Carapanolides C-I from the seeds of andiroba (Carapa guianensis, Meliaceae) - PubMed (original) (raw)
Carapanolides C-I from the seeds of andiroba (Carapa guianensis, Meliaceae)
Takanobu Inoue et al. Fitoterapia. 2014 Jul.
Abstract
Five new mexicanolide-type limonoids, carapanolides C-G (1-5), together with two new phragmalin-type limonoids, carapanolides H-I (6, 7), were isolated from the oil of Carapa guianasis AUBLET (Meliaceae) seeds. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR spectra and FABMS. Carapanolides C (1), E (3), and I (7) exhibited moderate activity in the P388 (IC50 17.9 μM in 1, 15.8 μM in 3) and L1210 cell lines (IC50 13.3 μM in 1, 18.1 μM in 3, 16.9 μM in 7). On the other hand, Carapanolide D (2) exhibited a strong inhibitory effect in the HL-60 cell line (IC50 11.0 μM), Carapanolides F (4) showed inhibitory activity in the L1210 cell line (IC50 15.9 μM), and the cytotoxic activity of Carapanolides I (7) was moderate in all cell lines.
Keywords: Carapa guianensis; Carapanolides C–I; Limonoid; Meliaceae; Seed.
Copyright © 2014 Elsevier B.V. All rights reserved.
Similar articles
- Carapanosins A-C from Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production.
Higuchi K, Miyake T, Ohmori S, Tani Y, Minoura K, Kikuchi T, Yamada T, Tanaka R. Higuchi K, et al. Molecules. 2017 Mar 22;22(3):502. doi: 10.3390/molecules22030502. Molecules. 2017. PMID: 28327530 Free PMC article. - Carapanolides T-X from Carapa guianensis (Andiroba) Seeds.
Miyake T, Ishimoto S, Ishimatsu N, Higuchi K, Minoura K, Kikuchi T, Yamada T, Muraoka O, Tanaka R. Miyake T, et al. Molecules. 2015 Nov 24;20(11):20955-66. doi: 10.3390/molecules201119737. Molecules. 2015. PMID: 26610460 Free PMC article. - Andirolides Q-V from the flower of andiroba (Carapa guianensis, Meliaceae).
Sakamoto A, Tanaka Y, Inoue T, Kikuchi T, Kajimoto T, Muraoka O, Yamada T, Tanaka R. Sakamoto A, et al. Fitoterapia. 2013 Oct;90:20-9. doi: 10.1016/j.fitote.2013.07.001. Epub 2013 Jul 10. Fitoterapia. 2013. PMID: 23850542 - The therapeutic properties of Carapa guianensis.
Henriques Md, Penido C. Henriques Md, et al. Curr Pharm Des. 2014;20(6):850-6. doi: 10.2174/13816128113199990048. Curr Pharm Des. 2014. PMID: 23701562 Review. - Effects of andiroba oil (Carapa guianensis aublet) on the immune system in inflammation and wound healing: A scoping review.
Fonseca ASAD, Monteiro IS, Dos Santos CR, Carneiro MLB, Morais SS, Araújo PL, Santana TF, Joanitti GA. Fonseca ASAD, et al. J Ethnopharmacol. 2024 Jun 12;327:118004. doi: 10.1016/j.jep.2024.118004. Epub 2024 Mar 1. J Ethnopharmacol. 2024. PMID: 38432579 Review.
Cited by
- Bioactive limonoids from Carapa guianensis seeds oil and the sustainable use of its by-products.
Pereira da Silva V, de Carvalho Brito L, Mesquita Marques A, da Cunha Camillo F, Raquel Figueiredo M. Pereira da Silva V, et al. Curr Res Toxicol. 2023 Mar 20;4:100104. doi: 10.1016/j.crtox.2023.100104. eCollection 2023. Curr Res Toxicol. 2023. PMID: 37020602 Free PMC article. - A Gedunin-Type Limonoid, 7-Deacetoxy-7-Oxogedunin, from Andiroba (Carapa guianensis Aublet) Reduced Intracellular Triglyceride Content and Enhanced Autophagy in HepG2 Cells.
Nagatomo A, Ninomiya K, Marumoto S, Sakai C, Watanabe S, Ishikawa W, Manse Y, Kikuchi T, Yamada T, Tanaka R, Muraoka O, Morikawa T. Nagatomo A, et al. Int J Mol Sci. 2022 Oct 28;23(21):13141. doi: 10.3390/ijms232113141. Int J Mol Sci. 2022. PMID: 36361930 Free PMC article. - Carapa guianensis Aublet (Andiroba) Seed Oil: Chemical Composition and Antileishmanial Activity of Limonoid-Rich Fractions.
Oliveira IDSDS, Moragas Tellis CJ, Chagas MDSDS, Behrens MD, Calabrese KDS, Abreu-Silva AL, Almeida-Souza F. Oliveira IDSDS, et al. Biomed Res Int. 2018 Sep 6;2018:5032816. doi: 10.1155/2018/5032816. eCollection 2018. Biomed Res Int. 2018. PMID: 30258850 Free PMC article. - Carapanosins D-F from the Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production.
Inoue T, Ohmori S, Kikuchi T, Yamada T, Tanaka R. Inoue T, et al. Molecules. 2018 Jul 19;23(7):1778. doi: 10.3390/molecules23071778. Molecules. 2018. PMID: 30029521 Free PMC article. - Carapanosins A-C from Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production.
Higuchi K, Miyake T, Ohmori S, Tani Y, Minoura K, Kikuchi T, Yamada T, Tanaka R. Higuchi K, et al. Molecules. 2017 Mar 22;22(3):502. doi: 10.3390/molecules22030502. Molecules. 2017. PMID: 28327530 Free PMC article.
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources