Tronoharine, a novel hexacyclic indole alkaloid from a Malayan Tabernaemontana

Kam, Toh‐Seok; Sim, Kooi‐Mow; Lim, Tuck‐Meng

doi:10.1016/s0040-4039(99)01018-7

Cited by 36 publications

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References 8 publications

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“…The UV spectrum showed absorption maxima at 239 and 313 nm, characteristic of a 2-acylindole chromophore [26]. The EI-MS of 5 showed a molecular ion at m/z 282, which corresponds to C 17 (6), which is also in a-position to the indole moiety. The H-atoms at C(21) are found upfield from the HÀC(6) signals, at d(H) 2.68 and 3.65.…”

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Biologically Active Ibogan and Vallesamine Derivatives from Tabernaemontana divaricata

Kam

Pang

Choo

et al. 2004

Chemistry & Biodiversity

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Six new indole alkaloids, viz., (3S)-3-cyanocoronaridine (2), (3S)-3-cyanoisovoacangine (3), conolobine A (5), conolobine B (6), conolidine (7), and (3R/3S)-3-ethoxyvoacangine (8), in addition to 36 known ones, were obtained from the stem-bark extract of the Malayan Tabernaemontana divaricata. The structures were determined by NMR and MS analysis. The CN-substituted alkaloids showed appreciable cytotoxicity towards the KB human oral epidermoid carcinoma cell-line.

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confidence: 99%

Biologically Active Ibogan and Vallesamine Derivatives from Tabernaemontana divaricata

Kam

Pang

Choo

et al. 2004

Chemistry & Biodiversity

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“…[1][2][3] We have reported many examples of new alkaloids from various Malaysian representatives of this genus that are distinguished by their structural novelty, as well as useful bioactivity. [4][5][6][7][8][9][10][11][12][13][14][15] For instance, we have previously reported the structure of the novel tetracyclic indole voaharine 1, as well as the novel bisindoles, conophylline 2, conophyllidine 3, and conofoline 4 from the leaf extract of T. divaricata (L.) R. Br. ex Roem.…”

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Biologically active indole and bisindole alkaloids from Tabernaemontana divaricata

2003

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The ethanol extract of the leaves of Tabernaemontana divaricata (double flower variety) provided a total of 23 alkaloids, including the new aspidosperma alkaloids, taberhanine, voafinine, N-methylvoafinine, voafinidine, voalenine and the new bisindole alkaloid, conophyllinine in addition to the previously known, biologically active bisindole, conophylline and its congener, conofoline. The structures of the new alkaloids were established by spectroscopic methods. The preparation and characterization of the corresponding quinones of the biologically active bisindoles are also described in relation to a structure-activity study of these compounds with respect to their action in stimulating insulin expression.

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“…Phytochemical studies on leaves and stem bark of T. corymbosa employing complex isolation techniques have produced a pool of novel structured alkaloids with interesting anticancer activities that include the reversal of drug resistance in vincristine‐resistant KB/VJ300 cells as shown in Table . Majority of these isolated alkloids are indoles of different types such as aspidosperma, pentacyclic, hexacyclic, iboga‐pyrrolidone conjugate, iboga, bis‐vobasinyl‐chippiine, hexacylic chippiine derivative, chippiine, vobasine and tacaman . The bisindoles constituted the second largest group of alkaloids comprising mainly of vobasinyl‐ibogan types.…”

Section: Phytochemistrymentioning

confidence: 99%

A review on ethnobotany, pharmacology and phytochemistry of Tabernaemontana corymbosa

Abubakar

Loh

2016

Journal of Pharmacy and Pharmacology

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Objectives Tabernaemontana is a genus from the plant family, Apocynaceae with vast medicinal application and widespread distribution in the tropics and subtropics of Africa, Americas and Asia. The objective of this study is to critically evaluate the ethnobotany, medicinal uses, pharmacology and phytochemistry of the species, Tabernaemontana corymbosa (Roxb. ex Wall.) and provide information on the potential future application of alkaloids isolated from different parts of the plant. Key findings T. corymbosa (Roxb. ex Wall.) parts are used as poultice, boiled juice, decoctions and infusions for treatment against ulceration, fracture, postnatal recovery, syphilis, fever, tumours and orchitis in Malaysia, China, Thailand and Bangladesh. Studies recorded alkaloids as the predominant phytochemicals in addition to phenols, saponins and sterols with vast bioactivities such as antimicrobial, analgesic, anthelmintic, vasorelaxation, antiviral and cytotoxicity. Summary An evaluation of scientific data and traditional medicine revealed the medicinal uses of different parts of T. corymbosa (Roxb. ex Wall.) across Asia. Future studies exploring the structure-bioactivity relationship of alkaloids such as jerantinine and vincamajicine among others could potentially improve the future application towards reversing anticancer drug resistance.

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Tronoharine, a novel hexacyclic indole alkaloid from a Malayan Tabernaemontana

Cited by 36 publications

References 8 publications

Biologically Active Ibogan and Vallesamine Derivatives from Tabernaemontana divaricata

Biologically Active Ibogan and Vallesamine Derivatives from Tabernaemontana divaricata

Biologically active indole and bisindole alkaloids from Tabernaemontana divaricata

A review on ethnobotany, pharmacology and phytochemistry of Tabernaemontana corymbosa

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