A novel sunscreen agent having antimelanoma activity

Nogueira, Marisa A.; Magalhães, Eva G.; Magalhães, Aderbal F.; Biloti, Débora Nakai; Laverde, Antônio; Pessine, Francisco Benedito Teixeira; Carvalho, João Ernesto de; Kohn, Luciana Konecny; Antônio, Márcia Aparecida; Marsaioli, Anita Jocelyne

doi:10.1016/s0014-827x(03)00195-2

Cited by 21 publications

(20 citation statements)

References 7 publications

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“…Dibenzoylmethane (DBM), a β-diketone, a constituent of licorice ( Glycyrrhiza glabra ), is used in sunscreens as an anti-melanoma agent [1]. It exhibits anti-cancer effects in vitro and in vivo and has been shown to suppress the proliferation of breast, colon [2], and prostate cancer cells [3].…”

Section: Introductionmentioning

confidence: 99%

RETRACTED: Suppression of pro-inflammatory and proliferative pathways by diferuloylmethane (curcumin) and its analogues dibenzoylmethane, dibenzoylpropane, and dibenzylideneacetone: Role of Michael acceptors and Michael donors

Anand

Sung

Kunnumakkara

et al. 2011

Biochemical Pharmacology

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Curcumin, a diferuloylmethane, has been shown to exhibit anti-inflammatory and anti-proliferative activities. Whereas curcumin has both a Michael acceptor and a Michael donor units, its analogues dibenzoylmethane (DBM, a component of licorice) and dibenzoylpropane (DBP) have a Michael donor but not a Michael acceptor unit, and the analogue dibenzylideneacetone (DBA) has a Michael acceptor unit. In the current report, we investigated the potency of DBM, DBP, and DBA in relation to curcumin for their ability to suppress TNF-induced NF-κB activation, NF-κB-regulated gene products, and cell proliferation. We found that all four agents were active in suppressing NF-κB activation; curcumin was most active and DBM was least active. When examined for its ability to inhibit the direct DNA binding activity of p65, a subunit of NF-κB, only DBP inhibited the binding. For inhibition of TNF-induced IKK activation, DBA was most active. For suppression of TNF-induced expression of NF-κB regulated gene products such as COX-2 (inflammation marker), cyclin D1 (proliferation marker), and VEGF (angiogenesis marker), DBA and curcumin were more active than DBM. Similarly for suppression of proliferation of leukemia (KBM-5), T cell leukemia (Jurkat), prostate (DU145), and breast (MDA-MB-231) cancer cells, curcumin and DBA were most active and DBP was least active. Overall, our results indicate that although curcumin and its analogues exhibit activities to suppress inflammatory pathways and cellular proliferation, a lack of Michael acceptor units in DBM and DBP can reduce their activities.

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Section: Introductionmentioning

confidence: 99%

RETRACTED: Suppression of pro-inflammatory and proliferative pathways by diferuloylmethane (curcumin) and its analogues dibenzoylmethane, dibenzoylpropane, and dibenzylideneacetone: Role of Michael acceptors and Michael donors

Anand

Sung

Kunnumakkara

et al. 2011

Biochemical Pharmacology

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“…6,8,17,18 Estão descritos em literatura apenas treze derivados de dibenzoilmetanos em Lonchocarpus, desde seu primeiro relato no gênero até a presente data. 4,6,8,17,18 Devido à pouca ocorrência dessas substâncias, suas propriedades biológicas ainda são pouco exploradas mas, eles vêm se destacando por apresentarem fortes atividades fotoprotetoras e antitumorais. 18,19 Os resultados do ensaio de toxicidade sobre a Artemia salina (1), (2) , seguida da lanceolatina B (1) com DL 50 = 6,72 µg mL -1 e pongamol (2) com DL 50 = 13,22 µg mL -1 .…”

Section: Resultsunclassified

“…4,6,8,17,18 Devido à pouca ocorrência dessas substâncias, suas propriedades biológicas ainda são pouco exploradas mas, eles vêm se destacando por apresentarem fortes atividades fotoprotetoras e antitumorais. 18,19 Os resultados do ensaio de toxicidade sobre a Artemia salina (1), (2) , seguida da lanceolatina B (1) com DL 50 = 6,72 µg mL -1 e pongamol (2) com DL 50 = 13,22 µg mL -1 . As atividades destas substâncias estão muito próximas com as descritas na literatura.…”

Section: Resultsunclassified

Toxicidade e atividade antioxidante de flavonoides das cascas das raízes de Lonchocarpus filipes

Santos¹,

Costa²,

Marques³

et al. 2009

Quím. Nova

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Recebido em 17/3/08; aceito em 24/5/09; publicado na web em 6/11/09 TOXICITY AND ANTIOXIDANT ACTIVITY OF FLAVONOIDS FROM Lonchocarpus filipes ROOT BARK. The phytochemical investigation of dichloromethane extract from root bark of Lonchocarpus filipes Benth (Leguminosae) afforded four flavonoids including three dibenzoylmethane derivatives rarely found in nature. The structures were established based on their spectral data ( 1 H and 13 C NMR, 2D-NMR) as being: lanceolatin B (1), pongamol (2), (E)-7-O-methylpongamol (3) and (E)-9-O-methylpongamol (4). Compound (4) is described herein for the first time as a natural product. The extracts and the isolated compounds (1), (2) and (3) displayed high toxicity in the brine shrimp lethality assay. Only compound (2) showed antioxidant activity using a DPPH radical scavenging assay. This is the first report on the phytochemical study of Lonchocarpus filipes.Keywords: Lonchocarpus filipes; flavonoids; dibenzoylmethanes. INTRODUÇÃOO gênero Lonchocarpus Kunth (Leguminosae), conhecido comumente como "Timbó", compreende cerca de 120 espécies, das quais 23 são nativas do Brasil.1 Várias espécies desse gênero são utilizadas na medicina popular como, por exemplo, as raízes e caules de L. chrysophyllus, L. martynii e L. spruceanus no tratamento de tumores, AIDS, eczema, dores de cabeça e doenças de pele.2 As raízes dessas espécies e as de L. urucu e L. utilis também são consideradas tóxicas para insetos e peixes, fato atribuído à presença da rotenona. 2,3Estudos prévios em espécies de Lonchocarpus revelaram a presença de flavonoides, triterpenos, derivados de ácido benzoico, aminoácidos e alcaloides, 4,5 sendo os flavonoides considerados os constituintes predominantes em espécies desse gênero. [6][7][8] Os flavonoides são considerados um dos maiores grupos de metabólitos secundários e têm se destacado por apresentarem diversas propriedades farmacológicas, agindo como antitumorais, anti-inflamatórios, antioxidantes, antivirais, fungicidas, antiprotozoários, bem como na redução de riscos de doenças cardiovasculares. 8,9 O gênero Lonchocarpus é subdividido em dois subgêneros: Lonchocarpus subgênero Punctati o qual não está subdividido em seções, e Lonchocarpus subgênero Lonchocarpus, subdividido em cinco seções: Laxiflori, Unguiflori, Pubiflori, Lonchocarpus e Densiflori. 10 De acordo com essa classificação botânica, Lonchocarpus filipes Benth pertence ao subgênero Lonchocarpus, seção Laxiflori, ao lado de L. campestris. 11Lonchocarpus filipes é uma árvore tipicamente brasileira, variando de 2 a 4 m de altura, com distribuição restrita ao estado do Rio de Janeiro. É encontrada em matas e bosques da capital, estendendo-se até Petrópolis.10 Atualmente é cultivada no Parque Ecológico da Universidade Estadual de Campinas (UNICAMP).Neste trabalho são descritos o isolamento, a avaliação da toxicidade e da atividade antioxidante dos extratos e substâncias isoladas das cascas das raízes de L. filipes. Este é o primeiro relato de estudo fitoquímico dessa espécie. RESULTADOS E DISCUSSÃOO fracion...

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“…DB, a β-diketone analogue of curcumin, belongs to the flavonoid family. Skin cancer frequently occurs at sun-exposed sites of the body, and sunscreen derivatives from DB have been used for protection against ultraviolet radiation (27). DB modulates the phase I/phase II detoxification (10,28) and with its analogues, HDB and HMDB, induces apoptosis in various types of cancer (15)(16)(17)(18).…”

Section: Discussionmentioning

confidence: 99%

Dibenzoylmethane, hydroxydibenzoylmethane and hydroxymethyldibenzoylmethane inhibit phorbol-12-myristate 13-acetate-induced breast carcinoma cell invasion

Liao

Tzeng

Hung

et al. 2015

Molecular Medicine Reports

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Dibenzoylmethane (DB), a minor constituent of the root extract of licorice, belongs to the flavonoid family. Hydroxydibenzoylmethane (HDB) and hydroxymethyldibenzoylmethane (HMDB) have an identical structure to DB, but also possess a hydroxyl group and a hydroxyl and methyl group bonded to aromatic rings, respectively. They inhibit cellular proliferation and induce apoptosis in a variety of types of cancer cell, however, the antimetastatic effects of DB, HDB and HMDB on human breast carcinoma cells remain to be elucidated. The present study aimed to clarify the molecular mechanisms underlying the effects of DB and its analogues on phorbol‑12‑myristate 13‑acetate (PMA)‑induced MCF‑7 cell metastasis. The results revealed that DB, HDB and HMDB inhibited cell migration and invasion. In addition, PMA‑mediated MCF‑7 cell invasion was inhibited by DB, HDB and HMDB by inhibiting the expression of matrix metalloproteinase (MMP)‑9. Rottlerin, a protein kinase C (PKC)δ inhibitor and LY294002, a phosphatidylinositide 3‑kinase (PI3K) inhibitor, reduced the PMA‑mediated expression of MMP‑9 and cell invasion. Furthermore, DB, HDB and HMDB prevented the activation of PKCδ and PI3K by inhibiting their phosphorylation. The present study was the first, to the best of our knowledge, to demonstrate the antimetastatic potential of DB, HDB and HDMB, which decreased cancer cell invasion through the PI3K/PKCδ‑mediated MMP‑9 pathway.

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A novel sunscreen agent having antimelanoma activity

Cited by 21 publications

References 7 publications

RETRACTED: Suppression of pro-inflammatory and proliferative pathways by diferuloylmethane (curcumin) and its analogues dibenzoylmethane, dibenzoylpropane, and dibenzylideneacetone: Role of Michael acceptors and Michael donors

RETRACTED: Suppression of pro-inflammatory and proliferative pathways by diferuloylmethane (curcumin) and its analogues dibenzoylmethane, dibenzoylpropane, and dibenzylideneacetone: Role of Michael acceptors and Michael donors

Toxicidade e atividade antioxidante de flavonoides das cascas das raízes de Lonchocarpus filipes

Dibenzoylmethane, hydroxydibenzoylmethane and hydroxymethyldibenzoylmethane inhibit phorbol-12-myristate 13-acetate-induced breast carcinoma cell invasion

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