Two new protopines argemexicaines A and B and the anti-HIV alkaloid 6-acetonyldihydrochelerythrine from Formosan Argemone mexicana

Yuh Chwen Chang; Pei Wen Hsieh; Fang Rong Chang; Ru Rong Wu; Chih Chuang Liaw; Kuo Hsiung Lee; Yang Chang Wu

doi:10.1055/s-2003-37710

Two new protopines argemexicaines A and B and the anti-HIV alkaloid 6-acetonyldihydrochelerythrine from Formosan Argemone mexicana

Yuh Chwen Chang, Pei Wen Hsieh, Fang Rong Chang, Ru Rong Wu, Chih Chuang Liaw, Kuo Hsiung Lee, Yang Chang Wu^*

^*Corresponding author for this work

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

88 Scopus citations

Abstract

Two new protopine-type alkaloids, argemexicaine A (1) and argemexicaine B (2), along with thirteen known alkaloids, were isolated from MeOH extracts of Formosan Argernone mexicana L. (Papaveraceae). Physical and spectral analyses, particularly IR and thermo-modulated 1D and 2D NMR, were used to determine the transannular conformations of the isolated protopine-type alkaloids. The known benzo[c]phenanthridine (±)-6-acetonyldihydrochelerythrine (5) exhibited significant anti-HIV activity in H9 lymphocytes with EC₅₀ and TI (Therapeutic Index) values of 1.77 μg/mL and 14.6, respectively.

Original language	English
Pages (from-to)	148-152
Number of pages	5
Journal	Planta Medica
Volume	69
Issue number	2
DOIs	https://doi.org/10.1055/s-2003-37710
State	Published - 01 02 2003
Externally published	Yes

Keywords

(±)-6- acetonyldihydrochelerythrine
Anti-HIV activity
Argemexicaine A
Argemexicaine B
Argemone mexicana
Benzo[c]phenanthridine
Papaveraceae
Protopine

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10.1055/s-2003-37710

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title = "Two new protopines argemexicaines A and B and the anti-HIV alkaloid 6-acetonyldihydrochelerythrine from Formosan Argemone mexicana",

abstract = "Two new protopine-type alkaloids, argemexicaine A (1) and argemexicaine B (2), along with thirteen known alkaloids, were isolated from MeOH extracts of Formosan Argernone mexicana L. (Papaveraceae). Physical and spectral analyses, particularly IR and thermo-modulated 1D and 2D NMR, were used to determine the transannular conformations of the isolated protopine-type alkaloids. The known benzo[c]phenanthridine (±)-6-acetonyldihydrochelerythrine (5) exhibited significant anti-HIV activity in H9 lymphocytes with EC50 and TI (Therapeutic Index) values of 1.77 μg/mL and 14.6, respectively.",

keywords = "(±)-6- acetonyldihydrochelerythrine, Anti-HIV activity, Argemexicaine A, Argemexicaine B, Argemone mexicana, Benzo[c]phenanthridine, Papaveraceae, Protopine",

author = "Chang, \{Yuh Chwen\} and Hsieh, \{Pei Wen\} and Chang, \{Fang Rong\} and Wu, \{Ru Rong\} and Liaw, \{Chih Chuang\} and Lee, \{Kuo Hsiung\} and Wu, \{Yang Chang\}",

year = "2003",

month = feb,

day = "1",

doi = "10.1055/s-2003-37710",

language = "英语",

volume = "69",

pages = "148--152",

journal = "Planta Medica",

issn = "0032-0943",

publisher = "Georg Thieme Verlag",

number = "2",

}

TY - JOUR

T1 - Two new protopines argemexicaines A and B and the anti-HIV alkaloid 6-acetonyldihydrochelerythrine from Formosan Argemone mexicana

AU - Chang, Yuh Chwen

AU - Hsieh, Pei Wen

AU - Chang, Fang Rong

AU - Wu, Ru Rong

AU - Liaw, Chih Chuang

AU - Lee, Kuo Hsiung

AU - Wu, Yang Chang

PY - 2003/2/1

Y1 - 2003/2/1

N2 - Two new protopine-type alkaloids, argemexicaine A (1) and argemexicaine B (2), along with thirteen known alkaloids, were isolated from MeOH extracts of Formosan Argernone mexicana L. (Papaveraceae). Physical and spectral analyses, particularly IR and thermo-modulated 1D and 2D NMR, were used to determine the transannular conformations of the isolated protopine-type alkaloids. The known benzo[c]phenanthridine (±)-6-acetonyldihydrochelerythrine (5) exhibited significant anti-HIV activity in H9 lymphocytes with EC50 and TI (Therapeutic Index) values of 1.77 μg/mL and 14.6, respectively.

AB - Two new protopine-type alkaloids, argemexicaine A (1) and argemexicaine B (2), along with thirteen known alkaloids, were isolated from MeOH extracts of Formosan Argernone mexicana L. (Papaveraceae). Physical and spectral analyses, particularly IR and thermo-modulated 1D and 2D NMR, were used to determine the transannular conformations of the isolated protopine-type alkaloids. The known benzo[c]phenanthridine (±)-6-acetonyldihydrochelerythrine (5) exhibited significant anti-HIV activity in H9 lymphocytes with EC50 and TI (Therapeutic Index) values of 1.77 μg/mL and 14.6, respectively.

KW - (±)-6- acetonyldihydrochelerythrine

KW - Anti-HIV activity

KW - Argemexicaine A

KW - Argemexicaine B

KW - Argemone mexicana

KW - Benzo[c]phenanthridine

KW - Papaveraceae

KW - Protopine

UR - https://www.scopus.com/pages/publications/0037303055

U2 - 10.1055/s-2003-37710

DO - 10.1055/s-2003-37710

M3 - 文章

C2 - 12624820

AN - SCOPUS:0037303055

SN - 0032-0943

VL - 69

SP - 148

EP - 152

JO - Planta Medica

JF - Planta Medica

IS - 2

ER -

Two new protopines argemexicaines A and B and the anti-HIV alkaloid 6-acetonyldihydrochelerythrine from Formosan Argemone mexicana

Abstract

Keywords

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