Occurrence of two epimeric alkaloids and metabolism compared with lycorine in Crinum latifolium

Ghosal, Shibnath; Unnikrishnan, Sankara G.; Singh, Suman Kumar

doi:10.1016/s0031-9422(00)98030-0

Cited by 18 publications

(5 citation statements)

References 7 publications

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“…The nonchiral benzannulated anhydrolycorinium chloride ( 3a , R = H) is effective in vivo against murine P-388 lymphocytic leukemia, and ungeremine ( 3b , R = OH) is active against some types of carcinoma . The indolic 3,4-dehydroanhydrolycorine ( 4a , X = H, H) and hippadine ( 4b , X = O) are both biosynthetically derived from 2- epi -lycorine, and 4b reversibly inhibits fertility in male rats. , The structurally related ABC tricyclic lycoricidine ( 5 ) exhibits in vitro antiviral activity against RNA-containing flaviviruses and bunyaviruses, as well as antitumoral activity against Ehrlich carcinoma 1 …”

Section: Introductionmentioning

confidence: 99%

Iodine(III)-Mediated Generation of Nitrogen-Tethered Orthoquinol Acetates for the Construction of Oxygenated Indole, Quinoline, and Phenanthridine Alkaloid Motifs

2002

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Functionalized indole and quinoline derivatives are conveniently prepared from nitrogen-tethered 2-methoxyphenols via phenyliodine(III) diacetate mediated oxidative acetoxylation, followed by a fluoride- or base-induced intramolecular nucleophilic addition reaction. This regioselective Michael-type addition step is further discussed in view of the rearrangement of orthoquinol acetate intermediates into paraquinol acetates that is sometimes observed in situ. Application of this methodology to the synthesis of a functionalized phenanthridine, and its potential for the construction of polyoxygenated lycorine-type alkaloid skeleta are here described.

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Section: Introductionmentioning

confidence: 99%

Iodine(III)-Mediated Generation of Nitrogen-Tethered Orthoquinol Acetates for the Construction of Oxygenated Indole, Quinoline, and Phenanthridine Alkaloid Motifs

2002

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“…The [M − H 2 O] + at m/z 269 is the base ion in 2‐ epi ‐lycorine. Ghosal et al, however, reports a MS spectrum for 2‐ epi ‐lycorine similar to that of lycorine 25 …”

Section: Resultsmentioning

confidence: 99%

GC–MS of some lycorine‐type Amaryllidaceae alkaloids

Berkov

Torras-Claveria²,

Viladomat³

et al. 2021

J Mass Spectrom

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The search for novel bioactive compounds and the identification of known ones in the plant kingdom are a challenge for the scientists working in different fields of plant science. In the recent years, mass spectrometry is the most frequently applied method for analysis of complex mixtures of plant metabolites. Twenty‐two alkaloids of different lycorine skeleton subtypes (with a Δ3,4 double bond, with a Δ4,11 double bond, with saturated rings C and D, and with aromatic ring C) were subjected to separation with gas chromatography and studied with electron impact mass spectrometry including single quadropole (GC‐EIMS), tandem mass (GC‐EIMS/MS) and high resolution mass (EI‐HRMS) detectors in order to determine their fragmentation pattern. The compounds showed excellent separation and specific MS fragmentation allowing structural determination. The GC–MS can be successfully applied for searching new and identification of known bioactive molecules, chemotaxonomical and chemoecological studies, among others, within the Amaryllidoideae subfamily.

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“…japonicum (17) was found to inhibit the cytopathic effect (ED 50 , 12.5 mg/mL) induced by HIV-1 infection of MT-4 cells with a high SI value (SI, 16.0). Crinum species are reported to contain phenanthridine alkaloids (Likhitwitayawuid et al, 1993;Razafimbelo et al, 1996;Ghosal et al, 1989;Bastida et al, 1995), which showed cytotoxicities against cancer cell lines (Likhitwitayawuid et al, 1993;Abd El Hafiz et al, 1991), and a moderate inhibition of RT activity (IC 50 = 72.5 mg/mL). Hence, we evaluated phenanthridine alkaloids, which form a plain structure, and had anti-HIV-1 replication and inhibition of RT activity by intercalation.…”

Section: Discussionmentioning

confidence: 99%

Inhibitory effects of Korean plants on HIV‐1 activities

Min

Kim

Tomiyama

et al. 2001

Phytotherapy Research

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In the search for novel anti-human immunodeficiency virus type 1 (anti-HIV-1) agents from natural sources, 49 MeOH extracts of Korean plants were screened for their inhibitory effects against RNA-dependent DNA polymerase (RT) and ribonuclease H (RNase H) activities of HIV-1 reverse transcriptase and HIV-1 protease, and anti-HIV-1 activity. Regarding the HIV-1 reverse transcriptase, Agrimonia pilosa (whole plant), Cornus kousa (stem and leaf), Limonium tetragonum (root) and Mallotus japonicus (stem) showed significant inhibitory activity on RT activity with 50% inhibitory activity (IC(50)) of 8.9, 6.3, 7.5 and 11.9 microg/mL, respectively, whereas Agrimonia pilosa was also active against RNase H activity (IC(50) = 98.4 microg/mL). Four plants, namely Agrimonia pilosa (whole plant), Atractylodes japonica (root), Clematis heracleifolia (whole plant) and Syneilesis palmata (whole plant), were appreciably active (<35%) against recombinant HIV-1 protease at a concentration of 100 microg/mL. Crinum asiaticum var. japonicum (root) showed significant anti-HIV-1 activity (ED(50) = 12.5 microg/mL) with a favourable SI value of 16.

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Occurrence of two epimeric alkaloids and metabolism compared with lycorine in Crinum latifolium

Cited by 18 publications

References 7 publications

Iodine(III)-Mediated Generation of Nitrogen-Tethered Orthoquinol Acetates for the Construction of Oxygenated Indole, Quinoline, and Phenanthridine Alkaloid Motifs

Iodine(III)-Mediated Generation of Nitrogen-Tethered Orthoquinol Acetates for the Construction of Oxygenated Indole, Quinoline, and Phenanthridine Alkaloid Motifs

GC–MS of some lycorine‐type Amaryllidaceae alkaloids

Inhibitory effects of Korean plants on HIV‐1 activities

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