A new indole alkaloid, 7-hydroxyspeciociliatine, from the fruits of Malaysian Mitragyna speciosa and its opioid agonistic activity

被引:46
作者
Kitajima, Mariko
Misawa, Kaori
Kogure, Noriyuki
Said, Ikram M.
Horie, Syunji
Hatori, Yoshio
Murayama, Toshihiko
Takayama, Hiromitsu
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
[2] Univ Kebangsaan Malaysia, Fac Sci & Technol, Bangi 43600, Selangor, Malaysia
[3] Josai Int Univ, Fac Pharmaceut Sci, Pharmacol Lab, Chiba 2838555, Japan
关键词
Mitragyna speciosa; indole alkaloid; 7-hydroxyspeciociliatine; structure determination; opioid agonist; mu-opioid receptor;
D O I
10.1007/s11418-005-0001-7
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A new indole alkaloid, 7-hydroxyspeciociliatine (1), was isolated from the fruits of Malaysian Mitragyna speciosa Korth., together with 11 known indole and oxindole alkaloids (3-13). The structure of the new compound was determined by spectroscopic analysis and chemical conversion. The opioid agonistic activity of the new alkaloid was investigated in guinea-pig ileum experiments. The compound was found to have a weak stimulatory effect of mu-opioid receptors.
引用
收藏
页码:28 / 35
页数:8
相关论文
共 24 条
[1]   OXIDATIVE TRANSFORMATIONS OF INDOLE ALKALOIDS .2. PREPARATION OF OXINDOLES FROM CIS-DE-YOHIMBINOID - PARTIAL SYNTHESIS OF CARAPANAUBINE [J].
FINCH, N ;
HSU, IHC ;
GEMENDEN, CW ;
TAYLOR, WI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (10) :1520-&
[2]   AGONIST AND ANTAGONIST ACTIONS OF MORPHINE-LIKE DRUGS ON GUINEA-PIG ISOLATED ILEUM [J].
GYANG, EA ;
KOSTERLITZ, HW .
BRITISH JOURNAL OF PHARMACOLOGY AND CHEMOTHERAPY, 1966, 27 (03) :514-+
[3]   Indole alkaloids of a Thai medicinal herb, Mitragyna speciosa, that has opioid agonistic effect in guinea-pig ileum [J].
Horie, S ;
Koyama, F ;
Takayama, H ;
Ishikawa, H ;
Aimi, N ;
Ponglux, D ;
Matsumoto, K ;
Murayama, T .
PLANTA MEDICA, 2005, 71 (03) :231-236
[4]   ALKALOIDS FROM MITRAGYNA-SPECIOSA [J].
HOUGHTON, PJ ;
LATIFF, A ;
SAID, IM .
PHYTOCHEMISTRY, 1991, 30 (01) :347-350
[5]   CORYNANTHEIDINE-TYPE ALKALOIDS .2. ABSOLUTE CONFIGURATION OF MITRAGYNINE SPECIOCILIATINE MITRACILIATINE AND SPECIOGYNINE [J].
LEE, CM ;
TRAGER, WF ;
BECKETT, AH .
TETRAHEDRON, 1967, 23 (01) :375-&
[6]   Preparation of (±)-hirsutine and (±)-3-isocorynantheidine [J].
Lounasmaa, M ;
Jokela, R ;
Laine, C ;
Hanhinen, P .
HETEROCYCLES, 1998, 49 :445-450
[7]   Antinociceptive effect of 7-hydroxymitragynine in mice:: Discovery of an orally active opioid analgesic from the Thai medicinal herb Mitragyna speciosa [J].
Matsumoto, K ;
Horie, S ;
Ishikawa, H ;
Takayama, H ;
Aimi, N ;
Ponglux, D ;
Watanabe, K .
LIFE SCIENCES, 2004, 74 (17) :2143-2155
[8]  
Patrick L, 1999, Altern Med Rev, V4, P220
[9]   A NEW INDOLE ALKALOID, 7-ALPHA-HYDROXY-7H-MITRAGYNINE, FROM MITRAGYNA-SPECIOSA IN THAILAND [J].
PONGLUX, D ;
WONGSERIPIPATANA, S ;
TAKAYAMA, H ;
KIKUCHI, M ;
KURIHARA, M ;
KITAJIMA, M ;
AIMI, N ;
SAKAI, S .
PLANTA MEDICA, 1994, 60 (06) :580-581
[10]   Effect of oxindole alkaloids from the hooks of Uncaria macrophylla on thiopental-induced hypnosis [J].
Sakakibara, I ;
Takahashi, H ;
Terabayashi, S ;
Yuzurihara, M ;
Kubo, M ;
Ishige, A ;
Higuchi, M ;
Komatsu, Y ;
Okada, M ;
Maruno, M ;
Biqiang, C ;
Jiang, HX .
PHYTOMEDICINE, 1998, 5 (02) :83-86