11010-04-1Relevant articles and documents
TRITERPENOID SAPONINS FROM CENTIPEDA MINIMA
Gupta, Dipti,Singh, J.
, p. 1197 - 1202 (1989)
Four new triterpenoid saponins were isolated from the whole plant of Centipeda minima.They were characterized as 1α,3β,19α,23-tetrahydroxyurs-12-en-28-oic acid-28-O-β-D-xylopyranoside, 1β,2α,3β-19α-23-pentahydroxyurs-12-en-28-oic acid-28-O-β-D-xylopyranoside, 3α,21α,22α,28-tetrahydroxyolean-12-en-28-O-β-D-xylopyranoside and 3α,16α,21α,22α-28-pentahydroxyolean-12-en-28-O-β-D-xylopyranoside.Structrures of all compounds were elucidated by spectroscopic methods with emphasis on mass spectra, 1H and 13C NMR spectra.Key Word Index - Centipeda minima; Compositae; triterpenoid saponins; ursane and oleanane derivatives.
Self gelating isoracemosol A, new racemosaceramide A, and racemosol E from Barringtonia racemosa
Ponnapalli, Mangala Gowri,Dangeti, Nalini,Sura, Madhu Babu,Kothapalli, Haribabu,Akella, V. S. Sarma,Shaik, Jeelani Basha
supporting information, p. 63 - 69 (2016/11/29)
Phytochemical investigation into the CHCl3extract of the fruits of Barringtonia racemosa resulted in the isolation of two new metabolites along with isoracemosol A and betulinic acid as known metabolites. The new compounds were characterised as phytosphingosine-type ceramide [(2S,3S,4R)-2-[(2R)-2-hydroxyhexadecanoyl amino]-hexacos-8(E)-ene-1,3,4-triol, 1] and racemosol E [21β-acetoxy-22α-(2-methylbutyroxy)-olean-12-ene-3β,16α,28-triol, 2] on the basis of extensive spectroscopic data analysis and chemical modifications. In addition, the self-gelating property of isoracemosol A (3) was investigated for the first time, which leads to the unexpected agglomerated porous-like morphology.
α-Glucosidase inhibitory monoacylated polyhydroxytriterpenoids from the fruits of Barringtonia racemosa
Ponnapalli, Mangala Gowri,Sukki, Sushma,Rao Annam, S.Ch.V. Appa,Ankireddy, Madhu,Tirunagari, Harini,Tuniki, V. Raju,Bobbili, V.V. Pardhasaradhi
supporting information, p. 1570 - 1574 (2015/03/14)
Chemical investigation of a lipophilic CHCl3 extract of the dried fruits of Barringtonia racemosa resulted in the isolation of two unusual monoacylated polyhydroxy oleanane triterpenoid congeners named racemosols C-D (1-2) along with three known compounds. Their structures were determined by comprehensive spectroscopic analysis coupled with chemical modifications as 21β-acetoxy-3β, 16α,22α,28-tetrahydroxyolean-12-ene (1) and 22α-(2-methylbutyryl)-3β, 15α,16α,21β,28-pentahydroxyolean-12-ene (2). Compounds (1-3, 1a, and 2a) were subjected to α-glucosidase inhibitory assay and 1 showed the most potent α-glucosidase inhibition with an IC50 value of 5.6 μM.
PROCESS FOR THE PREPARATION OF PROTOESCIGENIN
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Paragraph 0174; 0175; 0176, (2013/07/31)
A process for the preparation of protoescigenin by hydrolysis of escin isolated from Aesculus hippocastanum. The process includes the following steps: a two-step hydrolysis first under acidic and then basic conditions, enrichment of the crude mixture of sapogenins with protoescigenin, an isolation of the mixture of sapogenins in a solid form, and a purification of the obtained solid and isolation of high purity protoescigenin. The invention also relates to protoescigenin monohydrate in a crystalline form and the preparation thereof. Protoescigenin is a polyhydroxy aglycone, which can be used as a synthon in the chemical modifications of naturally occurring saponins.
PREPARATION OF PROTOESCIGENIN FROM ESCIN
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Page/Page column 23, (2013/04/25)
The invention relates to the process for preparation of protoescigenin from escin isolated from Aesculum hippocastanum. The process comprises the following steps: two-step hydrolysis under acidic and basic conditions, enrichment of the crude mixture of sapogenins with protoescigenin, isolation of the mixture of sapogenins in a solid form, purification of the obtained solid and isolation of high purity protoescigenin. The present invention also relates to protoescigenin monohydrate in a crystalline form and the preparation thereof. Protoescigenin is a polyhydroxyl aglycone, which can be used as the synthon in the chemical modifications of naturally occurring saponis.
Medicinal flowers. XXXVI.1) Acylated oleanane-type triterpene saponins with inhibitory effects on melanogenesis from the flower buds of Chinese Camellia japonica
Nakamura, Seikou,Fujimoto, Katsuyoshi,Nakashima, Souichi,Matsumoto, Takahiro,Miura, Tomoko,Uno, Kaoru,Matsuda, Hisashi,Yoshikawa, Masayuki
experimental part, p. 752 - 758 (2012/09/25)
Four acylated oleanane-type triterpene oligoglycosides, sanchakasaponins E-H, were isolated from the flower buds of Camellia japonica cultivated in Yunnan province, China, together with four known triterpene oligoglycosides. The chemical structures of the new triterpene oligoglycosides were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of the triterpene oligoglycoside constituents on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were investigated.
Triterpene saponins of Maesa lanceolata leaves
Manguro, Lawrence Onyango A.,Midiwo, Jacob O.,Tietze, Lutz F.,Hao, Pang
experimental part, p. 172 - 198 (2011/06/09)
Chemical investigation of Maesa lanceolata leaves aqueous MeOH extract has led to the isolation of eight new triterpene glycosides identified as 16-oxo-28-hydroxyolean-12-ene 3-O-β-glucopyranosyl-(1''→6')-β- glucopyranoside 1, 16α, 28-dihydroxyolean-12-ene 3-O-β-[(6"-O- galloylglucopyranosyl-(1"→2')][β-glucopyranosyl-(1'''→6')] -β-glucopyranoside 2, 16α, 22α, 28-trihydroxyolean-12-ene 3-O-[β-glucopyranosyl-(1"→2')] [α-rhamnopyranosyl- (1'''→6']-β-glucopyranoside 3, 22α-acetyl-16α- hydroxyolean-12-en-28-al 3-O-[α-rhamnopyranosyl- (1""→6"')-β-glucopyranosyl-(1"'→3')] [β-glucopyranosyl-(1"→2')]-β-arabinopyranoside 4, 22α-acetyl-16α,21 β-dihydroxyoleanane-13β:28-olide 3-O-[β-glucopyranosyl-(1'''→6')] [6''-O-coumaroylglucopyranosyl- (1''→2')]-β-glucopyranoside 5, 16α,22α-diacetyl-21β- angeloyloleanane-13β:28-olide 3 β-O-[β-glucopyranosyl- (1''→2')][β-glucopyranosyl-(1'''→4')]-β-glucopyranoside 6, 16α, 22α, 28-trihydroxy-21β-angeloyloleanan-12-ene 3 β-O-[α-rhamnopyranosyl-(1'''→6'')][β-glucopyranosyl- (1''→2')]-β-xylopyranoside 7, 16α, 28-dihydroxy-22α- acetyl-21β-angeloylolean-12-ene 3-O-[β-galactopyranosyl- (1"→2')] [α-rhamnopyranosyl-(1'"→4')]-α- arabinopyranoside 8. Together with these were known compounds quercetin, myricetin, quercetin 3-O-rhamnopyranoside, myricetin 3-O-β-glucopyranoside, gallic acid, sistosterol 3-O-β-glucopyranoside, rutin, myricetin 3-O-α-rhamnopyranosyl-(1"→3')-β-glucopyranoside and quercetin 3,7-O-β-diglucopyranoside. Their structures were determined using spectroscopic methods as well as comparison with data from known compounds. The in vitro antibacterial activity of aqueous MeOH extract of the leaves of M. lanceolata was also investigated and zones of inhibition ranging from 28±0.1 to 10±0.2 mm were observed. The minimum inhibitory concentration (MIC) for the extract ranged between 100 to 1000 μg/ml with the highest activity being observed with Vibro cholerae. Among the pure isolates, compound 6 was the most active and its highest recorded MIC value was 62.5 μg/ml against V. cholerae. ARKAT-USA, Inc.
Medicinal flowers. XXVI.1 structures of acylated oleanane-type triterpene oligoglycosides, yuchasaponins A, B, C, and D, from the flower buds of camellia oleifera-gastroprotective, aldose reductase inhibitory, and radical scavenging effects
Sugimoto, Sachiko,Chi, Guihua,Kato, Yasuyo,Nakamura, Seikou,Matsuda, Hisashi,Yoshikawa, Masayuki
experimental part, p. 269 - 275 (2009/11/30)
The methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia oleifera Abel were found to exhibit inhibitory effects on ethanol- and indomethacin-induced gastric mucosal lesions in rats. The ethyl acetate- and 1-butanol-solubl
A triterpenoid saponin possessing antileishmanial activity from the leaves of Careya arborea
Mandal, Debayan,Panda, Nilendu,Kumar, Shrabanti,Banerjee, Sukdeb,Mandal, Nirup B.,Sahu, Niranjan P.
, p. 183 - 190 (2008/02/07)
Bioguided-fractionation of the methanol extract of the leaves of Careya arborea led to isolation of a triterpenoid saponin, designated arborenin, and characterized as 3-O-β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl- 2α,3β-dihydroxy-taraxast-20-en-28-oic acid (1), together with desacylescin III (2). The structures were determined on the basis of extensive 2D NMR spectroscopic analysis. The saponin showed in vitro antileishmanial activity against Leishmania donovani (strain AG 83).
Two new glycosides from Sanicula lamelligera
Zhou, Ling-Yun,Liu, Hai-Yang,Xie, Bai-Bo,Liu, Zhi-Hai,Chen, Chang-Xiang
, p. 607 - 610 (2008/01/27)
Two new glycosides, 21-O-β-D-glucopyranosyl-olean-12-ene-3β, 16α, 21β, 22α, 28-pentol-3-O-β-D-glucopyranosyl (1 → 2)-[β-D-arabinopyranosyl (1 → 3)]-β-D-glucopyranoside-(1) and 4-O-β-D-glucopyranosyl rosmarinic acid (3), along with the known compound rosmarinic acid (2) were isolated from the whole plants of Sanicula lamelligera Hance. Their structures were elucidated by spectroscopic analysis and chemical means.
