Premium
New Monoterpene‐Substituted Dihydrochalcones from Piper aduncum
Author(s) -
Orjala Jimmy,
Wright Anthony D.,
Erdelmeier Clemens A. J.,
Sticher Otto,
Rali Topul
Publication year - 1993
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.19930760409
Subject(s) - chemistry , furan , monoterpene , stereochemistry , piperaceae , piper , organic chemistry , botany , biology
Five New unusual monoterpene‐substituted dihydrochalcones, the adunctins A–E (1″ S )‐1‐{2′‐hydroxy‐4′‐methoxy‐6′‐[4″‐methyl‐1″‐(1‴‐methylethyl)cyclohex‐3″ ‐en‐1″ ‐yloxy]phenyl}‐3‐phenylpropan‐1‐one ( 1 ), (5a R *,8 R *,9a R *)‐3‐phenyl‐1‐[5′,8′,9′,9′a‐tetrahydro‐3′‐hydroxy‐1′‐methoxy‐8′‐(1″‐methylethyl)‐5′‐a‐methyldibenzo‐[ b,d ]furan‐4′‐yl]propan‐1‐one ( 2 ), (2′ R *,4″ S *)‐1‐{6′‐hydroxy‐4′‐methoxy‐4″‐(1‴‐methylethyl)spiro[benzo[b]‐furan‐2′(3′ H ),1″ ‐cyclohex‐2″ ‐en]‐7′‐yl}‐3‐phenylpropan‐1‐one ( 3 ), (2′R*,4″ R *)‐1‐{6′‐hydroxy‐4′‐methylethyl‐4″‐(1‴‐methylethyl)spiro[benzo[ b ]furan‐2′(3′ H ),1″‐cyclohex‐2″‐en]‐7′‐yl}‐3‐phenypropan‐1‐one ( 4 ), and (5′aR*,6′ S *, 9′ R *,9′a S *)‐1‐[5′a,6′,7′,8′,9′a‐hexahydro‐3′,6′‐methoxy‐6′‐methyl‐9′‐(1″‐methylethyl)dibenzo[ b,d ]‐furan‐4′‐yl]‐3‐phenylpropan‐1‐one ( 5 ) were isolated from the leaves of Piper aduncum (Piperaceae) by preparative liquid chromatography. In addition, (−)‐methyllindaretin ( 6 ), trans ‐phytol, and α‐tocopherol ( = vitamin E) were also isolated and identified. The structures were elucidated by spectroscopic methods, including 1D‐ and 2D‐NMR spectroscopy as well as single‐crystal X‐ray diffraction analysis. The antibacterial and cytotoxic potentials of the isolates were also investigated.