Lupane-Triterpene Esters from the Leaves of Ceriops decandra (Griff.) Ding Hou

2005 ◽  
Vol 58 (8) ◽  
pp. 615 ◽  
Author(s):  
Chanita Ponglimanont ◽  
Pakakrong Thongdeeying
Keyword(s):  
Ursolic Acid ◽  
Betulinic Acid ◽  
Spectroscopic Methods ◽  
Ceriops Decandra ◽  
New Compounds ◽  
First Time ◽  
Triterpene Esters

Two novel triterpene esters were isolated from the leaves of Ceriops decandra in addition to 16 known triterpenes: lupenone 3, lupeol 4, betulinaldehyde 5, 3β-Z-coumaroyllupeol 6, 3β-E-coumaroyllupeol 7, 3-epi-betulinic acid 8, betulin 9, betulinic acid 10, 3β-E-feruloylbetulin 11, 30-nor-lup-3β-ol-20-one 12, 3β-E-caffeoyllupeol 13, lup-20(29)-en-3β,30-diol 14, 3β-hydroxylupan-29-oic acid 15, 3β,20-dihydroxylupane 16, and a mixture of oleanolic and ursolic acid 17 and 18. The new compounds were determined by spectroscopic methods to be 3β-E-feruloyllupeol 1 and 3β-Z-feruloyllupeol 2. Compounds 3 and 5–16 were reported for the first time as metabolites of C. decandra.

Limonoids from Aphanamixis polystachya Leaves and Their Interaction with Hsp90

Planta Medica ◽  
2018 ◽  
Vol 84 (12/13) ◽  
pp. 964-970 ◽  
Author(s):  
César Muñoz Camero ◽  
Antonio Vassallo ◽  
Marinella De Leo ◽  
Abeer Temraz ◽  
Nunziatina De Tommasi ◽  
...  
Keyword(s):  
Molecular Chaperone ◽  
Natural Compounds ◽  
Spectroscopic Methods ◽  
Phytochemical Study ◽  
Phenolic Derivatives ◽  
New Compounds ◽  
Type 3 ◽  
First Time

AbstractA phytochemical study of n-hexane, CHCl3, and CHCl3-MeOH extracts of Aphanamixis polystachya leaves led to the isolation of 10 compounds. Five of them turned out to be new natural compounds, including two mexicanolide-type (1, 2) and three polyoxyphragmalin-type (3–5) limonoids, together with two known andirobin-type limonoids (6, 7) and three phenolic derivatives. The structures of the new compounds were established on the basis of spectroscopic methods to be 8-hydro-14,15-en-cabralin (1), 3-deacetyl-8-hydro-cabralin-14,15-en-3-one (2), 20,22-dihydroxy-21,23-dimethoxytetrahydrofuran khayanolide A (3), 1-deacetyl-3-dehydroxy-3-oxokhaysenelide E (4), and meliaphanamixin A (5). All compounds were isolated for the first time from this species. The ability of the isolated limonoids to interact with the molecular chaperone Hsp90 was tested. Compounds 6 and 7 were the most active.

scholarly journals Antileishmanial Phenylpropanoids from the Leaves ofHyptis pectinata(L.) Poit

2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
Rosangela A. Falcao ◽  
Patricia L. A. do Nascimento ◽  
Silvana A. de Souza ◽  
Telma M. G. da Silva ◽  
Aline C. de Queiroz ◽  
...  
Keyword(s):  
Rosmarinic Acid ◽  
Bacterial Infections ◽  
Ethanol Extract ◽  
Spectroscopic Methods ◽  
Etoh Extract ◽  
Promastigote Form ◽  
Water Fractions ◽  
New Compounds ◽  
First Time

Hyptis pectinata, popularly known in Brazil as “sambacaitá” or “canudinho,” is an aromatic shrub largely grown in the northeast of Brazil. The leaves and bark are used in an infusion for the treatment of throat and skin inflammations, bacterial infections, pain, and cancer. Analogues of rosmarinic acid and flavonoids were obtained from the leaves ofHyptis pectinataand consisted of two new compounds, sambacaitaric acid (1) and 3-O-methyl-sambacaitaric acid (2), and nine known compounds, rosmarinic acid (3), 3-O-methyl-rosmarinic acid (4), ethyl caffeate (5), nepetoidin A (6), nepetoidin B (7), cirsiliol (8), circimaritin (9), 7-O-methylluteolin (10), and genkwanin (11). The structures of these compounds were determined by spectroscopic methods. Compounds1–5, and7were evaluatedin vitroagainst the promastigote form ofL. braziliensis, and the ethanol extract. The hexane, ethyl acetate, and methanol-water fractions were also evaluated. The EtOH extract, the hexane extract, EtOAc, MeOH:H2O fractions; and compounds1,2and4exhibited antileishmanial activity, and compound1was as potent as pentamidine. In contrast, compounds3,5, and7did not present activity against the promastigote form ofL. braziliensisbelow 100 µM. To our knowledge, compounds1and2are being described for the first time.

scholarly journals A Pair of Novel Sulfonyl-Containing N-Acetyldopamine Dimeric Enantiomers From Aspongopus chinensis

2020 ◽  
Vol 15 (3) ◽  
pp. 1934578X2091127
Author(s):  
Li Liao ◽  
Yong-Ming Yan ◽  
Te Xu ◽  
Hou-Lin Xia ◽  
Yong-Xian Cheng
Keyword(s):  
High Performance Liquid Chromatography ◽  
Biological Activity ◽  
Liquid Chromatography ◽  
Renal Fibrosis ◽  
High Performance ◽  
Racemic Mixture ◽  
Spectroscopic Methods ◽  
Liquid Chromatography Separation ◽  
New Compounds ◽  
First Time

A pair of novel sulfonyl-containing N-acetyldopamine dimer enanitomers, (±)-aspongamide E (1), a new ester 2-aminoethyl ( E)-hex-2-enoate (2), along with 3 known compounds (3-5) were isolated from Aspongopus chinensis. Their structures were determined by spectroscopic methods. Compound 1 is a racemic mixture, chiral high-performance liquid chromatography separation followed by electronic circular dichroism calculations assigned the absolute configurations of 2 enantiomers of 1. Compounds 3-5 were isolated from A. chinensis for the first time. The biological activity of the selected new compounds against renal fibrosis was evaluated.

scholarly journals Pyranocoumarin and Triterpene from Millettia Richardiana

2013 ◽  
Vol 8 (8) ◽  
pp. 1934578X1300800
Author(s):  
Manitriniaina Rajemiarimiraho ◽  
Jean Théophile Banzouzi ◽  
Stéphane Richard Rakotonandrasana ◽  
Pierre Chalard ◽  
Françoise Benoit-Vical ◽  
...  
Keyword(s):  
Linoleic Acid ◽  
Stearic Acid ◽  
Palmitic Acid ◽  
Betulinic Acid ◽  
Stem Bark ◽  
Spectroscopic Methods ◽  
Endemic Plant ◽  
First Time

From the stem bark of a Madagascan endemic plant, Millettia richardiana Baill., lonchocarpenin and betulinic acid were isolated and their structures established by spectroscopic methods. The analysis of dichloromethane fractions suggested the presence of β-amyrin, lupeol, palmitic acid, linoleic acid and stearic acid. Except for β-amyrin and lupeol, these compounds are described for the first time for the Millettia genus.

scholarly journals 177 Saponins, Including 11 New Compounds in Wild Ginseng Tentatively Identified via HPLC-IT-TOF-MSn, and Differences among Wild Ginseng, Ginseng under Forest, and Cultivated Ginseng

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3371
Author(s):  
Chao-Qun Wang ◽  
Li-Wei Yi ◽  
Lin Zhao ◽  
Yu-Zhen Zhou ◽  
Fang Guo ◽  
...  
Keyword(s):  
Natural Environment ◽  
Mountain Forest ◽  
Characteristic Peak ◽  
Chromatographic Fingerprints ◽  
New Compounds ◽  
First Time ◽  
Peak Pattern ◽  
Wild Ginseng

Wild ginseng (W-GS), ginseng under forest (F-GS, planted in mountain forest and growing in natural environment), and cultivated ginseng (C-GS) were compared via HPLC-DAD and HPLC-IT-TOF-MSn. A total of 199 saponins, including 16 potential new compounds, were tentatively identified from 100 mg W-GS (177 saponins in W-GS with 11 new compounds), F-GS (56 saponins with 1 new compound), and C-GS (60 saponins with 6 new compounds). There were 21 saponins detected from all the W-GS, F-GS, and C-GS. Fifty saponins were only detected from W-GS, including 23 saponins found in ginseng for the first time. Contents of ginsenosides Re (12.36–13.91 mg/g), Rh1 (7.46–7.65 mg/g), Rd (12.94–12.98 mg/g), and the total contents (50.52–55.51 mg/g) of Rg1, Re, Rf, Rb1, Rg2, Rh1, and Rd in W-GS were remarkably higher than those in F-GS (Re 1.22–3.50 mg/g, Rh1 0.15–1.49 mg/g, Rd 0.19–1.49 mg/g, total 5.69–18.74 mg/g), and C-GS (Re 0.30–3.45 mg/g, Rh1 0.05–3.42 mg/g, Rd 0.17–1.68 mg/g, total 2.99–19.55 mg/g). Contents of Re and Rf were significantly higher in F-GS than those in C-GS (p < 0.05). Using the contents of Re, Rf, or Rb1, approximately a half number of cultivated ginseng samples could be identified from ginseng under forest. Contents of Rg1, Re, Rg2, Rh1, as well as the total contents of the seven ginsenosides were highest in ginseng older than 15 years, middle–high in ginseng between 10 to 15 years old, and lowest in ginseng younger than 10 years. Contents of Rg1, Re, Rf, Rb1, Rg2, and the total of seven ginsenosides were significantly related to the growing ages of ginseng (p < 0.10). Similarities of chromatographic fingerprints to W-GS were significantly higher (p < 0.05) for F-GS (median: 0.824) than C-GS (median: 0.745). A characteristic peak pattern in fingerprint was also discovered for distinguishing three types of ginseng. Conclusively, wild ginseng was remarkably superior to ginseng under forest and cultivated ginseng, with ginseng under forest slightly closer to wild ginseng than cultivated ginseng. The differences among wild ginseng, ginseng under forest, and cultivated ginseng in saponin compositions and contents of ginsenosides were mainly attributed to their growing ages.

scholarly journals Fusarins G–L with Inhibition of NO in RAW264.7 from Marine-Derived Fungus Fusarium solani 7227

Marine Drugs ◽  
2021 ◽  
Vol 19 (6) ◽  
pp. 305
Author(s):  
Guangyuan Luo ◽  
Li Zheng ◽  
Qilin Wu ◽  
Senhua Chen ◽  
Jing Li ◽  
...  
Keyword(s):  
Fusarium Solani ◽  
2D Nmr ◽  
Inflammatory Activity ◽  
Raw264.7 Cells ◽  
Spectroscopic Methods ◽  
X Ray ◽  
X Ray Crystallography ◽  
Structure Activity ◽  
Ic50 Values ◽  
New Compounds

Six new fusarin derivatives, fusarins G–L (1–6), together with five known compounds (5–11) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 5–11 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 μM. The structure–activity relationships of the fusarins are discussed herein.

scholarly journals 21,28-Epoxy-18β,21β-Dihydroxbaccharan-3-one and Other Terpenoids from the Liverwort Lepidozia Chordulifera T. Taylor

2008 ◽  
Vol 3 (11) ◽  
pp. 1934578X0800301
Author(s):  
Hildegard Zapp ◽  
Kerstin Orth ◽  
Josef Zapp ◽  
Joseph D. Connolly ◽  
Hans Becker
Keyword(s):  
Ursolic Acid ◽  
Betulinic Acid ◽  
Spectroscopic Properties ◽  
Betulonic Acid ◽  
Side Chain

A new triterpenoid, 21,28-epoxy-18β,21β-dihydroxybaccharan-3-one (1), with a spiro-hemiketal side-chain, has been isolated from the liverwort Lepidozia chordulifera. The plant also yielded (6S*, 7S*)-3-norhimachal-1-en-3-one (3), an epimer of a known norhimachalane, the rare 3β-hydroxy-22,23,24,25,26,27-hexanordammaran-20-one and the triterpenoids shoreic acid, taraxerol, betulinic acid, betulonic acid and ursolic acid. Their structures have been assigned on the basis of their spectroscopic properties.

scholarly journals Phenolic Constituents of Knautia arvensis Aerial Parts

2011 ◽  
Vol 6 (11) ◽  
pp. 1934578X1100601 ◽  
Author(s):  
Jaroslaw Moldoch ◽  
Barbara Szajwaj ◽  
Milena Masullo ◽  
Lukasz Pecio ◽  
Wieslaw Oleszek ◽  
...  
Keyword(s):  
Chlorogenic Acid ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Flavone Glycoside ◽  
Aerial Parts ◽  
Dicaffeoylquinic Acid ◽  
Phenolic Constituents ◽  
First Time

A new C-6 flavone glycoside (6), together with seven known compounds, cryptochlorogenic acid (1), chlorogenic acid (2), 2- O- trans-caffeoylhydrocitric acid (3), isovitexin 7-β-D-glucopyranoside (4), 7,4′-dihydroxy-5-methoxyflavone-6- C-β-D-glucopyranoside (5), 3,5- O-dicaffeoylquinic acid (7) and 4,5- O-dicaffeoylquinic acid (8), were isolated from the aerial parts of Knautia arvensis. Their structures were elucidated by extensive spectroscopic methods including 1D- (1H, 13C and TOCSY) and 2D-NMR (DQF-COSY, HSQC, HMBC) experiments, as well as ESIMS analysis. Compounds 1, 3-5 and 8 are reported for the first time in Knautia arvensis.

Flavon- and Flavonolglycosides from Achillea pannonica Scheele

2001 ◽  
Vol 56 (7-8) ◽  
pp. 521-525 ◽  
Author(s):  
Denata Kasaj ◽  
Liselotte Krenn ◽  
Sonja Prinz ◽  
Antje Hüfner ◽  
Shi Shan Yuc ◽  
...  
Keyword(s):  
Methanolic Extract ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Spectroscopic Methods ◽  
Esi Ms ◽  
Aerial Parts ◽  
Nmr Techniques ◽  
Chemotaxonomic Study ◽  
First Time ◽  
C Nmr

The detailed investigation of a methanolic extract of aerial parts of Achillea pannonica SCHEELE. within a chemotaxonomic study led to the isolation of 6 flavonoid glycosides. Besides rutin, apigenin-7-O-glucopyranoside, luteolin-7-O-glucopyranoside, apigenin-7-O-rutinoside and acacetin-7-O-rutinoside, an unusual flavondiglucoside was isolated. Its structure was established by UV, 1HNMR and 13C NMR spectroscopic methods including 2D-NMR techniques and ESI-MS as luteolin-7,4′-O-β-diglucoside. This substance is reported for the first time in the genus Achillea. Chemotaxonomic aspects are discussed briefly

Chemical components of the rhizomes of Drynaria fortunei (KUNZE) J. Sm. (polypodiaceae) in Vietnam

2011 ◽  
Vol 76 (9) ◽  
pp. 1133-1139 ◽  
Author(s):  
Pham Thi Nhat Trinh ◽  
Nguyen Cong Hao ◽  
Phan Thanh Thao ◽  
Le Tien Dung
Keyword(s):  
Data Analysis ◽  
Spectral Data ◽  
Phenolic Acid ◽  
Ethanol Extract ◽  
Chemical Components ◽  
Spectroscopic Methods ◽  
Phenylpropanoid Glycoside ◽  
Spectral Data Analysis ◽  
First Time

From the ethanol extract of Drynaria fortunei (KUNZE) J. Sm., a new phenylpropanoid glycoside, fortunamide (1), was isolated and characterized by spectroscopic methods. Together with a new glycoside, 9 known compounds, including three curcuminoids (2–4), two isoprenylated flavonoids (5, 6), two flavonoids (7, 8), one monoterpenoid (9) and one phenolic acid (10) were isolated and identified by spectral data analysis from the rhizomes of Drynaria fortunei (KUNZE) J. Sm. Eight of them were isolated from Drynaria fortunei (KUNZE) J. Sm. for the first time.

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