Chemical Constituents of Heteroplexis micocephala

Eleven new compounds including two sesquiterpenes with an unusual 2,2,5,9-tetramethylbicyclo[6.3.0]undecane carbon skeleton (1 and 2), five phytane-type diterpene dilactones (3−7), an ent-clerodane diterpene dilactone (8), and three phenylpropenol esters (9−11), together with a diacylphenol (12) and...

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Published inJournal of natural products (Washington, D.C.) Vol. 72; no. 6; pp. 1184 - 1190
Main Authors Fan, Xiaona, Zi, Jiachen, Zhu, Chenggen, Xu, Wendong, Cheng, Wei, Yang, Sen, Guo, Ying, Shi, Jiangong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society and American Society of Pharmacognosy 26.06.2009
Amer Chemical Soc
American Society of Pharmacognosy
Subjects
Anti-HIV Agents
Anti-HIV Agents - chemistry
Anti-HIV Agents - isolation & purification
Anti-HIV Agents - pharmacology
antiviral properties
Asteraceae
Asteraceae - chemistry
Biological and medical sciences
cell lines
chemical structure
chemistry
Chemistry, Medicinal
cytotoxicity
Diterpenes
Diterpenes - chemistry
Diterpenes - isolation & purification
Diterpenes - pharmacology
diterpenoids
drug crops
drug effects
Drug Screening Assays, Antitumor
Drugs, Chinese Herbal
Drugs, Chinese Herbal - chemistry
Drugs, Chinese Herbal - isolation & purification
Drugs, Chinese Herbal - pharmacology
General pharmacology
herbal medicines
Heteroplexis micocephala
HIV-1
HIV-1 - drug effects
Human immunodeficiency virus 1
Humans
Inhibitory Concentration 50
isolation & purification
lactones
Life Sciences & Biomedicine
Medical sciences
medicinal plants
medicinal properties
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pharmacognosy. Homeopathy. Health food
pharmacology
Pharmacology & Pharmacy
Pharmacology. Drug treatments
plant extracts
Plant Sciences
Plants, Medicinal
Plants, Medicinal - chemistry
Science & Technology
Sesquiterpenes
Sesquiterpenes - chemistry
Sesquiterpenes - isolation & purification
Sesquiterpenes - pharmacology
sesquiterpenoids
virus replication
Asia
China
GLYCOSIDES
DITERPENOIDS
COLORIMETRIC ASSAY
BARK
HYDROXYACETOPHENONE
IMMUNODEFICIENCY-VIRUS TYPE-1
GAMMA-LACTONES
DERIVATIVES
TERPENOIDS
SESQUITERPENE LACTONES
Antineoplastic agent
Five membered ring
HIV-1 virus
Epimer
Ketol
Cytotoxicity
Compositae
Oxygen heterocycle
Medicinal plant
Ester
Ovary
Ketoether
Folk medicine
Dicotyledones
Sesquiterpenes
Angiospermae
Bicyclic compound
Antiviral
Inhibition
Secondary alcohol
Tumor cell
Human
Terpenoid
Ether
Aliphatic compound
Pharmacognosy
Retroviridae
Virus replication cycle
Lactone
Tetracyclic compound
Lentivirus
Ketone
In vitro
Biological activity
Virus
Cell line
Absolute configuration
Plant origin
Diterpene
Phenols
Isolation
Spermatophyta
Human immunodeficiency virus
Enone
Structural analysis
Online AccessGet full text
ISSN0163-3864
1520-6025
1520-6025
DOI10.1021/np900213w

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Abstract Eleven new compounds including two sesquiterpenes with an unusual 2,2,5,9-tetramethylbicyclo[6.3.0]undecane carbon skeleton (1 and 2), five phytane-type diterpene dilactones (3−7), an ent-clerodane diterpene dilactone (8), and three phenylpropenol esters (9−11), together with a diacylphenol (12) and 38 known compounds, have been isolated from an ethanolic extract of Heteroplexis micocephala. Their structures including absolute configurations were elucidated by spectroscopic and chemical analyses. In the in vitro assays, compound 6 showed a selective cytotoxic activity against A2780 with an IC50 value of 4.37 μM, while sinapyl diangelate (13) showed a potent activity inhibiting HIV-1 replication with an IC50 value of 4.04 μM.
AbstractList Eleven new compounds including two sesquiterpenes with an unusual 2,2,5,9-tetramethylbicyclo[6.3.0]undecane carbon skeleton (1 and 2), five phytane-type diterpene dilactones (3-7), an ent-clerodane diterpene dilactone (8), and three phenylpropenol esters (9-11), together with a diacylphenol (12) and 38 known compounds, have been isolated from an ethanolic extract of Heteroplexis micocephala. Their structures including absolute configurations were elucidated by spectroscopic and chemical analyses. In the in vitro assays, compound 6 showed a selective cytotoxic activity against A2780 with an IC50 value of 4.37 mu M, while sinapyl diangelate (13) showed a potent activity inhibiting HIV-1 replication with an IC50 value of 4.04 mu M.
Eleven new compounds including two sesquiterpenes with an unusual 2,2,5,9-tetramethylbicyclo[6.3.0]undecane carbon skeleton (1 and 2), five phytane-type diterpene dilactones (3-7), an ent-clerodane diterpene dilactone (8), and three phenylpropenol esters (9-11), together with a diacylphenol (12) and 38 known compounds, have been isolated from an ethanolic extract of Heteroplexis micocephala. Their structures including absolute configurations were elucidated by spectroscopic and chemical analyses. In the in vitro assays, compound 6 showed a selective cytotoxic activity against A2780 with an IC(50) value of 4.37 microM, while sinapyl diangelate (13) showed a potent activity inhibiting HIV-1 replication with an IC(50) value of 4.04 microM.
Eleven new compounds including two sesquiterpenes with an unusual 2,2,5,9-tetramethylbicyclo[6.3.0]undecane carbon skeleton (1 and 2), five phytane-type diterpene dilactones (3-7), an ent-clerodane diterpene dilactone (8), and three phenylpropenol esters (9-11), together with a diacylphenol (12) and 38 known compounds, have been isolated from an ethanolic extract of Heteroplexis micocephala. Their structures including absolute configurations were elucidated by spectroscopic and chemical analyses. In the in vitro assays, compound 6 showed a selective cytotoxic activity against A2780 with an IC(50) value of 4.37 microM, while sinapyl diangelate (13) showed a potent activity inhibiting HIV-1 replication with an IC(50) value of 4.04 microM.Eleven new compounds including two sesquiterpenes with an unusual 2,2,5,9-tetramethylbicyclo[6.3.0]undecane carbon skeleton (1 and 2), five phytane-type diterpene dilactones (3-7), an ent-clerodane diterpene dilactone (8), and three phenylpropenol esters (9-11), together with a diacylphenol (12) and 38 known compounds, have been isolated from an ethanolic extract of Heteroplexis micocephala. Their structures including absolute configurations were elucidated by spectroscopic and chemical analyses. In the in vitro assays, compound 6 showed a selective cytotoxic activity against A2780 with an IC(50) value of 4.37 microM, while sinapyl diangelate (13) showed a potent activity inhibiting HIV-1 replication with an IC(50) value of 4.04 microM.
Eleven new compounds including two sesquiterpenes with an unusual 2,2,5,9-tetramethylbicyclo[6.3.0]undecane carbon skeleton (1 and 2), five phytane-type diterpene dilactones (3−7), an ent-clerodane diterpene dilactone (8), and three phenylpropenol esters (9−11), together with a diacylphenol (12) and 38 known compounds, have been isolated from an ethanolic extract of Heteroplexis micocephala. Their structures including absolute configurations were elucidated by spectroscopic and chemical analyses. In the in vitro assays, compound 6 showed a selective cytotoxic activity against A2780 with an IC50 value of 4.37 μM, while sinapyl diangelate (13) showed a potent activity inhibiting HIV-1 replication with an IC50 value of 4.04 μM.
Author Zi, Jiachen
Guo, Ying
Fan, Xiaona
Cheng, Wei
Xu, Wendong
Yang, Sen
Zhu, Chenggen
Shi, Jiangong
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DocumentTitleAlternate Chemical Constituents of Heteroplexis micocephala
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Issue 6
Keywords GLYCOSIDES
DITERPENOIDS
COLORIMETRIC ASSAY
BARK
HYDROXYACETOPHENONE
IMMUNODEFICIENCY-VIRUS TYPE-1
GAMMA-LACTONES
DERIVATIVES
TERPENOIDS
SESQUITERPENE LACTONES
Antineoplastic agent
Five membered ring
HIV-1 virus
Epimer
Ketol
Cytotoxicity
Compositae
Oxygen heterocycle
Medicinal plant
Ester
Ovary
Ketoether
Folk medicine
Dicotyledones
Sesquiterpenes
Angiospermae
Bicyclic compound
Antiviral
Inhibition
Secondary alcohol
Tumor cell
Human
Terpenoid
Ether
Aliphatic compound
Pharmacognosy
Retroviridae
Virus replication cycle
Lactone
Tetracyclic compound
Lentivirus
Ketone
In vitro
Biological activity
Virus
Cell line
Absolute configuration
Plant origin
Diterpene
Phenols
Isolation
Spermatophyta
Human immunodeficiency virus
Enone
Structural analysis
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Snippet Eleven new compounds including two sesquiterpenes with an unusual 2,2,5,9-tetramethylbicyclo[6.3.0]undecane carbon skeleton (1 and 2), five phytane-type...
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SubjectTerms Anti-HIV Agents
Anti-HIV Agents - chemistry
Anti-HIV Agents - isolation & purification
Anti-HIV Agents - pharmacology
antiviral properties
Asteraceae
Asteraceae - chemistry
Biological and medical sciences
cell lines
chemical structure
chemistry
Chemistry, Medicinal
cytotoxicity
Diterpenes
Diterpenes - chemistry
Diterpenes - isolation & purification
Diterpenes - pharmacology
diterpenoids
drug crops
drug effects
Drug Screening Assays, Antitumor
Drugs, Chinese Herbal
Drugs, Chinese Herbal - chemistry
Drugs, Chinese Herbal - isolation & purification
Drugs, Chinese Herbal - pharmacology
General pharmacology
herbal medicines
Heteroplexis micocephala
HIV-1
HIV-1 - drug effects
Human immunodeficiency virus 1
Humans
Inhibitory Concentration 50
isolation & purification
lactones
Life Sciences & Biomedicine
Medical sciences
medicinal plants
medicinal properties
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pharmacognosy. Homeopathy. Health food
pharmacology
Pharmacology & Pharmacy
Pharmacology. Drug treatments
plant extracts
Plant Sciences
Plants, Medicinal
Plants, Medicinal - chemistry
Science & Technology
Sesquiterpenes
Sesquiterpenes - chemistry
Sesquiterpenes - isolation & purification
Sesquiterpenes - pharmacology
sesquiterpenoids
virus replication
Title Chemical Constituents of Heteroplexis micocephala
URI http://dx.doi.org/10.1021/np900213w
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https://www.ncbi.nlm.nih.gov/pubmed/19453174
https://www.proquest.com/docview/46359839
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https://www.proquest.com/docview/771910210
Volume 72
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