An iboga alkaloid chemotaxonomic marker from endemic Tabernaemontana ternifolia with antitubercular activity

Garcellano, Rhea C.; Cort, John R.; Moinuddin, Syed G. A.; Franzblau, Scott G.; Ma, Rui; Aguinaldo, Alicia M.

doi:10.1080/14786419.2018.1550759

Title: An iboga alkaloid chemotaxonomic marker from endemic Tabernaemontana ternifolia with antitubercular activity

Journal Article · Sun Feb 17 00:00:00 EST 2019 · Natural Product Research

DOI:https://doi.org/10.1080/14786419.2018.1550759· OSTI ID:1642384

Garcellano, Rhea C. ^[1];

^[2]; Moinuddin, Syed G. A. ^[3]; Franzblau, Scott G. ^[4]; Ma, Rui ^[4]; Aguinaldo, Alicia M. ^[5]

Univ. of Santo Tomas, Manila (Philippines); Palawan State Univ., Palawan (Philippines)
Pacific Northwest National Lab. (PNNL), Richland, WA (United States); Washington State Univ., Pullman, WA (United States)
Washington State Univ., Pullman, WA (United States)
University of Illinois at Chicago, IL (United States). Inst. for Tuberculosis Research
Univ. of Santo Tomas, Manila (Philippines). Phytochemistry Lab., Research Center for the Natural and Applied Sciences

In this work, coronaridine (1) was isolated from the CH₂Cl₂ root extract of Tabernaemontana ternifolia. The structure of 1 was established from 1D- and 2D-NMR and HR-ESIMS experiments, and by comparison with reported spectroscopic data. To date, this is the first report of compound 1 from T. ternifolia, introduced as new Tabernaemontana species from Philippines in 2005 on the basis of morphological characters. Coronaridine, an iboga-type indole alkaloid, has been isolated from over 50 Tabernaemontana species and can thus be inferred as a chemotaxonomic marker of the genus. T. ternifolia has a distinct arrangement of leaves not known in the genus, but is variable in other genera. Its isolation from endemic T. ternifolia establishes its position in the genus and supports the claim that coronaridine is a chemical marker of the genus Tabernaemontana. Interestingly, coronaridine exhibited relatively weak activity against Mycobacterium tuberculosis H₃₇Rv (MIC 82.64 μg/mL) (Rifampicin MIC 0.05 μg/mL).

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Research Organization:: Pacific Northwest National Lab. (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER)

Grant/Contract Number:: AC05-76RL01830

OSTI ID:: 1642384

Report Number(s):: PNNL-SA-139640

Journal Information:: Natural Product Research, Vol. 34, Issue 8; ISSN 1478-6419

Publisher:: Taylor & FrancisCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 6 works

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Contortamide, a new anti-colon cancer cerebroside and other constituents from Tabernaemontana contorta Stapf (Apocynaceae) Ebede, Guy R.; Ndongo, Joseph T.; Mbing, Joséphine N. Taylor & Francis https://doi.org/10.6084/m9.figshare.8791325	text	January 2019
Contortamide, a new anti-colon cancer cerebroside and other constituents from Tabernaemontana contorta Stapf (Apocynaceae) Ebede, Guy R.; Ndongo, Joseph T.; Mbing, Joséphine N. Taylor & Francis https://doi.org/10.6084/m9.figshare.8791325.v1	text	January 2019
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Related Subjects

59 BASIC BIOLOGICAL SCIENCES
NMR
alkaloid
plants
endemic
Tabernaemontana ternifolia
Apocynaceae
coronaridine
syringaldehyde
Mycobacterium tuberculosis