Prenylated 9,10-dihydrophenanthrenes from <i>Macaranga javanica</i>

Ilmiawati, Auliya; Hakim, Euis H.; Syah, Yana Maolana

doi:10.1515/znb-2015-0062

Cited by 10 publications

(9 citation statements)

References 14 publications

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“…Prenyl-substituted phenanthrenes are relatively uncommon. However, Ilmiawati et al reported five prenylated compounds, including three new prenyl-substituted phenanthrenes ( 62 , 63 , 161 ) from Macaranga javanica (Euphorbiaceae) …”

Section: Compound Structural Diversity and Biological Activitymentioning

confidence: 99%

Phenanthrenes: A Promising Group of Plant Secondary Metabolites

2017

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Although phenanthrenes are considered to constitute a relatively small group of natural products, discovering new phenanthrene derivatives and evaluating their prospective biological activities have become of great interest to many research groups worldwide. Based on 160 references, this review covers the phytochemistry and pharmacology of 213 naturally occurring phenanthrenes that have been isolated between 2008 and 2016. More than 40% of the 450 currently known naturally occurring phenanthrenes were identified during this period. The family Orchidaceae is the most abundant source of these compounds, although several new plant families and genera have been involved in the search for phenanthrenes. The presence of certain substituent patterns may be restricted to specific families; vinyl-substituted phenanthrenes were reported only from Juncaceae plants, and prenylated derivatives occur mainly in Euphorbiaceae species. Therefore, these compounds also can serve as chemotaxonomic markers. Almost all of the newly isolated compounds have been studied for their biological activities (e.g., potential cytotoxic, antimicrobial, anti-inflammatory, and antioxidant effects), and many of them showed multiple activities. According to the accumulated data, denbinobin, with a novel mechanism of action, has great potential as a lead compound for the development of a new anticancer agent.

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Section: Compound Structural Diversity and Biological Activitymentioning

confidence: 99%

Phenanthrenes: A Promising Group of Plant Secondary Metabolites

2017

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“…5). The antibacterial assay on laevifolins A (1) and B (2) on S.aureus (clinical isolate) have been reported before by Ilmiawati and co-workers [14] with MIC values 35 As for cytotoxicity, laevifolin A (1) displayed pronounced inhibition on HT-29 cells with an IC 50 value of but no IC 50 observed in laevifolin B (2). The steric hindrance enhanced the activity due to the accessibility of laevifolin A (1) to exert its effect on the cancer cells [21].…”

Section: Resultsmentioning

confidence: 55%

“…As for the biological activities, laevifolins A (1) and B (2) were reported for their antibacterial activity (Bacillus subtilis, Enterobacter aerogenes, Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi, Shigella dysenteriae, Staphylococcus aureus, and Vibrio cholera) and cytotoxicity of murine leukemia (P-388 cells). Meanwhile, macarubiginosin C (3) was only tested on P-388 cells [14,20]. In this study, the compounds were assayed on different bacteria and cancer cells.…”

Section: Resultsmentioning

confidence: 99%

“…M. heynei belongs to the Javanica group which consists of 13 species such as M. costulata, M. cumingii, M. javanica, M. kinabaluensis and M. loheri [13]. Amongst the species, only M. javanica has been phytochemically studied and was reported to contain prenylated dihydrostilbenes as well as dihydrophenanthrenes [14]. This genus consists a large number of species, however, only 10% have been phytochemically investi-gated [15].…”

Section: Introductionmentioning

confidence: 99%

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Isolation of Dihydrostilbenes from Macaranga Heynei and their Bioactivities

Kamarozaman¹,

Ahmat²,

Low³

et al. 2019

IJET

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Macaranga is known to contain abundant sources of prenylated flavonoids and stilbenoids which possessed broad spectrum of biological activities including anti-inflammatory, antimicrobial, antioxidant and cytotoxicity. These species are widely distributed in New Guinea, Borneo and from West Africa to the south Pacific islands. Although Macaranga comprises a large number of species, this genus has not been widely investigated which prompted us to conduct a study on Macaranga heynei. This research is conducted to isolate and characterise the compounds from M. heynei as well as to access the antibacterial and cytotoxicity of the isolates. The purification from the leaves of M. heynei has successfully yielded three dihydrostilbenes which were analysed by means of NMR, UV-Vis, FTIR, MS and comparison with the literature data. These compounds were characterised as laevifolins A (1) and B (2) as well as macarubiginosin C (3). Laevifolin A (1) exhibited good activity against S.cohnii subsp. urealyticum and moderate activity against S.aureus ATCC 25923 with the IC50 values of 11.65 and 27.13 M respectively. It also displayed pronounced inhibition against HT-29 cells with an IC50 value of 21.20 M. Meanwhile, laevifolin B (2) displayed moderate activity on S.cohnii subsp. urealyticum but strong inhibition against S.aureus ATCC 25923 with the IC50 values of 20.71 and 1.64 M respectively.

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“…Similarly, flavonoids displayed significant role in dietary antioxidant by reducing the oxidative stress in the body [15]. Meanwhile, the stilbenoids namely laevifolins A and B which were isolated from M. javanica possessed significant activities against S. aureus with MIC values 35 μM [16].…”

Section: Introductionmentioning

confidence: 99%

PRENYLATED DIHYDROSTILBENES FROM Macaranga heynei (EUPHORBIACEAE)

Kamarozaman

Ahmat

Fariza

et al. 2018

MJAS

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Macaranga is the largest genus in Euphorbiaceae which consists of approximately 300 species and are widely distributed in New Guinea, Borneo and from West Africa to the south Pacific islands. Phytochemical study on the leaves of Macaranga heynei has been conducted. The powder of the leaves of M. heynei was macerated in methanol at room temperature for 24 hours and repeated three times. The crude extract obtained was dissolved in aqueous methanol (80:20) and partitioned with hexane and ethyl acetate. The ethyl acetate crude extract was fractionated by vacuum liquid chromatography (VLC) with hexane:ethyl acetate in increasing polarity to give seven combined fractions (MH 1-7). Fraction MH 2 (1000 mg) was further purified by radial chromatography (RC) with hexane:ethyl acetate in increasing polarity to give six combined subfractions . Fraction MH 23 (693.7 mg) was further purified by the same chromatographic technique but with different eluent which was chloroform:ethyl acetate in increasing polarity to afford two pure compounds (1) (10 mg) and (2) (12 mg). Based on spectroscopy analysis, the pure compounds were characterized as laevifolins A (1) and B (2). Keywords: Laevifolin A, laevifolin B, leaves, Macaranga heynei AbstrakMacaranga merupakan genus terbesar dalam famili Euphorbiaceae yang mengandungi kira-kira 300 spesies dan taburannya meliputi New Guinea, Borneo dan dari Afrika Selatan ke utara kepulauan Pasifik. Kajian fitokimia ke atas daun Macaranga heynei telah dijalankan. Serbuk daun M. heynei direndam dalam metanol pada suhu bilik selama 24 jam dan pengesktrakan diulang sebanyak tiga kali. Ekstrak mentah yang diperolehi telah dilarutkan dalam larutan metanol (80:20) dan dipisahkan dengan heksana dan etil asetat. Etil asetat mentah difraksinasi menggunakan kromatografi cecair vakum (KCV) dengan heksana:etil asetat mengikut peningkatan kekutuban menghasilkan tujuh fraksi gabungan (MH 1-7). Fraksi MH 2 (1000 mg) selanjutnya ditulenkan dengan menggunakan kromatografi radial (RC) dengan heksana:etil asetat mengikut peningkatan kekutuban menghasilkan enam subfraksi gabungan . Fraksi MH 23 (693.7 mg) seterusnya ditulenkan dengan menggunakan teknik kromatografi yang sama tetapi menggunakan eluen yang berbeza iaitu kloroform:etil asetat mengikut peningkatan kekutuban menghasilkan dua sebatian tulen (1) (10 mg) dan (2) (12 mg). Berdasarkan analisis spektroskopi, sebatian tulen tersebut dicirikan sebagai laevifolin A (1) dan B (2). Kata kunci: Laevifolin A, laevifolin B, daun, Macaranga heynei

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Prenylated 9,10-dihydrophenanthrenes from Macaranga javanica

Cited by 10 publications

References 14 publications

Phenanthrenes: A Promising Group of Plant Secondary Metabolites

Phenanthrenes: A Promising Group of Plant Secondary Metabolites

Isolation of Dihydrostilbenes from Macaranga Heynei and their Bioactivities

PRENYLATED DIHYDROSTILBENES FROM Macaranga heynei (EUPHORBIACEAE)

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