Carbazole alkaloids from Clausena hainanensis with their potential antiproliferative activities

Ma, Yanlei; Liu, Yan-Ping; Zhang, Chao; Zhao, Wan-Hui; Shi, Shi; He, Dan-Nv; Zhang, Pan; Liu, Xiaohong; Han, Tingting; Fu, Yan-Hui

doi:10.1016/j.bioorg.2017.12.016

Cited by 40 publications

(16 citation statements)

References 18 publications

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“…Previous chemical investigations on F. carica resulted in the separation of a series of natural products, such as isoflavonoids, flavonoids, triterpenoids, lignans, alkaloids, coumarins, and sesquiterpenes, which account for a wide variety of biological activities, including antispasmodic, hypoglycemic, anti-inflammatory, antiplatelet, antioxidant, hemostatic antitumor, and hypolipidemic activities. − Our preliminary findings indicated that the 90% ethanol extract of the fruits of F. carica collected from Shandong Province of China displayed a pronounced inhibitory effect against NO production induced by lipopolysaccharide in mouse macrophage RAW 264.7 cells with an IC 50 value of 4.58 ± 0.08 μg/mL, and antiproliferative activities with the IC 50 values ranged from 5.62 ± 0.09 to 28.19 ± 0.12 μM in vitro. In our ongoing research into natural products with structural diversity and biological diversity from tropical medicinal plants and fruits in China, − a systematic phytochemical study on the fruits of F. carica was therefore implemented and resulted in the isolation and characterization of four new prenylated isoflavone derivatives, ficucaricones A–D ( 1 – 4 ), along with 12 known prenylated isoflavone derivatives. The structures of 1 – 4 were ambiguously established based on comprehensive spectroscopic data analyses, and the known compounds were determined via comparing their NMR and mass spectrometry (MS) data with those data reported in the literature.…”

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory and Antiproliferative Prenylated Isoflavone Derivatives from the Fruits of Ficus carica

Liu

Guo

Gui

et al. 2019

J. Agric. Food Chem.

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Ficus carica is an Asian species of flowering plant belonging to the genus Ficus of the family Moraceae, native to Western Asia and the Middle East. Its fruits, usually known as common fig or fig, have been consumed as a very popular healthpromoting fruit worldwide since ancient times. To investigate the potential health-promoting chemical constituents of the fruits of F. carica, a systematic phytochemical study on its fruits was therefore carried out. In our study, four new structurally diverse prenylated isoflavone derivatives, ficucaricones A−D (1−4), along with 12 known analogues (5−16) were separated from the fruits of F. carica. Their chemical structures were ambiguously elucidated based on extensive spectroscopic methods. The antiinflammatory effects and antiproliferative activities of these isolated prenylated isoflavone derivatives were tested. Prenylated isoflavone derivatives (1−16) displayed remarkable inhibitory effects against nitric oxide (NO) production with the IC 50 values ranging from 0.89 ± 0.05 to 8.49 ± 0.18 μM, comparable to that of the positive control (hydrocortisone). Furthermore, compounds 1−16 also exhibited pronounced antiproliferative activities against diverse human cancer cell lines in vitro, holding the IC 50 values ranging from 0.18 ± 0.03 to 18.76 ± 0.09 μM. These findings indicate that regular consumption of the fruits of F. carica may help to prevent the occurrence of inflammatory diseases and tumors. Moreover, the isolation and characterization of these prenylated isoflavone derivatives possessing remarkable anti-inflammatory effects and antiproliferative activities could be meaningful to the discovery of new anti-inflammatory and antitumor agents.

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Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory and Antiproliferative Prenylated Isoflavone Derivatives from the Fruits of Ficus carica

Liu

Guo

Gui

et al. 2019

J. Agric. Food Chem.

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“…Phytochemical studies on Clausena species revealed the preponderance of prenylated/geranylated coumarins and carbazole alkaloids with interesting bioactivities (Ito et al 2000;Sripisut et al 2012;Cao et al 2018;Yan et al 2019). Generally, prenylation of specialised metabolites seems to be common within rutaceous species and might be of chemotaxonomic importance for the subfamily Aurantioideae (Lukaseder et al 2009;Sakunpak et al 2013;Ma et al 2018a). The studied species Clausena lenis occurs in the border region between China, Thailand and Burma.…”

Section: Introductionmentioning

confidence: 94%

Chemical constituents of Clausena lenis

Wongthet

Schinnerl

Brecker

et al. 2020

Natural Product Research

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Phytochemical examination of Clausena lenis Drake (Rutaceae), collected in Thailand, led to the isolation of seven coumarins, four furoquinolines, two amides, and one flavonoid glycoside. Four of these compounds, one coumarine derivative named as gravelliferone A (3), two furoquinoline derivatives (kokusagenin A (8) and B (9)) and one amide, clausenalansamide H (13), are reported for the first time. Compound 3 was isolated from the root bark, compound 8 from the stem bark and compounds 9 and 13 from the leaves. The molecular structures of all isolated compounds were established by means of NMR experiments combined with mass spectrometry. Preliminary tests of the lipophilic stem bark extract against various human pathogenic bacteria strains revealed promising effects against Staphylococcus aureus ATCC 43300.

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“…To investigate the chemical constituents from the fresh young leaves and buds of T. sinensis and their potential health benefits, as a part of our continuing efforts to identify active natural products from the tropical fruits together with tropical medicinal plants, − a phytochemical study on the fresh young leaves and buds of T. sinensis was thus undertaken and led to the isolation and identification of four new limonoids, toonasinenoids A–D ( 1 – 4 ), a new naturally occurring limonoid, toonasinenoid E ( 5 ), and 11 known limonoids.…”

Section: Introductionmentioning

confidence: 99%

Limonoids from the Fresh Young Leaves and Buds of Toona sinensis and Their Potential Neuroprotective Effects

Xie

Wang

et al. 2020

J. Agric. Food Chem.

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Toona sinensis, popularly known as Chinese toon or Chinese mahogany, is a perennial deciduous arbor belonging to the genus Toona in the Meliaceae family, which is widely distributed and cultivated in eastern and southeastern Asia. Its fresh young leaves and buds have been consumed as a very popular nutritious vegetable in China and confirmed to display a wide variety of biological activities. To investigate the chemical constituents and their potential health benefits from the fresh young leaves and buds of T. sinensis, a phytochemical study on its fresh young leaves and buds was therefore undertaken. In our current investigation, 16 limonoids (1–16), including four new limonoids, toonasinenoids A–D (1–4), and a new naturally occurring limonoid, toonasinenoid E (5), were isolated and characterized from the fresh young leaves and buds of T. sinensis. The chemical structures and absolute configurations of limonoids 1–5 were elucidated by comprehensive spectroscopic data analyses. All known limonoids (6–16) were identified via comparing their experimental spectral data containing mass spectrometry data, 1H and 13C nuclear magnetic resonance data, and optical rotation values to the data reported in the literature. All known limonoids (6–16) were isolated from T. sinensis for the first time. Furthermore, the neuroprotective effects of all isolated limonoids 1–16 against 6-hydroxydopamine-induced cell death in human neuroblastoma SH-SY5Y cells were assessed in vitro. Limonoids 1–16 exhibited notable neuroprotective activities, with EC50 values in the range from 0.27 ± 0.03 to 17.28 ± 0.16 μM. These results suggest that regular consumption of the fresh young leaves and buds of T. sinensis might prevent the occurrence and development of Parkinson’s disease (PD). Moreover, the isolation and characterization of these limonoids that exhibit notable neuroprotective activities from the fresh young leaves and buds of T. sinensis could be very significant for researching and developing new neuroprotective drugs used for the prevention and treatment of PD.

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Carbazole alkaloids from Clausena hainanensis with their potential antiproliferative activities

Cited by 40 publications

References 18 publications

Anti-Inflammatory and Antiproliferative Prenylated Isoflavone Derivatives from the Fruits of Ficus carica

Anti-Inflammatory and Antiproliferative Prenylated Isoflavone Derivatives from the Fruits of Ficus carica

Chemical constituents of Clausena lenis

Limonoids from the Fresh Young Leaves and Buds of Toona sinensis and Their Potential Neuroprotective Effects

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