COSMOSIL HILIC Application Notebook contains about 200 chromatograms for the separation of polar compounds using COS-

MOSIL HILIC column It also describes hoZ the mobile phase conditions such as buffer pH and salt concentration inÀuence the
separation in HILIC mode

Contents
Hydrophilic Interaction Chromatography P2
COSMOSIL HILIC P3
COSMOSIL 2.5HILIC P5
COSMOSIL Applications P8
COSMOSIL Applications on Website P11
COSMOSIL Chromatogram Index P12
Reference List P34
INDEX P36

Hydrophilic Interaction Chromatography

The hydrophilic interaction chromatography is a variation of normal phase chromatography. The elution order is similar to that of
normal phase and the sample elution is in the order of increasing hydrophilicity.

Separation Mode Hydrophilic interaction Hydrophobic interaction

chromatography chromatography
Stationary Phase Hydrophilic Group (or Silica Gel) Hydrophobic group (C18 etc.)

Mobile Phase Organic Solvent (CH3CN etc.) / H2O

Main Interaction Hydrophilic interaction Hydrophobic interaction
Target Sample Hydrophilic compounds Hydrophilic and hydrophobic compounds
Features 䞉 for separation of Hydrophilic compounds 䞉 for the widest range of compounds
䞉 Suitable for LC/MS 䞉 High separation ability
䞉 A wide range of applications

Comparison with C18

COSMOSIL HILIC can separate glycine and glycylglycine without ion-pair reagent. Although C18 column can separate them with
ion-pair reagents, there are some disadvantages such as longer column equilibration time, time-consuming preparation of mo-
bile phase and earlier column deterioration.

COSMOSIL HILIC COSMOSIL 5C18-PAQ Column Size 4.6 mm I.D. x 250 mm

Flow Rate 1.0 ml/min
Temperature 30Υ
Detection UV 210 nm
without Ion-pair Reagents without Sample 1. Glycine (5.0 mg/ml)
2. Glycylglycine (0.125 mg/ml)
Injection Volume 2.0 μl

with Ion-pair Reagents

Mobile Phase Mobile Phase Mobile Phase

Acetonitrile : 10 mmol/l CH3COONH4 = 60 : 40 20 mmol/l Phosphatase Buffer (pH2.5) 20 mmol/l Phosphatase Buffer (pH2.5)
- 5 mmol/l Sodium 1-Octanesulfonate (Ion-pair Reagent)

2
 HPLC Column for Hydrophilic Interaction

COSMOSIL HILIC

・Triazole bonded stationary phase N

・Enhanced hydrophilic interaction NH
・Alternative selectivity to other HILIC columns
N
Triazole
Different Interactions
・Separation of Anionic Compounds
Anionic compounds were used to evaluate the anion-exchange capability. The only COSMOSIL HILIC showed strong
selectivity of anionic compounds against competitors' columns

COSMOSIL HILIC M company T company W company Column Size 4.6 mm I.D. x 250 mm
(HILIC column) (Amide column) (HILIC column) Mobile Phase Acetonitrile : 10 mmol/l Phosphate Buffer (pH7.0) = 50 : 50
Flow Rate 1.0 ml/min
Temperature 30Υ
Detection UV 210 nm
Sample 1. Oxamic Acid (0.4 mg/ml)
2. Oxalic Acid (2.0 mg/ml)
Injection Volume 1.0 μl
NH2 O
HO HO
O OH
3 O O
1. Oxamic Acid 2. Oxalic Acid

・Separation of Acidic, Basic and Neutral Compounds

Acidic (Glyceric Acid), basic (Tris) and neutral (meso-Erythritol) compounds were used for evaluation of anion and cation-
exchange characteristics. The separation factor D(Acid/Neutral) indicates its anion-exchange capability and the factor D(Basic/
Neutral) shows its cation-exchange effect.

COSMOSIL HILIC M companyHILIC column) Ș(Basic/Neutral) = 4.45

Ș(Acidic/Neutral) = 1.71

Ș(Basic/Neutral) = 1.48
Ș(Acidic/Neutral) = 4.36

T company (Amide column) Ș(Basic/Neutral) = 3.07

Ș(Acidic/Neutral) = 2.04

Column Size 4.6 mm I.D. x 250 mm

Mobile Phase Acetonitrile : 50mmol/l CH3COONH4 = 80 : 20
Flow Rate 1.0 ml/min
Temperature 30Υ
Detection ELSD
Sample 1. meso-Erythritol (1.0 mg/ml)
2. Tris(hydroxymethyl)aminomethane (1.0 mg/ml)
3. Glyceric Acid (2.0 mg/ml) W company (HILIC column) Ș(Basic/Neutral) = 5.03
Injection Volume 3.0 μl Ș(Acidic/Neutral) = 1.47

OH
OH
HOOC
HO OH OH
OH H2N OH
OH
OH

1. meso-Erythritol 2. Tris(hydroxymethyl) 3. Glyceric Acid

Neutral aminomethane ࠉAcidic
Basic

3
 Different Interactions
・Separation by Hydrophilic Interaction
The retention mechanism of COSMOSIL HILIC is the combination of hydrophilic interaction and anion-exchange capability, and
the retention can be controlled by changing the mobile phase.

Hydrophilic Interaction (Low)

Ionic Interaction (Low)

Hydrophilic Interaction (Low) Hydrophilic Interaction (High)

Ionic Interaction (High) Ionic Interaction (Low)

Suppress ionic Enhance hydrophilic interaction

interaction by by increasing organic solvent concentration.
increasing salt
concentration

Mobile Phase Mobile Phase Mobile Phase

Acetonitrile : 10 mmol/l CH3COONH4 = 50 : 50 Acetonitrile : 100 mmol/l CH3COONH4 = 50 : 50 Acetonitrile : 100 mmol/l CH3COONH4 = 80 : 20

HO HO
Column Size 4.6 mm I.D. x 250 mm 1. Isoascorbic Acid 2. Ascorbic Acid
Flow Rate 1.0 ml/min 䚷䚷䛊Erythorbic Acid䛋 HO H
Temperature 30Υ H H H
Detection UV 245 nm OH
HO HO
Sample 1. Isoascorbic AcidࠝErythrbic Acidࠞ (0.5 mg/ml) O O
2. Ascorbic Acid (0.5 mg/ml)
Injection Volume 2.0 μl HO O HO O

Melamine Analysis
Melamine analysis and LC/MS/MS using COSMOSIL HILIC.

7.5e4

7.0e4
TIC
6.5e4
Melamine(Positive ESI)
6.0e4

5.5e4

5.0e4

4.5e4

4.0e4

3.5e4

3.0e4

2.5e4

2.0e4

1.5e4

1.0e4

5000.0 1.88 4.92

0.0
0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8.5 9.0 9.5 10.0
Time,min

Combination with C18 Columns

Column Size 4.6 mm I.D. x 250 mm
Mobile Phase 5C18-AR-Ⅱ A: Acetonitrile/0.1%TFA = 10/90
3,4,5 B: Acetonitrile/0.1%TFA = 30/70
      B: 0→100％ 20min linear gradient
HILIC Acetonitrile/10mmol/l Phosphate Buffer(pH7)= 70/30
Flow Rate 1.0 ml/min
Temperature 30Υ
Detection UV 220 nm
Sample
1. Angiotensin II, [Sar1, Thr8] (0.5 μg)
1 2 2. Angiotensin II, [Sar1, Ala8] (0.5 μg)
6
COSMOSIL 5C18-AR-II 7 COSMOSIL HILIC 3. Angiotensin II, Des-Asp - [Ile ] (0.5 μg)
1
4. Angiotensin II, [Asn1, Val5]
8
(0.5 μg)
5. Angiotensin II, [Sar1, Ile8] (0.5 μg)
6. Angiotensin II, [Val5] (0.5 μg)
3 7. Angiotensin II, (Human) (0.5 μg)
4
Separate peak No.3-6 5
6
by COSMOSIL HILIC

0 5 10 15 20 (min)

4
 Ordering Information
Product Name Column Size Product Number Product Name Column Size Product Number
COSMOSIL HILIC 1.0 mm I.D. x 150 mm 07869-11 COSMOSIL HILIC 4.6 mm I.D. x 250 mm 07057-41
Packed Column 1.0 mm I.D. x 250 mm 07870-71 Packed Column 10.0 mm I.D. x 150 mm 05564-51
2.0 mm I.D. x 30 mm 08568-21 10.0 mm I.D. x 250 mm 07059-21
2.0 mm I.D. x 50 mm 07052-91 20.0 mm I.D. x 250 mm 07060-81
2.0 mm I.D. x 100 mm 08569-11 28.0 mm I.D. x 250 mm 07875-21
2.0 mm I.D. x 150 mm 07054-71 COSMOSIL HILIC 4.6 mm I.D. x 10 mm 07055-61
2.0 mm I.D. x 250 mm 07489-91 Guard Column 10.0 mm I.D. x 20 mm 07058-31
3.0 mm I.D. x 150 mm 07871-61 20.0 mm I.D. x 20 mm 07854-91
3.0 mm I.D. x 250 mm 07872-51 20.0 mm I.D. x 50 mm 07873-41
4.6 mm I.D. x 150 mm 07056-51 28.0 mm I.D. x 50 mm 07874-31
4.6 mm I.D. x 150 mm
09385-23
3 lots set

Ultra-High Performance Column for HILIC Analysis

COSMOSIL 2.5HILIC
・8OWUD+LJK3HUIRUPDQFHXVLQJȝPSDUWLFOHV

Ultra-High-Speed Analysis (Oxidation marker analysis)

COSMOSIL 2.5HILIC can be used with any conventional LC systems.

COSMOSIL Application Data

HILIC (5䃛m) 2.5HILIC (2.5䃛m)
(4.6mmI.D.-250mm) (3.0mmI.D.-100mm)
Column:
Column size:
Mobile phase: Acetonitrile/ 10mmol/l Ammonium Acetate = 80/20
Flow rate: 1.0 ml/min Analysis time: 1/6
Temperature: 40°C
Detection: UV249nm

Sample: 1; Creatinine (0.1mg/ml)

2; 2'-Deoxyguanosine (0.1mg/ml)
3; 8-Hydroxy-2'-Deoxyguanosine (0.1mg/ml)
4; 8-Hydroxy Guanosine (0.1mg/ml)
Inj. Vol: 1.0μl

NACALAI TESQUE, INC

Ordering Information
Product Name Column Size Product Number Product Name Column Size Product Number
COSMOSIL 2.5HILIC 2.0 mm I.D. x 50 mm 11766-21 COSMOSIL 2.5HILIC 3.0 mm I.D. x 50 mm 11771-41
Packed Column 2.0 mm I.D. x 75 mm 11768-01 Packed Column 3.0 mm I.D. x 75 mm 11772-31
2.0 mm I.D. x 100 mm 11769-91 3.0 mm I.D. x 100 mm 11773-21
2.0 mm I.D. x 150 mm 11770-51 3.0 mm I.D. x 150 mm 11774-11

5
 Selection guide of mobile phase
COMOSIL HILIC column generates retention and separation by hydrophilic interaction (mainly hydrogen bond) and anion-ex-
change. Refer to following recommendations to select an appropriate mobile phase condition.

(1) The effect of organic solvent type and content

‡ In general, acetonitrile/water is used as mobile phase.
‡ Retention increases as water content in the mobile phase decreased. (Fig.1)
‡ Use acetonitrile content in the mobile phase within the range of 0-95% (in general 50-95%).
‡ Methanol/water generates shorter retention than acetonitrile/water. (Fig.2)
‡ Use only HPLC grade solvent

8
meso-Erythritol 8
meso-Erythritol
7
Leucine
6 6 Leucine
Tris(hydroxymethyl)
Aminomethane 5
Tris(hydroxymethyl)
k'

4 Guanidoacetic Acid

k'
4 Aminomethane
3
2
2

1
0
65 70 75 80 85 90 95 100 0
Acetonitrile content(%) Acetonitorile Methanol

Fig.1 The effect of acetonitrile content on retention Fig.2 Difference of acetonitrile and methanol on retention
Column; COSMOSIL HILIC Column; COSMOSIL HILIC
Mobile phase; Acetonitrile/ 10mmol/l CH3COONH4 Mobile phase; Organic solvent/ 10mmol/l CH3COONH4 = 90/10

(2) The effect of buffer pH

‡ Keep pH of the mobile phase within the range of 2-7.5.
‡ The buffer around neutrality generates larger retention. (Fig.3)

4.5
meso-Erythritol
4
3.5 Leucine
3 Tris(hydroxymethyl)
2.5 Aminomethane
k'

2 Guanidoacetic Acid
1.5
1
0.5 Fig.3 The effect of buffer pH on retention
0
2 3 4 5 6 7 8 9
Column; COSMOSIL HILIC
pH
Mobile phase; Acetonitrile / 10mmol/l buffer = 90/10

(3) The effect of salt type and concentration

‡ When analyze ionic compounds, add salts or buffers in the mobile phase.
‡ When mobile phase has high acetonitrile content, note dissolubility of the salt. The dissolubility of phosphate buffers used
widely in reversed phase chromatography is low in acetonitrile. Therefore use of phosphate buffers is not recommended.
Keep the concentration of acetonitrile under 70% if use a phosphate buffer. Check that the salt does not precipitate when
mixed with acetonitril before use.
‡ Ammonium acetate or formic acid ammonium buffers are recommended because they are soluble in high acetonitrile content.
‡ Use the buffer concentration within the range of 5 - 100mmol/l. Moreover, check that the salt does not precipitate after mixing
buffer and acetonitrile.
‡ High salt concentration inhibits ion exchange capability and decreases retention. (Fig.4)
‡ Run mobile phase through membrane ¿lter (less than 0.45ȝm in pore size) before use.

10
Benzoic Acid
8

6
k'

0
Fig.4 The effect of salt concentration on retention
0 25 50 75 100

Buffrer Concentration(mmol/l) Column; COSMOSIL HILIC

Mobile phase; Acetonitrile / 10mmol/l CH3COONH4 = 50/50

6
(4) Selection of mobile phase
Following are the recommended mobile phases for different compound types.

Neutral compounds → Acetonitrile / Water = 90/10

Basic compounds → Acetonitrile / 10mmol/l CH3COONH4 = 90/10
Amphoteric compounds → Acetonitrile / 10mmol/l CH3COONH4 = 70/30
Acidic compounds → Acetonitrile / 10mmol/l CH3COONH4 = 50/50
↓ not eluted
Acetonitrile / 10mmol/l Phosphate buffer (pH7.0)= 50/50

(5) Two interactions (hydrophilic interaction and anion exchange capability)

The retention mechanism of COSMOSIL HILIC is the combination of hydrophilic interaction and anion-exchange, and the reten-
tion can be controlled by changing the mobile phase. More speci¿cally, the hydrophilic interaction can be enhanced by increas-
ing the organic solvent concentration while suppressing the ionic interaction with high salt concentration.

Hydrophilic Interaction (Low)

Ionic Interaction (Low)

Hydrophilic Interaction (Low) Hydrophilic Interaction (High)

Ionic Interaction (High) Ionic Interaction (Low)

Suppress ionic Enhance hydrophilic interaction

interaction by by increasing organic solvent concentration.
increasing salt
concentration

Mobile Phase Mobile Phase Mobile Phase

Acetonitrile : 10 mmol/l CH3COONH4 = 50 : 50 Acetonitrile : 100 mmol/l CH3COONH4 = 50 : 50 Acetonitrile : 100 mmol/l CH3COONH4 = 80 : 20

Column Size 4.6 mm I.D. x 250 mm

Flow Rate 1.0 ml/min
Temperature 30Υ
Detection UV 245 nm
Sample 1. Isoascorbic AcidࠝErythrbic Acidࠞ (0.5 mg/ml)
2. Ascorbic Acid (0.5 mg/ml)
Injection Volume 2.0 μl

(6) Improvement of peak shape

Try following if peak shape is tailing. The peak shape might improve.
‡ Add 5mmol/l EDTA to mobile phase.
‡ Change to citrate buffer. (i. e. 10 mmol/l citrate buffer pH7.0)

80%Acetonitrile/ 80%Acetonitrile/
10 mM CH3COONH4 10 mM CH3COONH4+5 mmol/l EDTA

Column COSMOSIL HILIC(4.6mmI.D.-250mm)

Flow rate 1.0ml/min
Temperature 30oC
Detection UV254nm
Sample Tryptophan(1ng)

Fig.5 Improvement of peak shape

(7) Others
‡ Use scrupulously degassed mobile phase. Air bubbles generate detection noise and accelerate column deterioration.
‡ We recommend keeping the chromatography conditions constant, since frequent changes of mobile phase shorten column life.

7
8
9
10
 COSMOSIL Applications
COSMOSIL Application has more than 7,000 applications using COSMOSIL columns. Setting optimal HPLC experimen-
tal parameters is the one of the most important processes that requires experience and time. COSMOSIL Application
provides you with sample analysis conditions with widely used ODS columns and other specialty columns.

Visit COSMOSIL top page at

http://www.nacalai.co.jp/global/cosmosil/ Search Result

Click

Click
Application are search by
Applications
1. Sample Category
2. Sample Name
3. CAS No., OSMOSIL Application
COSMOSIL Applicat
4. Column Name
COSMOSIL Application Data
5. Particle Size 5C18-MS-II 5PE-MS NAP

Column:
Column size: 4.6mmI.D.-150mm
Mobile phase: Methanol/ 20mmol/l Phosphate
buffer(pH2.5)
5C18-MS-II = 40/60
5PE-MS = 60/40
NAP = 80/20
Flow rate: 1.0 ml/min
Temperature: 30 C
Detection: UV254nm

Sample: 1; Palmatine (0.2 g)

2; Berberine (0.2 g)
OMe O
OMe O

N+ N+
NACALAI TESQUE, INC
MeO MeO
Cl- Cl-
OMe OMe
AP-1024

Click

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 Reference List

References list
No. Title AUTHOR JOURNAL ISSUE PAGE YEAR
Characterization of the decomposition
of compounds derived from Takahiro Doi, Akihiro Takeda, Akiko
1 Contact Dermatitis 67 (5) 284–292 2012
imidazolidinyl urea in cosmetics and Asada, Keiji Kajimura
patch test materials
A simple graphical representation of
Mohammed E.A. Ibrahim, Yang Liu, Journal of
2 selectivity in hydrophilic interaction 1260 126-131 2012
Charles A. Lucy Chromatography A
liquid chromatography
Comparison of 2-amino-[3-11C] Tsuji, Atsushi B; Kato, Koichi;
isobutyric acid and 2-deoxy-2- Sugyo, Aya; Okada, Maki; Sudo,
Nuclear Medicine 1058–
3 [18F]Àuoro-D-glucose in nude mice Hitomi; Yoshida, Chisato; Wakizaka, 33 (10) 2012
Communications 1064
with xenografted tumors and acute Hidekatsu; Zhang, Ming-Rong; Saga,
inÀammation Tsuneo
Min Gi Kim, Deok-Kyu Hwang, Hyeon-
In Vitro and in Vivo Metabolism of Uk Jeong, Hye Young Ji, Sei-Ryang 11990-
4 Molecules 17 (10) 2012
Verproside in Rats Oh , Yongnam Lee, Ji Seok Yoo, Dae 12002
Hee Shin and Hye Suk Lee
Functional expression of carnitine/ Noritaka Nakamichi, Takayuki
organic cation transporter OCTN1 Taguchi, Hiroshi Hosotani, Tomohiko Neurochemistry
5 In Press 2012
in mouse brain neurons: Possible Wakayama, Takuya Shimizu, Tomoko International
involvement in neuronal differentiation Sugiura, Shoichi Iseki, Yukio Kato,
Characterization and use of hydrophilic
interaction liquid chromatography type Caroline West, Syame Khater, Eric Journal of
6 1250 182-195 2012
stationary phases in supercritical Àuid Lesellier Chromatography A
chromatography
Analysis of 8-hydroxy-2ƍ- Chiemi Hosozumi, Akira Toriba,
deoxyguanosine in human urine using Thanyarat Chuesaard, Takayuki Journal of
7 893-894 173-176 2012
hydrophilic interaction chromatography Kameda, Ning Tang, Kazuichi Chromatography B
with tandem mass spectrometry Hayakawa
A NOVEL NORMAL PHASE
HPLC METHOD FOR THE
QUANTIFICATION OF N-FORMYL T. Satyanarayana Raju, L. Journal of Liquid
1070-
8 IMPURITY IN AZACITIDINE ACTIVE Kalyanaraman, K. S. V. Raghavachary Chromatography & 35 (8) 2012
1080
PHARMACEUTICAL INGREDIENTS & P. Yadagiri Swamy Related Technologies
AND PHARMACEUTICAL DOSAGE
FORMS
Determination of Histamine in Tatsuo YOSHIDA, Hirotoshi HAMADA,
Seafood by Hydrophilic Interaction Hiroshi MURAKAWA, Hidekazu
9 Analytical Sciences 28 (2) 179-182 2012
Chromatography/Tandem Mass YOSHIMOTO, Toshiaki TOBINO, Kei
Spectrometry TODA
Dr. Tomoko Fujino, Dr. Ken-ichi
Triazole-Linked DNA as a Primer
Yasumoto, Naomi Yamazaki, Ai Chemistry – An Asian 2956-
10 Surrogate in the Synthesis of First- 6 (11) 2011
Hasome, Prof. Kazuhiro Sogawa, Prof. Journal 2960
Strand cDNA
Hiroyuki Isobe
Retention and selectivity of stationary
Journal of 5920-
11 phases for hydrophilic interaction Yong Guo, Sheetal Gaiki 1218 (35) 2011
Chromatography A 5938
chromatography
Chromatographic characterization
of hydrophilic interaction liquid Yuusuke Kawachi, Tohru Ikegami,
Journal of 5903-
12 chromatography stationary phases: Hirotaka Takubo, Yuka Ikegami, 1218 (35) 2011
Chromatography A 5919
Hydrophilicity, charge effects, structural Masatoshi Miyamoto, Nobuo Tanaka
selectivity, and separation ef¿ciency
The different decomposition properties
Takahiro Doi, Keiji Kajimura, Shuzo
13 of diazolidinyl urea in cosmetics and Contact Dermatitis 65 (2) 81-91 2011
Taguchi
patch test materials
Stationary and mobile phases
14 in hydrophilic interaction Pavel Jandera Analytica Chimica Acta 692 (1-2) 1-25 2011
chromatography: a review
Degradation of N-Acetyl-D-
glucosamine and D-Glucosamine in Rongchun WANG, Takashi Food Science and
15 17 (4) 273-278 2011
Subcritical Water and Properties of the KOBAYASHI and Shuji ADACHI Technology Research
Degradation Products
Determination of isoascorbic acid in
¿sh tissue by hydrophilic interaction Spyros Drivelos, Marilena E. Dasenaki Analytical and 2199-
16 397 (6) 2010
liquid chromatography–ultraviolet and Nikolaos S. Thomaidis Bioanalytical Chemistry 2210
detection
Toshiyuki AKACHI, Yasuyuki SHIINA,
Hepatoprotective Effects of Flavonoids
Yayoi OHISHI, Takumi KAWAGUCHI,
from Shekwasha (Citrus depressa)
17 Hirokazu KAWAGISHI, Tatsuya J. Nutr Sci Vitaminol 56 (1) 60-67 2010
against D-Galactosamine-Induced
MORITA, Makoto MORI and Kimio
Liver Injury in Rats
SUGIYAMA

34
 Reference List

No. Title AUTHOR JOURNAL ISSUE PAGE YEAR

Yuki Matsuba, Nobuhiro Sasaki,
A Novel Glucosylation Reaction Masayuki Tera, Masachika Okamura,
on Anthocyanins Catalyzed Yutaka Abe, Emi Okamoto, Haruka
3374-
18 by Acyl-Glucose–Dependent Nakamura, Hisakage Funabashi, The Plant Cell 22 (10) 2010
3389
Glucosyltransferase in the Petals of Makoto Takatsu, Mikako Saito, Hideaki
Carnation and Delphinium Matsuoka, Kazuo Nagasawa and
Yoshihiro Ozekia
Molecular identi¿cation of unsaturated
Ryuichi Takasea, Akihito Ochiai, Bunzo Biochimica et Biophysica
uronate reductase prerequisite for 1925-
19 Mikami, Wataru Hashimoto, Kousaku Acta (BBA) - Proteins & 1804 (9) 2010
alginate metabolism in Sphingomonas 1936
Murata, Proteomics
sp. A1
Inhibitory Effects of Acylated Acyclic
Toshio Morikawa, Yuanyuan Xie,
Sesquiterpene Oligoglycosides from
Kiyofumi Ninomiya, Masaki Okamoto, 1276-
20 the Pericarps of Sapindus rarak on Chem. Pharm. Bull. 58 (9) 2010
Osamu Muraoka, Dan Yuan, Masayuki 1280
Tumor Necrosis Factor-Į-Induced
Yoshikawa and Takao Hayakawa
Cytotoxicity
Approach to hydrophilic interaction
chromatography column selection: Raluca-Ioana Chirita, Caroline West, Journal of 3091-
21 1217 (18) 2010
Application to neurotransmitters Adriana-Luminita Finaru, Claire Elfakir Chromatography A 3104
analysis
Medicinal Flowers. Part 29.
Toshio Morikawa, Xuezheng Li, Eriko
Acylated Oleanane-Type Triterpene
Nishida, Seikou Nakamura, Kiyofumi
Bisdesmosides: Perennisaponins G,
22 Ninomiya, Hisashi Matsuda, Yoshimi Helvetica Chimica Acta 93 (3) 573-586 2010
H, I, J, K, L, and M with Pancreatic
Oda, Osamu Muraoka, Masayuki
Lipase Inhibitory Activity from the
Yoshikawa
Flowers of Bellis perennis
Takumi Kawaguchi, Tomohiro Suzuki,
Unusual amino acid derivatives from Yuka Kobayashi, Shinya Kodani,
23 Tetrahedron 66 (2) 504-507 2010
the mushroom Pleurocybella porrigens Hirofumi Hirai, Kaoru Nagai, Hirokazu
Kawagishi
Structures of Acetylated Oleanane- Yasunobu Asao, Toshio Morikawa,
Type Triterpene Saponins, Yuanyuan Xie, Masaki Okamoto,
24 Rarasaponins IV, V, and VI, and Anti- Makoto Hamao, Hisashi Matsuda, Chem. Pharm. Bull. 57 (2) 198-203 2009
hyperlipidemic Constituents from the Osamu Muraoka, Dan Yuan and
Pericarps of Sapindus rarak Masayuki Yoshikawa
Development and validation of a
reversed-phase high-performance S. Mutalik, A.K. Hewavitharana, P.N.
Journal of 3556-
25 liquid chromatographic method for Shaw, Y.G. Anissimov, M.S. Roberts, 877 (29) 2009
Chromatography B 3562
quanti¿cation of peptide dendrimers in H.S. Parekh,
human skin permeation experiments
Determination of para-aminohippuric
acid (PAH) in human plasma and urine Phey Yen Han, P. Nicholas Shaw, Carl Journal of 3215-
26 877 (27) 2009
by liquid chromatography–tandem M.J. Kirkpatrick Chromatography B 3220
mass spectrometry
Oxidation of Methionine to
Alexander V. Peskin, Rufus Turner,
Dehydromethionine by Reactive 10175–
27 Ghassan J. Maghzal, Christine C. Biochemistry 48 (42) 2009
Halogen Species Generated by 10182
Winterbourn and Anthony J. Kettle
Neutrophils
Toshio Morikawa, Yuanyuan Xie,
Oleanane-type triterpene Yasunobu Asao, Masaki Okamoto,
oligoglycosides with pancreatic lipase Chihiro Yamashita, Osamu 1166-
28 Phytochemistry 70 (9) 2009
inhibitory activity from the pericarps of Muraoka, Hisashi Matsuda, Yutana 1172
Sapindus rarak Pongpiriyadacha, Dan Yuan, Masayuki
Yoshikawa
Direct Evidence for Ef¿cient
Keisuke Mitsuoka, Ikumi Tamai,
Transport and Minimal Metabolism
Yasushi Morohashi, Yoshiyuki Kubo, 1459-
29 of L-Cephalexin by Oligopeptide Biol. Pharm. Bull. 32 (8) 2009
Ryoichi Saitoh, Akira Tsuji and Yukio 1461
Transporter 1 in Budded Baculovirus
Kato
Fraction
Simultaneous measurement of
Takahiro Doi, Keiji Kajimura, Satoshi
diazolidinyl urea, urea, and allantoin Journal of 1005-
30 Takatori, Naoki Fukui, Shuzo Taguchi, 877 (10) 2009
in cosmetic samples by hydrophilic Chromatography B 1010
Shozo Iwagami
interaction chromatography
A Perspective of Hydrophilic Interaction
Chromatography -Development and Tohru Ikegami, Hirotaka Takubo,
31 Chromatography 29 (2) 2008
the Characteristics of the separation Nobuo Tanaka
mode
Tetrodotoxin poisoning evidenced by
Hsiao-Chin Jen, Shin-Jung Lin, Yung-
solid-phase extraction combining with Journal of
32 Hsiang Tsai, Chun-Hsiang Chen, Zu- 871 (1) 95-100 2008
liquid chromatography–tandem mass Chromatography B
Chun Lin, Deng-Fwu Hwang,
spectrometry

35
 INDEX

Sample name Page Sample name Page

A Acesulfame 10 C Choline Hydrogen Tartrate 11
Acetamide 12 Creatine 17
Acetazolamide 12 Creatinine 10, 17
Acetrizoic Acid 12 Cyanoacetic Acid 17
Acrylic Acid 12 Cyanuric Acid 8, 17
L-Į-Alanine 12 L-Cysteine 17
ȕ-Alanine 12 L-(-)-Cystine 18
Allantoic Acid 11 Cytidine 18
Allantoin 11, 12 Cytosine 18
p-Aminobenzamidine 12 D 2'-Deoxyguanosine 10
p-Aminobenzoic Acid 13 3,4-Diaminobenzoic Acid 18
4-Amino-n-butyric Acid [GABA] 13 3,5-Diaminobenzoic Acid 18
6-Aminohexanoic Acid [6-Amino-n-caproic Acid] 13 2,4-Diaminophenol 18
5-Aminolevulinic Acid 13 DL-2,6-Diaminopimelic Acid 18
2-Aminopyridine 13 DL-2,3-Diaminopropionic Acid 18
3-Aminopyridine 13 Diatrizoic Acid 19
5-Amino-1H-tetrazole 13 Diethylene Glycol 8
3-Amino-1H-1,2,4-triazole 13 Dipicolinic Acid 19
5-Aminouracil 14 Dithiouracil 19
Ammelide 8 L-DOPA 19
Ammeline 8 Dopamine 19
Amphotericin B 14 E L-(+)-Ergothioneine 19
Angiotensin I (Human) 14 meso-Erythritol 3, 9, 19
Angiotensin II (Human) 5, 14 Ethylene Glycol 9
Angiotensin II, [Asn ,Val ]
1 5
5, 8, 14 F Famotidine 19
Angiotensin II, [Sar1,Ala8] 5, 14 Folic Acid 20
Angiotensin II, [Sar1,Ile8] 5, 8, 14 Folinic Acid 20
Angiotensin II, [Sar ,Thr ]
1 8
5, 14 Formamide 20
Angiotensin II, [Val5] 5, 8, 15 D-Fructose-6-phosphate 9, 20
Angiotensin II, Des-Asp1-[Ile8] 5, 8, 15 Fuchsine, Acid [Rubin S] 20
L-Arginine 15 Fumaric Acid 20
Ascorbic Acid 4, 7, 8 G GABA[4-Amino-n-butyric Acid] 13
L-(+)-Ascorbic Acid[Vitamin C] 8, 15 Gluconic Acid 20
L-Asparagine 15 Glucose 9
Aspartame 10 D-Glucose-6-phosphate 9, 20
L-Aspartic Acid 15 Į-D-Glucose-1-phosphate 9, 21
6-Azauracil 15 D-Glucuronic Acid 21
Aztreonam 15 L-Glutamic Acid 21
B Benzamidine 16 L-Glutamine 21
Benzenesulfonic Acid 16 Glutaric Acid 21
Benzoic Acid 10, 16 Glutathione(Reduced Form) 21
Benzylamine 16 Glyceric Acid 3,9
Bromoacetic Acid 16 DL-Glyceric Acid 21
C Cacotheline 16 Glycerol 8,9
Caffeine 10 Glycinamide 21
Camostat 16 Glycine 2, 9, 22
L-Carnitine 16 Glycolic Acid 22
Ceftriaxone 17 Glycylglycine 2, 9, 22
Chloroacetic Acid 17 Guanidoacetic Acid 22
Citrazinic Acid 17 H 1,2,6-Hexanetriol 22
L-Citrulline 8 L-Histidine 22
Choline Chloride 11 L-Homocystine 22

36
 INDEX

Sample name Page Sample name Page

H L-Homoserine 22 P Perennisaponin K 34, 35
Hydantoic Acid 23 L-(-)-Phenylalanine 28
Hydantoin 23 p-Phenylenediamine 28
Hydroxylamine-O-sulfonic Acid 23 L-(+)-Į-Phenylglycine 28
8-Hydroxy-2'-Deoxyguanosine 10 Phosphocreatine 28
8-Hydroxy Guanosine 10 O-Phospho-L-serine 28
cis-4-Hydroxy-D-proline 23 Picolinic Acid 28
L-Hydroxyproline [trans-4-Hydroxy-L-proline] 23 Pivalic Acid 28
N-Hydroxysuccinimide 23 Procaterol 28
I Indigo carmine 23 L-Proline 29
Isoascorbic Acid[Erythorbic Acid] 4, 7, 8 Propionic Acid 29
D-Isoascorbic Acid 23 Pyridoxine[Vitamin B6] 8, 29
Isocinchomeronic Acid [Pyridine-2,5-dicarboxylic Acid] 24 Pyruvic Acid 29
Isoleucine 9 Q Quinine 10
L-Isoleucine 24 R RiboÀavin[Vitamin B2] 8, 32
Isonicotinic Acid  24 Ribose-5-phosphate 29
Isonicotinohydrazide 24 S D-Saccharic Acid 29
Isopropyl -ȕ-D-1-thiogalactopyranoside [IPTG] 24 Saccharin 10
K Kojic Acid 24 Sarcosine 29
L Leucine 9 Sebacic Acid 29
L-Leucine 24 L-Serine 30
D-Leucyl-L-tyrosine 24 Sinigrin 30
L-Lysine 25 Sorbic Acid 8, 10, 30
M Melamine 4, 8, 25 Succinic Acid 30
Maleic Acid 25 Sulbactam 30
Malic Acid 8 Sulfanilic Acid 30
L-(-)-Malic Acid 25 T L-(+)-Tartaric Acid 30
Malonic Acid 25 Taurine 10, 30
Mecobalamin 25 L-Theanine 31
Metanilic Acid 25 Thiamine[Vitamin B1] 32
L-Methionine 25 2-Thiobarbituric Acid 31
N-Methylglucamine 26 2-Thiouracil 31
N-Methylhydroxylamine 26 L-Threonine 31
2-Methylimidazole 10 Todralazine 31
4-Methylimidazole 10 Trichloroacetic Acid 31
6-Methyl-2-thiouracil 26 Trimethylene Glycol 9
Mucic Acid 26 Tris(hydroxymethyl)aminomethane 3, 9, 31
Murexide 26 Tryptophan 7
N 1,5-Naphthalenedisulfonic Acid 11 L-Tryptophan 31
Nicotinamide 8, 26 L-Tyrosine 32
Nicotinic Acid 8, 26 U Uracil 10, 32
L-Noradrenaline [Norepinephrine] 26 Urea 10, 32
Norepinephrine [L-Noradrenaline] 26 Uridine 10, 32
DL-Norleucine 27 V Valine 9
DL-Norvaline 27 L-Valine 28
O L-Ornithine 27 Vitamin B1[Thiamine] 28
Orotic Acid 27 Vitamin B2 [RiboÀavin] 8, 32
Oxalic Acid 3, 9, 27 Vitamin B6[Pyridoxine] 8, 29
Oxamic Acid 3, 9, 27 Vitamin C[L-(+)-Ascorbic Acid] 8, 15
Oxytocin 27
P D-Pantothenic Acid 8, 27
Perennisaponin J 34, 35

37
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