Chemistry of Myzodendraceae, I. Myzodendrone, a New Phenylbutanone of Myzodendron punctulatum

Reyes, Adelfo; Muñoz, Manuel; Garcia, H.; Cox, Christopher D.

doi:10.1021/np50044a021

Cited by 10 publications

(8 citation statements)

References 1 publication

(1 reference statement)

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“…side (17, 0.00008%), 20) eugenyl vicianoside (18,0.00096%), 21) 2,6-dimethoxy-4-(2-propenyl)phenol 6-O-b -D-glucopyranosyl-b-D-glucopyranoside (19, 0.00011%), 22) coniferin (20, 0.00024%), 23) syringin (21, 0.0032%), 24) cis-syringin (22, 0.00024%), 25) dihydrosyringin (23, 0.00024%), 26) trans-psinapoyl-b-D-glucopyranoside (24, 0.00068%), 27) (E)-coumaroyl-1-O-b-D-glucopyranoside (25, 0.00026%), 28) 1-[(2Z)-3-(4-hydroxyphenyl)-2-propenoate]-b -D-glucopyranoside (26, 0.00005%), 28) myzodendrone (27, 0.00024%), 29,30) hovetrichoside A (28, 0.00010%), 31) 4,7,9-trihydroxy-3,3Ј-dimethoxy-8-O-4Ј-neolignan-9Ј-O-b -D-glucopyranoside[7S, 8R-erythro form] (29, 0.00019%), 32) syringaresinol mono-b-D-glucopyranoside (30, 0.00049%), 33) eleutheroside E 2 (31, 0.00017%), 34) 7R,8S-dihydrodehydrodiconiferyl alcohol 4-Ob-D-glucopyranoside (32, 0.00028%), 35) (2S)-2,3-O-di-(9,12, 15-octadecatrienoyl)-glyceryl-b -D-galactopyranoside (33, 0.0066%), 36) and 1,2-di-9,12,15-octadecatrienoyl-sn-glycerol (34, 0.00023%). 37) Structures of Foliachinenosides, E, F, G, H, and I, and Foliasalaciosides J, K, and L Foliachinenoside E (1) was obtained as a colorless amorphous powder with positive optical rotation ([a] D 27 ϩ9.8°in MeOH).…”

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confidence: 99%

Chemical Structures and Hepatoprotective Effects of Constituents from the Leaves of Salacia chinensis

Nakamura

Zhang

Matsuda

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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In the course of our characterization studies on bioactive constituents from Salacia species (Hippocrateaceae), [1][2][3][4][5][6] we have reported the isolation and absolute stereostructure elucidation of 13 megastigmane glycosides, 7 phenolic glycosides, and 11 triterpenes from the leaves of Salacia chinensis collected in Thailand together with 40 known constituents. 7-11)As a continuning study on the leaves of Salacia chinensis, the methanolic (MeOH) extract was found to show a protective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the MeOH 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. Furthermore, we examined the hepatoprotective effects of the isolated compounds on D-galactosamine-induced cytotoxicity. In this paper, we describe the isolation and structure elucidation of the new constituents (1-8) and the hepatoprotective effects of isolated compounds from the leaves of Salacia chinensis.The dried leaves of S. chinensis, which were collected at Nakhon Si Thammarat province, Thailand, were finely cut and extracted with MeOH to furnish a MeOH extract (13.0%). The MeOH extract was partitioned into an EtOAc-H 2 O (1 : 1, v/v) mixture to furnish an EtOAc-soluble fraction (4.1%) and an aqueous phase. The aqueous phase was further extracted with n-BuOH to give an n-BuOH-soluble fraction (2.4%) and a H 2 O-soluble fraction (6.6%). The n-BuOH-soluble fraction was subjected to Diaion HP-20 column chromatography (H 2 O→MeOH) to give the water-and MeOHeluted fractions as previously reported.7) The EtOAc-soluble fraction and the MeOH-eluted fraction were respectively subjected to normal-and reversed-phase silica gel column chromatographies, and finally HPLC to give eight new compounds, foliachinenosides E (1, 0.00009%), F (2, 0.00013%), G (3, 0.00017%), H (4, 0.00048%), and I (5, 0.0018%), and foliasalaciosides J (6, 0.00017%), K (7, 0.00016%), and L (8, 0.00007%), together with 26 known compounds, 3-methyl-2-but-2-en-1-ol 6-O-a-L-arabinopyranosyl-b-D-glucopyranoside (9, 0.0017%), 12) (3Z)-3-hexen-1-ol 6-O-a-L-arabinopyranosyl-b-D-glucopyranoside (10, 0.0014%), 13) 2,4,6-trimethoxyphenol 1-O-b-D-glucopyranoside (11, 0.00016%), 14) benzyl alcohol b-D-glucopyranoside (12, 0.00003%), 15) benzyl alco- Yamashina-ku, Kyoto 607-8412, Japan: and b Pharmaceutical Research and Technology Institute, Kinki University; 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. Received April 27, 2011; accepted May 26, 2011; published

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confidence: 99%

Chemical Structures and Hepatoprotective Effects of Constituents from the Leaves of Salacia chinensis

Nakamura

Zhang

Matsuda

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Subfraction 6-8 (n-hexane/DCM 1:1) (73 mg) afforded pure myzodendrone (2, 26 mg) after repetitive CC over Sephadex LH-20. It was identified by spectroscopic means as well as by comparison of spectroscopic data with those reported in the literature (Reyes et al, 1986;Pabst et al, 1990). .4 (C-4″), 62.4 (C-6″), 45.3 (C-3), 29.9 (C-4), 29.5 (C-1).…”

Section: Introductionmentioning

confidence: 77%

“…Chromatographic separations were achieved by Misodendrum punctulatum B. et S. (Myzodendraceae) is an important hemiparasitic shrublet that preferentially lives on Fagaceae such as andean Nothofagus spp., commonly found in the south of Argentina and Chile. Misodendrum punctulatum was previously investigated under the name of Myzodendron punctulatum, as a result of this study the phenolic glycoside myzodendrone was isolated together with other known compounds (Reyes et al, 1986). As part of a continuing program aimed to study the antioxidant potential of South vacuum-liquid chromatography (VLC) and column chromatography (CC) using silica gel 60 (70-230 µm) (Merck, USA), or Sephadex LH-20 (Pharmacia, Sweden).…”

Section: Methodsmentioning

confidence: 99%

“…Free radical scavenging activity was concentrated in the two final fractions. After further purification, the radical scavenger metabolites were identified and their chemical structure confirmed by spectral analysis ( 1 H-NMR and FABMS) as catechin (1) and myzodendrone (2), the latter was previously isolated from M. punctulatum (Reyes et al, 1986) and from Rubus idaeus, raspberry fruit (Pabst et al, 1990). Both catechin (1) and myzodendrone (2), together with a group of synthetic related phenols (Fig.…”

Section: Peroxyl Radical Scavenging Activitymentioning

confidence: 99%

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Antioxidant and free radical scavenging activities ofMisodendrum punctulatum, myzodendrone and structurally related phenols

Desmarchelier¹,

Pacciaroni²,

Abate-Daga³

et al. 2005

Phytother. Res.

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The peroxyl radical scavenging activity of a dry methanol extract of Misodendrum punctulatum was determined by means of luminol-enhanced chemiluminescence assay, allowing to calculate the total reactive antioxidant potential (TRAP) index equal to 239 +/- 26 microm, expressed in Trolox equivalents. The flavan-3-ol catechin (1) and the phenylbutanone derivative myzodendrone (2) were identified through assay-guided fractionation as active metabolites present in the extract, and their structures were elucidated by chemical and spectroscopic analysis. Three other structurally related synthetic phenols, dehydrozingerone (3), zingerone (4) and myzodendrone aglycone (5), were also analysed using this method. Compounds 1 and 2 were highly effective as free radical scavengers (TRAP = 1257 microm and 1018 microm, respectively) when compared with Trolox (TRAP = 144 microm), used as a standard. Compounds 3 and 5 were also active showing TRAP values of 229 microm and 219 microm, respectively, similarly to that observed for the dry extract. On the other hand, 4 was inactive. Catechin (1) also reduced the production of thiobarbituric acid reactive substances (TBARS) in rat liver homogenates, with IC50 = 26 microg/mL, superior to that obtained for Trolox, IC50 = 73 microg/mL. Compounds 2 and 5 showed IC50 values > 1000 microg/mL, while no activity could be observed for 3, 4, or the extract.

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“…Compound 4 had a molecular formula C 33 H 36 O 11 , as deduced from HR-FABMS. Its 1 H NMR spectrum was similar to that of 1, except for the presence of additional signals corresponding to a cinnamoyl moiety, which was attached to the 2-positon of a xylopyranosyl moiety, as indicated by the downfield shifted H-2''' signal, [11,12]. Compounds 6-10 were flavonoids and identified as quercetin (6) [13], and rhamnetin-3-O-α-rhamnoside (10) [16], respectively.…”

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confidence: 88%

Chemical Constituents from Alnus formosana Burk. II. Polar Constituents from the Leaves

Lee

Chen

et al. 2006

Natural Product Communications

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This study was aimed to explore the n-BuOH soluble constituents of the leaves of Alnus formosana Burk. A total of 13 compounds were isolated and characterized. Of these, 2'''-cinnamoyloregonin is a new diaryl heptanoid glycoside. Ten of the remaining twelve known compounds, i.e. platyphylloside, aceroside VII, myzodendrone, quercetin, kaempferol-3-Orhamnoside, quercetin-3-O-rhamnoside, quercetin-3-O-glucoside, rhamnetin-3-O-rhamnoside, inositol, and shikimic acid, are reported for the first time for an Alnus species. The structures were characterized by spectral analysis.

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Chemistry of Myzodendraceae, I. Myzodendrone, a New Phenylbutanone of Myzodendron punctulatum

Cited by 10 publications

References 1 publication

Chemical Structures and Hepatoprotective Effects of Constituents from the Leaves of Salacia chinensis

Chemical Structures and Hepatoprotective Effects of Constituents from the Leaves of Salacia chinensis

Antioxidant and free radical scavenging activities ofMisodendrum punctulatum, myzodendrone and structurally related phenols

Chemical Constituents from Alnus formosana Burk. II. Polar Constituents from the Leaves

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