New monoterpene glycosides and phenolic compounds from Distylium racemosum and their inhibitory activity against ribonuclease H

Jeong Ah Kim; Seo Young Yang; Anthony Wamiru; James B. McMahon; Stuart F.J. Le Grice; John A. Beutler; Young Ho Kim

doi:10.1016/j.bmcl.2011.03.091

New monoterpene glycosides and phenolic compounds from Distylium racemosum and their inhibitory activity against ribonuclease H

Jeong Ah Kim, Seo Young Yang, Anthony Wamiru, James B. McMahon, Stuart F.J. Le Grice, John A. Beutler, Young Ho Kim

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

Two new monoterpene glycosides, distyloside A-B (1-2), and a new megastigmane glucoside, iso-dihydrodendranthemoside A (3) were isolated from twigs and leaves of Distylium racemosum, along with five known phenolic compounds (4-8). The structures were established via spectroscopic techniques and chemical transformations, and the absolute stereochemistry of 3 was determined by Mosher's esterification. A homogeneous fluorescence resonance energy transfer (FRET) quenching assay was used to determine the inhibitory activity of isolates (1-8) on the ribonuclease H enzymes from HIV-1, 2, human, and Escherichia coli. Among them, 6″-O-galloylsalidroside (6) showed potent inhibitory effects with an IC₅₀ value of 3.5 μM on HIV-2, and 1.7 μM on human RNase H, respectively.

Original language	English
Pages (from-to)	2840-2844
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	10
DOIs	https://doi.org/10.1016/j.bmcl.2011.03.091
State	Published - 15 May 2011

Keywords

Distylium racemosum
Megastigmane glucoside
Monoterpene glycosides
Ribonuclease H

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmcl.2011.03.091

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title = "New monoterpene glycosides and phenolic compounds from Distylium racemosum and their inhibitory activity against ribonuclease H",

abstract = "Two new monoterpene glycosides, distyloside A-B (1-2), and a new megastigmane glucoside, iso-dihydrodendranthemoside A (3) were isolated from twigs and leaves of Distylium racemosum, along with five known phenolic compounds (4-8). The structures were established via spectroscopic techniques and chemical transformations, and the absolute stereochemistry of 3 was determined by Mosher's esterification. A homogeneous fluorescence resonance energy transfer (FRET) quenching assay was used to determine the inhibitory activity of isolates (1-8) on the ribonuclease H enzymes from HIV-1, 2, human, and Escherichia coli. Among them, 6″-O-galloylsalidroside (6) showed potent inhibitory effects with an IC50 value of 3.5 μM on HIV-2, and 1.7 μM on human RNase H, respectively.",

keywords = "Distylium racemosum, Megastigmane glucoside, Monoterpene glycosides, Ribonuclease H",

author = "Kim, {Jeong Ah} and Yang, {Seo Young} and Anthony Wamiru and McMahon, {James B.} and {Le Grice}, {Stuart F.J.} and Beutler, {John A.} and Kim, {Young Ho}",

year = "2011",

month = may,

day = "15",

doi = "10.1016/j.bmcl.2011.03.091",

language = "English",

volume = "21",

pages = "2840--2844",

journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - New monoterpene glycosides and phenolic compounds from Distylium racemosum and their inhibitory activity against ribonuclease H

AU - Kim, Jeong Ah

AU - Yang, Seo Young

AU - Wamiru, Anthony

AU - McMahon, James B.

AU - Le Grice, Stuart F.J.

AU - Beutler, John A.

AU - Kim, Young Ho

PY - 2011/5/15

Y1 - 2011/5/15

N2 - Two new monoterpene glycosides, distyloside A-B (1-2), and a new megastigmane glucoside, iso-dihydrodendranthemoside A (3) were isolated from twigs and leaves of Distylium racemosum, along with five known phenolic compounds (4-8). The structures were established via spectroscopic techniques and chemical transformations, and the absolute stereochemistry of 3 was determined by Mosher's esterification. A homogeneous fluorescence resonance energy transfer (FRET) quenching assay was used to determine the inhibitory activity of isolates (1-8) on the ribonuclease H enzymes from HIV-1, 2, human, and Escherichia coli. Among them, 6″-O-galloylsalidroside (6) showed potent inhibitory effects with an IC50 value of 3.5 μM on HIV-2, and 1.7 μM on human RNase H, respectively.

AB - Two new monoterpene glycosides, distyloside A-B (1-2), and a new megastigmane glucoside, iso-dihydrodendranthemoside A (3) were isolated from twigs and leaves of Distylium racemosum, along with five known phenolic compounds (4-8). The structures were established via spectroscopic techniques and chemical transformations, and the absolute stereochemistry of 3 was determined by Mosher's esterification. A homogeneous fluorescence resonance energy transfer (FRET) quenching assay was used to determine the inhibitory activity of isolates (1-8) on the ribonuclease H enzymes from HIV-1, 2, human, and Escherichia coli. Among them, 6″-O-galloylsalidroside (6) showed potent inhibitory effects with an IC50 value of 3.5 μM on HIV-2, and 1.7 μM on human RNase H, respectively.

KW - Distylium racemosum

KW - Megastigmane glucoside

KW - Monoterpene glycosides

KW - Ribonuclease H

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U2 - 10.1016/j.bmcl.2011.03.091

DO - 10.1016/j.bmcl.2011.03.091

M3 - Article

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AN - SCOPUS:79955552011

SN - 0960-894X

VL - 21

SP - 2840

EP - 2844

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 10

ER -

New monoterpene glycosides and phenolic compounds from Distylium racemosum and their inhibitory activity against ribonuclease H

Abstract

Keywords

UN SDGs

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