Two New Sesquiterpene Lactones fromMontanoa tomentosassp.microcephala

Abstract

Two new sesquiterpene lactones: 8alpha-(4'-acetoxymethacryloyloxy)-3alpha,9beta-dihydroxy-1(10)E,4Z,11(13)-germacratrien-12,6alpha-olide (1) and 8alpha-(2'E)-(2'-acetoxymethyl-2'-butenoyloxy)-3alpha,9beta-dihydroxy-1(10)E,4Z,11(13)-germacratrien-12,6alphaolide (2), together with the known zoapatanolide A were isolated from the aerial parts of Montanoa tomentosa Cerv. in La Llave et Lex ssp. microcephala (Sch. Bip. In K. Koch) V.A. Funk (Asteraceae). The structures of all compounds were established on the basis of 1D, 2D NMR, and EIMS analysis.

Antibacterial Activity and Reversal of Multidrug Resistance of Tumor Cells by Essential Oils from Fresh Leaves, Flowers, and Stems of Montanoa quadrangularis Schultz Bipontinus (Asteraceae) Collected in Mérida—Venezuela

“…Previous investigations carried out with the essential oil of M. quadrangularis collected from a different location in Mérida at 1800 m.a.s.l showed limonene (18.83%), sabinene (11.63%), α-pinene (9.90%), and α-tujene (9.27%) as main components from the essential oil of the flowers while the essential oil of the leaves was composed mainly by limonene (18.01%), trans-caryophyllene (16.07%), germacrene-D (7.63%), and mircene (6.37%). [15] Additionally, the essential oil of the inforescence of Montanoa grandiflora revealed β-phellandrene (6.63%) and α-pinene (2.70%) as major compounds. The essential oil of the stems showed β-phellandrene (7.74%), limonene (4.80%), α-pinene (4.43%), and citronellal (3.50%), while the leaves showed α-pinene (4.27%), β-phellandrene (4.22%), limonene (2.37%), and citronellal (2.82%) as main components [24].…”

“…Previous phytochemical investigations have reported sesquiterpene lactones such as eudesmanolides and germacrolides as major class of chemical compounds present in Montanoa species [9,15,16]. However, flavonoids such as luteolin and apigenin have also been isolated [9].…”

<em>Montanoa tomentosa</em>. A review of the new scientific evidence on pharmacological properties

“…The ground uproots, mixed with lukewarm water, is used in the treatment of dysentery. 2,3 The volatile constituents of the aerial parts (leaves and flowers) of this medicinal plant were analyzed by SPME-GC-MS. 3 The major constituents of the volatile fraction were monoterpenes, such sabinene, α-pinene and α-thujene, which accounted for 65% of the total fraction. [4][5][6][7] Other identified compounds were sesquiterpenes, like α-gurjunene, caryophyllene and germacrene D, but in minor amount.…”

“…The characterization of volatile from M. tomentosa was established in that study for the first time, therefore their utility in different aspects opens an interesting area to carry out further investigation of the plant. 3,4 In a recent study, the pro-sexual effect of the aqueous crude extracts from M. tomentosa (cihuapatli) and its possible proejaculatory properties in spinal male rats were examined. 14 Systemic administration of the aqueous crude extracts of Montanoa tomentosa exerted a pro-ejaculatory effect and produced an increase in the number of discharges in the ejaculatory motor patterns in the spinal rats.…”

Biosynthesis of uterotonic diterpenes from Montanoa tomentosa (zoapatle)

“…Recently, aphrodisiac effects were reported in male rats (Carro-Juárez et al, 2006). At least 20 different active compounds have been isolated from zoapatle (Braca et al, 2001) including the three tetracyclic diterpenes KA ([4a]-kaur-6-en-18-oic acid), GF ([4a]-kaura-9 [11]-16-dien-18-oic acid), and MO (13-methyl-[4a]-norkaur-15-en-18-oic acid) (Enriquez et al, 1997). These three compounds have shown uterotonic (CamposBedolla et al, 1997), anti-inflammatory (Paiva et al, 2002), anti-spasmodic (Tirapelli et al, 2005), and anti-cancer effects (Cavalcanti et al, 2006) in mammals.…”