CHEMICAL STUDY OF LEAVES OF<i>Trichilia silvatica</i>Meliaceae

Soares, Aloízio de Oliveira; Ferreira, Adrienn Gianny Leguizamon; Soares, Luzinátia Ramos; Corsino, Joaquim; Garcez, Fernanda Rodrigues; Garcez, Walmir Silva

doi:10.5935/0100-4042.20140231

Cited by 4 publications

(5 citation statements)

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“…The spectroscopic data were identical with those reported in the literature [22]. In addition, 1 H-NMR and 13 C-NMR data of compounds 5 and 6 were identical to those of stigmasterol and daucosterol (β-sitosterol-3-O-glucoside) in the literature [26][27][28][29]. Compounds 3-6 have been isolated here for the first time from this species.…”

Section: Resultssupporting

confidence: 82%

Inhibitory Activity of Extract, Fractions, and Compounds from Zingiber montanum Rhizomes on the Migration of Breast Cancer Cells

et al. 2020

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Zingiber montanum rhizomes are traditionally used for the treatment of numerous human ailments. The present study was carried out to investigate the inhibitory activity of the crude extract, chromatographic fractions, and purified compounds from Z. montanum rhizomes on the migration of MDA-MB-231 cells. The effect of the extract on cell migration was investigated by a scratch assay, which showed significant inhibition in a concentration-dependent manner. Vacuum liquid chromatography on silica gel afforded four fractions (Frs. 1 – 4), which were tested on cell migration in the scratch assay. Frs. 1 and 2 showed the most significant inhibition of MDA-MB-231 cell migration. The effect of the most potent fraction (Fr. 2) was further confirmed in a transwell migration assay. The study of Frs. 1 and 2 by gelatin zymography showed significant inhibition of MMP-9 enzyme activity. Chromatographic separation of Frs. 1 and 2 afforded buddledone A (1), zerumbone (2), (2E,9E)-6-methoxy-2,9-humuradien-8-one (3), zerumbone epoxide (4), stigmasterol (5), and daucosterol (6). In a cell viability assay, compounds 1 – 4 inhibited the viability of MDA-MB-231 cells in a concentration-dependent manner. The study of buddledone A (1) and zerumbone epoxide (4) on cell migration revealed that 4 significantly inhibited the migration of MDA-MB-231 cells in both scratch and transwell migration assays. The results of the present study may lead to further molecular studies behind the inhibitory activity of zerumbone epoxide (4) on cell migration and support the traditional use of Z. montanum rhizomes for the treatment of cancer.

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Section: Resultssupporting

confidence: 82%

Inhibitory Activity of Extract, Fractions, and Compounds from Zingiber montanum Rhizomes on the Migration of Breast Cancer Cells

et al. 2020

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“…Purification and structural characterization of both compounds by NMR (Figs S20 – S23 and Tables S6 & S7) revealed that SsSS removes the diphosphate and forms a tertiary alcohol, ent -kolavelool ( 35 )(Soares et al, 2014), while KgTS removes the diphosphate and forms an additional carbon-carbon double bond, producing the exo -methylene containing (5 R ,8 R ,9 S ,10 R )-cleroda-3,13(16),14-triene ( 36 ), which has been previously observed (Nagashima et al, 1998). Notably, SsSS and KgTS also readily react with kolavenyl diphosphate ( 13 ) resulting in enantiomeric products to those observed with 12 , as indicated by their identical retention times and mass spectra upon non-chiral GC-MS analysis (Fig.…”

Section: Resultsmentioning

confidence: 99%

Extreme promiscuity of a bacterial and a plant diterpene synthase enables combinatorial biosynthesis

Jia

Potter

Peters

2016

Metabolic Engineering

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Diterpenes are widely distributed across many biological kingdoms, where they serve a diverse range of physiological functions, and some have significant industrial utility. Their biosynthesis involves class I diterpene synthases (DTSs), whose activity can be preceded by that of class II diterpene cyclases (DTCs). Here, a modular metabolic engineering system was used to examine the promiscuity of DTSs. Strikingly, both a bacterial and plant DTS were found to exhibit extreme promiscuity, reacting with all available precursors with orthogonal activity, producing an olefin or hydroxyl group, respectively. Such DTS promiscuity enables combinatorial biosynthesis, with remarkably high yields for these unoptimized non-native enzymatic combinations (up to 15 mg/L). Indeed, it was possible to readily characterize the 13 unknown products. Notably, 16 of the observed diterpenes were previously inaccessible, and these results provide biosynthetic routes that are further expected to enable assembly of more extended pathways to produce additionally elaborated ‘non-natural’ diterpenoids.

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“…Cneorubin X (1) was isolated from sample Bazzania harpago. Literature reviews showed that 1 was initially isolated and reported from Cneorum tricoccon (Trautmann et al 1980), Guarea guidonia (Brochini & Roque 2000), Ptaeroxylon obliquum (Mulholland & Mahomed 2000) and Trichilia sylvatica (Soares et al 2014), that are all vascular plants. To the best of our knowledge, this is the first report of Cneorubin X been reported from a non-vascular plant.…”

Section: Resultsmentioning

confidence: 99%

Structural Diversity, Anti-Fungal Activity and Chemosystematics of Bornean Liverwort Bazzania harpago (De Not.) Schiffner

Ng¹,

Ang²,

Hau³

et al. 2021

JSM

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Two terpenes; cneorubin X (1), (-)-gymnomitr-3(15)-en-4β-ol (2) as well as one benzoic compound; caffeic acid (3) were isolated from Bazzania harpago collected from Mt. Trus Madi, Sabah, Malaysia. The structures of these secondary metabolites were elucidated based on spectroscopic data (Infra-Red (IR), 1D and 2D Nuclear Magnetic Resonance (NMR), and Mass Spectrum (MS)). This is the first record that cneorubin X (1) was isolated from non-vascular plants and it exhibited active anti-fungal activity against Haliphthoros sabahensis and Haliphthoros milfordensis. Chemosystematics finding suggests that the Marchantiophyta (liverworts) genus Bazzania might have a closer chemical relationship to its sister group Bryophyta (mosses) genus Brachythecium, Kindbergia and Mnium, as well as Anthocerophyta (hornworts) genus Anthocerosin their evolutionary history.

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CHEMICAL STUDY OF LEAVES OFTrichilia silvaticaMeliaceae

Cited by 4 publications

References 0 publications

Inhibitory Activity of Extract, Fractions, and Compounds from Zingiber montanum Rhizomes on the Migration of Breast Cancer Cells

Inhibitory Activity of Extract, Fractions, and Compounds from Zingiber montanum Rhizomes on the Migration of Breast Cancer Cells

Extreme promiscuity of a bacterial and a plant diterpene synthase enables combinatorial biosynthesis

Structural Diversity, Anti-Fungal Activity and Chemosystematics of Bornean Liverwort Bazzania harpago (De Not.) Schiffner

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