Chemical Constituents from Fruits and Stem Bark of Celtis australis L.

Abstract

Four triterpenoids named (9b,31R)-9,25-cyclo-30-propylhopan-31-ol (1), (3b)-3-hydroxy-30-propylhopan-31-one (2), (3b)-oleanan-3-ol (3), and (3b,9b)-9,25-cycloolean-12-en-3-yl b-d-glucofuranoside (4), a steroid named (3b,9b,14b)-14-hydroxy-9,19-cyclocholan-3-yl b-d-glucopyranoside (5), and an anthraquinone named 6-hydroxy-5,7,8-trimethoxy-9,10-dioxo-9,10-dihydroanthracen-2-yl acetate (6) have been isolated from the fruits and bark of Celtis australis (Ulmaceae), along with apigenin, quercetin, and its glucoside. Their structures were elucidated by means of chemical and spectral analysis including COSY, NOESY, and HMBC experiments.Introduction. -Celtis australis L. of Ulmaceae is a deciduous tree distributed from montane to submontane Himalaya. The plant has been used as remedy for bone fracture, pimples, contusions, sprains, and joints pain in the traditional Indian medicine [1]. Previous studies on the plants of the genus Celtis led to the isolation of phenolic glycosides [2], steroids [3], terpenoids [4] [5], and tannins, saponins, and alkaloids [6]. From the leaves of C. australis, three phenol derivatives, acacetin 7-O-glucoside, isovitexin, and cytisoside were reported [7]. Recently, we have isolated a novel sulfonated phenolic celtisanin from the fruits [8] and a bacteriohopanoid, (3b)-33-ethyl-3-hydroxy-34-methyl-35-(3-propanoylcyclohex-1-yl)bacteriohopane from the stem bark [9] of this plant. Here, we describe the isolation and structure elucidation of four triterpenoids, 1 -4, one steroid, 5, and one anthraquinone, 6, for the first time from this source.

Triterpenoids

“…296 The unusual 9,25-cyclo-29-propylhopan-31-ol 533 and 3b-hydroxy-29-propylhopan-31-one 534 have been identied in Celestris australis. 176 The same group claim that the cyclohexylhopane derivative 535 is also found in Celestris australis 297 and that the 29-ethylhopane derivative 536 and 32,33,34-trimethylbacteriohopan-3b-yl b-D-glucopyranoside 537 are constituents of Symplocos paniculata. 177 Several N-acylated bacteriohopanehexol mannosamine derivatives 538 have been identi-ed in the thermophilic bacterium Alicyclobacillus acidoterrestris.…”

“…171 6 The oleanane group Several ring-A seco-oleanane triterpenoids have been isolated, including the 2,3-seco-oleanenetrioic acid 406 from Dillenia philippinensis, 172 dysoxyhainic acid F 407, G 408, I 409 and J 410 from Dysoxylum hainanense, 159 the 12-ketone 411 and 13(18)-ene 412 from Betula pendula, 173 the 3-methyl ester 413 from Kalopanax pictus 174 and ivorengenin B 414 from Terminalia ivorensis. 175 The unusual 9,25-cycloolean-12-en-3b-yl b-D-glucofuranoside 415 has been reported to be a constituent of Celestris australis 176 and the same group has identied 9,25-cyclo-3b-(b-D-glucopyranosyloxy)-16a-hydroxyolean-12-en-28-oic acid 416 in Symplocos paniculata. 177 The 24,30-dinoroleanane 417, 30-noroleanane 418 and 24-noroleanane 419 derivatives are present in the roots of Paeonia rockii ssp.…”

Bioassay‐guided isolation of anti‐inflammatory constituents from Celtis sinensis leaves

“…The plants of genus Celtis are also employed as a folk medicine for the treatment of lumbago, gastric disease, abdominal pain, and urticarial eczema, among other diseases in eastern Asia, including China, Korea, and Japan. Previous studies on the plants of the genus Celtis led to the isolation of flavonoids (Kaltenhauser et al., 2010; Spitaler et al., 2009; Zehrmann et al., 2010), terpenoids (Badoni et al., 2011; Hwang et al., 2003; Kim et al., 2005), phenolic acids (Badoni et al., 2010; Hoang et al., 2012), and amide compounds (Al‐Taweel et al., 2012; Kim & Lee, 2003; Kim, Lee, et al., 2005). Recently, two new flavanol dimers were isolated from the bark of Celtis tetrandra (Seephonkai et al., 2018).…”

Seasonal variations in phenolics and antioxidant properties of leaves extract from Celtis australis

“…In Moroccan traditional medicine, C. australis commonly called "Taghzaz" is also used to treat various gastro-intestinal ailments 9 . Phytochemical investigations have shown the plant to contain several chemical species of secondary metabolites such as terpenoids, amides, lignin glycosides and steroids 10 , flavonoids 11 , sulphonated phenolic 12 , bacteriohopanoid 13 , terpenoids, steroids and anthraquinones 14 , glycosyl-flavonoids 15 , phenolic amides 16 , -sitosterol, -sitosterol-glucoside and vanilic acid 17 , among others.…”