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Ergostane-type steroids from the Cameroonian ‘white tiama’ Entandrophragma angolense

Happi, Gervais Mouthé ; Wouamba, Steven Collins N. ; Ismail, Mohamed LU orcid ; Kouam, Simeon Fogue ; Frese, Marcel ; Lenta, Bruno Ndjakou and Sewald, Norbert (2020) In Steroids 156.
Abstract

Two new ergostane-type steroids named tiamenones A and B (1–2) were isolated from the bark of Entandrophragma angolense (Meliaceae) along with ten known compounds identified as 20S-hydroxy-4,6,24(28)-ergostatrien-3-one (3), 3β,7α,20β-trihydroxyergosta-5,24(28)-diene (4), 3β,5α-dihydroxyergosta-7,22-diene (5), stigmasterol, β-sitosterol, β-amyrin, oleanolic acid, asperphenamate, sucrose and daucosterol. The structures of the isolated compounds have been established using NMR spectroscopic and mass spectrometric analyses. The assignment of relative and absolute configurations of compound 1 was achieved by a NOESY experiment and comparison of its NMR data with those of known compound reported in literature. Compounds 1–3, β-amyrin and... (More)

Two new ergostane-type steroids named tiamenones A and B (1–2) were isolated from the bark of Entandrophragma angolense (Meliaceae) along with ten known compounds identified as 20S-hydroxy-4,6,24(28)-ergostatrien-3-one (3), 3β,7α,20β-trihydroxyergosta-5,24(28)-diene (4), 3β,5α-dihydroxyergosta-7,22-diene (5), stigmasterol, β-sitosterol, β-amyrin, oleanolic acid, asperphenamate, sucrose and daucosterol. The structures of the isolated compounds have been established using NMR spectroscopic and mass spectrometric analyses. The assignment of relative and absolute configurations of compound 1 was achieved by a NOESY experiment and comparison of its NMR data with those of known compound reported in literature. Compounds 1–3, β-amyrin and asperphenamate were evaluated for their antibacterial potencies against five bacterial model strains viz. Escherichia coli DSMZ 1058, Pseudomonas agarici DSMZ 11810, Bacillus subtilis DSMZ 704, Micrococcus luteus DMSZ 1605 and Staphylococcus warneri DSMZ 20036 and their cytotoxicity on two cell lines KB3-1 and HT-29. No potencies were exhibited by the tested compounds even at the highest concentration of 0.5 mg/mL. Compounds 1–3 were found to be potential HIV-1 inhibitors based on their molecular docking analyses.

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author
; ; ; ; ; and
publishing date
type
Contribution to journal
publication status
published
keywords
Antibacterial, Cytotoxicity, Entandrophragma angolense, HIV-1 inhibitors, Meliaceae, Tiamenones A and B
in
Steroids
volume
156
article number
108584
publisher
Elsevier
external identifiers
  • pmid:31982421
  • scopus:85079198680
ISSN
0039-128X
DOI
10.1016/j.steroids.2020.108584
language
English
LU publication?
no
id
15cdda0e-bc63-4c2e-bcf2-4d67c5b97c33
date added to LUP
2023-08-28 11:46:28
date last changed
2024-04-05 23:41:01
@article{15cdda0e-bc63-4c2e-bcf2-4d67c5b97c33,
  abstract     = {{<p>Two new ergostane-type steroids named tiamenones A and B (1–2) were isolated from the bark of Entandrophragma angolense (Meliaceae) along with ten known compounds identified as 20S-hydroxy-4,6,24(28)-ergostatrien-3-one (3), 3β,7α,20β-trihydroxyergosta-5,24(28)-diene (4), 3β,5α-dihydroxyergosta-7,22-diene (5), stigmasterol, β-sitosterol, β-amyrin, oleanolic acid, asperphenamate, sucrose and daucosterol. The structures of the isolated compounds have been established using NMR spectroscopic and mass spectrometric analyses. The assignment of relative and absolute configurations of compound 1 was achieved by a NOESY experiment and comparison of its NMR data with those of known compound reported in literature. Compounds 1–3, β-amyrin and asperphenamate were evaluated for their antibacterial potencies against five bacterial model strains viz. Escherichia coli DSMZ 1058, Pseudomonas agarici DSMZ 11810, Bacillus subtilis DSMZ 704, Micrococcus luteus DMSZ 1605 and Staphylococcus warneri DSMZ 20036 and their cytotoxicity on two cell lines KB3-1 and HT-29. No potencies were exhibited by the tested compounds even at the highest concentration of 0.5 mg/mL. Compounds 1–3 were found to be potential HIV-1 inhibitors based on their molecular docking analyses.</p>}},
  author       = {{Happi, Gervais Mouthé and Wouamba, Steven Collins N. and Ismail, Mohamed and Kouam, Simeon Fogue and Frese, Marcel and Lenta, Bruno Ndjakou and Sewald, Norbert}},
  issn         = {{0039-128X}},
  keywords     = {{Antibacterial; Cytotoxicity; Entandrophragma angolense; HIV-1 inhibitors; Meliaceae; Tiamenones A and B}},
  language     = {{eng}},
  publisher    = {{Elsevier}},
  series       = {{Steroids}},
  title        = {{Ergostane-type steroids from the Cameroonian ‘white tiama’ <i>Entandrophragma angolense</i>}},
  url          = {{http://dx.doi.org/10.1016/j.steroids.2020.108584}},
  doi          = {{10.1016/j.steroids.2020.108584}},
  volume       = {{156}},
  year         = {{2020}},
}