Tropane alkaloids from the Australian plant Triunia montana (Proteaceae)

Yang, Fan; Zhao, Huijun; Carroll, Anthony R.

doi:10.1016/j.tetlet.2017.01.021

Cited by 6 publications

(5 citation statements)

References 20 publications

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“…Adding these criteria (CH 3 (doublet) = 2, CH 3 N = 1, CH−O (all) = 1, and CO (all) = 1) to the search reduced the hits to one compound, 2,3-dihydrodarlingine (3), and comparison of its NMR data with the literature confirmed its structure. 30 Many marine natural products are proton poor and can often contain isolated proton spin systems. However, even these groups of molecules can be identified with a limited number of search criteria.…”

Section: ■ Results and Discussionmentioning

confidence: 78%

“…The 1 H NMR spectrum indicated that two of the methyls are doublets, the HSQC spectrum (Figure S4, Supporting Information) suggested that one of the methyls is attached to a nitrogen and one of the methines is oxygenated, while the HMBC spectrum (Figure S5, Supporting Information) indicated the molecule also contains a ketone carbonyl adjacent to one of the methyl groups. Adding these criteria (CH 3 (doublet) = 2, CH 3 N = 1, CH–O (all) = 1, and CO (all) = 1) to the search reduced the hits to one compound, 2,3-dihydrodarlingine ( 3 ), and comparison of its NMR data with the literature confirmed its structure …”

Section: Resultsmentioning

confidence: 99%

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Database for Rapid Dereplication of Known Natural Products Using Data from MS and Fast NMR Experiments

Zani

Carroll

2017

J. Nat. Prod.

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The discovery of novel and/or new bioactive natural products from biota sources is often confounded by the reisolation of known natural products. Dereplication strategies that involve the analysis of NMR and MS spectroscopic data to infer structural features present in purified natural products in combination with database searches of these substructures provide an efficient method to rapidly identify known natural products. Unfortunately this strategy has been hampered by the lack of publically available and comprehensive natural product databases and open source cheminformatics tools. A new platform, DEREP-NP, has been developed to help solve this problem. DEREP-NP uses the open source cheminformatics program DataWarrior to generate a database containing counts of 65 structural fragments present in 229 358 natural product structures derived from plants, animals, and microorganisms, published before 2013 and freely available in the nonproprietary Universal Natural Products Database (UNPD). By counting the number of times one or more of these structural features occurs in an unknown compound, as deduced from the analysis of its NMR (H, HSQC, and/or HMBC) and/or MS data, matching structures carrying the same numeric combination of searched structural features can be retrieved from the database. Confirmation that the matching structure is the same compound can then be verified through literature comparison of spectroscopic data. This methodology can be applied to both purified natural products and fractions containing a small number of individual compounds that are often generated as screening libraries. The utility of DEREP-NP has been verified through the analysis of spectra derived from compounds (and fractions containing two or three compounds) isolated from plant, marine invertebrate, and fungal sources. DEREP-NP is freely available at https://github.com/clzani/DEREP-NP and will help to streamline the natural product discovery process.

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Section: ■ Results and Discussionmentioning

confidence: 78%

Section: Resultsmentioning

confidence: 99%

Database for Rapid Dereplication of Known Natural Products Using Data from MS and Fast NMR Experiments

Zani

Carroll

2017

J. Nat. Prod.

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“…It may take up to two decades to develop HCC (Afum et al, 2016) but being chronically exposed to aflatoxin and hepatitis B may shorten this period. A study from the Africa Liver Cancer Consortium shows that HCC tends to develop at a younger age in Africa than in other regions of the world (Yang et al, 2017) but the relation between HCC and aflatoxin exposure was not studied.…”

Section: Disease Burdenmentioning

confidence: 99%

The aflatoxin situation in Africa : Systematic literature review

Meijer¹,

Kleter

Safitri

et al. 2018

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This research has been carried out by Wageningen University & Research and financed by Partnership for Aflatoxin Control in Africa (PACA) through funds made available to PACA by the Bill and Melinda Gates Foundation and Mars, Incorporated (project number 1277360301). PACA acknowledges the contribution of the Technical Centre for Agricultural and Rural Cooperation (CTA) in producing this report which is a follow up to the CTA/PACA 2016 Working Paper "Improving the evidence base on aflatoxin contamination and exposure in Africa" written by

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“…Furthermore, phytochemical studies have revealed the presence of various classes of compounds in the family members. [35][36][37] Stenocarpus sinuatus (A. CUNN.)…”

Section: Introductionmentioning

confidence: 99%

In vivo hepatoprotective and nephroprotective effects ofStenocarpus sinuatusleaf extract against ifosfamide‐induced toxicity in rats

Younis,

Ayoub,

George

et al. 2023

Archiv der Pharmazie

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Ifosfamide (IFOS) is a broad‐spectrum chemotherapeutic agent that has been extensively used for breast cancer and other solid tumors. Unfortunately, its use is associated with toxicities of several organs. Stenocarpus sinuatus is an Australian tree belonging to the Proteaceae family. In the current study, the phytochemical constituents of S. sinuatus methanol leaf extract (SSLE) were assessed. In addition, the protective effect of SSLE against IFOS‐induced nephrotoxicity and hepatotoxicity was evaluated. Rats were randomly divided into six groups: control, IFOS (50 mg/kg), IFOS + SSLE (100 mg/kg), IFOS + SSLE (200 mg/kg), IFOS + SSLE (400 mg/kg), and SSLE (400 mg/kg). Hepatoprotective and nephroprotective potency of SSLE was assessed using different biochemical parameters. The phytochemical investigation resulted in the isolation of four flavonoid glycosides (kaempferol 3‐O‐β‐ d‐glucopyranosyl‐(1→2)‐α‐ l‐rhamnopyranoside, kaempferol 3‐O‐α‐rhamnopyranoside, isorhamnetin 3‐O‐β‐ d‐glucopyranosyl‐(1→2)‐α‐ l‐rhamnopyranoside, and quercetin 3‐O‐β‐ d‐glucopyranosyl‐(1→2)‐α‐ l‐rhamnopyranoside) and a coumarin (scopoletin). This is the first report on the isolated compounds from the genus Stenocarpus. SSLE showed enhancement of kidney and liver functions and reduction of oxidative stress and inflammation. The histopathology of the investigated organs confirmed the protective effect of SSLE. In conclusion, SSLE is considered as a promising candidate that can be used in defense against the toxic effects of IFOS after further clinical trials.

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Tropane alkaloids from the Australian plant Triunia montana (Proteaceae)

Cited by 6 publications

References 20 publications

Database for Rapid Dereplication of Known Natural Products Using Data from MS and Fast NMR Experiments

Database for Rapid Dereplication of Known Natural Products Using Data from MS and Fast NMR Experiments

The aflatoxin situation in Africa : Systematic literature review

In vivo hepatoprotective and nephroprotective effects ofStenocarpus sinuatusleaf extract against ifosfamide‐induced toxicity in rats

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