Antimycobacterial Activity of Phorbol Esters from the Fruits of Sapium indicum

Chumkaew, Parinuch; Karalai, Chatchanok; Ponglimanont, Chanita; Chantrapromma, Kan

doi:10.1021/np0204489

Cited by 64 publications

(53 citation statements)

References 11 publications

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“…2). The coupling constant between H-11 and H-12 was 9.7 Hz, confirming the a configuration of H-12 (Chumkaew et al, 2003). Other characteristic resonances included signals for a tiglyl group and an acetyl moiety.…”

Section: Introductionmentioning

confidence: 59%

“…In addition, NMR signals for a hexadecanoyl group in 2 were observed to replace those for an acetyl moiety in 1. Other characteristic resonances included signals for a tiglyl group (Zhang et al, 2013;Chumkaew et al, 2003). In the HMBC spectrum, H-12 proton showed a 3 J correlation with the carbonyl carbon of the tiglyl group, confirming the location of the tiglyl group at C-12.…”

Section: Introductionmentioning

confidence: 72%

“…A continuous study of this plant led to the purification of four new phorbol diesters (1-4) having a 4-deoxy-4b-phorbol skeleton, which had only been reported in S. indicum (Chumkaew et al, 2003). The present paper deals with the isolation, structural elucidation and cytotoxic activities of these compounds.…”

Section: Introductionmentioning

confidence: 96%

“…These signals suggested that compound 1 possessed the 4-deoxy-4a-phorbol or 4-deoxy-4b-phorbol backbone (Taylor et al, 1981;Chumkaew et al, 2003 (Zhang et al, 2013). The chemical shift values of C-1, C-2 and C-10 at d C 159.7, 136.4 and 54.1 also verified the b configuration of H-4 in compound 1 (Chumkaew et al, 2003). In addition, the proposed stereochemistry of compound 1 was supported from NOE correlations between H-4/H-8/H-11 on the b face and H-1, H-7, H-14 and H-18 on the other side of the molecule (Fig.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Four new phorbol diesters from Croton tiglium and their cytotoxic activities

Zhang

Khan²,

Wang

et al. 2016

Phytochemistry Letters

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Section: Introductionmentioning

confidence: 59%

Section: Introductionmentioning

confidence: 72%

Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Four new phorbol diesters from Croton tiglium and their cytotoxic activities

Zhang

Khan²,

Wang

et al. 2016

Phytochemistry Letters

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“…Therefore, J. curcas seeds are unsuitable for being used in animal feeding [11]. Despite their toxicity, phorbol esters also offer many interesting activities including insecticidal, molluscicidal and anti-mycobacterial [12][13][14]. A recent study has demonstrated that Casbene Synthase plays a significant role in the synthesis of phorbol esters [15].…”

Section: Introductionmentioning

confidence: 99%

Reverse Transcription-PCR analysis of geranylgeranyl diphosphate synthase (JcGGPPS) in Jatropha curcas L. and in silico analysis of Casbene Synthase (JcCS) among Euphorbiaceae

Jadid

Mardika

Nurhidayati

et al. 2016

AIP Conference Proceedings

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Abstract. Recently, Euphorbiaceae have attracted much attention for their potential uses in biodiesel production. Their seeds have been well known as the principal resource for oil production. The seed-derived oil content ranged from 28 % to 39 % by dry weight for all Euphorbiaceae species. Meanwhile, their seed also possesses relatively high protein content, ranged from 22 % to 35 %, making them a new alternative for livestock animal feed resources. Nevertheless, the development of this new animal feed resource is limited to the toxicity of the seeds. Its toxicity is mainly caused by the presence of anti-nutrient agents and toxins, such as curcin, trypsin inhibitor and phorbol ester (PE). The later is known to be tetracyclic diterpenes, which represents the primary toxic substances in one of the Euphorbiaceae plants, Jatropha curcas L. To date, little is known about the biosynthesis of these toxic substances. This research aims to analyze the expression of JcGGPPS gene encoding the geranylgeranyl diphosphate synthase involved in the production of the primary precursor for diterpenoid substances. In addition, the phylogram was presented to show the Euphorbiaceae Casbene Synthase (CS). The RT-PCR analysis showed that JcGGPPS is expressed both in seeds and leaves of J. curcas. Meanwhile, in silico analysis of six Euphorbiaceae species showed that CS from Euphorbia esula, Euphorbia resinifera, Euphorbia peplus and Euphorbia fischeriana are highly identical. In addition, CS from J. curcas derives from a different origin than other Euphorbiaceae plants.

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Preparation of Sixteen 3‐Hydroxy‐4‐ and 7‐Hydroxy‐1‐hydrindanones and 3‐Hydroxy‐4‐ and 8‐Hydroxy‐1‐hydroazulenones

et al. 2006

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3‐Hydroxyoctahydro‐4H‐inden‐4‐ones and 7‐hydroxyoctahydro‐1H‐inden‐1‐ones (1, 2 and 3, 4, respectively), as well as the homologous 3‐hydroxyoctahydro‐4(1H)‐azulenones (5, 6) and 8‐hydroxyoctahydro‐1(2H)‐azulenones (7, 8), were prepared diastereoselectively either from the precursor α,β‐enones 9, 10, 11, and 12 or by an isoxazoline method. Unmasking of the isoxazolines 13i, 14i, and 14j with O3 proved a more stereoselective process than hydrogenolysis. In many cases epimerization with 100 % completeness was observed on passing the epimerizable diastereomers once through a column filled with silica gel, the trans‐fused hydrindanones thus in most cases furnishing the cis‐fused epimers and the cis‐fused hydroazulenones the trans forms. These results have been corroborated by AM1 theoretical computations, which indicate that the cis‐fused epimers in these hydrindanone systems are more stable than the trans‐fused variants, whereas the reverse was calculated for the hydroazulenone homologues. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Antimycobacterial Activity of Phorbol Esters from the Fruits of Sapium indicum

Cited by 64 publications

References 11 publications

Four new phorbol diesters from Croton tiglium and their cytotoxic activities

Four new phorbol diesters from Croton tiglium and their cytotoxic activities

Reverse Transcription-PCR analysis of geranylgeranyl diphosphate synthase (JcGGPPS) in Jatropha curcas L. and in silico analysis of Casbene Synthase (JcCS) among Euphorbiaceae

Preparation of Sixteen 3‐Hydroxy‐4‐ and 7‐Hydroxy‐1‐hydrindanones and 3‐Hydroxy‐4‐ and 8‐Hydroxy‐1‐hydroazulenones

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