Carbazole-pyranocoumarin conjugate and two carbazole alkaloids from the stems of <i>Clausena excavata</i>

Chakthong, Suda; Bindulem, Nitima; Raknai, Sirorat; Yodwaree, Sariya; Kaewsanee, Soonthorn; Kanjana‐Opas, Akkharawit

doi:10.1080/14786419.2015.1135143

Cited by 19 publications

(10 citation statements)

References 27 publications

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“…This type of binary compounds previously has been reported from C. excavata as carbazomarin-A 10 and carbazomarin-B. 11 The spectral data of 1 in pyranocoumarin unit are the same as the previously reported compounds. However, the carbazole unit is different from 1 .…”

supporting

confidence: 77%

Carbazomarin: A New Potential of α-Glucosidase Inhibitor From Clausena excavata Roots

Aminah

Thant

Kristanti

et al. 2019

Natural Product Communications

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Continuing our exploration for dual functions antidiabetic and antioxidant agents from Myanmar medicinal plant , a new carbazole-pyranocoumarin conjugate, carbazomarin-C (1) along with a known carbazole alkaloid, mukonine (2) and a pyranocoumarin, xanthoxyletin (3), was isolated from the roots of Clausena excavata. The chemical structures of these compounds were identified using a combination of spectroscopic methods. Among isolates, there was a strong inhibition of compounds (1) and (3) on yeast α-glucosidase in a dose-dependent manner. It was shown when p-nitrophenyl-α-d-glucopyranoside was used as a substrate in vitro with IC50 values 0.22 and 4.81 mM, respectively. However, all isolated compounds displayed no inhibition against DPPH (2,2-diphenyl-1-picrylhydrazyl) radicals.

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supporting

confidence: 77%

Carbazomarin: A New Potential of α-Glucosidase Inhibitor From Clausena excavata Roots

Aminah

Thant

Kristanti

et al. 2019

Natural Product Communications

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“…Its molecular formula was determined as C 32 H 28 N 2 O 3 base on its 13 C NMR and HRESIMS data ( m / z 487.2016 [M − H] − , calcd for C 32 H 27 N 2 O 3 , 487.2022). The 1 H and 13 C NMR data ( Table 2 and Table 3 ) analysis revealed that the structure of 17 is a dimeric carbazole formed by murrayamine A [ 16 ] and murrayafoline A [ 22 , 23 ] units. Additionally, the HMBC correlations from the 3″-CH 2 protons to C-5/C-6/C-7/C-2″/C-3″/C-4″, and H-5/H-2″/H-4″ to 3″-CH 2 revealed a C-6–C-3″-methyl linkage between the two carbazole moieties ( Figure 2 ).…”

Section: Resultsmentioning

confidence: 99%

Trimeric and Dimeric Carbazole Alkaloids from Murraya microphylla

Chen

Zhu

et al. 2021

Molecules

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Seventeen new carbazole alkaloid derivatives, including a trimeric carbazole racemate, (±)-microphyltrine A (1), 15 dimeric carbazole racemates, (±)-microphyldines A–O (2–16), and a C-6–C-3″-methyl-linked dimeric carbazole, microphyldine P (17), were isolated from the leaves and stems of Murraya microphylla (Merr. et Chun) Swingle. The structures of the new compounds were elucidated on the basis of HRESIMS and NMR data analysis. The optically pure isomers of these isolated carbazole alkaloids were obtained by chiral HPLC separation and their absolute configurations were determined by electronic circular dichroism (ECD) data analysis.

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“…Due to the sensitivity of brine shrimp to a variety of chemical substances, many researchers had considered this assay for searching potent noncytotoxic natural compounds having biological and pharmacological properties [23][24][25]. Although previous studies showed antimicrobial activity of the bark, leaf, and stem of this plant [26,27], there is no recorded data for anti-Enterococcus faecalis.…”

Section: Introductionmentioning

confidence: 99%

Anti‐Enterococcus Faecalis, Cytotoxicity, Phytotoxicity, and Anticancer Studies on Clausena excavata Burum. f. (Rutaceae) Leaves

Albaayit

Maharjan

Abdullah

et al. 2021

BioMed Research International

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Background. Clausena excavata Burum. f. has long been applied in ethnomedicine for the treatment of various disorders like rhinitis, headache, cough, wound healing, fever, and detoxification. This study is aimed at investigating the antibacterial activity against Enterococcus faecalis ATCC 49532 using AlamarBlue assay and atomic force microscopy (AFM) as well as the cytotoxicity, anticancer, and phytotoxicity of C. excavata. Method. Bacterial cell viability was performed by using microplate AlamarBlue assay. Atomic force microscopy was used to determine morphological changes in the surface of bacterial cells. Cytotoxicity and phytotoxicity were determined by brine shrimp lethality and Lemna minor bioassay. Caco-2 (colorectal adenocarcinoma) cell line was used for the evaluation of the anticancer effects. Result. Among the fractions tested, ethyl acetate (EA) fraction was found to be active with minimum inhibitory concentration (MIC) of 750 μg/mL against E. faecalis, but other fractions were found to be insensitive to bacterial growth. Microscopically, the EA fraction-treated bacteria showed highly damaged cells with their cytoplasmic content scattered all over. The L C 50 value of the EA fraction against brine shrimp was more than 1000 μg/mL showing the nontoxic nature of this fraction. Chloroform (CH), EA, and methanol (MOH) fractions of C. excavata were highly herbicidal at the concentration of 1000 μg/mL. EA inhibited Caco-2 cell line with an I C 50 of 20 μg/mL. Conclusions. This study is the first to reveal anti-E. faecalis property of EA fraction of C. excavata leaves, natural herbicidal, and anticancer agents thus highlight the potential compound present in its leaf which needs to be isolated and tested against multidrug-resistant E. faecalis.

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Carbazole-pyranocoumarin conjugate and two carbazole alkaloids from the stems of Clausena excavata

Cited by 19 publications

References 27 publications

Carbazomarin: A New Potential of α-Glucosidase Inhibitor From Clausena excavata Roots

Carbazomarin: A New Potential of α-Glucosidase Inhibitor From Clausena excavata Roots

Trimeric and Dimeric Carbazole Alkaloids from Murraya microphylla

Anti‐Enterococcus Faecalis, Cytotoxicity, Phytotoxicity, and Anticancer Studies on Clausena excavata Burum. f. (Rutaceae) Leaves

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