New natural barrigenol-like triterpenoid isolated from the husks of Xanthoceras sorbifolia Bunge.

Published on May 1, 2018in Natural Product Research2.158
· DOI :10.1080/14786419.2017.1375916
Da Wang4
Estimated H-index: 4
(SPU: Shenyang Pharmaceutical University),
Bin Yu2
Estimated H-index: 2
(SPU: Shenyang Pharmaceutical University)
+ 5 AuthorsHuiyuan Gao12
Estimated H-index: 12
(SPU: Shenyang Pharmaceutical University)
Sources
Abstract
AbstractThe Xanthoceras sorbifolia Bunge husks were known for their abundant triterpenoids resource, which contributed to many bioactivities, such as antitumor, antiinflammatory and neuroprotection. The present study has led to the purification of a new triterpenoid saponin, 21β-O-acetyl-xanthohuskiside A (1), together with six known barrigenol derivatives (2–7), whose structures were authenticated on the basis of NMR, HR-MS, IR spectrum and acid hydrolysis experiment. Compound 7 showed more noteworthy cytotoxicity towards three human tumour cell lines (HCT-116, HepG-2 and U87-MG) than other compounds.
📖 Papers frequently viewed together
20172.53Fitoterapia
9 Authors (Da Wang, ..., Xiaobo Wang)
12 Citations
20122.53Fitoterapia
9 Authors (Lili Yu, ..., Feng Qiu)
11 Citations
22 Citations
References16
Newest
#1Da Wang (SPU: Shenyang Pharmaceutical University)H-Index: 4
#2Dan Su (SPU: Shenyang Pharmaceutical University)H-Index: 7
Last. Xiaobo WangH-Index: 9
view all 9 authors...
Abstract The high edible oil content of Xanthoceras sorbifolia Bunge seeds contributes to its economic value. In this study, we analysed the barrigenol-like triterpenoids derived from X. sorbifolia husks. We also identified anti-tumour agents that could enhance the health benefits and medicinal value of X. sorbifolia. We isolated 10 barrigenol triterpenoids, including six new compounds (1–6) and four known compounds (7–10). New compounds 3 and 5 showed significant inhibitory activity against the...
12 CitationsSource
#1Da Wang (SPU: Shenyang Pharmaceutical University)H-Index: 4
#2Dan Su (SPU: Shenyang Pharmaceutical University)H-Index: 7
Last. Xiaobo WangH-Index: 9
view all 7 authors...
Barrigenol-like triterpenoids containing angeloyl residues in their structures are unusual natural products. To discover the chemical constituents responsible for the antitumor activity of Xanthoceras sorbifolia Bunge, the present study was carried out using the husk of this crop. Ten angeloyl barrigenol triterpenoids, including seven new (1–7) and three known compounds (8–10), were isolated from the active fraction via the bioassay-guided method. The structures of the compounds were established...
16 CitationsSource
#1Yuan Du (Yantai University)H-Index: 11
#2Yanqin Song (Yantai University)H-Index: 4
Last. Fenghua Fu (Yantai University)H-Index: 21
view all 5 authors...
Abstract The present study was aimed at investigating whether low dose oral prednisone combined with escin could inhibit the progression of adjuvant-induced arthritis (AIA) in rats. Adjuvant arthritis was induced in SD rats began day 1 for 28 days. Prednisone at doses of 2, 10 mg/kg/day alone or escin at doses of 5, 10 mg/kg/day alone, or prednisone at dose of 2 mg/kg/day with escin at doses of 5 or 10 mg/kg/day were given to different groups of rats intragastrically from day 13 to 28 respective...
12 CitationsSource
#1Yulin RenH-Index: 17
#2Andrew VanSchoiackH-Index: 1
Last. A. Douglas KinghornH-Index: 79
view all 5 authors...
Two new [(+)-cyrillins A (1) and B (2)] and four known barrigenol-like triterpenoids (3–6), along with betulinic acid and (+)-3β-O-trans-feruloylbetulinic acid, were isolated from a sample-restricted CH2Cl2-soluble extract of the bark of Cyrilla racemiflora, collected in Dominica. The structures of the new compounds were elucidated by interpretation of their spectroscopic data, and the absolute configuration of the cyclic 1,2-diol unit of (+)-cyrillin A (1) was ascertained by analysis of the ele...
8 CitationsSource
#1Ge Jin (SPU: Shenyang Pharmaceutical University)H-Index: 7
#2Li-Hua Wang (CAS: Chinese Academy of Sciences)H-Index: 8
Last. Libo Zou (SPU: Shenyang Pharmaceutical University)H-Index: 13
view all 10 authors...
Abstract Xanthoceraside, a triterpenoid saponin, has been shown to reverse cognitive deficits in several Alzheimer's disease (AD) animal models. However, the effects of xanthoceraside on the Aβ deposition pathology and the APP processing in AD are unclear. Here, we show that xanthoceraside at doses of 0.08 and 0.32 mg/kg/d for 6 months significantly improved learning and memory impairment in APP transgenic mice assessed by the Y maze and novel object recognition tests. Immunohistochemical analys...
33 CitationsSource
#1Mariusz KowalczykH-Index: 20
#2Milena MasulloH-Index: 21
Last. Wieslaw OleszekH-Index: 53
view all 6 authors...
Saponin composition of the roots of Eryngium planum L. was investigated. Triterpene saponins found in E. planum and also present in Eryngium maritimum were different from those described previously in Eryngium campestre L. Three primary saponins were isolated and their tentative identifications, based on the electrospray MS/MS fragmentation patterns, were subsequently confirmed by 1D and 2D NMR analyses. Their structures were established as 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-glucuronopyranosyl-2...
12 CitationsSource
#1Ji Li (NEFU: Northeast Forestry University)H-Index: 19
#2Yuangang Zu (NEFU: Northeast Forestry University)H-Index: 71
Last. Yu-Jie Fu (NEFU: Northeast Forestry University)H-Index: 61
view all 7 authors...
Abstract In this study, aqueous enzymatic process (AEP) assisted by microwave extraction (ME) of oil from yellow horn ( Xanthoceras sorbifolia Bunge.) seed kernel was investigated. Central composite design (CCD) and response surface methodology (RSM) were used to optimise an enzyme cocktail (cellulase, hemicellulase, pectinase) for AEP. The main factors of ME were also studied. A maximal oil extraction yield of 55.8% was achieved under optimal conditions. Moreover, scanning electron microscope (...
46 CitationsSource
#1Ying-Ying Li (LNUTCM: Liaoning University of Traditional Chinese Medicine)H-Index: 2
#2Zheng Xiang (LNUTCM: Liaoning University of Traditional Chinese Medicine)H-Index: 3
Last. Hai-Xue Kuang (Heilongjiang University)H-Index: 6
view all 7 authors...
Two new oleanane-type pentacyclic triterpenoid saponins were isolated from the husks of Xanthoceras sorbifolia Bunge and their structures were elucidated as 3-O-β-D-glucopyranosyl (1 → 6)-β-D-glucopyranosyl-28-O-α-L-rhamnopyranosyl (1 → 2) [β-D-glucopyranosyl (1 → 6)] β-D-glucopyranosyl-21β,22α-dihydroxyl-olean-12,15-diene and 3-O-β-D-glucopyranosyl (1 → 2)-β-D-glucopyranosyl-28-O-α-L-rhamnopyranosyl (1 → 2) [β-D-glucopyranosyl (1 → 6)] β-D-glucopyranosy-21β,22α-dihydroxyl-olean-12-ene. Meanwhil...
3 CitationsSource
#1Zhan-Lin Li (SPU: Shenyang Pharmaceutical University)H-Index: 23
#2Dan-Yi Li (SPU: Shenyang Pharmaceutical University)H-Index: 7
Last. Hui-Ming Hua (SPU: Shenyang Pharmaceutical University)H-Index: 25
view all 4 authors...
Two new oleanane triterpenoid saponins, xanthohuskisides A (1) and B (2), were isolated from the husks of Xanthoceras sorbifolia. The structures of these two compounds were established as 3-O-β-D-glucopyranosyl (1→6)-[β-D-glucopyranosyl (1→2)]-β-D-glucopyranosyl, 28-O-β-D-glucopyranosyl (1→6)-[α-L-rhamnopyranosyl (1→2)]-β-D-glucopyranosyl 16-deoxybarringtogenol C (1) and 3-O-β-D-glucopyranosyl (1→6)-[β-D-glucopyranosyl (1→2)]-β-D-glucopyranosyl, 28-O-β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl 1...
7 CitationsSource
#1Consolacion Y. Ragasa (DLSU: De La Salle University)H-Index: 18
#2Dinah L. Espineli (DLSU: De La Salle University)H-Index: 6
Last. Chien-Chang ShenH-Index: 21
view all 3 authors...
The freeze-dried bark of Barringtonia asiatica afforded a new triterpene: (3β,11α)-11-hydroxyolean-12-en-3-yl palmitate (1). The bark also yielded mixtures of (3β)-olean-12-en-3-yl palmitate (2a), (3β)-urs-12-en-3-yl palmitate (2b) and (3β)-olean-18-en-3-yl palmitate (2c) in a 2 : 1 : 4 ratio; β-amyrin (3a), α-amyrin (3b) and germanicol (3c) in a 3 : 1 : 4 ratio; 22-O-tigloylcamelliagenin A (4a) and betulinic acid (4b) in a 2 : 1 ratio; olean-12-en-3β,16β,22α-triol (5), β-sitosterol, spinasterol...
12 CitationsSource
Cited By7
Newest
#1Armand Emmanuel Moffi Biang (University of Yaoundé I)H-Index: 1
#2Lin Marcellin Messi (University of Toulouse)H-Index: 1
Last. Mohamed Haddad (University of Toulouse)H-Index: 13
view all 9 authors...
Abstract null null In our continuing search of saponins from the plant of Sapindaceae family, phytochemical investigation of the stem barks of Pancovia turbinata Radlk., led to the isolation and structural characterization of two new triterpenoid saponins, named turbinatosides A-B (1–2), one new farnesyl glycoside, named turbinoside A (3), one new coumarin glucoside, named panturboside A (4), together with a known saponin (5). The structures of the new compounds were established, using extensive...
Source
#1Kewen DingH-Index: 2
#1Ding Kewen (Shenyang)
Last. Bi Kaishun (Shenyang)
view all 8 authors...
: A new triterpenoid saponin (1), 3-O-[β-D-glucopyranosyl(1→6)]-(2'-angeloyl)-β-D-glucopyranosyl-28-O-β-D-glucopyranosyl(1→6)[α-L-rhamnopyranosyl(1→2)-β-D-glucopyranosyl]-21-O-acetyl-16-deoxybarringtogenol C, together with four known saponins (2 ∼ 5) were isolated from the husks of Xanthoceras sorbifolium Bunge. Their structures were characterized by HR-ESI-MS, 1D-NMR, 2D-NMR spectra and chemical methods. Compound 1 exhibited excellent neuroprotection on PC12 cells injury induced by Aβ25-35 at t...
Source
#1Armand Emmanuel Moffi Biang (University of Yaoundé I)H-Index: 1
#2Eutrophe Le Doux Kamto (University of Yaoundé I)H-Index: 2
Last. Mohamed Haddad (University of Toulouse)H-Index: 13
view all 9 authors...
Abstract In our continuing studies on saponins from Cameroonian medicinal plants, phytochemical investigation of Chytranthus klaineanus stem barks led to the isolation of three new oleanane-type saponins, named Klaineanosides A–C (1–3). Their structures were established by extensive analysis of their spectral data, mainly 1D (1H, 13C NMR, and DEPT) and 2D (COSY, HSQC, NOESY, HSQC-TOCSY, and HMBC) NMR experiments, and mass spectrometry as 3-O-β- d -glucopyranosyl-(1→3)-β- d -xylopyranosyl-(1→4)[-...
4 CitationsSource
#1Zi-Jian Rong (SPU: Shenyang Pharmaceutical University)H-Index: 3
#2Gaosheng Hu (SPU: Shenyang Pharmaceutical University)H-Index: 3
Last. An-Hua Wang (SPU: Shenyang Pharmaceutical University)H-Index: 5
view all 8 authors...
Three new isoflavone glucosides, kudonol A−C (1–3), two new ester derivatives of phenylpropanoid, kudolignan A and B (4–5) and five known compounds, (−)-maackiain (6), neoliquiritin (7), methyl 4-coumarate (8), methyl ferulate (9) and (+)-wikstromol (10), were isolated from an extract of dried seeds of the traditional Chinese medicinal plant Sophora alopecuroides L. Their structures were established by NMR and HRESIMS data analyses. The monosaccharide part’s configuration of isoflavone glucoside...
3 CitationsSource
#1Yiren Yang (SPU: Shenyang Pharmaceutical University)H-Index: 4
#2Liping Long (SPU: Shenyang Pharmaceutical University)H-Index: 3
Last. Luping Sha (SPU: Shenyang Pharmaceutical University)H-Index: 2
view all 8 authors...
Barrigenol-like triterpenoids (BATs) showed promising anti-tumor, anti-inflammatory and anti-Alzheimer's activities, while, the inhibitory strength was usually affected by their states with aglycones or glycosides. In order to find more BATs as new anti-tumor agents with much more efficiency, the chemical and pharmaceutical studies were carried out on the acid hydrolysate product (AHP) of Semen Aesculi crude extract. Thirteen BATs, including three new aglycones (1–3), two new glycosides (4, 5) a...
1 CitationsSource
#1Xinxin Zhang (SPU: Shenyang Pharmaceutical University)H-Index: 3
#2Song Zhang (SPU: Shenyang Pharmaceutical University)H-Index: 1
Last. Huiyuan Gao (SPU: Shenyang Pharmaceutical University)H-Index: 12
view all 5 authors...
Abstract Barrigenol-like triterpenoids (BATs), which contain an unusual oleanane substituted by many hydroxyl groups as the skeleton, are subdivided into five subtypes: barrigenol A 1 , barrigenol A 2 , barrigenol R 1 , barringtogenol C, and 16-deoxybarringtogenol C. The variations in acyl derivatives, hydroxyl groups, and carbohydrate chains in their structures have enhanced the diversity of BATs. Moreover, the stable polyhydroxy-replaced pentacyclic skeleton provides an ideal platform for stru...
19 CitationsSource
#1Zhan-Lin Li (SPU: Shenyang Pharmaceutical University)H-Index: 23
#2Dan-Dan Zhao (SPU: Shenyang Pharmaceutical University)
Last. Dan-Yi Li (SPU: Shenyang Pharmaceutical University)
view all 3 authors...
Abstract Four tyrosine-derived spiro-isoxazoline analogues, including two new ones (3–4), were isolated from the flowers of Xanthoceras sorbifolia Bunge. The planar structures and the conformations were established by the analyses of the 1D and 2D NMR spectroscopic data, and the absolute configuration of compound 4 was determined via ECD calculation by time-dependent density functional theory (TDDFT). The biosynthetic pathway involving oxidative cyclization of the aldoxime precursor and the subs...
Source