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Mitrariosides, Five Bitter Labdane Glycosides from Mitraria coccinea (Gesneriaceae)
Author(s) -
Cárdenas Luz Clarena,
Rodríguez Jaime,
Riguera Ricardo,
Chamy Maria Cristina
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1992199201113
Subject(s) - labdane , gesneriaceae , chemistry , glycoside , stereochemistry , diene , diterpene , botany , organic chemistry , biology , natural rubber
From Mitraria coccinea Cav. (Gesneriaceae), five strongly bitter labdane glycosides named mitrariosides A 1 , A 2 , B, C and D ( 1 — 5 ) were obtained. The structures were deduced by chemical and spectroscopic evidence (COSY, 13 C‐ 1 H CORR, NOESY and MS‐FAB) and found to be: mitrarioside A 1 ( 1 ): (6 S )‐19‐(β‐ D ‐galactopyranosyloxy)‐6‐hydroxy‐15‐(α‐ L rhamno‐pyranosyloxy)labda‐8(17),13‐diene, mitrarioside A 2 ( 2 ): (6 S )‐19‐(β‐ D ‐glucopyranosyloxy)‐6‐hydroxy‐15‐(α‐ L ‐rhamnopyranosyloxy)labda‐8(17),13‐diene, mitrarioside B ( 3 ):(6 S )‐19‐(β‐ D ‐glucopyranosyloxy)‐6‐hydroxy‐15‐(β‐ D ‐glucopyranosyloxy)‐labda‐8(17),13‐diene, mitrarioside C ( 4 ): (6 S )‐19‐(β‐ D ‐glucopyranosyloxy)‐6,15‐dihydroxylabda‐8(17), 13‐diene, and mitrarioside D ( 5 ): (6 S )‐19‐(α‐ L ‐rhamnopyranosyloxy)‐6,15‐dihydroxy‐labda‐8(17),13‐diene. The known compounds acteoside and calceolarioside C were also isolated.