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1.
Natural Product Sciences ; : 134-139, 2021.
Artigo em Inglês | WPRIM | ID: wpr-902775

RESUMO

A new cipadesin limonoid, i.e. 3-epi-cipadonoid C (1), and a new tirucallane triterpene, i.e. hispidol B 3-palmitate (3), have been isolated from the seeds and fruit peels extract of Sandoricum koetjape, respectively. Along with these compounds the known limonoid, cipaferen G (2), and two pentacyclic triterpenes, bryonolic (4) and bryononic (5) acids, were also isolated. The strucrures of the new compounds were elucidated by the analysis of NMR and mass spectral data. Compounds 1 - 5 were evaluated as the inhibitor of receptor tyrosine kinases (EGFR, Epidermal Growth Factor Receptor; HER2, HER4, Human Epidermal growth factor Receptor 2, -4; IGFR, Insulin-like Growth Factor Receptor; InsR, Insulin Receptor; KDR, Kinase insert Domain Receptor; PDGFRα, and PDGFRβ, Platelet-Derived Growth Factor Receptor-α and -β). The results showed only 1 and 3 that have weak activity against InsR.

2.
Natural Product Sciences ; : 134-139, 2021.
Artigo em Inglês | WPRIM | ID: wpr-895071

RESUMO

A new cipadesin limonoid, i.e. 3-epi-cipadonoid C (1), and a new tirucallane triterpene, i.e. hispidol B 3-palmitate (3), have been isolated from the seeds and fruit peels extract of Sandoricum koetjape, respectively. Along with these compounds the known limonoid, cipaferen G (2), and two pentacyclic triterpenes, bryonolic (4) and bryononic (5) acids, were also isolated. The strucrures of the new compounds were elucidated by the analysis of NMR and mass spectral data. Compounds 1 - 5 were evaluated as the inhibitor of receptor tyrosine kinases (EGFR, Epidermal Growth Factor Receptor; HER2, HER4, Human Epidermal growth factor Receptor 2, -4; IGFR, Insulin-like Growth Factor Receptor; InsR, Insulin Receptor; KDR, Kinase insert Domain Receptor; PDGFRα, and PDGFRβ, Platelet-Derived Growth Factor Receptor-α and -β). The results showed only 1 and 3 that have weak activity against InsR.

3.
Artigo | IMSEAR | ID: sea-210738

RESUMO

Two triterpenoid and alkaloid compounds have been isolated, namely, 3-acetyl-12-en-28-oic acid and (R)-N-transferuloyloctopamine from Melochia umbellata (Houtt.) Stapf var Visenia. Both of these compounds were tested asan antimicrobial and anti-HCV activity. Isolation has been done by maceration, fractionation, and purification. Themolecular structure was determined by IR spectroscopy and nuclear magnetic resonance (NMR) 1,2D (1H-NMR, 13C-NMR, HSQC, and HMBC). Antimicrobial assay of 3-acetyl-12-en-28-oic acid showed a zone of inhibition in thecriteria of moderate to active against Escherichia coli (8.4 mm), Salmonella thypi (11.2 mm), Staphylococcus aureus(10.8 mm), and Candida albicans (8.5 mm), as well as compounds (R)-N-trans-feruloyloctopamine that is againstE. coli (7.0 mm), S. thypi (10.55 mm), S. aureus (9.1 mm), and C. albicans (7.9 mm). Anti-HCV tests on the twocompounds showed IC50 values of 52.07 and 45.02 μg/ml, respectively. The results of these tests indicate that the twocompounds are potential as an antibiotic candidate.

4.
Natural Product Sciences ; : 345-350, 2020.
Artigo em Inglês | WPRIM | ID: wpr-902763

RESUMO

In recent years, tyrosine kinases (TKs) have been the target to combat cancers, and most of the developed inhibitors are of synthetic origin. Natural compounds that have the properties as the TK’s inhibitors are very limited. This paper described the isolation of a new dammarane triterpene from the tree bark of Sandoricum koetjape, along with three known related dammaranes from the damar resin of Shorea javanica, as well as their inhibitory properties against eight receptor TKs (RTKs: EGFR, HER2, HER4, IGF1R, InsR, KDR, PDGFRα, and PDGFRβ). Based on the NMR and mass spectral data the new compound was identified as (12β,20S)-12,20-dihydroxy-3,4-seco-dammaran-4,24-dien-3-oic acid (12β-hydroxydammarenolic acid) (1), while the three known compounds were identified as (20S)-20-hydroxy-3,4-seco-dammaran-4,24-dien-3-oic acid (dammarenolic acid) (2), (3β,20S)-3,20-dihydroxydammaran-24-ene (3), and (20S)-3-oxo-20-hydroxydammaran-24-ene (4). The tyrosine kinase assay of the four compounds resulted only 1 and 2 at concentration of 10 μM that had weak activity against EGFR and InsR, with their % inhibitory were 30%, 27% (1), 45%, and 32% (2), respectively.The results suggested that the presence of a linear carboxylic acid group in both compounds could be of significance to the inhibitory properties against the two RTKs.

5.
Natural Product Sciences ; : 345-350, 2020.
Artigo em Inglês | WPRIM | ID: wpr-895059

RESUMO

In recent years, tyrosine kinases (TKs) have been the target to combat cancers, and most of the developed inhibitors are of synthetic origin. Natural compounds that have the properties as the TK’s inhibitors are very limited. This paper described the isolation of a new dammarane triterpene from the tree bark of Sandoricum koetjape, along with three known related dammaranes from the damar resin of Shorea javanica, as well as their inhibitory properties against eight receptor TKs (RTKs: EGFR, HER2, HER4, IGF1R, InsR, KDR, PDGFRα, and PDGFRβ). Based on the NMR and mass spectral data the new compound was identified as (12β,20S)-12,20-dihydroxy-3,4-seco-dammaran-4,24-dien-3-oic acid (12β-hydroxydammarenolic acid) (1), while the three known compounds were identified as (20S)-20-hydroxy-3,4-seco-dammaran-4,24-dien-3-oic acid (dammarenolic acid) (2), (3β,20S)-3,20-dihydroxydammaran-24-ene (3), and (20S)-3-oxo-20-hydroxydammaran-24-ene (4). The tyrosine kinase assay of the four compounds resulted only 1 and 2 at concentration of 10 μM that had weak activity against EGFR and InsR, with their % inhibitory were 30%, 27% (1), 45%, and 32% (2), respectively.The results suggested that the presence of a linear carboxylic acid group in both compounds could be of significance to the inhibitory properties against the two RTKs.

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