Ficuschlorins A – D, Lactone Chlorins from the Leaves of <i>Ficus microcarpa</i>

Lin, Hsiao‐Yun; Chiu, Hao-Chieh; Lan, Yu-Hsuang; Tzeng, Chih-Ying; Lee, Tzong-Huei; Lee, Ching-Kuo; Shao, Yiming; Chen, Chiy‐Rong; Chang, Ching‐Cheng; Kuo, Yueh‐Hsiung

doi:10.1002/cbdv.201000175

Cited by 4 publications

(3 citation statements)

References 19 publications

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“…As a result, the structure of compound 1 was identical to methyl 10-epi-pheophorbide A that was originally isolated from spinach leaves [32] and later in Ficus microcarpa leaves [23,24]. Meanwhile, this is the first report of methyl 10-epi-pheophorbide A from F. deltoidea.…”

Section: Fig 1: Structure and Key Noesy Signals Of 1 (3d Model) Measmentioning

confidence: 70%

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Methyl 10-Epi-Pheophorbide a From McF-7 Cells Active Layer of the Indonesian Ficus Deltoidea Jack Leaves

Murni

Hanif

Kita

et al. 2017

Int J Pharm Pharm Sci

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Objective: To isolate and elucidate a cytotoxic principle against breast tumor MCF-7 cells of the Indonesian terrestrial plant Ficus deltoidea Jack leaves. Methods:F. deltoidea leaves collected at National Park of mount Gede-Pangrango, Indonesia have been subjected to chemical and biological work. F. deltoidea leaves were extracted with 96% aqueous ethanol (EtOH) and was then partitioned into three layers n-hexane, dichloromethane (CH2Cl2), and n-butanol (n-BuOH). All layers were checked for their activity against breast tumor MCF-7 cells using MTT assay method. A portion of the most active layer was purified using open column chromatography to give fraction that has toxicity against zebra fish embryos. Based on the assay-guided isolation, compound 1 was isolated. The chemical structure of 1 was elucidated using nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS) data as well as comparing data with literature. Results:The CH2Cl2 layer of F. deltoidea leaves was found to inhibit breast tumor MCF-7 cells with IC50 10 µg/ml which was the most toxic among the layers. A portion of the most active layer was purified using open column chromatography to give 7 fractions. The fraction 5 showed toxicity against zebrafish embryos (LC50 35 µg/ml, 48 hpf). This fraction was purified using high performance liquid chromatography (HPLC) octadecylsilyl (ODS) column with gradient elution 70% aqueous acetonitrile (MeCN) to 100% MeCN (linear gradient) for 40 min with UV detection at 254 nm (tR = 30.99 min) to give compound 1. The chemical structure of 1 was revealed as a chlorin-type compound named methyl 10-epi-pheophorbide A. Conclusion:Methyl 10-epi-pheophorbide A was isolated for the first time from the active fraction of the Indonesian F. deltoidea leaves or tabat barito. The chemical structure including absolute stereochemistry was elucidated using NMR and HRMS data as well as by comparison with the literature values. The 13 C NMR data has been added to complete the previous report.

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Section: Fig 1: Structure and Key Noesy Signals Of 1 (3d Model) Measmentioning

confidence: 70%

“…The molecules showed in vivo α-glucosidase inhibition. Moreover, the Ficus genus contained alkaloid such as chlorin as ficusmicrochlorin A-C [23] and ficuschlorin A-D [24] have been discovered from Taiwanese Ficus microcarpa. All the compounds were elucidated using detailed analysis of 1D and 2D NMR spectroscopy as well as MS data.…”

Section: Introductionmentioning

confidence: 99%

Methyl 10-Epi-Pheophorbide a From McF-7 Cells Active Layer of the Indonesian Ficus Deltoidea Jack Leaves

Murni

Hanif

Kita

et al. 2017

Int J Pharm Pharm Sci

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“…39,32,40 In the same context, lactone chlorines with the molecular formula C 55 H 74 N 4 O 6 were characterized as cuschlorine A (16) and B (17) that was previously detected in F. microcarpa. 41…”

Section: Metabolic Prolingmentioning

confidence: 99%

Isolation and characterization of novel acetylcholinesterase inhibitors from Ficus benghalensis L. leaves

et al. 2020

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Chemical compounds isolated from Talinum triangulare (Portulacaceae)

et al. 2014

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This first phytochemical study of Talinum triangulare Leach (Portulacaceae), also known as 'cariru', which is a commonly consumed food in Northern Brazil, allowed the isolation and structural determination of four new compounds: one acrylamide, 3-N-(acryloyl, N-pentadecanoyl) propanoic acid (5), and three new phaeophytins named (15(1)S, 17R, 18R)-Ficuschlorin D acid (3(1),3(2)-didehydro-7-oxo-17(3)-O-phytyl-rhodochlorin-15-acetic acid), (13), Talichorin A (17R, 18R)-phaeophytin b-15(1)-hidroxy, 15(2),15(3)-acetyl-13(1)-carboxilic acid (14), and (15(1)S, 17R, 18R)-phaeophytin b peroxylactone or (15(1)S, 17R, 18R)-hydroperoxy-ficuschlorin D (16), together with twelve known compounds, including four phaeophytins (11,12, 15 and 17). The structures of the compounds were established on the basis of 1D and 2D NMR, IR, HRESI-MS spectra, including GC-MS, and HPLC-UV analysis, as well as comparisons with the literature data. The CD spectra data analysis were used to define the absolute configuration of phaeophytins 12 (13(2)R, 17R, 18R)-13(2)-hydroxyphaeophytin a, 13 and 16, 15 (15(1)S, 17R, 18R)-3(1),3(2)-didehydro-15(1)-hydroxyrhodochlorin-15-acetic acid δ-lactone-15(2)-methyl-17(3)-phytyl ester and 17 (17R, 18R)-purpurin 18-phytyl ester.

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Ficuschlorins A – D, Lactone Chlorins from the Leaves of Ficus microcarpa

Cited by 4 publications

References 19 publications

Methyl 10-Epi-Pheophorbide a From McF-7 Cells Active Layer of the Indonesian Ficus Deltoidea Jack Leaves

Methyl 10-Epi-Pheophorbide a From McF-7 Cells Active Layer of the Indonesian Ficus Deltoidea Jack Leaves

Isolation and characterization of novel acetylcholinesterase inhibitors from Ficus benghalensis L. leaves

Chemical compounds isolated from Talinum triangulare (Portulacaceae)

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