Abstract
The crude petroleum‐ether extract of the aerial parts of Hypericum calycinum L. (Guttiferae) exhibited in vitro growth‐inhibitory activity against the Co‐115 human colon carcinoma cell line. Bioassay‐guided fractionation of this extract allowed the isolation of the cyclohexadienone derivatives 1–5, four of which are previously undescribed compounds. The structures of the known chinesin II (1) and of 2 (hypercalin A) were established by 1H‐ and 13C‐NMR spectroscopy and were confirmed by X‐ray analysis of their crystalline mixture which revealed the complete relative configuration of both compounds. The structure of 3 (hypercalin B) was elucidated by means of extensive 1D‐ and 2D‐NMR experiments, including DQ‐COSY, HETCOR and LR‐HETCOR. The structure of compound 4 (hypercalin C) was established by 1H‐ and 13C‐NMR spectroscopy and confirmed by X‐ray analysis to be the 3,5‐dihydroxy‐4‐{[(1R*,2S*, 5S*)‐2‐hydroxy‐2‐methyl‐5‐(1‐methylethenyl)cyclopentyl]methyl}‐6,6‐bis‐(3‐methylbut‐2‐enyl)‐2‐(2‐methylpropanoyl)cyclohexa‐2,4‐dien‐1‐one. The structures of the higher isomeric homologues 5a/5b were deduced by comparison of their UV, 1H‐, and 13C‐NMR spectra with those of 4. The isolated compounds appeared to be related to chinesin I and II previously isolated from Hypericum chinense L. and were responsible for the growth‐inhibitory activity of the extract against the Co‐115 human carcinoma cell line. Moreover, 1/2 and 3 showed molluscicidal activity against the schistosomiasis‐transmitting snail Biomphalaria glabrata.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1833-1845 |
| Number of pages | 13 |
| Journal | Helvetica Chimica Acta |
| Volume | 72 |
| Issue number | 8 |
| DOIs | |
| State | Published - Jan 1 1989 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Catalysis
- Biochemistry
- Drug Discovery
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
Cite this
New Cell Growth‐Inhibitory Cyclohexadienone Derivatives from Hypericum calycinum L. / Decosterd, Laurent A.; Stoeckli‐Evans, Helen; Chapuis, Jean; Sordat, Bernard; Hostettmann, Kurt.
In: Helvetica Chimica Acta, Vol. 72, No. 8, 01.01.1989, p. 1833-1845.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - New Cell Growth‐Inhibitory Cyclohexadienone Derivatives from Hypericum calycinum L.
AU - Decosterd, Laurent A.
AU - Stoeckli‐Evans, Helen
AU - Chapuis, Jean
AU - Sordat, Bernard
AU - Hostettmann, Kurt
PY - 1989/1/1
Y1 - 1989/1/1
N2 - The crude petroleum‐ether extract of the aerial parts of Hypericum calycinum L. (Guttiferae) exhibited in vitro growth‐inhibitory activity against the Co‐115 human colon carcinoma cell line. Bioassay‐guided fractionation of this extract allowed the isolation of the cyclohexadienone derivatives 1–5, four of which are previously undescribed compounds. The structures of the known chinesin II (1) and of 2 (hypercalin A) were established by 1H‐ and 13C‐NMR spectroscopy and were confirmed by X‐ray analysis of their crystalline mixture which revealed the complete relative configuration of both compounds. The structure of 3 (hypercalin B) was elucidated by means of extensive 1D‐ and 2D‐NMR experiments, including DQ‐COSY, HETCOR and LR‐HETCOR. The structure of compound 4 (hypercalin C) was established by 1H‐ and 13C‐NMR spectroscopy and confirmed by X‐ray analysis to be the 3,5‐dihydroxy‐4‐{[(1R*,2S*, 5S*)‐2‐hydroxy‐2‐methyl‐5‐(1‐methylethenyl)cyclopentyl]methyl}‐6,6‐bis‐(3‐methylbut‐2‐enyl)‐2‐(2‐methylpropanoyl)cyclohexa‐2,4‐dien‐1‐one. The structures of the higher isomeric homologues 5a/5b were deduced by comparison of their UV, 1H‐, and 13C‐NMR spectra with those of 4. The isolated compounds appeared to be related to chinesin I and II previously isolated from Hypericum chinense L. and were responsible for the growth‐inhibitory activity of the extract against the Co‐115 human carcinoma cell line. Moreover, 1/2 and 3 showed molluscicidal activity against the schistosomiasis‐transmitting snail Biomphalaria glabrata.
AB - The crude petroleum‐ether extract of the aerial parts of Hypericum calycinum L. (Guttiferae) exhibited in vitro growth‐inhibitory activity against the Co‐115 human colon carcinoma cell line. Bioassay‐guided fractionation of this extract allowed the isolation of the cyclohexadienone derivatives 1–5, four of which are previously undescribed compounds. The structures of the known chinesin II (1) and of 2 (hypercalin A) were established by 1H‐ and 13C‐NMR spectroscopy and were confirmed by X‐ray analysis of their crystalline mixture which revealed the complete relative configuration of both compounds. The structure of 3 (hypercalin B) was elucidated by means of extensive 1D‐ and 2D‐NMR experiments, including DQ‐COSY, HETCOR and LR‐HETCOR. The structure of compound 4 (hypercalin C) was established by 1H‐ and 13C‐NMR spectroscopy and confirmed by X‐ray analysis to be the 3,5‐dihydroxy‐4‐{[(1R*,2S*, 5S*)‐2‐hydroxy‐2‐methyl‐5‐(1‐methylethenyl)cyclopentyl]methyl}‐6,6‐bis‐(3‐methylbut‐2‐enyl)‐2‐(2‐methylpropanoyl)cyclohexa‐2,4‐dien‐1‐one. The structures of the higher isomeric homologues 5a/5b were deduced by comparison of their UV, 1H‐, and 13C‐NMR spectra with those of 4. The isolated compounds appeared to be related to chinesin I and II previously isolated from Hypericum chinense L. and were responsible for the growth‐inhibitory activity of the extract against the Co‐115 human carcinoma cell line. Moreover, 1/2 and 3 showed molluscicidal activity against the schistosomiasis‐transmitting snail Biomphalaria glabrata.
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U2 - 10.1002/hlca.19890720820
DO - 10.1002/hlca.19890720820
M3 - Article
AN - SCOPUS:0024796848
VL - 72
SP - 1833
EP - 1845
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
SN - 0018-019X
IS - 8
ER -