2. Academic Validation
  3. Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata

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

  • J Nat Prod. 2018 Sep 28;81(9):1976-1983. doi: 10.1021/acs.jnatprod.8b00191.
You-Sheng Cai 1 2,  Ariel M Sarotti 3,  Ting-Lan Zhou 1,  Rong Huang 1,  Guofu Qiu 1,  Congkui Tian 4,  Ze-Hong Miao 5,  Attila Mándi 6,  Tibor Kurtán 6,  Shugeng Cao 2,  Sheng-Ping Yang 1
Affiliations

Affiliations

  • 1 Institute of TCM and Natural Products, School of Pharmaceutical Sciences , Wuhan University , 185 Donghu Road , Wuhan 430071 , People's Republic of China.
  • 2 Department of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy , University of Hawai'i at Hilo , 200 West Kawili Street , Hilo , Hawaii 96720 , United States.
  • 3 Instituto de Química Rosario (CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas , Universidad Nacional de Rosario , Suipacha 531 , Rosario 2000 , Argentina.
  • 4 Wuling Mountain Institute of Natural Medicine, Hubei University for Nationalities, Key Laboratory of Biological Resources Protection and Utilization of Hubei Province , 39 Xueyuan Road , Enshi 445000 , People's Republic of China.
  • 5 State Key Laboratory of Drug Research Institute of Materia Medica, Chinese Academy of Sciences , Zu Chong Zhi Road 555 Zhangjiang Hi-Tech Park , Shanghai 201203 , People's Republic of China.
  • 6 Department of Organic Chemistry , University of Debrecen , POB 400, H-4002 Debrecen , Hungary.
PMID: 30169038 DOI: 10.1021/acs.jnatprod.8b00191
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.

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