- Self gelating isoracemosol A, new racemosaceramide A, and racemosol E from Barringtonia racemosa
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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.
- Ponnapalli, Mangala Gowri,Dangeti, Nalini,Sura, Madhu Babu,Kothapalli, Haribabu,Akella, V. S. Sarma,Shaik, Jeelani Basha
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supporting information
p. 63 - 69
(2016/11/29)
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- α-Glucosidase inhibitory monoacylated polyhydroxytriterpenoids from the fruits of Barringtonia racemosa
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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.
- Ponnapalli, Mangala Gowri,Sukki, Sushma,Rao Annam, S.Ch.V. Appa,Ankireddy, Madhu,Tirunagari, Harini,Tuniki, V. Raju,Bobbili, V.V. Pardhasaradhi
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supporting information
p. 1570 - 1574
(2015/03/14)
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- PREPARATION OF PROTOESCIGENIN FROM ESCIN
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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.
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Page/Page column 23
(2013/04/25)
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- Medicinal flowers. XXXVI.1) Acylated oleanane-type triterpene saponins with inhibitory effects on melanogenesis from the flower buds of Chinese Camellia japonica
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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.
- Nakamura, Seikou,Fujimoto, Katsuyoshi,Nakashima, Souichi,Matsumoto, Takahiro,Miura, Tomoko,Uno, Kaoru,Matsuda, Hisashi,Yoshikawa, Masayuki
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experimental part
p. 752 - 758
(2012/09/25)
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- Triterpene saponins of Maesa lanceolata leaves
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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.
- Manguro, Lawrence Onyango A.,Midiwo, Jacob O.,Tietze, Lutz F.,Hao, Pang
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experimental part
p. 172 - 198
(2011/06/09)
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- 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
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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
- Sugimoto, Sachiko,Chi, Guihua,Kato, Yasuyo,Nakamura, Seikou,Matsuda, Hisashi,Yoshikawa, Masayuki
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experimental part
p. 269 - 275
(2009/11/30)
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- A triterpenoid saponin possessing antileishmanial activity from the leaves of Careya arborea
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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).
- Mandal, Debayan,Panda, Nilendu,Kumar, Shrabanti,Banerjee, Sukdeb,Mandal, Nirup B.,Sahu, Niranjan P.
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p. 183 - 190
(2008/02/07)
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- Two new glycosides from Sanicula lamelligera
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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.
- Zhou, Ling-Yun,Liu, Hai-Yang,Xie, Bai-Bo,Liu, Zhi-Hai,Chen, Chang-Xiang
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p. 607 - 610
(2008/01/27)
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- Triterpenoid saponins from Berneuxia thebetica
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Four triterpenoid saponins were isolated from Berneuxia thibetica. On the basis of chemical and spectroscopic evidence, three new saponins, berneuxia saponins A, B and C, were elucidated as 21-tigloylbarringtogenol C- 3β-O-α-L-rhamnopyranosyl(1 → 2)-β-D-galactopyranosyl(l → 3)[β-D- glucopyranosyl (1 → 2)-β-D-glucuronopyranoside], 28-tigloylbarringtogenol C-3β-O-α-L-rhamnopyranosyl(1 → 2)-β-D-galactopyranosyl(1 → 3)[β-D- glucopyranosyl(1 → 2)-β-D-glucuronopyranoside] and 16α-28-dihydroxyolean- 12-en-21-one-3-O-α-L-rhamnopyranosyl(1 → 2)-β-D-galactopyranosyl(1 → 3)[β-D-glucopyranosyl(1 → 2)-β-D-glucuronopyranoside]. The known saponin was desacyl jegosaponin.
- Wang, Ming-Kui,Cai, Hong,Peng, Shu-Lin,Ding, Li-Sheng,Wu, Feng-E,Chen, Yao-Zu
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p. 1411 - 1414
(2007/10/03)
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- A triterpenoid saponin from Maesa ramentacea
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The structure of a piscicidal triterpenoid saponin (saponin A) isolated from the leaves of Maesa ramentacea has been shown to be 3-O-{[(α-L- rhamnopyranosyl(1→2)-a-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl(1→3)]- [β-D-glucopyranosyl-(1→2)]-β-D-glucuronopyranosyl}barringtogenol C21, 22- O-diangeloate. Extensive use was made of homo- and heteronuclear 2D NMR techniques.
- Tuntiwachwuttikul, Pittaya,Pancharoen, Orasa,Mahabusarakam, Wilawan,Wiriyachitra, Pichaet,Taylor, Walter C.,Bubb, William A.,Towers
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p. 491 - 495
(2007/10/03)
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- Studies on the Constituents of Xanthoceras sorbifolia BUNGE. III. Minor Prosapogenins from the Fruits of Xanthoceras sorbifolia BUNGE
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The prosapogenins from the fruits of Xanthoceras sorbifolia BUNGE (Sapindaceae) were examined.On the basis of chemical and spectral analyses, the structures of three minor prosapogenins, obtained by acid hydrolysis of crude saponin fraction, were characterized as 21-O-(3,4-di-O-angeloyl)-β-D-fucopyranosyl theasapogenol B (1), 21-O-(4-O-acetyl-3-O-angeloyl)-β-D-fucopyranosyl theasapogenol B (2) and 21-O-(4-O-acetyl-3-O-angeloyl)-β-D-fucopyranosyl-22-O-acetyl protoaescigenin (3), respectively.
- Chen, Yingjie,Takeda, Tadahiro,Ogihara, Yukio
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p. 127 - 134
(2007/10/02)
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