LC-ToF-ESI-MS Patterns of Hirsutinolide-like Sesquiterpenoids Present in the Elephantopus mollis Kunth Extract and Chemophenetic Significance of Its Chemical Constituents

Abstract

A total of nine sesquiterpenoid lactones together with phenolic compounds and other terpenes were identified from the crude methanol extract of Elephantopus mollis Kunth. Compounds were isolated using different chromatographic techniques and their structures were determined by NMR and IR spectroscopy as well as mass spectrometry. The structures of some detected compounds were assigned based on LC-ToF-ESI-MS screening of main fractions/subfractions from flash chromatography and comparison with isolated analogues as standards. The findings revealed not only the in-source loss of water as the base peak in hirsutinolides but also the in-source loss of corresponding alcohol when the oxygen at position 1 is alkylated. The present study also draws up a complement of data with respect to hirsutinolide-like sesquiterpene lactones whose LC-MS characteristics are not available in the literature. The chemophenetic significance is also discussed. Some of the isolated compounds were reported for the first time to be found in the species, the genus as well as the plant family. The medium-polar fractions of the crude extract, also containing the larger amount of sesquiterpenoid lactones, exhibited activity both against a cancer cell line and bacterial strains. Isolated lactones were also active against the cancer cell line, while the chlorogenic derivatives also valuable in Elephantopus genus showed potent radical scavenging activity. This is the first report of cytotoxic and antibacterial activities of our samples against the tested strains and cell line. The present study follows the ongoing research project dealing with the characterization of taxa with antibacterial and antiparasitic activities from Cameroonian pharmacopeia.

Elemane‐Type Sesquiterpene, Acetonide Derived Polyacetylene and Other Constituents from the Whole Plant of Gymnanthemum theophrastifolium (Schweinf. ex Oliv. & Hiern) H.Rob. and Their Chemophenetic Significance

“…The seventeen known isolates of G. theophrastifolium were identified by comparison of their spectroscopic data with those reported in the literature for chondrosterin G ( 3 ), [20] 1,2‐ O ‐isopropylidene‐ β ‐D‐fructopyranose ( 4 ), [28] 1,2 : 4,5‐Di‐ O ‐isopropylidene‐ β ‐D‐fructopyranose ( 5 ), [28] glycerol ( 6 ), [29] and 1‐ O ‐hex‐3‐enyl β ‐D‐glucopyranosyl ( 7 ), [30] 1‐ O ‐benzyl β ‐D‐glucopyranoside ( 8 ), [31] pinoresinol ( 9 ), [32] Balanophonin B ( 10 ), [33] syringaresinol ( 11 ), [34] (−)‐glaberide I ( 12 ), [35] 4‐hydroxybenzoic acid ( 13 ), [36] methyl 4‐hydroxybenzoate ( 14 ), [37] apigenin ( 15 ), [38] luteolin ( 16 ), [39] diosmetin ( 17 ), [40] lutein ( 18 ), [41] and β ‐sitosterol‐3‐ O ‐ β ‐D‐glucopyranoside‐6′‐ O ‐palmitate ( 19 ) [38] ( Figure 1).…”

“…[44] Apigenin could be said to be one of the markers of the family since it has been found in almost every plant species of Asteraceae. [38,45] Syringaresinol (11) was isolated from V. lanceolata, while pineresinol (9) was reported from Centaurea aegyptiaca (Asteraceae). [46] Both lignans were also isolated from Carduus assoi (Asteraceae).…”

“…Luteolin ( 16 ) was reported from the crude extract leaves of V. amygdalina and V. cinerea with strong antioxidant activity and anti‐inflammatory effects, [42,43] while apigenin ( 15 ) and diosmetin ( 17 ) were also reported from Chrysanthemum morifolium Ramat [44] . Apigenin could be said to be one of the markers of the family since it has been found in almost every plant species of Asteraceae [38,45] . Syringaresinol ( 11 ) was isolated from V. lanceolata , while pineresinol ( 9 ) was reported from Centaurea aegyptiaca (Asteraceae) [46] .…”

EVALUASI INVITRO AKTIVITAS ANTIOKSIDAN DAN TABIR SURYA DARI EKSTRAK DAUN DAN AKAR TUMBUHAN Elephantopus mollis Kunth

“…Komponen kimia yang terdapat pada daun dan akar dapat diduga memiliki kemiripan yang mengakibatkan aktivitas antioksidan yang diperoleh dari kedua bagian tumbuhan ini menjadi tidak berbeda. Penelusuran pada beberapa penelitian lain diperoleh informasi kandungan senyawa-senyawa kimia yang beberapa diantaranya aktif antioksidan seperti lupeol, lupeol asetat, 2-de-ethoxy-2-hydroxyphantomolin, epifriedelinol, molephantin, dan 2-de-ethoxy-2methoxyphantomolin (Bitchagno et al, 2021).…”

Polyoxygenated Stigmastane-Type Steroids from Vernonia kotschyana Sch. Bip. ex Walp. and Their Chemophenetic Significance

“…Unlike sesquiterpene lactones, which are distributed throughout the genus, stigmastanes instead occur in few species, including V. guineensis and V. amygdalina [ 4 , 5 , 6 , 7 , 8 ]. Sesquiterpene lactones are able to alkylate cysteine-containing enzymes and proteins, inducing apoptosis in malignant cells [ 9 , 10 ]. Sesquiterpene lactones and related enriched extracts have shown significant potential against various cancer cells [ 11 , 12 ].…”