New sesquiterpenes from Litsea verticillata

Hongjie ZHANG; Ghee Teng Tan; Bernard D. Santarsiero; Andrew D. Mesecar; Nguyen Van Hung; Nguyen Manh Cuong; D. Doel Soejarto; John M. Pezzuto; Harry H.S. Fong

doi:10.1021/np020508a

New sesquiterpenes from Litsea verticillata

Hongjie ZHANG, Ghee Teng Tan, Bernard D. Santarsiero, Andrew D. Mesecar, Nguyen Van Hung, Nguyen Manh Cuong, D. Doel Soejarto, John M. Pezzuto, Harry H.S. Fong^*

^*Corresponding author for this work

School of Chinese Medicine

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

100 Citations (Scopus)

Abstract

Seven new sesquiterpenes, named litseagermacrane (1), 7-epi-eudesm-4(15)-ene-1α,6α-diol (2), 5-epi- eudesm-4(15)-ene-1β,6β-diol (4), litseahumulanes A (6) and B (7), and litseachromolaevanes A (11) and B (12), as well as the known compounds 7-epi-eudesm-4(15)-ene-1β,6β-diol (3), eudesm-4(15)-ene-1β,6α-diol (5), octahydro-4-hydroxy-3α-methyl-7-methylene-α-(1-methylethyl)- 1H-indene-1-methanol (8), 10-hydroxyl-15-oxo-α-cadinol (9), and aphanamol II (10), were isolated from an anti-HIV fraction of the leaves and twigs of Litsea verticillata Hance (Figure 1). Isolates 1, 4, and 12 were found to inhibit HIV-1 replication in a green fluorescent protein (GFP)-based reporter cell line (HOG.R5) with IC₅₀ values of 6.5 (27.5), 17.4 (73.1), and 28.0 (119.7) μg/mL (μM), respectively. The structures of these isolates were determined by spectral data including 1D and 2D NMR spectra. Compound 11 was confirmed by X-ray crystallographic analysis.

Original language	English
Pages (from-to)	609-615
Number of pages	7
Journal	Journal of Natural Products
Volume	66
Issue number	5
DOIs	https://doi.org/10.1021/np020508a
Publication status	Published - 1 May 2003

Scopus Subject Areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/np020508a

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title = "New sesquiterpenes from Litsea verticillata",

abstract = "Seven new sesquiterpenes, named litseagermacrane (1), 7-epi-eudesm-4(15)-ene-1α,6α-diol (2), 5-epi- eudesm-4(15)-ene-1β,6β-diol (4), litseahumulanes A (6) and B (7), and litseachromolaevanes A (11) and B (12), as well as the known compounds 7-epi-eudesm-4(15)-ene-1β,6β-diol (3), eudesm-4(15)-ene-1β,6α-diol (5), octahydro-4-hydroxy-3α-methyl-7-methylene-α-(1-methylethyl)- 1H-indene-1-methanol (8), 10-hydroxyl-15-oxo-α-cadinol (9), and aphanamol II (10), were isolated from an anti-HIV fraction of the leaves and twigs of Litsea verticillata Hance (Figure 1). Isolates 1, 4, and 12 were found to inhibit HIV-1 replication in a green fluorescent protein (GFP)-based reporter cell line (HOG.R5) with IC50 values of 6.5 (27.5), 17.4 (73.1), and 28.0 (119.7) μg/mL (μM), respectively. The structures of these isolates were determined by spectral data including 1D and 2D NMR spectra. Compound 11 was confirmed by X-ray crystallographic analysis.",

author = "Hongjie ZHANG and Tan, {Ghee Teng} and Santarsiero, {Bernard D.} and Mesecar, {Andrew D.} and {Van Hung}, Nguyen and Cuong, {Nguyen Manh} and Soejarto, {D. Doel} and Pezzuto, {John M.} and Fong, {Harry H.S.}",

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doi = "10.1021/np020508a",

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T1 - New sesquiterpenes from Litsea verticillata

AU - ZHANG, Hongjie

AU - Tan, Ghee Teng

AU - Santarsiero, Bernard D.

AU - Mesecar, Andrew D.

AU - Van Hung, Nguyen

AU - Cuong, Nguyen Manh

AU - Soejarto, D. Doel

AU - Pezzuto, John M.

AU - Fong, Harry H.S.

PY - 2003/5/1

Y1 - 2003/5/1

N2 - Seven new sesquiterpenes, named litseagermacrane (1), 7-epi-eudesm-4(15)-ene-1α,6α-diol (2), 5-epi- eudesm-4(15)-ene-1β,6β-diol (4), litseahumulanes A (6) and B (7), and litseachromolaevanes A (11) and B (12), as well as the known compounds 7-epi-eudesm-4(15)-ene-1β,6β-diol (3), eudesm-4(15)-ene-1β,6α-diol (5), octahydro-4-hydroxy-3α-methyl-7-methylene-α-(1-methylethyl)- 1H-indene-1-methanol (8), 10-hydroxyl-15-oxo-α-cadinol (9), and aphanamol II (10), were isolated from an anti-HIV fraction of the leaves and twigs of Litsea verticillata Hance (Figure 1). Isolates 1, 4, and 12 were found to inhibit HIV-1 replication in a green fluorescent protein (GFP)-based reporter cell line (HOG.R5) with IC50 values of 6.5 (27.5), 17.4 (73.1), and 28.0 (119.7) μg/mL (μM), respectively. The structures of these isolates were determined by spectral data including 1D and 2D NMR spectra. Compound 11 was confirmed by X-ray crystallographic analysis.

AB - Seven new sesquiterpenes, named litseagermacrane (1), 7-epi-eudesm-4(15)-ene-1α,6α-diol (2), 5-epi- eudesm-4(15)-ene-1β,6β-diol (4), litseahumulanes A (6) and B (7), and litseachromolaevanes A (11) and B (12), as well as the known compounds 7-epi-eudesm-4(15)-ene-1β,6β-diol (3), eudesm-4(15)-ene-1β,6α-diol (5), octahydro-4-hydroxy-3α-methyl-7-methylene-α-(1-methylethyl)- 1H-indene-1-methanol (8), 10-hydroxyl-15-oxo-α-cadinol (9), and aphanamol II (10), were isolated from an anti-HIV fraction of the leaves and twigs of Litsea verticillata Hance (Figure 1). Isolates 1, 4, and 12 were found to inhibit HIV-1 replication in a green fluorescent protein (GFP)-based reporter cell line (HOG.R5) with IC50 values of 6.5 (27.5), 17.4 (73.1), and 28.0 (119.7) μg/mL (μM), respectively. The structures of these isolates were determined by spectral data including 1D and 2D NMR spectra. Compound 11 was confirmed by X-ray crystallographic analysis.

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JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 5

ER -

New sesquiterpenes from Litsea verticillata

Abstract

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