Locomotor-Reducing Effects and Structural Characteristics of Inhaled Zerumbone and Tetrahydrozerumbone Derivatives

被引：12

作者：

Ogawa, Kakuyou ^{[1
]}

Miyoshi, Takashi ^{[1
]}

Kitayama, Takashi ^{[2
]}

Ito, Michiho ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Dept Pharmacognosy, Sakyo Ku, Kyoto 6068501, Japan

[2] Kinki Univ, Grad Sch Agr, Dept Adv Biosci, Nara 6318505, Japan

来源：

BIOLOGICAL & PHARMACEUTICAL BULLETIN | 2014年 / 37卷 / 09期

关键词：

zerumbone; tetrahydrozerumbone; sedative effect; inhalation; structure-activity relationship; IDENTIFICATION; SMITH; OIL;

D O I：

10.1248/bpb.b14-00314

中图分类号：

R9 [药学];

学科分类号：

1007 ;

摘要：

Zerumbone 1 is an 11-membered cyclic sesquiterpene obtained from the rhizomes of Zingiber zerumbet SMITH (Zingiberaceae). In this study, we investigated the structure activity relationship of 1, alpha-humulene (2), tetrahydrozerumbone stereoisomers (3-5), and tetrahydrozerumbone derivatives (6-9). The oxygen-containing functional groups and the configurations at Cl and C2 contributed to the spontaneous locomotor activity reduction of zerumbone 1 and derivatives 2-9.

引用

页码：1559 / 1563

页数：5

共 23 条

[1]

Akira N., 2007, JAPANESE SOC AROMATH, V6, P13

[2] Chemical composition of the essential oil from rhizomes, leaves and flowers of Zingiber zerumbet Smith from Reunion Island [J].

Chane-Ming, J ;

Vera, R ;

Chalchat, JC .

JOURNAL OF ESSENTIAL OIL RESEARCH, 2003, 15 (03) :202-205

[3] Anti-inflammatory constituents of Zingiber zerumbet [J].

Chien, T. Y. ;

Chen, L. G. ;

Lee, C. J. ;

Lee, F. Y. ;

Wang, C. C. .

FOOD CHEMISTRY, 2008, 110 (03) :584-589

[4] Essential oils in practice to the dispensary [J].

Couic-Marinier, Francoise ;

Lobstein, Annelise .

ACTUALITES PHARMACEUTIQUES, 2013, 52 (525) :31-33

[5]

Fleming MF, 2006, GOODMAN GILMANS PHAR, P600

[6] Species-specific AFLP markers for identification of Zingiber officinale, Z. montanum and Z. zerumbet (Zingiberaceae) [J].

Ghosh, S. ;

Majumder, P. B. ;

Sen Mandi, S. .

GENETICS AND MOLECULAR RESEARCH, 2011, 10 (01) :218-229

[7] CRYSTAL-STRUCTURE OF ZERUMBONE [(E,E,E)-2,6,9,9-TETRAMETHYLCYCLOUNDECA-2,6,10-TRIEN-1-ONE] [J].

HALL, SR ;

NIMGIRAWATH, S ;

RASTON, CL ;

SITTATRAKUL, A ;

THADANITI, S ;

THIRASASANA, N ;

WHITE, AH .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (10) :2243-2247

[8]

Ibrahim MY, 2010, AFR J BIOTECHNOL, V9, P4442

[9] The sedative effect of inhaled terpinolene in mice and its structure-activity relationships [J].

Ito, Ken ;

Ito, Michiho .

JOURNAL OF NATURAL MEDICINES, 2013, 67 (04) :833-837

[10] Efficient synthesis of an optically active tetrahydrozerumbone exhibiting a fragrance and the application of zerumbone derivatives with a medium ring structure [J].

Kitayama, Takashi ;

Saito, Ayumi ;

Ohta, Sayo .

TETRAHEDRON-ASYMMETRY, 2012, 23 (20-21) :1490-1495

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