Dolichocarpols A-F, Unprecedented Macrocyclic Humulene-Type Sesquiterpenoids from Anaxagorea dolichocarpa

Kaio Aragão Sales; Anderson Angel Vieira Pinheiro; Diego Igor Alves Fernandes de Araújo; Lucas Silva Abreu; Rodrigo Silva de Andrade; Maria de Fátima Agra; Marianna Vieira Sobral; Rafael Carlos Ferreira; Raimundo Braz-Filho; Marcus Tullius Scotti; Josean Fechine Tavares; Marcelo Sobral da Silva

doi:10.1021/acsomega.0c00690

Dolichocarpols A-F, Unprecedented Macrocyclic Humulene-Type Sesquiterpenoids from Anaxagorea dolichocarpa

ACS Omega. 2020 Jun 2;5(23):13656-13663. doi: 10.1021/acsomega.0c00690. eCollection 2020 Jun 16.

Affiliations

¹ Postgraduate Program in Natural and Synthetic Bioactive Products, Federal University of Paraíba, João Pessoa, 58051-900 Brazil.
² Biotechnology Department, Federal University of Paraíba, João Pessoa, 58051-900 Brazil.
³ Department of Chemistry, Institute of Chemistry, Federal Rural University of Rio de Janeiro, Seropédica, 23897-000 Brazil.

Abstract

Six sesquiterpenoids with unprecedented macrocyclic humulene-type structures, namely, dolichocarpols A-E (1-5) with ether-bridged bicyclic rings between C-10 and C-2, C-10 and C-7, C-10 and C-6 (×2), and C-6 and C-3 and dolichocarpol F (6) cyclized between C-7 and C-2 and with an ether bridge between C-10 and C-3, were isolated from Anaxagorea dolichocarpa roots. The structures of the compounds were elucidated by NMR, MS, and IR data. Absolute configurations of compounds 1-3 and 6 were established on the basis of data from electronic circular dichroism, whereas relative configurations of compounds 4 and 5 were suggested by the NOESY spectrum. In addition, a putative biosynthetic pathway of the compounds is proposed. Furthermore, the cytotoxicity of 3, 4, and 6 against HCT-116 (human colorectal carcinoma) and L929 (murine fibroblast) was evaluated.