Chemical Constituents from Andrographis echioides and Their Anti-Inflammatory Activity

Abstract

Phytochemical investigation of the whole plants of Andrographis echioides afforded two new 2′-oxygenated flavonoids (1) and (2), two new phenyl glycosides (3) and (4), along with 37 known structures. The structures of new compounds were elucidated by spectral analysis and chemical transformation studies. Among the isolated compounds, (1–2) and (6–19) were subjected into the examination for their iNOS inhibitory bioactivity. The structure-activity relationships of the flavonoids for their inhibition of NO production were also discussed.

The Constituents of the Stems of Cissus assamica and Their Bioactivities

“…The crude extract was suspended in water and then partitioned with chloroform and n -butanol successively to afford chloroform, n -butanol, and water layers, respectively. Purification of the three layers by column chromatography yielded a mixture of β-sitosterol ( 1 ) and stigmasterol ( 2 ) [27], β-sitosteryl glucoside ( 3 ) [28], a mixture of 3β-hydroxyl stigmast-5-en-7-one ( 4 ) and 3β-hydroxystigmast-5, 22-dien-7-one ( 5 ) [29], a mixture of β-sitostenone ( 6 ) [30] and stigmasta-4,22-dien-3-one ( 7 ) [31], 6β-hydroxy-β-sitostenone ( 8 ) [32], ergosterol peroxide ( 9 ) [33], 3,5,7,4′-tetramethoxyflavone ( 10 ) [34], 3′,4′,3,6,7-pentamethoxyflavone ( 11 ) [35], 3′,4′,5,6,7-pentamethoxyflavone ( 12 ) [35], 4′,5,6,7-tetramethoxy-flavone ( 13 ) [36], a mixture of oleanolic acid ( 14 ) [30] and ursolic acid ( 15 ) [28], betulinic acid ( 16 ) [37], friedelin ( 17 ) [38], epi -glut-5(6)-en-ol ( 18 ) [39], taraxerol ( 19 ) [9], epi -friedelinol ( 20 ) [40], glutinone ( 21 ) [41], lup-28-al-20(29)-en-3-ol ( 22 ) [42], a mixture of α-amyrin ( 23 ) and β-amyrin ( 24 ) [43], bergenin ( 25 ) [44], p -hydroxybenzaldehyde ( 26 ) [45], vanillin ( 27 ) [30], methyl gallate ( 28 ) [46], gallic acid ( 29 ) [47], 4-methoxybenzoic acid ( 30 ) [48], vanillic acid ( 31 ) [30], a mixture of 4-hydroxy- trans -cinnamic acid methyl ester ( 32 ) and 4-hydroxy- cis -cinnamic acid methyl ester ( 33 ) [49], a mixture of octadecyl- trans -ferulate ( 34 ) and octadecyl- cis -ferulate ( 35 ) [50], 1-(4-methoxy-phenyl)undecan-1-one ( 36 ) [51], 3-hydroxy-4-methoxybenzoic acid ( 37 ) [52], hexadecyl ferulate ( 38 ) [45], 2-hydroxybenzoquinone ( 39 ) [53], 2,6-dimethyoxybenzoquinone ( 40 ) [49], 3,3′,4-tri- O -methyl-ellagic acid ( 41 ) [54], 3,3′,4,4′-tetra- O -methylellagic acid ( 42 ) [55], methyl pheophorbide-a ( 43 ) [49], a mixture of methyl-21-hydroxy-(21 S )-pheophorbide-a ( 44 ) and methyl-21-hydroxy-(21 R )-pheophorbide-a ( 45 ) […”

A Review on the Phytochemistry, Medicinal Properties and Pharmacological Activities of 15 Selected Myanmar Medicinal Plants

“…From the whole plant of A. echioides , Jayaprakasam’s group characterized flavanone- dihydroechioidinin ( 82 ) (Figure 8) [55], flavones—echioidinin ( 83 ) [56], echioidin ( 84 ), skullcapflavone I 2′- O -methyl ether ( 85 )—flavone glucosides—skullcapflavone I 2′- O -glucoside ( 86 ) [57,58], and echioidinin 5- O -β- d -glucoside ( 87 ) [59] and a chalcone glucoside, androechin ( 88 ). 2′-Oxygenated flavonoids and phenyl glycosides from the whole plant of A. echioides include androgechosides A–B ( 89 , 90 ), androechiosides A–B ( 91 , 92 ) together with 2′,6′-dihydroxy-acetophenone 2′- O -β- d -glucopyranoside ( 93 ), pinostrobin ( 94 ), andrographidine C ( 95 ), dihydroechioidinin, tectochrysin 5-glucoside ( 96 ), methyl salicylate glucoside, 7,8-dimethoxy-5-hydroxyflavone ( 97 ), 5,7,8-trimethoxyflavone ( 98 ), skullcapflavone I 2′-methyl ether, acetophenone-2- O -β- d -glucopyranoside, androechin, skullcapflavone I 2′- O -β- d -glucopyranoside, tectochrysin ( 99 ), negletein 6- O -β- d -glucopyranoside, andrographidine E, 4-hydroxy-3-methoxy- trans -cinnamic acid methyl ester, 4-hydroxybenzaldehyde, 4-hydroxy- trans -cinnamic acid methyl ester, O -coumaric acid, 2,6-dihydrobenzoic acid, 132-hydroxy-(132- R )-phaeophytin, ( E )-phytyl epoxide, phytol, phytene 1,2-diol, (+)-dehydrovomifoliol, 3β-hydroxy-5α,6α-epoxy-7-megastigmen-9-one, β-sitosterol, β-sitosteryl-3- O -β-glucopyranoside, squalene, 1 H -indole-3-carbaldehyde, and loliolide were reported by Shen’s group [58]. Moreover, a variety of chemical compounds isolated from the petroleum ether, ethyl acetate and methanol extracts of A. echioides were analysed by GC-MS [60].…”

“…A flavanone, dihydroechioidinin ( 82 ), and 5,7,8-trimethoxyflavone ( 98 ) isolated from A. echioides are reported to possess potent anti-inflammatory activity, with IC 50 values of 37.6 ± 1.2 μM and 39.1 ± 1.3 μM, respectively, and to suppress NO inhibition activity [58].…”

Phyto mediated biogenic synthesis of silver nanoparticles using leaf extract of Andrographis echioides and its bio-efficacy on anticancer and antibacterial activities

“…They are 1. Androgechoside A, Androgechoside B, Androechioside A and Androechioside B [5]. Hence the present study aims to cost-effective, environment friendly AgNPs using aqueous leaf extract of A. echioides and to explore its anticancer and antibacterial potential.…”