Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata

You Sheng Cai, Ariel M. Sarotti, Ting Lan Zhou, Rong Huang, Guofu Qiu, Congkui Tian, Ze Hong Miao, Attila Mándi, T. Kurtán, Shugeng Cao, Sheng Ping Yang

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Four new monoterpenoid bisindole alkaloids, flabellipparicine (1), 19,20-dihydrovobparicine (2), 10′-demethoxy-19,20-dihydrovobatensine D (3), and 3′-(2-oxopropyl)ervahanine A (4), and 10 known monoterpenoid indole alkaloids were isolated from the stems of Tabernaemontana divaricata. All structures were elucidated based on spectroscopic methods, and the absolute configuration of 1 was established using conformational analysis and TDDFT-ECD calculation of selected stereoisomers. Compound 1 represents the first flabelliformide-apparicine-type bisindole alkaloid, in which the flabelliformide-like unit connects to the apparicine-like unit with a C-3-C-22′ bond and an N-1-C-16′ bond to form an uncommon five-membered ring between the two monomers. All alkaloids were evaluated for their cytotoxicity against two human cancer cell lines, MCF-7 and A-549. Compounds 2, 4, and 14 exhibited cytotoxicity against MCF-7 and A-549 with IC50 values in the range of 2 nM to 8 μM.

Original languageEnglish
JournalJournal of Natural Products
DOIs
Publication statusAccepted/In press - Jan 1 2018

Fingerprint

Tabernaemontana
Alkaloids
Cytotoxicity
Secologanin Tryptamine Alkaloids
Monoterpenes
Stereoisomerism
Inhibitory Concentration 50
Monomers
Cells
Cell Line
pericalline
Neoplasms

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata. / Cai, You Sheng; Sarotti, Ariel M.; Zhou, Ting Lan; Huang, Rong; Qiu, Guofu; Tian, Congkui; Miao, Ze Hong; Mándi, Attila; Kurtán, T.; Cao, Shugeng; Yang, Sheng Ping.

In: Journal of Natural Products, 01.01.2018.

Research output: Contribution to journalArticle

Cai, You Sheng ; Sarotti, Ariel M. ; Zhou, Ting Lan ; Huang, Rong ; Qiu, Guofu ; Tian, Congkui ; Miao, Ze Hong ; Mándi, Attila ; Kurtán, T. ; Cao, Shugeng ; Yang, Sheng Ping. / Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata. In: Journal of Natural Products. 2018.
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