Alstiphyllanines E-H, picraline and ajmaline-type alkaloids from Alstonia macrophylla inhibiting sodium glucose cotransporter

被引：56

作者：

Arai, Hiroko ^{[1
]}

Hirasawa, Yusuke ^{[1
]}

Rahman, Abdul ^{[2
]}

Kusumawati, Idha ^{[2
]}

Zaini, Noor Cholies ^{[2
]}

Sato, Seizo ^{[3
]}

Aoyama, Chihiro ^{[3
]}

Takeo, Jiro ^{[3
]}

Morita, Hiroshi ^{[1
]}

机构：

[1] Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 1428501, Japan

[2] Airlangga Univ, Fac Pharm, Jalan Dharmawangsa Dalam 60286, Surabaya, Indonesia

[3] Nippon Suisan Kaisha Ltd, Cent Res Lab, Tokyo 1920906, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2010年 / 18卷 / 06期

关键词：

Indole alkaloids; Alstonia macrophylla; Alstiphyllanines E-H; SGLT; AFFINITY NA+/GLUCOSE COTRANSPORTER; KOPSIA-FLAVIDA BLUME; INDOLE ALKALOIDS; IN-VITRO; SCHOLARIS; LEAVES;

D O I：

10.1016/j.bmc.2010.01.077

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Three new picraline-type alkaloids, alstiphyllanines E-G (1-3) and a new ajmaline-type alkaloid, alstiphyllanine H (4) were isolated from the leaves of Alstonia macrophylla together with 16 related alkaloids (5-20). Structures and stereochemistry of 1-4 were fully elucidated and characterized by 2D NMR analysis. Alstiphyllanines E and F (1 and 2) showed moderate Na+-glucose cotransporter (SGLT1 and SGLT2) inhibitory activity. A series of a hydroxy substituted derivatives 21-28 at C-17 of the picraline-type alkaloids have been derived as having potent SGLT inhibitory activity. 10-Methoxy-N(1)-methylburnamine-17-O-veratrate (6) exhibited potent inhibitory activity, suggesting that the presence of an ester side chain at C-17 may be important to show SGLT inhibitory activity. Structure activity relationship of alstiphyllanines on inhibitory activity of SGLT was discussed. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2152 / 2158

页数：7

共 25 条

[1]

ABE F, 1989, CHEM PHARM BULL, V37, P887, DOI 10.1248/cpb.37.887

[2]

ABE F, 1994, PHYTOCHEMISTRY, V35, P249, DOI 10.1016/S0031-9422(00)90544-2

[3]

Abe F, 1998, CHEM PHARM BULL, V46, P1235

[4] ALKALOIDS OF ASPIDOSPERMA CUSPA BLAKE [J].

BURNELL, RH ;

MEDINA, JD .

PHYTOCHEMISTRY, 1968, 7 (11) :2045-&

[5] PLANTS FROM NEW-CALEDONIA .87. ALKALOIDS OF ALSTONIA-SPHAEROCAPITATA [J].

CARON, C ;

YACHAOUI, Y ;

MASSIOT, G ;

LEMENOLIVIER, L ;

PUSSET, J ;

SEVENET, T .

PHYTOCHEMISTRY, 1984, 23 (10) :2355-2357

[6] Induction of antifertility with lupeol acetate in male albino rats [J].

Gupta, RS ;

Bhatnager, AK ;

Joshi, YC ;

Sharma, MC ;

Khushalani, V ;

Kachhawa, JBS .

PHARMACOLOGY, 2005, 75 (02) :57-62

[7] Alstiphyllanines A-D, Indole Alkaloids from Alstonia macrophylla [J].

Hirasawa, Yusuke ;

Arai, Hiroko ;

Zaima, Kazumasa ;

Oktarina, Rice ;

Rahman, Abdul ;

Ekasari, Wiwied ;

Widyawaruyanti, Aty ;

Indrayanto, Gunawan ;

Zaini, Noor Cholies ;

Morita, Hiroshi .

JOURNAL OF NATURAL PRODUCTS, 2009, 72 (02) :304-307

[8] Two new methyl chanofruticosinates from Kopsia flavida Blume [J].

Husain, K ;

Jantan, I ;

Said, IM ;

Aimi, N ;

Takayama, H .

JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2003, 5 (01) :63-67

[9] Methyl chanofruticosinates from leaves of Kopsia flavida blume [J].

Husain, K ;

Jantan, I ;

Kamaruddin, N ;

Said, IM ;

Aimi, N ;

Takayama, H .

PHYTOCHEMISTRY, 2001, 57 (04) :603-606

[10] Evaluation of anticancer activity of the alkaloid fraction of Alstonia scholaris (Sapthaparna) in vitro and in vivo [J].

Jagetia, GC ;

Baliga, MS .

PHYTOTHERAPY RESEARCH, 2006, 20 (02) :103-109

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