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1. (Article ID: 11892)
Shibano M, Nakamura S, Motoya N, Kusano G
Studies on the constituents of Broussonetia species. V. Two new pyrrolidine alkaloids, broussonetines K and L, as inhibitors of glycosidase, from Broussonetia kazinoki Sieb.
Chemical and Pharmaceutical Bulletin 47(4) (1999)
472-476
Two new pyrrolidine alkaloids, bronssonetines K and L, were isolated from the branches of Broussonetia kazinoki Sieb. (Moraceae). Broussonetines K and L were formulated as (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(1R)-1-hydroxy-10-oxo-13-(β-D-glucopyranosyloxy) tridecyl] pyrrolidine (1) and (2R,3R,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-[(1R)-1-hydroxy-9-oxo-13-(β-D-glucopyranosyloxy) tridecyl] pyrrolidine (2), respectively, by spectroscopic and chemical methods. 1 and 2 inhibited β-glucosidase, β-galactosidase and β-mannosidase.
Moraceae, pyrrolidine alkaloid, glycosidase inhibitor, Broussonetia kazinoki, broussonetine K, broussonetine L
Publication DOI: 10.1248/cpb.47.472Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan
Methods: 13C NMR, 1H NMR, IR, inhibition studies, TLC, HPLC, optical rotation measurement, acetylation, HMBC, acylation, HCl hydrolysis, HR-SI-MS
The publication contains the following compound(s):
- Compound ID: 30782
|
b-D-Glcp-(1-13)-Subst
Subst = bronssonetine K aglycone = SMILES O=C(CC{13}CO)CCCCCCCC{1}[C@@H](O)[C@H]1N[C@H]({51}CO){53}[C@@H](O){54}[C@@H]1O |
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Structure type: monomer
; 524.3073 [M+H]+
C24H45NO11
Trivial name: bronssonetine K
Compound class: alkaloid
- Compound ID: 30783
|
b-D-Glcp-(1-13)-Subst
Subst = bronssonetine L aglycone = SMILES O=C(CCC{13}CO)CCCCCCC{1}[C@@H](O)[C@H]1N[C@H]({51}CO){53}[C@@H](O){54}[C@@H]1O |
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Structure type: monomer
; 524.3074 [M+H]+
C24H45NO11
Trivial name: bronssonetine L
Compound class: alkaloid
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2. (Article ID: 12687)
Shibano M, Tsukamoto D, Fujimoto R, Masui Y, Sugimoto H, Kusano G
Studies on the constituents of Broussonetia species. VII. Four new pyrrolidine alkaloids, broussonetines M, O, P, and Q, as inhibitors of glycosidase, from Broussonetia kazinoki Sieb.
Chemical and Pharmaceutical Bulletin 48(9) (2000)
1281-1285
Four new pyrrolidine alkaloids, broussonetines M, O, P, and Q, were isolated from the branches of Broussonetia kazinoki SIEB. (Moraceae). Broussonetines M, O, P, and Q were formulated as (2R, 3R, 4R, 5R)-2-hydroxymethyl-3, 4-dihydroxy-5-[(10S)-10, 13-dihydroxy-tridecyl]pyrrolidine (1), (2R, 3R, 4R, 5R)-2-hydroxymethyl-3, 4-dihydroxy-5-[(E)9-oxo-13-hydroxy-3-tridecenyl]pyrrolidine (2), (2R, 3R, 4R, 5R)-2-hydroxymethyl-3, 4-dihydroxy-5-[(E)10-oxo-13-hydroxy-3-tridecenyl]pyrrolidine (3), and (2R, 3R, 4R, 5R)-2-hydroxymethyl-3-hydroxy-4-(β-D-glucopyranosyloxy)-5-[10-oxo-13-(β-D-glucopyranosyloxy)tridecyl]pyrrolidine (4) respectively, by spectroscopic and chemical methods. 1-4 inhibited β-glucosidase, β-galactosidase and β-mannosidase.
Moraceae, pyrrolidine alkaloid, glycosidase inhibitor, Broussonetia kazinoki
NCBI PubMed ID: 10993225Publication DOI: 10.1248/cpb.48.1281Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Correspondence: kusano
oups.ac.jp
Institutions: Osaka University of Pharmaceutical Sciences, Takatsuki, Japan
The publication contains the following compound(s):
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