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Anti‐TB polyynes from the roots of Angelica sinensis
Author(s) -
Deng Shixin,
Wang Yuehong,
Inui Taichi,
Chen Shaog,
Farnsworth Norman R.,
Cho Sanghyun,
Franzblau Scott G.,
Pauli Guido F.
Publication year - 2008
Publication title -
phytotherapy research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.019
H-Index - 129
eISSN - 1099-1573
pISSN - 0951-418X
DOI - 10.1002/ptr.2303
Subject(s) - phytochemical , angelica sinensis , vero cell , stereochemistry , chemistry , in vitro , traditional medicine , cytotoxicity , biochemistry , medicine , alternative medicine , pathology , traditional chinese medicine
Following chemotaxonomic evidence, the PE and CHCl 3 extracts of the roots of the botanical Angelica sinensis (Oliv.) Diels (Dang Gui) were investigated for in vitro anti‐TB activity, in parallel to studying their serotonergic and GABAergic potential. The activities were confirmed to overlap chemically with the neurotropic active principles present in medium lipophilic fractions. Phytochemical investigations led to the isolation of five polyynes: falcarindiol (1), 9Z ,17‐octadecadiene‐12,14‐diyne‐1,11,16‐triol,1‐acetate (2), oplopandiol (3), heptadeca‐1‐ene‐9,10‐epoxy‐4,6‐diyne‐3,8‐diol (4) and the new polyyne 8‐hydroxy‐1‐methoxy‐( Z )‐9‐heptadecene‐4,6‐diyn‐3‐one (5), as characterized by spectroscopic techniques including 1D, 2D NMR and HR‐MS. All compounds were tested against two pathogenic strains of Mycobacterium tuberculosis (H37R v and Erdman) in vitro in a microplate Alamar Blue assay (MABA). The most potent anti‐TB constituents were 1 and 2, exhibiting MIC values of 1.4–26.7 µg/mL; 3 showed moderate MICs (49.5 and 50.2 µg/mL, respectively) while 4 and 5 were weakly active (MIC > 60 µg/mL). Notably, none of the five compounds exhibited significant cytotoxicity against Vero cells. These findings not only reveal a new potential area of therapeutic value for A. sinensis , but also underline the role of polyynes as anti‐TB active principles in ethnobotanical preparations, and as lead compounds. Copyright © 2008 John Wiley & Sons, Ltd.