New flavan and alkyl alpha, beta-lactones from the stem bark of Horsfieldia superba.
In the present study phytochemical investigation of the methanol extract of the stem bark of Horsfieldia superba led to the isolation of twenty compounds (1-20), of which three (1-3) were new. However, compounds 2 and 3 were previously reported as synthetic alpha,beta-lactones. The compounds were ch...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Natural Product Communications
2013
|
| Online Access: | http://psasir.upm.edu.my/id/eprint/30491/1/New%20flavan%20and%20alkyl%20alpha.pdf |
| _version_ | 1825947717338136576 |
|---|---|
| author | Al-Mekhlafi, Nabil Ali Naji Shaari, Khozirah Abas, Faridah Jeyaraj, Ethel Jeyaseela Stanslas, Johnson Khalivulla, Shaik Ibrahim Lajis, Md Nordin |
| author_facet | Al-Mekhlafi, Nabil Ali Naji Shaari, Khozirah Abas, Faridah Jeyaraj, Ethel Jeyaseela Stanslas, Johnson Khalivulla, Shaik Ibrahim Lajis, Md Nordin |
| author_sort | Al-Mekhlafi, Nabil Ali Naji |
| collection | UPM |
| description | In the present study phytochemical investigation of the methanol extract of the stem bark of Horsfieldia superba led to the isolation of twenty compounds (1-20), of which three (1-3) were new. However, compounds 2 and 3 were previously reported as synthetic alpha,beta-lactones. The compounds were characterized as (-)-3,4',7-trihydroxy-3'-methoxyflavan (1), (-)-5,6-dihydro-6-undecyl-2H-pyran-2-one (2), and (-)-5,6-dihydro-6-tridecyl-2H-pyran-2-one (3). Seventeen other known compounds were also isolated and identified as (-)-viridiflorol (4), hexacosanoic acid (5), beta-sitosterol (6), methyl 2,4-dihydroxy-6-methylbenzoate (methylorsellinate) (7), methyl 2,4-dihydroxy-3,6-dimethylbenzoate (8), (-)-4'-hydroxy-7-methoxyflavan (9), (-)-4',7-dihydroxyflavan (10), (-)-4',7-dihydroxy-3'-methoxyflavan (11), (+)-3,4',7-trihydroxyflavan (12), (-)-catechin (13), (-)-epicatechin (14), (-)-7-hydroxy-3',4'-methylenedioxyflavan (15), 2',3,4-trihydroxy-4'-methoxydihydrochalcone (16), 3',4',7-trihydroxyflavone (17), (+)-4'-hydroxy-7-methoxyflavanone (18), hexadecanoic acid (palmitic acid) (19) and 3,4-dihydroxybenzoic acid (20). The structures of the compounds were fully characterized by various physical methods (melting point, optical rotation), spectral (UV, IR, ID and 2D NMR) and mass spectrometric techniques. In vitro assay of compounds 2 and 3 demonstrated moderate cytotoxic activities against human prostate (PC-3), colon (HCT-116) and breast (MCF-7) cancer cells, while the chloroform and ethyl acetate fractions of H. superba were found to exhibit moderate AChE inhibitory activity (IC50 72 and 60 microg/mL). |
| first_indexed | 2024-03-06T08:17:43Z |
| format | Article |
| id | upm.eprints-30491 |
| institution | Universiti Putra Malaysia |
| language | English |
| last_indexed | 2024-03-06T08:17:43Z |
| publishDate | 2013 |
| publisher | Natural Product Communications |
| record_format | dspace |
| spelling | upm.eprints-304912015-09-17T03:51:30Z http://psasir.upm.edu.my/id/eprint/30491/ New flavan and alkyl alpha, beta-lactones from the stem bark of Horsfieldia superba. Al-Mekhlafi, Nabil Ali Naji Shaari, Khozirah Abas, Faridah Jeyaraj, Ethel Jeyaseela Stanslas, Johnson Khalivulla, Shaik Ibrahim Lajis, Md Nordin In the present study phytochemical investigation of the methanol extract of the stem bark of Horsfieldia superba led to the isolation of twenty compounds (1-20), of which three (1-3) were new. However, compounds 2 and 3 were previously reported as synthetic alpha,beta-lactones. The compounds were characterized as (-)-3,4',7-trihydroxy-3'-methoxyflavan (1), (-)-5,6-dihydro-6-undecyl-2H-pyran-2-one (2), and (-)-5,6-dihydro-6-tridecyl-2H-pyran-2-one (3). Seventeen other known compounds were also isolated and identified as (-)-viridiflorol (4), hexacosanoic acid (5), beta-sitosterol (6), methyl 2,4-dihydroxy-6-methylbenzoate (methylorsellinate) (7), methyl 2,4-dihydroxy-3,6-dimethylbenzoate (8), (-)-4'-hydroxy-7-methoxyflavan (9), (-)-4',7-dihydroxyflavan (10), (-)-4',7-dihydroxy-3'-methoxyflavan (11), (+)-3,4',7-trihydroxyflavan (12), (-)-catechin (13), (-)-epicatechin (14), (-)-7-hydroxy-3',4'-methylenedioxyflavan (15), 2',3,4-trihydroxy-4'-methoxydihydrochalcone (16), 3',4',7-trihydroxyflavone (17), (+)-4'-hydroxy-7-methoxyflavanone (18), hexadecanoic acid (palmitic acid) (19) and 3,4-dihydroxybenzoic acid (20). The structures of the compounds were fully characterized by various physical methods (melting point, optical rotation), spectral (UV, IR, ID and 2D NMR) and mass spectrometric techniques. In vitro assay of compounds 2 and 3 demonstrated moderate cytotoxic activities against human prostate (PC-3), colon (HCT-116) and breast (MCF-7) cancer cells, while the chloroform and ethyl acetate fractions of H. superba were found to exhibit moderate AChE inhibitory activity (IC50 72 and 60 microg/mL). Natural Product Communications 2013 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/30491/1/New%20flavan%20and%20alkyl%20alpha.pdf Al-Mekhlafi, Nabil Ali Naji and Shaari, Khozirah and Abas, Faridah and Jeyaraj, Ethel Jeyaseela and Stanslas, Johnson and Khalivulla, Shaik Ibrahim and Lajis, Md Nordin (2013) New flavan and alkyl alpha, beta-lactones from the stem bark of Horsfieldia superba. Natural Product Communications, 8 (4). pp. 447-451. ISSN 1934-578X; ESSN: 1555-9475 |
| spellingShingle | Al-Mekhlafi, Nabil Ali Naji Shaari, Khozirah Abas, Faridah Jeyaraj, Ethel Jeyaseela Stanslas, Johnson Khalivulla, Shaik Ibrahim Lajis, Md Nordin New flavan and alkyl alpha, beta-lactones from the stem bark of Horsfieldia superba. |
| title | New flavan and alkyl alpha, beta-lactones from the stem bark of Horsfieldia superba. |
| title_full | New flavan and alkyl alpha, beta-lactones from the stem bark of Horsfieldia superba. |
| title_fullStr | New flavan and alkyl alpha, beta-lactones from the stem bark of Horsfieldia superba. |
| title_full_unstemmed | New flavan and alkyl alpha, beta-lactones from the stem bark of Horsfieldia superba. |
| title_short | New flavan and alkyl alpha, beta-lactones from the stem bark of Horsfieldia superba. |
| title_sort | new flavan and alkyl alpha beta lactones from the stem bark of horsfieldia superba |
| url | http://psasir.upm.edu.my/id/eprint/30491/1/New%20flavan%20and%20alkyl%20alpha.pdf |
| work_keys_str_mv | AT almekhlafinabilalinaji newflavanandalkylalphabetalactonesfromthestembarkofhorsfieldiasuperba AT shaarikhozirah newflavanandalkylalphabetalactonesfromthestembarkofhorsfieldiasuperba AT abasfaridah newflavanandalkylalphabetalactonesfromthestembarkofhorsfieldiasuperba AT jeyarajetheljeyaseela newflavanandalkylalphabetalactonesfromthestembarkofhorsfieldiasuperba AT stanslasjohnson newflavanandalkylalphabetalactonesfromthestembarkofhorsfieldiasuperba AT khalivullashaikibrahim newflavanandalkylalphabetalactonesfromthestembarkofhorsfieldiasuperba AT lajismdnordin newflavanandalkylalphabetalactonesfromthestembarkofhorsfieldiasuperba |