Subincanadines A-C, novel quaternary indole alkaloids from Aspidosperma subincanum

被引：78

作者：

Kobayashi, J ^{[1
]}

Sekiguchi, M

Shimamoto, S

Shigemori, H

Ishiyama, H

Ohsaki, A

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

[2] Tokyo Med & Dent Univ, Inst Biomat & Bioengn, Tokyo 1010062, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 18期

关键词：

D O I：

10.1021/jo025854b

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Three novel quaternary indole alkaloids with an unprecedented 1-azoniatricyclo[4.3.3.0(1,5)]undecane moiety, subincanadines A-C (1-3), as well as two new indole alkaloids with a 1-azabicyclo[5.2.2]undecane moiety, subincanadines D (4) and E (5), and a new indole alkaloid with a 1-azabicyclo[4.3.1]decane moiety, subincanadine F (6), have been isolated from the barks of Aspidosperma subincanum Mart, and the structures of 1-6 and the stereochemistry of 1-3 were elucidated by spectroscopic data and chemical means.

引用

收藏

页码：6449 / 6455

页数：7

相关论文

共 14 条

[1]

OPHIORRHIZINE, A NEW QUATERNARY INDOLE ALKALOID RELATED TO CINCHONAMINE, FROM OPHIORRHIZA-MAJOR RIDL [J].

ARBAIN, D ;

BYRNE, LT ;

PUTRA, DP ;

SARGENT, MV ;

SKELTON, BW ;

WHITE, AH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (06) :663-664

[2]

NOE CORRELATIONS IN MTPA, MNCB AND MBNC ESTERS [J].

FUKUSHI, Y ;

YAJIMA, C ;

MIZUTANI, J .

TETRAHEDRON LETTERS, 1994, 35 (50) :9417-9420

[3]

CURARE-ALKALOIDE CALEBASSEN .12. UBER EINIGE NEUE CALEBASSEN-ALKALOIDE [J].

GIESBRECHT, E ;

MEYER, H ;

BACHLI, E ;

SCHMID, H ;

KARRER, P .

HELVETICA CHIMICA ACTA, 1954, 37 (07) :1974-1982

[4]

Echinophyllins C-F, new nitrogen containing clerodane diterpenoids from Echinodorus macrophyllus [J].

Kobayashi, J ;

Sekiguchi, M ;

Shimamoto, S ;

Shigemori, H ;

Ohsaki, A .

JOURNAL OF NATURAL PRODUCTS, 2000, 63 (11) :1576-1579

[5]

Echinophyllins A and B, novel nitrogen-containing clerodane diterpenoids from Echinodorus macrophyllus [J].

Kobayashi, J ;

Sekiguchi, M ;

Shigemori, H ;

Ohsaki, A .

TETRAHEDRON LETTERS, 2000, 41 (16) :2939-2943

[6]

STUDIES ON INDOLE ALKALOID BIOSYNTHESIS .3. [J].

KUTNEY, JP ;

NELSON, VR ;

WIGFIELD, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (15) :4278-&

[7]

Final solution on the long-standing structural arguments on the C-3 stereochemistries of three glucoindole alkaloids: Palicoside, dolichantoside, and isodolichantoside - Through chemical conversions and spectroscopic studies [J].

Ohmori, O ;

Kumazawa, K ;

Hoshino, H ;

Suzuki, T ;

Morishima, Y ;

Kohno, H ;

Kitajima, M ;

Sakai, S ;

Takayama, H ;

Aimi, N .

TETRAHEDRON LETTERS, 1998, 39 (42) :7737-7740

[8]

Microanalysis of a selective potent anti-Helicobacter pylori compound in a Brazilian medicinal plant, Myroxylon peruiferum and the activity of analogues [J].

Ohsaki, A ;

Takashima, J ;

Chiba, N ;

Kawamura, M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (08) :1109-1112

[9]

HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].

OHTANI, I ;

KUSUMI, T ;

KASHMAN, Y ;

KAKISAWA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096

[10]

PETTIT GR, 1981, CAN J CHEM, V59, P216