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Curcumaromins A, B, and C, Three Novel Curcuminoids from Curcuma aromatica
Author(s) -
Qin XiangDong,
Zhao Yan,
Gao Yuan,
Ren FuCai,
Yang Shu,
Wang Fei
Publication year - 2015
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.201500080
Subject(s) - chemistry , curcuma , stereochemistry , sesquiterpene , monoterpene , traditional medicine , organic chemistry , medicine
Abstract Three novel curcuminoids, curcumaromins A–C ( 1 – 3 , resp.), along with a known compound, longiferone B ( 4 ) were isolated from Curcuma aromatica Salisb . The structures of the new compounds were elucidated as (1 E ,4 Z ,6 E )‐5‐hydroxy‐7‐{4‐hydroxy‐3‐[(1 R* ,6 R* )‐3‐methyl‐6‐(propan‐2‐yl)cyclohex‐2‐en‐1‐yl)phenyl}‐1‐(4‐hydroxyphenyl)hepta‐1,4,6‐trien‐3‐one ( 1 ), 2,3‐dihydro‐2‐(4‐hydroxyphenyl)‐6‐[( E )‐2‐(4‐hydroxyphenyl)ethenyl]‐5‐[(1 R* ,6 R* )‐3‐methyl‐6‐(propan‐2‐yl)cyclohex‐2‐en‐1‐yl]‐4 H ‐pyran‐4‐one ( 2 ), and (1 E ,6 E )‐1,7‐bis(4‐hydroxyphenyl)‐4‐[(1 R* ,6 R* )‐3‐methyl‐6‐(propan‐2‐yl)cyclohex‐2‐en‐1‐yl]hepta‐1,6‐diene‐3,5‐dione ( 3 ) on the basis of spectroscopic analysis. Curcumaromins A–C ( 1 – 3 ) represented the first examples of menthane monoterpene‐coupled curcuminoids. The known compound, longiferone B ( 4 ), was the first daucane sesquiterpene isolated from the genus Curcuma.