Isolation and Biological Evaluation of Jatrophane Diterpenoids from <i>Euphorbia dendroides</i>

Aljančić, Ivana; Pešić, Milica; Milosavljević, Slobodan; Todorović, Nina; Jadranin, Milka; Milosavljevic, Goran; Povrenović, Dragan; Banković, Jasna; Tanić, Nikola; Marković, Ivanka; Ruždijić, Sabera; Vajs, Vlatka; Tešević, Vele

doi:10.1021/np200241c

Cited by 56 publications

(41 citation statements)

References 22 publications

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“…Colorectal carcinoma cell lines (DLD1 and DLD1-TxR), as well as the glioma cell lines (U87 and U87-TxR), showed considerably lower sensitivity to the two jatrophanes. These results recapitulated those obtained in the previous study (Aljancic et al 2011) and indicated the potential of Euph H (225) and Euph S (236) for NSCLC treatment. 225 significantly sensitized NCI-H460/R and DLD1-TxR cells to Paclitaxel (PTX), similar to paclitaxel, R ± verapamil (Dex-VER), and tariquidar (TQ); while 236 demonstrated the moderate chemo-sensitizing effect.…”

Section: Mdr Reversing Activitysupporting

confidence: 90%

“…Both jatrophanes at 5 lM decreased the IC 50 values of doxorubicin significantly, showing a similar reversal potential to 'verapamil'. These results pointed to the potential of 396 and 397 to reverse paclitaxel and doxorubicin resistance in the MDR cancer cell line used (Aljancic et al 2011). Valente et al (2012) isolated three new jatrophanes euphomelliferine (293), euphomelliferenes A (294) and B (295) along with two known jatrophanes 306 and 302 from E. mellifera.…”

Section: Mdr Reversing Activitymentioning

confidence: 91%

“…Their efficacy was 25-fold higher than that of positive control 'verapamil' (FAR = 23.2 at 10 lg/mL); thus, both 185 and 188 appeared to be promising leads for drug development to overcome the MDR of cancer cells (Vasas et al 2011). Aljancic et al (2011) investigated the sensitivity of NCI-H460/R cells to another anticancer chemotherapeutic agent, doxorubicin, in the presence of six new jatrophanes, euphodendrophanes A-F (396-400, and 237) from E. dendroides. Moreover, the synergistic effect between these jatrophanes and the 'paclitaxel' was reported for the first time.…”

Section: Mdr Reversing Activitymentioning

confidence: 99%

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Jatrophane and rearranged jatrophane-type diterpenes: biogenesis, structure, isolation, biological activity and SARs (1984–2019)

et al. 2020

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Diterpene compounds specially macrocyclic ones comprising jatrophane, lathyrane, terracinolide, ingenane, pepluane, paraliane, and segetane skeletons occurring in plants of the Euphorbiaceae family are of considerable interest in the context of natural product drug discovery programs. They possess diverse complex skeletons and a broad spectrum of therapeutically relevant biological activities including anti-inflammatory, anti-chikungunya virus, anti-HIV, cytotoxic, and multidrug resistance-reversing activities as well as curative effects on thrombotic diseases. Among macrocyclic diterpenes of Euphorbia, the discovery of jatrophane and modified jatrophane diterpenes with a wide range of structurally unique polyoxygenated polycyclic derivatives and as a new class of powerful inhibitors of P-glycoprotein has opened new frontiers for research studies on this genus. In this review, an attempt has been made to give in-depth coverage of the articles on the naturally occurring jatrophanes and rearranged jatrophane-type diterpenes isolated from species belonging to the Euphorbiaceae family published from 1984 to March 2019, with emphasis on the biogenesis, isolation methods, structure, biological activity, and structureactivity relationship.

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Section: Mdr Reversing Activitysupporting

confidence: 90%

Section: Mdr Reversing Activitymentioning

confidence: 91%

Section: Mdr Reversing Activitymentioning

confidence: 99%

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Jatrophane and rearranged jatrophane-type diterpenes: biogenesis, structure, isolation, biological activity and SARs (1984–2019)

et al. 2020

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“…30,31 Compounds that stabilize MT represent potential therapeutic approach for the treatment of Alzheimer's disease and related tauopathies. 32 In this study 16 jatrophane diterpenoids isolated from Euphorbia dendroides 33,34 and latex extracts from E. dendroides and Euphorbia nicaeensis induced decrease in the frequency of MN and manifested protective effect on human lymphocytes DNA. Table 1.…”

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confidence: 75%

Jatrophane Diterpenoids With Protective Effect on Human Lymphocytes DNA

Krstić

Jadranin

Stanković³

et al. 2019

Natural Product Communications

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Two sets of structurally different jatrophanes (1-11 and 13-16), jatrophane 12, and latex extract of 2 Euphorbia species (17 and 18) were tested for in vitro protective effect against chromosome aberrations in peripheral human lymphocytes using the cytokinesis-block micronucleus (CBMN) assay. Jatrophanes 1-6 in minimal doses of 1 µg/mL prominently decreased micronuclei (MN) frequency in the range 44.86% to 34.29% and manifested considerable protective effect. From the other set of jatrophanes, 13 in the same minimal dose notably decreased MN frequency by 31.05%, while extracts 17 and 18 at a concentration of 4 µg/mL remarkably decreased the frequency of MN by 37.94% and 36.12%, respectively. Jatrophanes 12, 14, and 16 showed moderate protection, while 7-11 and 15 were less active than positive control. The structure-activity relationship (SAR) studies of the tested jatrophanes (1-16) indicated the favorable position of benzoate at C-8 or C-9 (3, 4, and 13) and a preference of isobutanoyloxy group at C-3 (1-3) rather than propanoyloxy at the same position (4-6) for pronounced protective effect on human lymphocytes DNA. In a previous SAR study on 11 jatrophanes (1, 3-8, and 13-16), the same structural features in 3, 4, and 13 influenced powerful inhibition of P-gp, while growth inhibition of cancer cells was more than doubled in 1 (isobutanoyloxy group at C-3) compared to 6 (propanoyloxy at C-3).

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“…Previous studies showed increasing application of herbal formulations for cardiovascular disease [1][2][3][4][5][6][7]. These formulations are made up of different herbs and extraction of herbal ingredients is conducted in boiling water.…”

Section: Introductionmentioning

confidence: 99%

Active Phytochemicals from Chinese Herbs as Therapeutic Agents for the Heart

Cheung²,

Yu³

2012

CHAMC

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Naturally occurring plant alkaloids, in particular those identified from herbal medicines, are finding therapeutic use. Heart diseases can be well managed with specific formulations of herbal medicines. The combined action of multiple constituents of herbal medicines works with therapeutic benefits in humans. The established formulations of Traditional Chinese medicines show efficacy in treatment of diseases. However, individual herbal principles seldom show pharmacological activity. Nevertheless, some of the active alkaloids and terpenoids from medicinal herbs have been identified. The pharmacological activities of these herbal compounds have been studied. These active constituents of herbal medicine are also used in nutrient supplements, but the modes of action of the active component remain sketchy. The present review describes the recent development of those active principles from herbal medicines as cardiovascular agents. The study will provide insights into herbal medicines for drug development for the treatment of cardiovascular disease.

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Isolation and Biological Evaluation of Jatrophane Diterpenoids from Euphorbia dendroides

Cited by 56 publications

References 22 publications

Jatrophane and rearranged jatrophane-type diterpenes: biogenesis, structure, isolation, biological activity and SARs (1984–2019)

Jatrophane and rearranged jatrophane-type diterpenes: biogenesis, structure, isolation, biological activity and SARs (1984–2019)

Jatrophane Diterpenoids With Protective Effect on Human Lymphocytes DNA

Active Phytochemicals from Chinese Herbs as Therapeutic Agents for the Heart

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