Two New Phenolic Amides from the Seeds of Pharbitis nil

Kim, Ki‐Hyun; Choi, Sang Un; Son, Miwon; Lee, Kang Ro

doi:10.1248/cpb.58.1532

Cited by 19 publications

(15 citation statements)

References 27 publications

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“…1,3-benzodioxol-acid IBAs like fagaramide (188) and derivatives (187, 188), however, possess no cytotoxicity against prostate tumor cell lines (Mbaze et al, 2009). (2E/Z)-N-(4-amino-2,3-dihydroxybutyl)-3-(4-hydroxyphenyl)prop-2-enamide (pharnilatin A (252) and B (342)) show in-vitro cytotoxicity against skin melanoma and lung, ovary and colon carcinoma (Kim et al, 2010a). Moreover, a sulfone-NAA (343) has anticancer activity against CEM-SS and KU812F (leukemia cells), HT29 (colon cancer) and UACC-62 (melanoma), and was found to be non-toxic to peripheral blood mononuclear cells (Astelbauer et al, 2010).…”

Section: Othersmentioning

confidence: 99%

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

132

109

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a b s t r a c tEthnopharmacological relevance: N-Alkylamides (NAAs) are a promising group of bioactive compounds, which are anticipated to act as important lead compounds for plant protection and biocidal products, functional food, cosmeceuticals and drugs in the next decennia. These molecules, currently found in more than 25 plant families and with a wide structural diversity, exert a variety of biologicalpharmacological effects and are of high ethnopharmacological importance. However, information is scattered in literature, with different, often unstandardized, pharmacological methodologies being used. Therefore, a comprehensive NAA database (acronym: Alkamid) was constructed to collect the available structural and functional NAA data, linked to their occurrence in plants (family, tribe, species, genus). Materials and methods: For loading information in the database, literature data was gathered over the period 1950-2010, by using several search engines. In order to represent the collected information about NAAs, the plants in which they occur and the functionalities for which they have been examined, a relational database is constructed and implemented on a MySQL back-end. Results: The database is supported by describing the NAA plant-, functional-and chemical-space. The chemical space includes a NAA classification, according to their fatty acid and amine structures. Conclusions: The Alkamid database (publicly available on the website http://alkamid.ugent.be/) is not only a central information point, but can also function as a useful tool to prioritize the NAA Q8 choice in the evaluation of their functionality, to perform data mining leading to quantitative structure-property relationships (QSPRs), functionality comparisons, clustering, plant biochemistry and taxonomic evaluations.

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Section: Othersmentioning

confidence: 99%

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Boonen

Bronselaer

Nielandt

et al. 2012

Journal of Ethnopharmacology

132

109

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“…), and the existence of the cis ‐feruloyl group was confirmed by detailed analysis of 2D‐NMR spectra ( 1 H, 1 H‐COSY, and HMBC; Fig. ), as well as by the typical chemical shifts of ( δ (H) 5.84)/( δ (C) 117.2) and ( δ (H) 6.83)/( δ (C) 144.4) for the C=C bond and the coupling constant ( J = 13.0 Hz) between the H‐atoms of the C=C bond . Thus, it was presumed that compound 2 is a derivative of 1 containing an O‐cis ‐feruloyl group.…”

Section: Resultsmentioning

confidence: 81%

“…The caffeoyl unit was confirmed by detailed analysis of 2D‐NMR spectra ( 1 H, 1 H‐COSY, and HMBC; Fig. ), and the cis configuration for the caffeoyl unit was assigned by the typical chemical shifts of ( δ (H) 5.71)/( δ (C) 117.0) and ( δ (H) 6.78)/( δ (C) 144.0) for the C=C bond and the coupling constant ( J = 13.0 Hz) between H‐atoms of the C=C bond . The complete structure of 3 was elucidated as shown in Fig.…”

Section: Resultsmentioning

confidence: 88%

“…). The chemical shifts of ( δ (H) 5.79)/( δ (C) 117.4) and ( δ (H) 6.83/( δ (C) 144.3) for the C=C bond and the coupling constant ( J = 13.0) between H‐atoms of the C=C bond suggested the presence of a cis ‐caffeoyl group . HMBC cross peaks from H–C(27) ( δ (H) 4.45) and ( δ (H) 4.63) to C(1′) ( δ (C) 168.5) revealed the connection of the cis ‐caffeoyl group to C(27) of the lupane‐type triterpenoid moiety ( Fig.…”

Section: Resultsmentioning

confidence: 99%

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Cytotoxic Triterpenoids from the Barks of Betula platyphylla var. japonica

Eom

Kang

Choi

et al. 2017

Chemistry & Biodiversity

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Phytochemical investigation on the barks of Betula platyphylla var. japonica (Betulaceae) was carried out, resulting in the isolation and identification of three new triterpenoids, 27-O-cis-caffeoylcylicodiscic acid (1), 27-O-cis-feruloylcylicodiscic acid (2), and 27-O-cis-caffeoylmyricerol (3), along with six known triterpenoids, obtusilinin (4), winchic acid (5), 27-O-trans-caffeoylcylicodiscic acid (6), uncarinic acid E (7), myriceric acid B (8), and 3-O-trans-caffeoyloleanolic acid (9). The structures of the new compounds were elucidated by extensive spectroscopic methods, including 1D- and 2D-NMR, and HR-ESI-MS. All of the isolated compounds were evaluated for cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and Bt549). Compounds 2, 6, 8, and 9 exhibited potent cytotoxicity against all of the tumor cells tested (IC < 10.0 μm), while compounds 3, 4, 5, and 7 showed moderate cytotoxicity against all of the tumor cells tested (IC < 20.0 μm).

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“…The HMBC ( Figure S5) and 1 H, 1 H-COSY correlations ( Figure S3) were further analyzed to indicate that theses peaks are consisted of two cis-p-coumaroyl units in this molecule. [19,20] The attachment of the cis-p-coumaroyl units to the icariol A 2 moiety was indicated with HMBCs of HÀ C(9)/C(9'') and HÀ C(9')/C(9''') ( Figure 2). Finally, the gross structure of 1 was established as a completely symmetrical (7) and HÀ C(7') implied that each hydroxymethylene group was conformed in a transorientation to the vicinal aryl group in the system of 2,5-diaryltetrahydrofuran lignan, [19] which concluded that the configuration of 1 was either all-trans or meso form of the lignan system.…”

Section: Structural Elucidation Of Compoundmentioning

confidence: 99%

Biological Evaluation of a New Lignan from the Roots of Rice (Oryza sativa)

Lee

et al. 2018

Chemistry & Biodiversity

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LC/MS-based phytochemical analysis of an EtOH extract of the roots of rice (Oryza sativa; Gramineae), which takes a crucial role in the stable crop population in Asia, resulted in the isolation of a new lignan, oryzativol C (1), as a minor component. The chemical structure of compound 1 was unambiguously confirmed using spectroscopic evidence (including 1D- and 2D-NMR data), HR-ESI-MS, and CD data analysis. Considering the traditional medicinal efficacy of O. sativa and its importance as a food crop, compound 1 was evaluated for effects on breast cancer cell lines (MDA-MB-231) and on glucose-stimulated insulin secretion in an INS-1 pancreatic β-cell line. Compound 1 showed mild cytotoxicity toward the MDA-MB-231. Furthermore, compound 1 stimulated insulin secretion in INS-1 pancreatic β-cells without inducing cytotoxicity. These results indicate that compound 1 is an active ingredient of O. sativa that offers health benefits including inhibition of breast cancer cell proliferation and hyperglycemia control.

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Two New Phenolic Amides from the Seeds of Pharbitis nil

Cited by 19 publications

References 27 publications

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Alkamid database: Chemistry, occurrence and functionality of plant N-alkylamides

Cytotoxic Triterpenoids from the Barks of Betula platyphylla var. japonica

Biological Evaluation of a New Lignan from the Roots of Rice (Oryza sativa)

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