Natural anti-HIV agents. Part 3: Litseaverticillols A-H, novel sesquiterpenes from Litsea verticillata

Hongjie ZHANG; Ghee Teng Tan; Vu Dinh Hoang; Nguyen Van Hung; Nguyen Manh Cuong; Djaja Doel Soejarto; John M. Pezzuto; Harry H.S. Fong

doi:10.1016/S0040-4020(02)01491-6

Natural anti-HIV agents. Part 3: Litseaverticillols A-H, novel sesquiterpenes from Litsea verticillata

Hongjie ZHANG, Ghee Teng Tan, Vu Dinh Hoang, Nguyen Van Hung, Nguyen Manh Cuong, Djaja Doel Soejarto, John M. Pezzuto, Harry H.S. Fong^*

^*Corresponding author for this work

School of Chinese Medicine

Research output: Contribution to journal › Journal article › peer-review

44 Citations (Scopus)

Abstract

Bioassay directed-fractionation led to the identification of litseaverticillols A-H (1-8) from the leaves and twigs of Litsea verticillata Hance. These new sesquiterpenes possess a unique skeleton that was recently designated as 'litseane'. The structures of these compounds were determined by spectroscopic means including 1D and 2D NMR data. Structural configurations were determined by ROESY experiments. Mosher ester reactions and optical rotation measurements established the sesquiterpenes 1-8 as racemates. Isolates 1-8 inhibited HIV-1 replication in HOG.R5 cells with IC₅₀ values ranging from 2 to 15μg/ml (8-58μM) while affecting the growth of HOG.R5 at concentrations 2-3-fold higher. Based on this data, structure-activity relationships can be discerned, suggesting compounds of this class are good candidates for analog production.

Original language	English
Pages (from-to)	141-148
Number of pages	8
Journal	Tetrahedron
Volume	59
Issue number	2
DOIs	https://doi.org/10.1016/S0040-4020(02)01491-6
Publication status	Published - 6 Jan 2003

Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

User-Defined Keywords

Anti-HIV activity
Bioassay-directed fractionation
Lauraceae
Litsea verticillata
Litseane
Litseaverticillols A-H
Sesquiterpenes

UN SDGs

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

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10.1016/S0040-4020(02)01491-6

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title = "Natural anti-HIV agents. Part 3: Litseaverticillols A-H, novel sesquiterpenes from Litsea verticillata",

abstract = "Bioassay directed-fractionation led to the identification of litseaverticillols A-H (1-8) from the leaves and twigs of Litsea verticillata Hance. These new sesquiterpenes possess a unique skeleton that was recently designated as 'litseane'. The structures of these compounds were determined by spectroscopic means including 1D and 2D NMR data. Structural configurations were determined by ROESY experiments. Mosher ester reactions and optical rotation measurements established the sesquiterpenes 1-8 as racemates. Isolates 1-8 inhibited HIV-1 replication in HOG.R5 cells with IC50 values ranging from 2 to 15μg/ml (8-58μM) while affecting the growth of HOG.R5 at concentrations 2-3-fold higher. Based on this data, structure-activity relationships can be discerned, suggesting compounds of this class are good candidates for analog production.",

keywords = "Anti-HIV activity, Bioassay-directed fractionation, Lauraceae, Litsea verticillata, Litseane, Litseaverticillols A-H, Sesquiterpenes",

author = "Hongjie ZHANG and Tan, {Ghee Teng} and Hoang, {Vu Dinh} and Hung, {Nguyen Van} and Cuong, {Nguyen Manh} and Soejarto, {Djaja Doel} and Pezzuto, {John M.} and Fong, {Harry H.S.}",

note = "Funding Information: All work involving plant sample collection, taxonomic identification, bioassay-guided chemical isolation, and structure elucidation in connection with this paper were carried out under a grant administered by the Fogarty International Center, NIH (Grant 1 UO1-TW01015-01), as part of an International Cooperative Biodiversity Group (ICBG) program. The authors are grateful to the Research Resources Center, University of Illinois at Chicago for access to the Bruker DRX 500 MHz instrument, and to the Center Research Group of the College of Pharmacy, University of Illinois at Chicago for the acquisition of MS data. The authors also wish to acknowledge the AIDS Research and Reference Reagent Program, NIAID, NIH for the supply of reagents critical to this study.",

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T2 - Litseaverticillols A-H, novel sesquiterpenes from Litsea verticillata

AU - ZHANG, Hongjie

AU - Tan, Ghee Teng

AU - Hoang, Vu Dinh

AU - Hung, Nguyen Van

AU - Cuong, Nguyen Manh

AU - Soejarto, Djaja Doel

AU - Pezzuto, John M.

AU - Fong, Harry H.S.

N1 - Funding Information: All work involving plant sample collection, taxonomic identification, bioassay-guided chemical isolation, and structure elucidation in connection with this paper were carried out under a grant administered by the Fogarty International Center, NIH (Grant 1 UO1-TW01015-01), as part of an International Cooperative Biodiversity Group (ICBG) program. The authors are grateful to the Research Resources Center, University of Illinois at Chicago for access to the Bruker DRX 500 MHz instrument, and to the Center Research Group of the College of Pharmacy, University of Illinois at Chicago for the acquisition of MS data. The authors also wish to acknowledge the AIDS Research and Reference Reagent Program, NIAID, NIH for the supply of reagents critical to this study.

PY - 2003/1/6

Y1 - 2003/1/6

N2 - Bioassay directed-fractionation led to the identification of litseaverticillols A-H (1-8) from the leaves and twigs of Litsea verticillata Hance. These new sesquiterpenes possess a unique skeleton that was recently designated as 'litseane'. The structures of these compounds were determined by spectroscopic means including 1D and 2D NMR data. Structural configurations were determined by ROESY experiments. Mosher ester reactions and optical rotation measurements established the sesquiterpenes 1-8 as racemates. Isolates 1-8 inhibited HIV-1 replication in HOG.R5 cells with IC50 values ranging from 2 to 15μg/ml (8-58μM) while affecting the growth of HOG.R5 at concentrations 2-3-fold higher. Based on this data, structure-activity relationships can be discerned, suggesting compounds of this class are good candidates for analog production.

AB - Bioassay directed-fractionation led to the identification of litseaverticillols A-H (1-8) from the leaves and twigs of Litsea verticillata Hance. These new sesquiterpenes possess a unique skeleton that was recently designated as 'litseane'. The structures of these compounds were determined by spectroscopic means including 1D and 2D NMR data. Structural configurations were determined by ROESY experiments. Mosher ester reactions and optical rotation measurements established the sesquiterpenes 1-8 as racemates. Isolates 1-8 inhibited HIV-1 replication in HOG.R5 cells with IC50 values ranging from 2 to 15μg/ml (8-58μM) while affecting the growth of HOG.R5 at concentrations 2-3-fold higher. Based on this data, structure-activity relationships can be discerned, suggesting compounds of this class are good candidates for analog production.

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KW - Bioassay-directed fractionation

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KW - Litseaverticillols A-H

KW - Sesquiterpenes

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JO - Tetrahedron

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ER -

Natural anti-HIV agents. Part 3: Litseaverticillols A-H, novel sesquiterpenes from Litsea verticillata

Abstract

Scopus Subject Areas

User-Defined Keywords

UN SDGs

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