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Open AccessArticle

Simalikalactone D, a Potential Anticancer Compound from Simarouba tulae, an Endemic Plant of Puerto Rico

1
Natural Sciences Program, University of Puerto Rico at Cayey, Cayey 00736, Puerto Rico
2
Department of Biochemistry, University of Puerto Rico, Medical Sciences Campus, San Juan 00936, Puerto Rico
3
Department of Pharmaceutical Sciences, University of Puerto Rico, School of Pharmacy, San Juan 00936, Puerto Rico
4
Department of Biology, University of Puerto Rico, Río Piedras Campus, San Juan 00936, Puerto Rico
5
Department of Chemistry, University of Puerto Rico, Río Piedras Campus, San Juan 00936, Puerto Rico
6
Department of Chemistry and Physics, Universidad Ana G Mendez, Gurabo 00778, Puerto Rico
*
Author to whom correspondence should be addressed.
Plants 2020, 9(1), 93; https://doi.org/10.3390/plants9010093
Received: 24 November 2019 / Revised: 4 January 2020 / Accepted: 6 January 2020 / Published: 11 January 2020
(This article belongs to the Special Issue Bioactive Compounds in Plants)
Species of the genus Simarouba have been studied because of their antimalarial and antileukemic activities. A group of oxygenated terpenes called quassinoids have been isolated from species of the Simarouba genus, and are responsible for its therapeutic properties. We hypothesized that Simarouba tulae, an endemic plant from Puerto Rico, is a natural source rich in quassinoid compounds with anticancer activity. The leaves were processed and extracted with solvents of different polarities. The extracts were screened for their antiproliferative activity, and it was shown that the chloroform extract was the most active extract. This extract was purified using different chromatographic techniques to afford the quassinoid simalikalactone D (SKD). This compound was further characterized using NMR and X-ray diffraction analysis. A reassessment of original structural assignments for SKD is proposed. SKD showed high cytotoxicity activity, with an IC50 of 55, 58, and 65 nM in A2780CP20 (ovarian), MDA-MB-435 (breast), and MDA-MB-231 (breast) cell lines, respectively. Exposure to SKD led to 15% inhibition of the migration of MDA-MB-231 cells. View Full-Text
Keywords: Simarouba tulae; quassinoids; simalikalactone D; breast cancer; ovarian cancer; medicinal plants; migration Simarouba tulae; quassinoids; simalikalactone D; breast cancer; ovarian cancer; medicinal plants; migration
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Mendez, B.; Reyes, J.; Conde, I.; Ramos, Z.; Lozada, E.; Cruz, A.M.; Asencio, G.; Carvajal, A.; Dharmawardhane, S.; Piñero-Cruz, D.M.; Hernández, E.; Vivas, P.; Ospina, C.A. Simalikalactone D, a Potential Anticancer Compound from Simarouba tulae, an Endemic Plant of Puerto Rico. Plants 2020, 9, 93.

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