Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana

Low, Yun‐Yee; Lim, Kuan‐Hon; Choo, Yeun‐Mun; Pang, Huey‐Shen; Etoh, Tadahiro; Hayashi, Masahiko; Komiyama, Kanki; Kam, Toh‐Seok

doi:10.1016/j.tetlet.2009.10.122

Cited by 29 publications

(15 citation statements)

References 33 publications

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“…Recently, Kam, Pang, Choo, and Komiyama () evaluated a total of 42 different types of bioactive alkaloids from Tabernaemontana divaricata with new ibogan (Conolabines A and B; 15 ) and vallesamine alkaloid (16) derivatives. Low et al () reported Lirofoline B (7) as a new pentacyclic indole alkaloid in its stem bark with a yield of 3.2 mg/kg. Another important member of this family, Catharanthus roseus , is reported to possess more than 130 alkaloids in different parts.…”

Section: Phytochemistrymentioning

confidence: 99%

Ethnopharmacology, phytochemistry, and biotechnological advances of family Apocynaceae: A review

Bhadane¹,

Patil²,

Maheshwari

et al. 2018

Phytotherapy Research

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The family Apocynaceae is one of the largest and important families in angiosperm. Several members of this family have medicinal properties and have been in the treatment of various ailments. Most of them are consumed as food by tribal people whereas a few plants are used as source of poison. Members of family Apocynaceae are rich in alkaloids, terpenoids, steroids, flavonoids, glycosides, simple phenols, lactones, and hydrocarbons. Other compounds such as sterols, lignans, sugars, lignans, and lactones have been isolated and systematically studied. Few studies have reported antioxidant, anti-inflammatory, antimicrobial, and cytotoxic activities of crude extracts as well as single compound(s) isolated from various members of the family Apocynaceae. Holarrhena antidysenterica, Rauvolfia serpentina, Carissa carandas, and Tabernaemontana divaricata are the extensively studied plants in this family. The present review provides a detailed outlook on ethnopharmacology, phytochemistry, and biological activities of selected members of this family. Moreover, it also covers the biotechnological advances used for large-scale production of bioactive compounds of therapeutic interest along with plant tissue culture-based approaches for conservation of this medicinally valuable family.

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Section: Phytochemistrymentioning

confidence: 99%

Ethnopharmacology, phytochemistry, and biotechnological advances of family Apocynaceae: A review

Bhadane¹,

Patil²,

Maheshwari

et al. 2018

Phytotherapy Research

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“…Similarly, as described for dihydropyridines,6 these intermediates are obvious candidates for Diels–Alder reactions, which would result in ring‐fused isoquinuclidines. The isoquinuclidine fragment is pharmaceutically interesting and is present in many biologically active natural products, such as ibogaine,7 dioscorine,8 and lirofoline B9 (Figure 2). Synthetic isoquinuclidines have also attracted attention as potential drugs, for example, compound 8 , which displays potent antimalarial activity 10…”

Section: Resultsmentioning

confidence: 99%

Four‐Component Assembly of Natural‐Product‐Like Ring‐Fused Isoquinuclidines

Sellstedt¹,

Dang²,

Prasad³

et al. 2013

Eur J Org Chem

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A four‐component reaction between formyl‐substituted 2‐pyridones, aldehydes, amines, and activated alkenes has been developed. The resulting products are ring‐fused natural‐product‐like isoquinuclidines. Three carbon–carbon bonds, two carbon–nitrogen bonds, and four or five stereocentres are formed in the reaction with overall product yields in the range 23–67 %. In most cases a single diastereomer was obtained. An intramolecular version of the reaction yielded analogues of the multi‐ring‐fused natural product catharanthine in a single step.

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“…The presence of a methine signal (G C 94.7, G H 6.94, br d, J = 2.4) in 1 implied that the methoxy group was located at C-11 (G C 158.7) ( Fig. 2), which was further line A [12] . The relative configuration of 1 established from the ROESY spectrum ( Fig.…”

Section: Introductionmentioning

confidence: 96%

“…. Detailed comparison of the NMR data of 1 with those of lirofoline A [12] suggested that their structures were closely related, except for the pattern of substitution of methoxy group. The presence of a methine signal (G C 94.7, G H 6.94, br d, J = 2.4) in 1 implied that the methoxy group was located at C-11 (G C 158.7) ( Fig.…”

Section: Introductionmentioning

confidence: 98%

A new monoterpenoid indole alkaloid from <I>Ervatamia chinensis</I>

Guo¹,

He²,

Li³

et al. 2012

Chinese Journal of Natural Medicines

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To study the chemical constituents of the whole plants of E. chinensis, and find new or effective components. METHODS: Compounds were isolated by repeated silica gel and Sephadex LH-20 column chromatography. The structures were elucidated by NMR and HRESI-MS spectrometry. RESULTS: Six alkaloids were isolated from whole plants of E. chinensis, and their structures were elucidated as ervachinine E (1), rutaecarpine (2), 1-methyl-2-nonyl-4(1H)-quinolone (3), dihydroevocarpine (4), evocarpine (5), and 1-methyl-2-[(Z)-6-undecenyl]-4(1H)-quinolone (6), respectively. CONCLUSION: Compound 1 is a new monoterpenoid indole alkaloid and with moderate anti-tumor activity, while compounds 2-6 are reported from this species for the first time.

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Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana

Cited by 29 publications

References 33 publications

Ethnopharmacology, phytochemistry, and biotechnological advances of family Apocynaceae: A review

Ethnopharmacology, phytochemistry, and biotechnological advances of family Apocynaceae: A review

Four‐Component Assembly of Natural‐Product‐Like Ring‐Fused Isoquinuclidines

A new monoterpenoid indole alkaloid from <I>Ervatamia chinensis</I>

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