Dendocarbin A: a sesquiterpene lactone fromDrimys winteri

Abstract

The natural compound dendocarbin A, C15H22O3, is a sesquiterpene lactone isolated for the first time from Drimys winteri for var chilensis. The compound crystallizes in the orthorhombic space group P2₁2₁2₁ and its X-ray crystal structure confirmed the S/R character of the chiral centres at C-5/C-10 and C-9/C-11, respectively. The α-OH group at C-11 was found to be involved in intermolecular hydrogen bonding, defining chains along the <100> 2₁ screw axis.

A monoclinic form of dendocarbin A: a borderline case of one-dimensional isostructural polymorphism

“…The rigid backbone of (II) is composed of three fused rings (see Scheme and Fig. 1) and fully matches its counterpart (I) (Paz Robles et al, 2014). Fig.…”

“…Dendrocarbin A was extracted from 1 kg of powdered Drimys winteri (collected at Concepcion, VIII Region, Chile, in February 2012) by maceration in ethanol for 3 d to yield a crude solid (20 g) which was purified by column chromatography and recrystallized from methanol. The previously reported orthorhombic phase, (I) (Paz Robles et al, 2014), was grown at $298 K, while the present monoclinic phase, (II), was obtained at $277 K.…”

“…= 0.00 for an ideal chair conformation (Boeyens, 1978)], the central B ring (atoms C5-C10) displays a half-chair conformation [ = 51.6 (3) and ' = 310.8 (4) = 5  60 + 10.8 ; = 50.8 and ' = k  60 + 30 for an ideal half-chair conformation (Boeyens, 1978)] and fivemembered lactone ring C (atoms C8/C9/C11/C12/O3) displays an envelope conformation [' = 62.9 (8) = 2  36 À 9.1 ; ' = k  36 + 0 for an ideal envelope conformation (Cremer & Pople, 1975)], the carbonyl group at atom C12 being conjugated with the 'outer' C7 C8 double bond. A full comparison of (I) was discussed previously (Paz Robles et al, 2014), and also applies to (II), with three related literature compounds, A view of the molecule of (I), with displacement ellipsoids drawn at the 30% probability level.…”

“…As part of a series of structural characterizations of naturally occurring molecules isolated from southern Andean flora, we have recently reported the crystal structure of dendrocarbin A in the orthorhombic phase (Paz Robles et al, 2014), (I), which was isolated for the first time from Drimys winteri var chilensis (Winteraceae). We present herein the monoclinic phase of dendrocarbin A, (II), from the same botanical origin.…”

Avaliação da atividade antiproliferativa de extratos hidroalcoólicos de plantas em linhagens celulares humanas de câncer de mama, fígado e próstata

“…No Brasil é comum na região Nordeste, onde é conhecida como "ciúme", "ciumeira" ou "flor de seda" (JOLY, 1979 ALENCAR 2017;IBRAHIM et al, 2014;JOSHI et al, 2015;KWON et al, 2018;SAMY et al, 2012 GROOT, 2004;MENDES et al, 1998;2000). Um estudo feito em salmões demonstrou um potencial imunoestimulador, onde o extrato de casca de anta estimulou o sistema imunológico de salmões afetados por parasitas a produzirem mais células imunes e atacarem seus invasores (PAZ ROBLES et al, 2014;PEREIRA-TORRES et al, 2016). OJEWOLE, 2009;LEBOEUF et al, 1980;YAJID et al, 2018;ZOROFCHIAN MOGHADAMTOUSI et al, 2014).…”