Two Pairs of Enantiomeric Alkaloid Dimers from <i>Macleaya cordata</i>

Sai, Chunmei; Li, Dahong; Xue, Chunmei; Wang, Kaibo; Hu, Ping; Pei, Yue‐Hu; Bai, Jiao; Jing, Yongkui; Li, Zhan‐Lin; Hua, Hui‐Ming

doi:10.1021/acs.orglett.5b02044

Cited by 48 publications

(29 citation statements)

References 24 publications

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“…1 and 2. These compositions are summarized along with their retention time, theoretical mass, molecular formula, observed mass, error and MS/MS fragments combined with literature reports [15,16] and previously isolated alkaloids from M. cordata [7,9,17,18]. A total of 14 possible alkaloids have been identified, of which 9 are known.…”

Section: Analysis Of Alkaloids From Fruits Of M Microcarpa By Uhplc-mentioning

confidence: 97%

“…The method can provide high resolution and accuracy data, as well as abundant structural information such as high-resolution second-stage mass fragment ions [5,6]. This study aimed to rapidly and conveniently characterize alkaloids from M. microcarpa by UHPLC-Q-TOF-MS using accurate mass weight and characteristic fragment ions, furthermore separate and identify the main alkaloids by chromatographic and spectral techniques, test antitumor activity in vitro using the trypan blue method and MTT method reported previously [7], and antiangiogenic activity in vivo using transgenic zebrafish [8].…”

Section: Introductionmentioning

confidence: 99%

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Isolation and identification of alkaloids from Macleaya microcarpa by UHPLC–Q-TOF-MS and their cytotoxic activity in vitro, antiangiogenic activity in vivo

Sai

Wang

et al. 2020

BMC Chemistry

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Background: Extensive bioactivities of alkaloids from the genus Macleaya (Macleaya cordata (Willd.) R. Br. and Macleaya microcarpa (Maxim.) Fedde) have been widely reported, as well as more and more concerned from the scientific communities. However, systematic research on the phytochemical information of M. microcarpa is incomplete. The aim of this study was to rapidly and conveniently qualitative analyze alkaloids from M. microcarpa by ultra-performance liquid chromatography/quadrupole-time-of-fight mass spectrometry (UHPLC-Q-TOF-MS) using accurate mass weight and characteristic fragment ions, furthermore separate and identify the main alkaloids, test antitumor activity in vitro and antiangiogenic activity in vivo. Results: A total of 14 alkaloids from fruits of M. microcarpa were identified by UHPLC-Q-TOF-MS, including 5 protopines, 2 benzophenanthridines, 1 dimer, 1 dihydrobenzophenanthridines and 5 unknown structure compounds. Two major alkaloids were isolated by various column chromatographic methods. Their structures were determined by NMR data and related literatures. The two major alkaloids were evaluated for intro cytotoxic activities against HL-60, MCF-7, A-549, and in vivo antiangiogenic activity using transgenic zebrafish. Conclusions: Current qualitative method based on UHPLC-Q-TOF-MS technique provided a scientific basis for isolation, structural identification, and in vitro or in vivo pharmacological further study of alkaloids from M. microcarpa in the future.

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Section: Analysis Of Alkaloids From Fruits Of M Microcarpa By Uhplc-mentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Isolation and identification of alkaloids from Macleaya microcarpa by UHPLC–Q-TOF-MS and their cytotoxic activity in vitro, antiangiogenic activity in vivo

Sai

Wang

et al. 2020

BMC Chemistry

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“…It has been found that quaternary benzo[c]phenanthridine alkaloids such as sanguinarine ( 11 a ) could produce architecturally intriguing alkaloids coupled with protopine alkaloid (Figure ). In 2015, Hua and co‐workers have reported two pairs of enantiomeric alkaloid dimers, (±)‐macleayins A ( 15 a ) and B ( 15 c ), from the aerial parts of Macleaya cordata . These alkaloids represent.…”

Section: Structure Of Hybrid Benzo[c]phenanthridine Alkaloidsmentioning

confidence: 99%

Biosynthetic Relationships and Total Syntheses of Naturally Occurring Benzo[c]Phenanthridine Alkaloids

et al. 2019

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Benzo[c]phenanthridine alkaloids sharing a tetracyclic structural motif, are an important class of nitrogencontaining small molecules and are used for the treatment of a number of diseases. This review presents a comprehensive survey of the occurrence, chemistry, biochemistry, and biological activity of benzophenanthridine alkaloids. Synthetic approaches to a number of benzo[c]phenanthridine are disclosed in this Minireview. Biosynthetic Relationship of Tetrahydroisoquinoline and Benzo[c]phenanthridine AlkaloidsA plausible biogenetic connection between tetrahydroisoquinoline and benzo[c]phenanthridine alkaloids is shown in Scheme 1. Protopine (3 a) can undergo a demethylation followed by reductive amination to generate tetrahydroisoquinoline alkaloid, stylopine (2 a). The latter can further undergo an [a] Dr. oxidative CÀ N bond cleavage leading to intermediate aldehyde 4 a, which can form a new CÀ C bond (see, 4 c) assisted by in-situ prepared enamine. An elimination followed by oxidation leads to the synthesis of norsanguinarine (1 a).

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“…Totally, 62 dihydrobenzophenanthridine alkaloids ( 38–99 ) were found in Macleaya species. Most of them are monomeric but interestingly, Sai et al () have isolated five pairs of new enantiomeric natural alkaloids (±)‐macleayins A‐E ( 91–95 ) from the aerial parts of M. cordata .…”

Section: Phytochemistrymentioning

confidence: 99%

Medicinal plants of the genusMacleaya(Macleaya cordata,Macleaya microcarpa): A review of their phytochemistry, pharmacology, and toxicology

Lin

Liang

Huang

et al. 2017

Phytotherapy Research

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In the genus Macleaya, Macleaya cordata and Macleaya microcarpa have been recognized as traditional herbs that are primarily distributed in China, North America, and Europe and have a long history of medicinal usage. These herbs have been long valued and studied for detumescence, detoxification, and insecticidal effect. This review aims to provide comprehensive information on botanical, phytochemical, pharmacological, and toxicological studies on plants in the genus Macleaya. Plants from the genus of Macleaya provide a source of bioactive compounds, primarily alkaloids, with remarkable diversity and complex architectures, thereby having attracted attention from researchers. To date, 291 constituents have been identified and/or isolated from this group. These purified compounds and/or crude extract possess antitumor, anti-inflammatory, insecticidal, and antibacterial activities in addition to certain potential toxicities. Macleaya species hold potential for medicinal applications. However, despite the pharmacological studies on these plants, the mechanisms underlying the biological activities of active ingredients derived from Macleaya have not been thoroughly elucidated to date. Additionally, there is a need for research focusing on in vivo medical effects of Macleaya compounds and, eventually, for clinical trials.

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Two Pairs of Enantiomeric Alkaloid Dimers from Macleaya cordata

Cited by 48 publications

References 24 publications

Isolation and identification of alkaloids from Macleaya microcarpa by UHPLC–Q-TOF-MS and their cytotoxic activity in vitro, antiangiogenic activity in vivo

Isolation and identification of alkaloids from Macleaya microcarpa by UHPLC–Q-TOF-MS and their cytotoxic activity in vitro, antiangiogenic activity in vivo

Biosynthetic Relationships and Total Syntheses of Naturally Occurring Benzo[c]Phenanthridine Alkaloids

Medicinal plants of the genusMacleaya(Macleaya cordata,Macleaya microcarpa): A review of their phytochemistry, pharmacology, and toxicology

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