and Iwashina, T. 2015.
Flavonoids and their qualitative variation in Calystegia
soldanella and related species (Convolvulaceae). Natural Product Communications 10: 429–432.
Nguyen, V. D., Nguyen, T. L., Tran, H. T., Ha, T. A., Bui,
V. H., Nguyen, H. N. and Nguyen, T. D. 2014. Flavan3-ols from the barks of Barringtonia acutangula. Biochemical Systematics and Ecology 55: 219–221.
Ragasa, C. Y., Espineli, D. L. and Shen, C.-C. 2011. New
triterpenes from Barringtonia asiatica. Chemical andPharmaceutical Bulletin 59: 778–782.
Setoguchi, H. 1999. Lecythidaceae. In: Iwatsuki, K.,
Boufford, D. E. and Ohba, H. (eds.), Flora of Japan,
Volume IIc. Angiospermae, Dicotyledoneae, Archichlamydeae (c.), pp. 216, Kodansha, Tokyo.
Uehara, A. and Iwashina, T. 2012. Flavonoids from theJapanese monotypic genus, Nipponanthemum. Natural
Product Communications 7: 1005–1006.
Uehara, A., Kitajima, J., Kokubugata, G. and Iwashina, T.
2014. Further characterization of foliar ﬂavonoids in
Crossostephium chinense and their geographic variation. Natural Product Communications 9: 163–164.
Ukachukwu, R., Efﬁom, E. O. and Uchechukwu, M. E.
2013. Characterization of alkaloid and ﬂavonoid bioactive compounds in methanolic root extract of Napoleona imperialis. International Journal of Science andResearch 4: 2817–2819.