- Megastigmanes from the aerial part of Euphorbia heterophylla
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Three unprecedented megastigmanes together with twelve known compounds were isolated from the aerial part of Euphorbia heterophylla. The structural elucidation was based on extensive uses of spectroscopic data. The absolute configuration assignment of 1 was based on NOESY correlations and comparison of the experimental and calculated ECD spectra. Selected isolates obtained in sufficient quantity were evaluated for their cytotoxic activity.
- Thapsut, Monnapa,Singha, Suriphon,Seeka, Chonticha,Sutthivaiyakit, Somyote
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- New Approach to the Synthesis of the Natural Product Aripuanin
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Aripuanin is a megastigmane that exists in the leaves of Ficus aripuanensis C.C. Berg (Moraceae). The present study describes a new approach to the total synthesis of this natural product starting from the readily available β-ionone. The proposed syntheti
- Lazaro, Aline S.,Ribeiro, Pedro H. Zana,Sairre, Mirela I.,Donate, Paulo M.
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supporting information
p. 1374 - 1378
(2015/05/26)
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- Inhibitory constituents from the aerial parts of Polygala tenuifolia on LPS-induced NO production in BV2 microglia cells in commemoration of Professor Xin-Sheng Yao's 80th Birthday
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Five new phenolic glycosides, tenuisides A-E (1-5), and a new megastigmane glycoside, tenuiside F (6), along with seventeen known compounds (7-23) were isolated from the aerial parts of Polygala tenuifolia Willd. Their structures were established by detailed analysis of NMR and HRESIMS spectroscopic data, and the absolute configurations of compounds 5 and 6 were determined by CD spectra and in-NMR-tube Mosher's method. The inhibitory effects of these compounds were evaluated on NO production in LPS-activated BV-2 microglia cells. Compound 17 showed the strongest activity, with an IC50 value of 7.4 μM, while compounds 1, 8, 14, and 18 showed the moderate activities, with IC50 values of 16.2-38.5 μM. And their primary structure-activity relationships (SARs) of NO inhibitory effects were also briefly discussed.
- Shi, Tian-Xing,Wang, Shu,Zeng, Ke-Wu,Tu, Peng-Fei,Jiang, Yong
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p. 5904 - 5908
(2013/10/22)
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- Chemical structures and hepatoprotective effects of constituents from the leaves of Salacia chinensis
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The methanolic extract from the leaves of Salacia chinensis collected in Thailand was found to show a protective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the methanolic extract, eight new glycosides, named foliachinenosides E, F, G, H, and I, and foliasalaciosides J, K and L, were isolated together with 26 known constituents. The structures of new glycosides were determined on the basis of physicochemical and chemical evidence. In addition, the hepatoprotective effects of the isolated compounds on D-galactosamine-induced cytotoxicity were examined. Among them, lignans, eleutheroside E2 and 7R,8S-dihydrodehydrodiconiferyl alcohol 4-O-β -D-glucopyranoside, were found to show the protective effects [inhibition (%) 41.4±3.6 (p0.01), 45.5±2.7 (p0.01) at 100 μM, respectively].
- Nakamura, Seikou,Zhang, Yi,Matsuda, Hisashi,Ninomiya, Kiyofumi,Muraoka, Osamu,Yoshikawa, Masayuki
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experimental part
p. 1020 - 1028
(2011/10/12)
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- Euodionosides A-G: Megastigmane glucosides from leaves of Euodia meliaefolia
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From a 1-BuOH-soluble fraction of the MeOH extract of leaves of Euodia meliaefolia, collected in Okinawa, seven megastigmane glucosides, named euodionosides A-G, were isolated together with three known megastgmane glucosides, and two aliphatic and three phenolic compounds. Their structures were elucidated through a combination of spectroscopic analyses and application of the modified Mosher's method.
- Yamamoto, Miwako,Akita, Takeyuki,Koyama, Yuka,Sueyoshi, Etsuko,Matsunami, Katsuyoshi,Otsuka, Hideaki,Shinzato, Takakazu,Takashima, Atsushi,Aramoto, Mitsunori,Takeda, Yoshio
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p. 1586 - 1596
(2008/09/21)
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- Stereochemistry of megastigmane glucosides from Glochidion zeylanicum and Alangium premnifolium
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From Glochidion zeylanicum, two megastigmane glucosides, 3- and 9-O-β-D-glucopyranosides of (3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol (1 and 2, respectively), were isolated. Their structures were different from those of kiwiionoside (3) and actinidioionoside (4), isolated from Actinidia chinensis and Actinidia polygama, respectively, in the stereochemistry at the 9-positions. Alangionosides E (5) and O (6), isolated from the leaves of Alangium premnifolium, are also megastigmane glucosides, and the latter is closely related to 1 and actinidioionoside (4). However, the absolute configurations of the 9-position remained to be determined. They were analyzed to be R by means of a modified Mosher's method. Alangionoside E (5) is identical with corchoionoside A in all aspects. The name of corchoionoside A must be retained thereafter.
- Otsuka, Hideaki,Hirata, Eiji,Shinzato, Takakazu,Takeda, Yoshio
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p. 763 - 768
(2007/10/03)
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