Goniolandrene A and B from Goniothalamus macrophyllus

Abdullah, Norkamilah; Sahibul-Anwar, Hamidah; Ideris, Sharinah; Hasuda, Tomoyo; Hitotsuyanagi, Yukio; Takeya, Koichi; Diederich, Marc; Choo, Chee Yan

doi:10.1016/j.fitote.2013.03.028

Cited by 16 publications

(6 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The absolute configuration of pinocembrin was further assigned by optical rotation and circular dichroism (CD) spectroscopy. Compared to the control (racemic pinocembrin ( 1 ) produced by strain 4), the CD spectrum of microbial pinocembrin exhibited a positive cotton effect at 325 nm and a negative cotton effect at 283 nm, which is consistent with the previous report [ 38 ]. Therefore, the absolute configuration of the microbial pinocembrin at C-2 was assigned to be 2S -configured (Fig.…”

Section: Resultssupporting

confidence: 91%

Transcriptome-enabled discovery and functional characterization of enzymes related to (2S)-pinocembrin biosynthesis from Ornithogalum caudatum and their application for metabolic engineering

Guo

Chen

et al. 2016

Microb Cell Fact

View full text Add to dashboard Cite

Background(2S)-Pinocembrin is a chiral flavanone with versatile pharmacological and biological activities. Its health-promoting effects have spurred on research effects on the microbial production of (2S)-pinocembrin. However, an often-overlooked salient feature in the analysis of microbial (2S)-pinocembrin is its chirality.ResultsHere, we presented a full characterization of absolute configuration of microbial (2S)-pinocembrin from engineered Escherichia coli. Specifically, a transcriptome-wide search for genes related to (2S)-pinocembrin biosynthesis from Ornithogalum caudatum, a plant rich in flavonoids, was first performed in the present study. A total of 104,180 unigenes were finally generated with an average length of 520 bp. The Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway mapping assigned 26 unigenes, representing three enzyme families of 4-coumarate:coenzyme A ligase (4CL), chalcone synthase (CHS) and chalcone isomerase(CHI), onto (2S)-pinocembrin biosynthetic pathway. A total of seven, three and one full-length candidates encoding 4CL, CHS and CHI were then verified by reverse transcription polymerase chain reaction, respectively. These candidates were screened by functional expression in E. coli individual or coupled multienzyme reaction systems based on metabolic engineering processes. Oc4CL1, OcCHS2 and OcCHI were identified to be bona fide genes encoding respective pathway enzymes of (2S)-pinocembrin biosynthesis. Then Oc4CL1, OcCHS2 and MsCHI from Medicago sativa, assembled as artificial gene clusters in different organizations, were used for fermentation production of (2S)-pinocembrin in E. coli. The absolute configuration of the resulting microbial pinocembrin at C-2 was assigned to be 2S-configured by combination of retention time, UV spectrum, LC–MS, NMR, optical rotation and circular dichroism spectroscopy. Improvement of (2S)-pinocembrin titres was then achieved by optimization of gene organizations, using of codon-optimized pathway enzymes and addition of cerulenin for increasing intracellular malonyl CoA pools. Overall, the optimized strain can produce (2S)-pinocembrin of 36.92 ± 4.1 mg/L.ConclusionsHigh titre of (2S)-pinocembrin can be obtained from engineered E. coli by an efficient method. The fermentative production of microbial (2S)-pinocembrin in E. coli paved the way for yield improvement and further pharmacological testing.Electronic supplementary materialThe online version of this article (doi:10.1186/s12934-016-0424-8) contains supplementary material, which is available to authorized users.

show abstract

Section: Resultssupporting

confidence: 91%

Transcriptome-enabled discovery and functional characterization of enzymes related to (2S)-pinocembrin biosynthesis from Ornithogalum caudatum and their application for metabolic engineering

Guo

Chen

et al. 2016

Microb Cell Fact

View full text Add to dashboard Cite

show abstract

“…On the other hand, only the 2D structure was proposed for cheliensisine; however, pinocembrin and its derivatives isolated from Goniothalamus sp. had been reported to have (2 S ) configurations. − Therefore, the absolute structure of cheliensisine was presumed to be the same as that of aquiledine ( 6 ). The specific rotations of 9 and 10 were calculated to assign the absolute structure of isoaquiledine in a similar manner.…”

Section: Results and Discussionmentioning

confidence: 99%

Computationally Assisted Structural Revision of Flavoalkaloids with a Seven-Membered Ring: Aquiledine, Isoaquiledine, and Cheliensisine

et al. 2020

View full text Add to dashboard Cite

Aquiledine and cheliensisine are flavoalkaloids isolated from Aquilegia ecalcarata and Goniothalamus cheliensis, respectively. Different structures have been proposed for these flavoalkaloids; however, their 1H and 13C NMR spectroscopic data were virtually identical. In this study, the structures of aquiledine and cheliensisine were revised on the basis of the DFT calculation of NMR data including DP4+ and J-DP4 analysis, as well as specific rotations. Similarly, the structure of isoaquiledine, a regioisomer of aquiledine, was also revised. A biosynthetic pathway of these flavoalkaloids is proposed.

show abstract

“…The extract contained 1-azaanthraquinone and naphthoquinone derivatives which possessed the high cytotoxicity against human tumor cell lines in the range of 0.04-3.03 µM 6 . Moreover, styryl-lactone and alkaloid compounds, isolated from other plants in this family also shown cytotoxic activity 7,8 . Thus, these finding compounds show a good opportunity to obtain new chemotherapeutic agents from G. marcanii stem barks in other fractions which also exhibited high cytotoxicity.…”

Section: Introductionmentioning

confidence: 95%

Cytotoxic effect of compounds isolated from Goniothalamus marcanii Craib stem barks

Thienthiti¹,

Tuchinda²,

Wongnoppavich³

et al. 2017

Pharm Sci Asia

View full text Add to dashboard Cite

Goniothalamus marcanii Craib (synonym of Goniothalamus tamirensis Pierre ex Finet & Gagnep), is locally known as Khao Lam in Thai. The previous study showed that the isolated compounds from stem barks exhibited high cytotoxicity to human tumor cell lines. The objective of the research was to investigate compounds which showed cytotoxic effect. Column chromatography was used for isolation. The structures of the compounds were investigated by spectroscopic methods. The bioactivity of the compounds was determined by SRB assay. The result showed that four compounds, a styryl-lactone: (+)-goniodiol (1); and three alkaloids: ouregidione (2); noraristolodione (3); velutinam (4) were isolated from G. marcanii stem barks. Compound 3 possessed the strongest activity (EC 50 35.56 and 50.75 μM), for A549 (lung) cells and HeLa (cervix) cells, respectively. Compound 1-3 displayed cytotoxic activity but less than that of doxorubicin, a conventional chemotherapeutic drug, the EC 50 levels of which were 0.13 and 0.12 μM for A549 and HeLa cells, respectively. On the other hand, compound 2 and 4 which could be evaluated from selective index values (SI 1.25 and 1.70, respectively) showed lower toxicity towards normal cells (MRC5) than doxorubicin (SI = 1.07). From this study, G. marcanii stem barks found to be a new source of compounds 1-4. In addition, the investigation of compound 3 in cytotoxic activity and the evaluation of compounds 1 and 2 for cytotoxic activity to HeLa cell line have been reported for the first time.

show abstract

Goniolandrene A and B from Goniothalamus macrophyllus

Cited by 16 publications

References 19 publications

Transcriptome-enabled discovery and functional characterization of enzymes related to (2S)-pinocembrin biosynthesis from Ornithogalum caudatum and their application for metabolic engineering

Transcriptome-enabled discovery and functional characterization of enzymes related to (2S)-pinocembrin biosynthesis from Ornithogalum caudatum and their application for metabolic engineering

Computationally Assisted Structural Revision of Flavoalkaloids with a Seven-Membered Ring: Aquiledine, Isoaquiledine, and Cheliensisine

Cytotoxic effect of compounds isolated from Goniothalamus marcanii Craib stem barks

Contact Info

Product

Resources

About