New Naphthalenyl Glucosides from the Roots of <i>Juglans mandshurica</i>

Joe, Yoon-Ki; Son, Jong‐Keun; Park, Sung-Hee; Lee, In-Ja; Moon, Dong-Chul

doi:10.1021/np9600356

Cited by 34 publications

(10 citation statements)

References 9 publications

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“…Its fresh rejuvenated fruit, commonly called "Qing Long Yi", has been used as a folk medicine for treatment of cancer and dermatosis and as an anodyne to relieve aches in China. Although phytochemical analyses were extensively carried out on not only the root [1][2][3][4][5] but also the stem bark 6) of J. mandshurica, little chemical work appears to have been done on the chemical composition of its fresh rejuvenated fruit. To our best knowledge, only two naphthalene glucosides, 4-hydroxynaphthalenyl b-D-glucopyranoside and 4,8-dihydroxy-1-naphthalenyl b-D-glucopyranoside have been isolated from the fruit of J. mandshurica.…”

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confidence: 99%

New .ALPHA.-Tetralonyl Glucosides from the Fruit of Juglans mandshurica

Liu

Koike

et al. 2004

Chem. Pharm. Bull.

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Juglans mandshurica MAXIM. (Juglandaceae) is widely distributed throughout urban and rural areas in northeast of China. Its fresh rejuvenated fruit, commonly called "Qing Long Yi", has been used as a folk medicine for treatment of cancer and dermatosis and as an anodyne to relieve aches in China. Although phytochemical analyses were extensively carried out on not only the root [1][2][3][4][5] but also the stem bark 6) of J. mandshurica, little chemical work appears to have been done on the chemical composition of its fresh rejuvenated fruit. To our best knowledge, only two naphthalene glucosides, 4-hydroxynaphthalenyl b-D-glucopyranoside and 4,8-dihydroxy-1-naphthalenyl b-D-glucopyranoside have been isolated from the fruit of J. mandshurica.7) The medicinal uses of "Qing Long Yi" prompted us to investigate its chemical constituents, resulting in the isolation of five new atetralonyl glucosides (1-5). This paper deals with the isolation and structural elucidation of the new compounds on the basis of spectroscopic analysis, including two-dimensional NMR spectroscopic data, and the results of hydrolysis. Results and DiscussionThe fresh rejuvenated fruit of J. mandshurica, which was collected in a mountain area of Heilongjiang Province, China, was decocted twice with water and extracted with hexane, EtOAc and n-BuOH, successively. The n-BuOH extract was chromatographed on a Diaion HP-20 column to give water and 40% methanol eluate fraction. The 40% methanol eluate fraction was chromatographed on an ODS column, and subjected to a combination of silica gel, Lobar RP-C 18 column chromatography, and HPLC. Then, five new compounds, named juglanosides A-E (1-5) were isolated, and their structures were characterized as follows.Juglanoside A (1) was isolated as an amorphous powder. Its molecular formula was determined to be C 16 H 20 O 7 by high-resolution (HR)-FAB-MS. On acid hydrolysis, 1 afforded D-glucose as a component sugar, which was identified by GLC analysis of its trimethylsilyl thiazolidine derivative. The 1 H-NMR spectrum of 1 showed a set of proton signals due to two methylenes at d 3.04 (1H, ddd, Jϭ17.8, 9.5, 4.8 Hz) and 2. 60 (1H, ddd, Jϭ17.8, 6.7, 4.8 Hz), and 2. 44 (1H, dddd, Jϭ13.3, 9.5, 4.8, 3.4 Hz) and 2.36 (1H, dddd, Jϭ13.3, 6.7, 6.2, 4.8 Hz), and an oxymethylene at d 5.10 (1H, dd, Jϭ6.2, 3.4 Hz). Moreover, the 13 C-NMR spectrum, in combination with distortionless enhancement by polarization transfer (DEPT) and Five new a a-tetralonyl glucosides, juglanosides A-E (1-5) were isolated from the fresh rejuvenated fruit of Juglans mandshurica. Their structures were elucidated as (4S)-4-hydroxy-a a-tetralone 4-O-b b-D-glucopyranoside (1), (4S)-4,5-dihydroxy-a a-tetralone 4-O-b b-D-glucopyranoside (2), (4S)-4,6-dihydroxy-a a-tetralone 4-O-b b-D-glucopyranoside (3), (4S)-4,5,8-trihydroxy-a a-tetralone 4-O-b b-D-glucopyranoside (4), and (4S)-4,5,8-trihydroxy-a

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confidence: 99%

New .ALPHA.-Tetralonyl Glucosides from the Fruit of Juglans mandshurica

Liu

Koike

et al. 2004

Chem. Pharm. Bull.

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“…mandshurica has been used as a folk medicine for treatment of cancer in Korea. 18) Several naphthoquinones, naph-thalenyl glucopyranosides, a-tetralonyl glucopyranosides and diarylheptanoyl glucopyranosides have been isolated from this plant [18][19][20] and these compounds have been shown to display cytotoxicity to human colon and lung carcinoma. 20) In this paper, we describe the characterization of compounds isolated from the stem-bark of this plant and their inhibitory potencies against HIV-1 RT and RNase H activities.…”

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confidence: 99%

Inhibition of Human Immunodeficiency Virus Type 1 Reverse Transcriptase and Ribonuclease H Activities by Constituents of Juglans mandshurica.

Min¹,

Nakamura²,

Miyashiro³

et al. 2000

CHEMICAL & PHARMACEUTICAL BULLETIN

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From the stem-bark of Juglans mandshurica, two new naphthalenyl glucopyranosides, 1,4,8-trihydroxynaphthalene 1-O-[alpha-L-arabinofuranosyl-(1-->6)-beta-D-glucopyranoside] (1) and 1,4,8-trihydroxynaphthalene 1-O-beta-D-[6'-O-(3",5"-dihydroxy-4"-methoxybenzoyl)]glucopyranosi de (4), and two new alpha-tetralonyl glucopyranosides, 4 alpha,5,8-trihydroxy-alpha-tetralone 5-O-beta-D-[6'-O-(3",5"-dihydroxy-4"-methoxybenzoyl)]glucopyranosi de (7) and 4 alpha,5,8-trihydroxy-alpha-tetralone 5-O-beta-D-[6'-O-(3",4",5"-trihydroxybenzoyl)]glucopyranoside (8), were isolated together with three known naphthalenyl glucopyranosides (2, 3 and 5), one alpha-tetralonyl glucopyranoside (6), four flavonoids (9-12), and two galloyl glucopyranosides (13, 14). Amongst the isolated compounds, 1,2,6-trigalloylglucopyranose (13) and 1,2,3,6-tertagalloylglucopyranose (14) exhibited the most potent inhibition of reverse transcriptase (RT) activity with IC50 values of 0.067 and 0.040 microM, respectively, while the latter compound also inhibited ribonuclease H (RNase H) activity with an IC50 of 39 microM, comparable in potency to illimaquinone used as a positive control. 1,4,8-Trihydroxy-naphthalene 1-O-beta-D-glucopyranoside (2), 1,4,8-trihydroxynaphthalene 1-O-beta-D-[6'-O-(4"-hydroxy-3",5"-dimethoxybenzoyl)]glucopyranoside (3) and 8 showed moderate inhibition against both enzyme activities, and inhibitory potency of 2 against RNase H activity (IC50 = 156 microM) was slightly greater than that against the RT activity (IC50 = 290 microM). The inhibitory potencies of 4 alpha,5,8-trihydroxy-alpha-tetralone 5-O-beta-D-[6'-O-(4"-hydroxy-3",5"-dimethoxybenzoyl)] glucopyranoside (6), 7 and 8 against RT activity increased accompanied by an increase in the number of free hydroxyls on the galloyl residues, as represented by the IC50 values of > 500, 330 and 5.8 microM, respectively.

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“…For the criteria of MIM triggering EPI spectra acquisition, the three most intensive MIM transitions exceeding 2000 cps in each scan cycle were selected for EPI spectra acquisition, respectively. For identification of targeted naphthoquinones, MIM‐EPI with specified precursor ions were conducted based on the 36 different molecular weights of all reported 52 naphthoquinones including isomers from family Juglandaceae (Gupta et al ., ; Hirakawa et al ., ; Binder et al ., ; Wu et al ., ; Son, ; Joe et al ., ; Kim et al ., ; Lee et al ., ; Min et al ., ; Liu et al ., , ; Machida et al ., ; Li et al ., ; Liu et al ., ; Liu et al ., ; Yu et al ., ; Cardona and Dorough, ; Konda and Kawazu, ). Various scan methods using MIM‐EPI were explored to maximize the detection and identification of targeted and untargeted naphthoquinones.…”

Section: Methodsmentioning

confidence: 99%