Three New Carbazole Alkaloids Isolated from Murraya siamensis

Ruangrungsi, Nijsiri; Ariyaprayoon, Jongjit; Lange, Gordon L.; Organ, Michael G.

doi:10.1021/np50070a025

Cited by 51 publications

(44 citation statements)

References 13 publications

(18 reference statements)

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“…Thec arbazole alkaloidsmukonal [15] and bis(2-hydroxy-3-methylcarbazole) [18] are isolated from the stem bark of Murraya koenigii.Girinimbilol [16] and heptaphylline [16] are isolated from both the stem bark of Murraya koenigii and root bark of Clausena heptaphylla.…”

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confidence: 99%

Synthesis of Carbazole Alkaloids by Ring‐Closing Metathesis and Ring Rearrangement–Aromatization

et al. 2015

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Aprocess for the assembly of carbazole alkaloids has been developed on the basis of ring-closing metathesis (RCM) and ringrearrangement-aromatization (RRA) as the key steps. This method is based on allyl Grignard addition to isatin derivatives to provide smooth access to 2,2-diallyl 3-oxindole derivatives through a 1,2-allyl shift. The diallyl derivatives were used as RCM precursors to afford a novel class of spirocyclopentene-3-oxindole derivatives, which underwent a novel RRA reaction to afford carbazole derivatives. The synthetic sequence to carbazoles was shortened by combining the RCM and RRA steps in an orthogonal tandem catalytic process. The utility of this methodology was further demonstrated by the straightforward synthesis of carbazole alkaloids, including amukonal derivative, girinimbilol, heptaphylline, and bis(2-hydroxy-3-methylcarbazole).

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confidence: 99%

Synthesis of Carbazole Alkaloids by Ring‐Closing Metathesis and Ring Rearrangement–Aromatization

et al. 2015

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“…Compound 4 was also obtained from the crude hexane extract and the crude ethanol extract of the rhizomes (5.3 mg% dry wt) and the crude hexane extract of the roots (5.6 mg% dry wt). All isolated compounds were identified by comparison of their mp, and IR, 1 H NMR and mass spectral data with those reported in the literature (Wu and Furukawa, 1982), and their structures were further confirmed by measurement of their 13 C NMR data which were the same as those in the literature (Huang et al, 1997;Ito et al, 1997;Ruangrungsi et al, 1990).…”

Section: Resultsmentioning

confidence: 61%

“…The carbazole, O-methylmukonal (1), has been isolated from this plant for the first time and showed a favourable potential therapeutic index. The other carbazoles, 3-formyl-2,7-dimethoxycarbazole (2) and clauszoline J (3), and a pyranocoumarin, clausenidin (4) have been reported from C. excavata in 1990 (Ruangrungsi et al, 1990(Ito et al, 1997) and 1982(Wu and Furukawa, 1982, respectively. These more recently isolated compounds as well as the limonoid (5), support the use of this traditional Thai medicinal plant to treat HIV/AIDS.…”

Section: Introductionmentioning

confidence: 99%

Anti‐HIV‐1 constituents from Clausena excavata: Part II. carbazoles and a pyranocoumarin

Kongkathip

Sunthitikawinsakul

et al. 2005

Phytotherapy Research

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Three carbazole derivatives, O-methylmukonal (1), 3-formyl-2,7-dimethoxycarbazole (2) and clauszoline J (3), and a pyranocoumarin, clausenidin (4), were isolated from the rhizomes and roots of Clausena excavata. Compound 1, isolated from this plant for the first time, has not been reported previously as having anti-HIV-1 activity. Compounds 1-4 displayed anti-HIV-1 activity in a syncytial assay with EC(50) values of 12, 29.1, 34.2 and 5.3 microm, respectively, and thus exhibited potential therapeutic index (PTI) values of 56.7, 8.0, 1.6 and 7.0, respectively. All isolated compounds demonstrated a lack of cytotoxicity against the KB and BC-1 cancer cell lines.

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“…7-Methoxy-O-methylmukonal has been isolated from the roots of Murraya siamensis (Ruangrungsi et al, 1990). Clausine O has been found in the root bark of the Chinese medicinal plant Clausena excavata (Wu et al, 1999).…”

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confidence: 99%

Transition metals in organic synthesis - Part 83#: Synthesis and pharmacological potential of carbazoles

et al. 2008

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A series of carbazole derivatives with promising pharmacological properties has been prepared using either an iron-mediated or a palladium-catalyzed synthetic approach. The carbazole alkaloids carbazoquinocin C, carbazomadurin A and B, epocarbazolin A and B, neocarazostatin B, and carquinostatin A are antioxidants acting as free-radical scavengers. Thus, they represent potential lead compounds for the development of novel drugs against diseases initiated by oxygenderived free radicals. Initiated by the first naturally occurring carbazole alkaloids with antituberculosis (anti-TB) activity, clausine K and micromeline, a study on the structure-activity relationships for anti-TB-active carbazole derivatives has been carried out. The 6-oxygenated carbazoles glycozoline and glycozolinine show antibiotic activity towards several microorganisms. The 7-oxygenated carbazole siamenol exhibits anti-HIV activity.

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Three New Carbazole Alkaloids Isolated from Murraya siamensis

Cited by 51 publications

References 13 publications

Synthesis of Carbazole Alkaloids by Ring‐Closing Metathesis and Ring Rearrangement–Aromatization

Synthesis of Carbazole Alkaloids by Ring‐Closing Metathesis and Ring Rearrangement–Aromatization

Anti‐HIV‐1 constituents from Clausena excavata: Part II. carbazoles and a pyranocoumarin

Transition metals in organic synthesis - Part 83#: Synthesis and pharmacological potential of carbazoles

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