Isolation and Structure Determination of Compounds from Stachys yemenensis Hedge

Abstract

In spite of several studies of Stachys species, the literature lacks any information about the constituents of S. yemenensis Hedge. We report here the isolation of a new sesquiterpenetriol, stachytriol (1), along with the known compounds β-sitosterol (2), ursolic acid (3), penduletin (4), and benghalensin B (5). The structure elucidation of all isolated compounds was performed by extensive 1D and 2D NMR spectroscopic investigation.

Sesquiterpenes From Oplopanax elatus Stems and Their Anti-Photoaging Effects by Down-Regulating Matrix Metalloproteinase-1 Expression via Anti-Inflammation

“…Combining the proton and proton correlations and the long-range cross-peaks from H 2 -3, H-4, H 2 -6, H 2 -9, C-1; H-5 to C-1, C-2, C-10; H 2 -8 to C-10; H 3 -12 to C-7, C-11, C-13; H 3 -13 to C-7, C-11, C-12; H 3 -14 to C-1, C-9, C-10 ( Figure 3 ), the planar structure of compound 8 was clarified, which was a guaiane type sesquiterpene. The chemical shifts of C-6–10 ( Table 2 ) were consistent with those of stachytriol ( 19 ) ( Soliman et al, 2007 ), which indicated that the configurations at C-1, 5, 7, 10 of them were identical. The main difference between 8 and 19 was that C-2 in the former was substituted by the hydroxyl.…”

“…19 sesquiterpenes, including nine new ones, named as eurylosesquiterpenosides A–D ( 1 – 4 ), eurylosesquiterpenols E – I ( 5 – 9 ) ( Figure 1 ), and ten known ones, oplodiol ( 10 ) ( Ono et al, 2008 ), 1( R ),4 β -dihydroxy -trans -eudesm-7-ene-1- O -β- d -glucopyranoside (11) ( Lee et al, 2010 ), massonside B ( 12 ) ( Xiao et al, 2016 ), massonside A ( 13 ) ( Xiao et al, 2016 ), (1 R ,4 S ,10 R )10,11-dimethyl-dicyclohex-5(6)-en-1,4-diol-7-one ( 14 ) ( Elmasri et al, 2016 ), cadinane-4 β ,5 α ,10 β -triol ( 15 ) ( Kuo et al, 2003 ; Fang et al, 2006 ), 7- epi -11-hydroxychabrolidione A ( 16 ) ( Pereira et al, 2012 ), (—)-4 α ,7 β -aromaden-dranediol ( 17 ) ( Beechan et al, 1978 ), aromadendrane-4 α ,10 α -diol ( 18 ) ( Moreira et al, 2003 ), stachytriol ( 19 ) ( Soliman et al, 2007 ) ( Figure 2 ) were isolated from the stems of O. elatus . The structures of them were identified by the comprehensive application of UV, IR, NMR, ( α ) D , MS, as well as electronic circular dichroism (ECD) spectra.…”

Table9.XLS

“…19 sesquiterpenes, including nine new ones, named as eurylosesquiterpenosides A-D (1-4), eurylosesquiterpenols E-I (5-9) (Figure 1), and ten known ones, oplodiol (10) (Ono et al, 2008), 1(R),4β-dihydroxy-trans-eudesm-7-ene-1-O-β-D-glucopyranoside (11) (Lee et al, 2010), massonside B (12) (Xiao et al, 2016), massonside A (13) (Xiao et al, 2016), (1R,4S,10R)10,11-dimethyl-dicyclohex-5(6)-en-1,4-diol-7-one ( 14) (Elmasri et al, 2016), cadinane-4β,5α,10β-triol (15) (Kuo et al, 2003;Fang et al, 2006), 7-epi-11-hydroxychabrolidione A ( 16) (Pereira et al, 2012), (-)-4α,7β-aromaden-dranediol (17) (Beechan et al, 1978), aromadendrane-4α,10α-diol (18) (Moreira et al, 2003), stachytriol (19) (Soliman et al, 2007) (Figure 2) were isolated from the stems of O. elatus. The structures of them were identified by the comprehensive application of UV, IR, NMR, (α) D , MS, as well as electronic circular dichroism (ECD) spectra.…”