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A Novel Type of Dimeric Secoiridoid Glycoside from Lisianthius jefensis R OBYNS et E LIAS
Author(s) -
Hamburger Matthias,
Hostettmanna Maryse,
StoeckliEvans Helen,
Soils Pablo N.,
Gupta Mahabir P.,
Hostettmanna Kurt
Publication year - 1990
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19900730706
Subject(s) - aglycone , chemistry , stereochemistry , glycoside , gentianaceae , botany , biology
A dimeric secoiridoid glucoside named lisianthioside ( l ) has been isolated from the roots of Lisianthius jefensis R OBYNS et E LIAS (Gentianaceae). The structure was established by spectroscopic analysis (UV, IR, 1 H‐ and 13 C‐NMR, DCI‐MS) of glycoside 1 , peracetate 1a , aglycone 3 and the dimethoxy derivatives 4a – c . Lisianthioside ( 1 ) is the first representative of a novel type of dimeric secoiridoids. Biogenetically derived from two sweroside ( 2 ) moieties, the tricyclic aglycone features a symmetrical 12‐membered bislactone ring. In contrast to the moderately bitter sweroside ( 2 ), lisianthioside ( 1 ) is tasteless.