(<i>R</i>)-3-(8'-Hydroxyfarnesyl)-indole and other chemical constituents from the flowers of <i>Anomianthus dulcis</i> and their antimalarial and cytotoxic activities

Promchai, Thanika; Thaima, Thanaphat; Rattanajak, Roonglawan; Kamchonwongpaisan, Sumalee; Pyne, Stephen G.; Limtharakul, Thunwadee

doi:10.1080/14786419.2019.1679139

Cited by 11 publications

(7 citation statements)

References 31 publications

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“…Pinocembrin is a flavonoid that can be isolated from propolis (bee glue) and plants in several families, for example, Piperaceae, Lauraceae, and Asteraceae. 5 It can also be biosynthesized using microorganisms and chemical reactions. 17 - 19 Our previous study reported a successful isolation of several flavonoids, including pinocembrin, from A. dulcis , a species belonging to the Annonaceae family.…”

Section: Discussionmentioning

confidence: 99%

“…It is indigenous to Southeast Asia and can be found in woods or grasslands of the Northeast of Thailand. 4 , 5 The flowers are salmon-pink, with a strongly sweet smell, and the fruit is edible ( Figure 1A ). The decoction of its stems and roots is used as an antipyretic and galactagogues in traditional Thai medicine.…”

Section: Introductionmentioning

confidence: 99%

“…The decoction of its stems and roots is used as an antipyretic and galactagogues in traditional Thai medicine. 5 The different parts of A. dulcis are rich sources of various phytochemicals with a wide range of bioactivities, for example, alkaloids, 4 - 6 flavonoids, 4 , 7 phenolic compounds, 4 , 7 , 8 and terpenoids. 4 , 7 Examples of the bioactivities of the phytochemicals obtained from A. dulcis are antiplasmodial, 5 antispasmodic, 7 and cytotoxic effects against oral squamous cell carcinoma, 5 lung adenocarcinoma, 4 colon adenocarcinoma, 4 and cervical cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

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Anti-proliferative Effects of Pinocembrin Isolated From Anomianthus dulcis on Hepatocellular Carcinoma Cells

Saengboonmee,

Thithuan,

Mahalapbutr

et al. 2024

Integr Cancer Ther

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Background: Hepatocellular carcinoma (HCC) is the most prevalent primary liver cancer. Anomianthus dulcis (Dunal) J.Sinclair (syn. Uvaria dulcis) has been used in Thai traditional medicine in various therapeutic indications. Phytochemical constituents of A. dulcis have been isolated and identified. However, their effects on liver cancer and the associated mechanisms have not been elucidated. Methods: Dry flowers of A. dulcis were extracted using organic solvents, and chromatographic methods were used to purify the secondary metabolites. The chemical structures of the pure compounds were elucidated by analysis of spectroscopic data. Cytotoxicity against HCC cells was examined using SRB assay, and the effects on cell proliferation were determined using flow cytometry. The mechanisms underlying HCC inhibition were examined by molecular docking and verified by Western blot analysis. Results: Among 3 purified flavonoids, pinocembrin, pinostrobin, and chrysin, and 1 indole alkaloid (3-farnesylindole), only pinocembrin showed inhibitory effects on the proliferation of 2 HCC cell lines, HepG2 and Li-7, whereas chrysin showed specific toxicity to HepG2. Pinocembrin was then selected for further study. Flow cytometric analyses revealed that pinocembrin arrested the HCC cell cycle at the G1 phase with a minimal effect on cell death induction. Pinocembrin exerted the suppression of STAT3, as shown by the molecular docking on STAT3 with a better binding affinity than stattic, a known STAT3 inhibitor. Pinocembrin also suppressed STAT3 phosphorylation at both Tyr705 and Ser727. Cell cycle regulatory proteins under the modulation of STAT3, namely cyclin D1, cyclin E, CDK4, and CDK6, are substantially suppressed in their expression levels. Conclusion: Pinocembrin extracted from A. dulcis exerted a significant growth inhibition on HCC cells via suppressing STAT3 signaling pathways and its downstream-regulated genes.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Anti-proliferative Effects of Pinocembrin Isolated From Anomianthus dulcis on Hepatocellular Carcinoma Cells

Saengboonmee,

Thithuan,

Mahalapbutr

et al. 2024

Integr Cancer Ther

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“…A new farnesylindole alkaloid was obtained from the flowers of Anomianthus dulcis (Dunal) J. Sinclair (Annonaceae) and was named (R)-3-(8'-hydroxyfarnesyl)-indole (63) [109]. The structure of the new compound is very similar to a known compound 3-(R)-3-(8'-hydroxyfarnesyl)-indole, differing by the presence of a hydroxyl in the new compound.…”

Section: Alkaloidsmentioning

confidence: 97%

New Compounds from Plants: A Perspective View

Oliveira,

Kohatsu,

Hufnagel

et al. 2023

Preprint

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In view of the diminishing contribution of natural products from plants to the discovery of new chemical structures, the aim of this study was to compile the articles from 2021 to 2022, assessing: (1) which classes of compounds these new structures belong to; (2) which plants and families these compounds belong to and (3) assessing the degree of novelty of the compound with an already known structure. The review was elaborate following the Preferred Reporting Items for System-atics Reviews and Meta-analyses (PRISMA) statement checklist for guide reporting of systematic reviews. A total of 464 articles were selected for the new compounds of natural origin survey. We included 117 complete articles in this review and reported approximately 109 new structures elucidated during the years 2021 and 2022. Many of the compounds showed small structural var-iations in relation to already known molecules. For some, however, this small modification was decisive for the biological activity reported, demonstrating the importance of descriptive phytochemical studies.

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“…Thus, 3-farnesylindole ( 90 , Fig. 17) was isolated from Anomianthus dulcis in 33% ee in favour of the R -enantiomer, 124 and the marine furanoditerpene 12-hydroxyambliofuran ( 91a ) and its acetate ( 91b ) were obtained from a Spongia species as a ca. 3 : 1 mixture of enantiomers.…”

Section: The Origin Of Scalemic Natural Productsmentioning

confidence: 99%