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Molecules 2017, 22(1), 118; doi:10.3390/molecules22010118

A Cytotoxic and Anti-inflammatory Campesterol Derivative from Genetically Transformed Hairy Roots of Lopezia racemosa Cav. (Onagraceae)

1
Centro Investigación en Biotecnología, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001 Col, Chamilpa C.P. 62209, Cuernavaca, Morelos, Mexico
2
Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001 Col, Chamilpa C.P. 62209, Cuernavaca, Morelos, Mexico
3
Centro de Investigación Biomédica del Sur (IMSS), Argentina No. 1, Xochitepec Centro C.P. 62790, Morelos, Mexico
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 12 November 2016 / Revised: 3 January 2017 / Accepted: 5 January 2017 / Published: 12 January 2017
(This article belongs to the Section Natural Products)
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Abstract

The genetically transformed hairy root line LRT 7.31 obtained by infecting leaf explants of Lopezia racemosa Cav with the Agrobacterium rhizogenes strain ATCC15834/pTDT, was evaluated to identify the anti-inflammatory and cytotoxic compounds reported previously for the wild plant. After several subcultures of the LRT 7.31 line, the bio-guided fractionation of the dichloromethane–methanol (1:1) extract obtained from dry biomass afforded a fraction that showed important in vivo anti-inflammatory, and in vitro cytotoxic activities. Chemical separation of the active fraction allowed us to identify the triterpenes ursolic (1) and oleanolic (2) acids, and (23R)-2α,3β,23,28-tetrahydroxy-14,15-dehydrocampesterol (3) as the anti-inflammatory principles of the active fraction. A new molecule 3 was characterized by spectroscopic analysis of its tetraacetate derivative 3a. This compound was not described in previous reports of callus cultures, in vitro germinated seedlings and wild plant extracts of whole L. racemosa plants. The anti-inflammatory and cytotoxic activities displayed by the fraction are associated to the presence of compounds 13. The present study reports the obtaining of the transformed hairy roots, the bioguided isolation of the new molecule 3, and its structure characterization. View Full-Text
Keywords: genetic transformation; Lopezia racemosa; Agrobacterium rhizogenes; hairy roots; cytotoxic; anti-inflammatory genetic transformation; Lopezia racemosa; Agrobacterium rhizogenes; hairy roots; cytotoxic; anti-inflammatory
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Moreno-Anzúrez, N.E.; Marquina, S.; Alvarez, L.; Zamilpa, A.; Castillo-España, P.; Perea-Arango, I.; Torres, P.N.; Herrera-Ruiz, M.; Díaz García, E.R.; García, J.T.; Arellano-García, J. A Cytotoxic and Anti-inflammatory Campesterol Derivative from Genetically Transformed Hairy Roots of Lopezia racemosa Cav. (Onagraceae). Molecules 2017, 22, 118.

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