Siamenol, a New Carbazole Alkaloid from <i>Murraya siamensis</i>

Meragelman, Karina M.; McKee, Tawnya C.; Boyd, Michael R.

doi:10.1021/np990570g

Cited by 91 publications

(79 citation statements)

References 13 publications

(20 reference statements)

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“…Aromoline and FK-3000 isolated from the root tuber of Stephania cepharantha, completely inhibited the cytopathic effects of HIV-1 on MT-4 cells at 31.3 and 7.8 µg/mL, and possessed a CC 0 at 62.5 and 15.6 µg/mL, respectively (Ma et al, 2002). Likewise, the carbazole alkaloid, siamenol from Murraya siamensis, inhibited HIV-1 induced cytopathic inhibitory activity in an XTT assay with an EC 50 of 2.6 µg/mL and TI of 2.4 (Meragelman et al, 2000). .…”

Section: Alkaloidsmentioning

confidence: 96%

Naturally derived anti‐HIV agents

Asres

Seyoum

Veeresham

et al. 2005

Phytotherapy Research

148

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The urgent need for new anti-HIV/AIDS drugs is a global concern. In addition to obvious economical and commercial hurdles, HIV/AIDS patients are faced with multifarious difficulties associated with the currently approved anti-HIV drugs. Adverse effects, the emergence of drug resistance and the narrow spectrum of activity have limited the therapeutic usefulness of the various reverse transcriptase and protease inhibitors that are currently available on the market. This has driven many scientists to look for new anti-retrovirals with better efficacy, safety and affordability. As has always been the case in the search for cures, natural sources offer great promise. Several natural products, mostly of plant origin have been shown to possess promising activities that could assist in the prevention and/or amelioration of the disease. Many of these anti-HIV agents have other medicinal values as well, which afford them further prospective as novel leads for the development of new drugs that can deal with both the virus and the various disorders that characterize HIV/AIDS. The aim of this review is to report new discoveries and updates pertaining to anti-HIV natural products. In the review anti-HIV agents have been classified according to their chemical classes rather than their target in the HIV replicative cycle, which is the most frequently encountered approach. Perusal of the literature revealed that most of these promising naturally derived anti-HIV compounds are flavonoids, coumarins, terpenoids, alkaloids, polyphenols, polysaccharides or proteins. It is our strong conviction that the results and experiences with many of the anti-HIV natural products will inspire and motivate even more researchers to look for new leads from plants and other natural sources.

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Section: Alkaloidsmentioning

confidence: 96%

Naturally derived anti‐HIV agents

Asres

Seyoum

Veeresham

et al. 2005

Phytotherapy Research

148

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“…A number of natural carbazole alkaloids were recognized to exhibit potential biological activities such as antimicrobial [1,2], anti-HIV [3], anticancer [4,5,6] activities. Among them, several compounds were used as drugs for treatment of cancer [7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Cytotoxic Activity Evaluation of Novel Derivatives of Murrayafoline A

Anh

2018

JST

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“…Some of these compounds show useful biological activities. For example, in 2000, Boyd et al [2] developed a bioassay-guided fractionation of the extract leading to the isolation of a new carbazole alkaloid, siamenol, which shows interesting anti-HIV activity (EC 50 = 2.6 mg mL À1 ), reaching 50-60 % maximum protection in the 2,3-bis-(2-methoxy-4-nitro-5-sulfophenyl)-2H-tetrazolium-5-carboxanilide (XTT) assay from Murraya siamensis collected in Thailand. 3-Formyl-7-hydroxycarbazole was isolated from the root bark of Murraya euchrestifolia (Scheme 1).…”

mentioning

confidence: 99%

“…Furthermore, in the first total synthesis of siamenol, [6] the coupling of 3-bromo-6-methyl-9H-carbazol-2-ol required 9.5 equiv of prenyl bromide and 12 equiv of NiA C H T U N G T R E N N U N G (cod) 2 (cod = 1,5-cyclooctadiene) for six days to yield siamenol in 47 % yield with a low purity. Thus, the pure siamenol had to be prepared by preparative HPLC, which makes this method much less attractive.…”

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confidence: 99%

General Au‐Catalyzed Benzannulation Towards Naturally Occurring Carbazole Alkaloids from Methoxypropadiene

Kong

2011

Chemistry A European J

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Accessible alkaloids: Naturally occurring carbazole alkaloids, such as clauszoline‐K, ‐L, ‐M, and ‐N, 3‐formyl‐7‐hydroxycarbazole, and siamenol, were synthesized through a gold‐catalyzed cyclization reaction of 1‐(indol‐2‐yl)‐2‐methoxy‐2,3‐allenols, which are readily available from indolecarbaldehydes and methoxypropadiene (see scheme; R1=Me, carboxylic acid/ester, or aldehyde; R2=prenyl or H; R3=H or Me). The reaction demonstrates atom economy, high selectivity, and high yields, mostly with catalytic reactions.

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Siamenol, a New Carbazole Alkaloid from Murraya siamensis

Abstract: A new carbazole alkaloid, siamenol (1), and two known alkaloids, mahanimbine (2) and mahanimbilol (3), have been isolated from the organic extract of Murraya siamensis. The novel compound exhibited HIV-inhibitory activity.

Cited by 91 publications

References 13 publications

Naturally derived anti‐HIV agents

Naturally derived anti‐HIV agents

Synthesis and Cytotoxic Activity Evaluation of Novel Derivatives of Murrayafoline A

General Au‐Catalyzed Benzannulation Towards Naturally Occurring Carbazole Alkaloids from Methoxypropadiene

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