Prenylated flavonoids of the leaves of Macaranga conifera with inhibitory activity against cyclooxygenase-2

Jang, Dae Sik; Cuendet, Muriel; Hawthorne, Michael; Kardono, Leonardus B.S.; Kawanishi, Kazuko; Fong, Harry H. S.; Mehta, Rajendra G.; Pezzuto, John M.; Kinghorn, A. Douglas

doi:10.1016/s0031-9422(02)00378-3

Cited by 81 publications

(64 citation statements)

References 31 publications

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“…Based on 1 H-, 13 C-NMR and EI-MS data as well as comparison to spectral data from the literature these compounds were identified as 3,5,4'-trimethoxy-4-prenylstilbene (1) [11], 4-methoxyderricidine (2) [11], 4-hydroxylonchocarpine (4) [11], 4-methoxylonchocarpine (5) [11], 4'-hydroxyisolonchocarpine (7) [12], 4'-methoxyisolonchocarpine (8) [13], 3',4'-methylenedioxy-7-methoxyflavone (10) [14] and 2,2-dimethylchromone-5,4'-dihydroxy-5'-methoxyflavone (11) [15]. The hexane extract from branches yielded two known flavonoids which were identified by the methods mentioned above as lonchocarpine (3) [11] and 3',4',7-trimethoxyflavone (9) [16].…”

Section: Isolation and Identification Of Flavonoids From D Duckeana mentioning

confidence: 99%

Isolation of Flavonoids from Deguelia duckeana and Their Effect on Cellular Viability, AMPK, eEF2, eIF2 and eIF4E

et al. 2016

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Preparations of Deguelia duckeana, known in Brazil as timbó, are used by indigenous people to kill fish. Reinvestigation of its extracts resulted in the isolation and identification of 11 known flavonoids identified as 3,5,4'-trimethoxy-4-prenylstilbene (1), 4-methoxyderricidine (2), lonchocarpine (3), 4-hydroxylonchocarpine (4), 4-methoxylonchocarpine (5), 5-hydroxy-4',7-dimethoxy-6-prenylflavanone (6), 4'-hydroxyisolonchocarpine (7), 4'-methoxyisolonchocarpine (8), 3',4',7-trimethoxyflavone (9), 3',4'-methylenedioxy-7-methoxyflavone (10), and 2,2-dimethyl-chromone-5,4'-hydroxy-5'-methoxyflavone (11). Except for 1, 3, and 4 all of these flavonoids have been described for the first time in D. duckeana and the flavanone 6 for the first time in nature. Compounds 2, 3, 4, 7, 9, and 10 were studied for their potential to induce cell death in neuronal SK-N-SH cells. Only the chalcone 4 and the flavanone 7 significantly induced lactate dehydrogenase (LDH) release, which was accompanied by activation of caspase-3 and impairment of energy homeostasis in the MTT assay and may explain the killing effect on fish. Interestingly, the flavone 10 reduced cell metabolism in the MTT assay without inducing cytotoxicity in the LDH assay. Furthermore, the flavonoids 2, 3, 4, 7, and 10 induced phosphorylation of the AMP-activated protein kinase (AMPK) and the eukaryotic elongation factor 2 (eEF2). The initiation factor eIF4E was dephosphorylated in the presence of these compounds. The initiation factor eIF2alpha was not affected. Further studies are needed to elucidate the importance of the observed effects on protein synthesis and potential therapeutic perspectives.

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Section: Isolation and Identification Of Flavonoids From D Duckeana mentioning

confidence: 99%

Isolation of Flavonoids from Deguelia duckeana and Their Effect on Cellular Viability, AMPK, eEF2, eIF2 and eIF4E

et al. 2016

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“…In folk medicine, traditional healers use fresh or dried leaves of some Macaranga species to treat swellings, cuts, sores, boils and bruises (Nick et al, 1995). A phytochemical review of literatures indicates the genus Macaranga to be a rich source of the isoprenylated, geranylated and farnesylated flavonoids (Schutz et al, 1995;Jang et al, 2002;Phormmart et al, 2005;Kawakami et al, 2008;Thanh et al, 2012) and stilbenes (Beutler et al, 1998;Yoder et al, 2007;Thanh et al, 2012). Furthermore, more classes of secondary metabolites like terpenes (Salah et al, 2003;Jang et al, 2004;Phormmart et al, 2005;Kawakami et al, 2008), tannins (Lin et al, 1990;Gunawan-Puteri and Kawabata, 2010;Ngoumfo et al, 2008), coumarins (Sutthivaiyakit et al, 2002;Darmawan et al, 2012) and other types of compounds (Ramaiah et al, 1979;Ngoumfo et al, 2008;Matsunami et al, 2009;Zakaria et al, 2010) are known to be isolated from different species of the genus Macaranga.…”

Section: Introductionmentioning

confidence: 99%

“…An increasing number of phytochemical studies are being carried out on plants belonging to the genus Macaranga due to their various traditional uses. Thus, the isolated natural products from this genus have been reported to display interesting biological activities including antitumor (Kaaden et al, 2001;Yoder et al, 2007;Zakaria et al, 2012), antioxidant (Sutthivaiyakit et al, 2002;Phormmart et al, 2005;Matsunami et al, 2009), antimicrobial (Salah et al, 2003;Lim et al, 2009) and anti-inflammatory (Jang, et al, 2002). This is a resourceful area of research as many species of Macaranga are used in traditional medicine as well as exhibits various pharmacological properties while their chemistry indicates varied chemical structures.…”

Section: Introductionmentioning

confidence: 99%

Phytochemistry and pharmacology of the genus Macaranga: A review

Magadula¹

2014

J. Med. Plants Res.

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“…[14,15] This is because previous reports demonstrated that flavonoids can suppress both pathways of arachidonic metabolism, namely lioxygenase and cyclooxygenase pathways. [17,18] In a separate study, Luyen and his colleagues (19) isolated twenty six compounds from Euphorbia humifusa. [19] Most of these compounds demonstrated anti-inflammatory activities as indicated by their inhibitory effects on soluble epoxide hydrolase, lipopolysaccharide-induced NO and TNF-α production.…”

Section: Discussionmentioning

confidence: 99%