Glutinane triterpenes from the stem bark of Euonymus hamiltonianus

Abstract

Plants of the Celastraceae family comprise 60 genera and 850 species worldwide [1]. Many of them have been used in traditional medicine [2, 3]. The genus Euonymus of the family Celastraceae is reported to be a rich source of sesquiterpene alkaloids [4], sesquiterpene esters [5], sesquiterpene pyridine alkaloids [6], sesquiterpene polyol esters [7], flavonoids, and coumarins [8]. The plant species belonging to this genus has well-known medicinal activity such as cytotoxic [9], antitumor [10], immunosuppressive [11], and insecticidal [12] and insect-antifeedant activity [13], and is capable of reversing multidrug resistance in cancer cells [14]. Euonymus hamiltonianus Wall. is a small tree growing wild in Kashmir at altitudes from 3000-4000 meters. By continuing the pursuit of active principles of the Celastraceae family, particularly of the genus Euonymus, the ethyl acetate extract of the stem bark of Euonymus hamiltonianus leads to the isolation and characterization of the three new glutinane-type triterpenes 19α-glutin-5-en-19-ol (1), 2β,15α,21β-glutin-11-ene-2,15,21-triol (2), and 2β,19α-glutin-7,21-diene-2,19-diol (3). In this paper the isolation and characterization of compounds 1-3 are presented.Column chromatography of the ethyl acetate extract of the stem bark of Euonymus hamiltonianus leads to the isolation and characterization of three new pentacyclic glutinane-type triterpenes, 19α-glutin-5-en-19-ol (1), 2β,15α,21β, glutin-11-ene-2,15,21-triol (2), and 2β,19α-glutin-7,21-diene-2,19-diol (3).

Bioactive Usual and Unusual Triterpenoids Derived from Natural Sources Used in Traditional Medicine

“…The glutinanes triterpenoids were reported in the terrestrial plants of the family Loranthaceae, Meliaceae, Asteraceae, Celastraceace, Betulaceae, and Rosaceae. The glutinanes, such as 19 α ‐glutin‐5‐en‐19‐ol, 2 β , 15 α ,21 β ‐glutin‐11‐ene‐2,15,21‐triol, and 2 β ,19 α ‐glutin‐7,21‐diene‐2,19‐diol were reported from Euonymus hamiltonianus Wall [101] …”

“…Medical experts and researchers have drawn attention to compound 100 because of its wide range of pharmacological activity, including anti-inflammatory, antiviral, antidiabetes, anticancer, and treating Chagas disease without causing significant toxicity. [79] One of the most popular lupane triterpenes is lupeol (101). Compound 101 can be discovered in several foods and botanical remedies, including grapes, birch bark, olive oil, white cabbage, mangoes, strawberries, and green pepper.…”

“…The glutinanes, such as 19α-glutin-5-en-19-ol, 2β, 15α,21β-glutin-11-ene-2,15,21-triol, and 2β,19α-glutin-7,21-diene-2,19-diol were reported from Euonymus hamiltonianus Wall. [101] The Rhaphiolepis indica var. tashiroi (Rosaceae) roots were isolated 3β,5β-dihydroxyglutinol, glutinol, and 5(6)-gluten-3α-ol, which had a lower inhibitory effect on superoxide formation generated by human neutrophils N-formyl-methionyl-leucyl-phenylalanine.…”

Neuroprotective Effects of Chemical Constituents of Leaves of Euonymus hamiltonianus Wall.

“…Previous studies have shown some of its phytochemicals by identifying novel coumarins in this indigenous plant, but these phytochemicals did not perform any related bioactivity [ 16 ]. Furthermore, to date, only three triterpenoids, six sesquiterpenoids, two flavonoids, and two coumarins have been identified in this plant species, and further in-depth phytochemical investigation of E. hamiltonianus is still needed [ 17 , 18 , 19 , 20 ].…”