Corynanthean, eburnan, secoleuconoxine, and pauciflorine alkaloids from Kopsia pauciflora

Gan, Chew‐Yan; Yoganathan, K.; Sim, Kae-Shin; Low, Yun‐Yee; Lim, Siew‐Huah; Kam, Toh‐Seok

doi:10.1016/j.phytochem.2014.09.014

Cited by 20 publications

(57 citation statements)

References 36 publications

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“…The present assignment of compound 10 as (−)-19(R)-hydroxy-O-ethylisoeburnamine has therefore also provided additional verification of the earlier assignment of the structure of (−)-19(R)-hydroxyisoeburnamine (21). 16 We recently reported the structures of the new indole alkaloids larutienine A (23) and its pseudoindoxyl, larutienine B (11), from the Malayan sample of K. paucif lora. 11 During the course of the present study, the pseudoindoxyl alkaloid larutienine B (11) was also independently isolated, although in this instance the precursor alkaloid, larutienine A (23), was not detected.…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

“…16 We recently reported the structures of the new indole alkaloids larutienine A (23) and its pseudoindoxyl, larutienine B (11), from the Malayan sample of K. paucif lora. 11 During the course of the present study, the pseudoindoxyl alkaloid larutienine B (11) was also independently isolated, although in this instance the precursor alkaloid, larutienine A (23), was not detected. In the previous report, the structure of compound 11 was determined based on analysis of the spectroscopic data.…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

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Aspidofractinine and Eburnane Alkaloids from a North Borneo Kopsia. Ring-Contracted, Additional Ring-Fused, and Paucidactine-Type Aspidofractinine Alkaloids from K. pauciflora

Yap¹,

Gan²,

Sim³

et al. 2015

J. Nat. Prod.

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Eleven new indole alkaloids (1-11) comprising seven aspidofractinine and four eburnane alkaloids, were isolated from the stem-bark extract of Kopsia pauciflora occurring in Malaysian Borneo. The aspidofractinine alkaloids include a ring-contracted, an additional ring-fused, a paucidactine regioisomer, two paucidactine, and one kopsine alkaloid. The structures of several of these alkaloids were also confirmed by X-ray diffraction analyses. The bisindole alkaloids isolated, norpleiomutine and kopsoffinol, showed in vitro growth inhibitory activity against human PC-3, HCT-116, MCF-7, and A549 cells and moderate effects in reversing multidrug-resistance in vincristine-resistant human KB cells.

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Section: Journal Of Natural Productsmentioning

confidence: 99%

Section: Journal Of Natural Productsmentioning

confidence: 99%

Aspidofractinine and Eburnane Alkaloids from a North Borneo Kopsia. Ring-Contracted, Additional Ring-Fused, and Paucidactine-Type Aspidofractinine Alkaloids from K. pauciflora

Yap¹,

Gan²,

Sim³

et al. 2015

J. Nat. Prod.

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“…Compounds 163 and 164 inhibited coughing by 88% and 76%, respectively [83]. Compound 163 was more active, with an ID 50 value = 0.11 mmoL/kg, whereas compound 164 exhibited an effect, with an ID 50 value = 0.45 mmol/kg, (Codeine, ID 50 = 0.1 mmol/kg) [90]. The link from C-2 to C-20 in compound 163 and the attachment of the methoxy carbonyl group at C-16 position promote the antitussive activity.…”

Section: Kopsiamentioning

confidence: 98%

“…Several species have been reported to have antitumor, antimanic, antitussive and antileishmanial effects [87][88][89]. A review published in 2017 was interested in reporting indole alkaloids from genus kopsia plants regarding reversing multidrug resistance in vincristine-resistant KB cells for example, kopsirensine B, arboloscine A [90], grandilodines A and C, and lapidilectine B [91,92].…”

Section: Kopsiamentioning

confidence: 99%

“…Compounds 198-227.Seven aspidofractinine -type alkaloids, paucidirinine(200), paucidirisine(201), paucidactinine(202), pauciduridine(203), paucidactine D(204), paucidactine E (205), and paucidisine(206), along with Additionally, four eburnane skeleton, (−)-19-oxoisoeburnamine (207), (−)-19(R)-hydroxyeburnamenine (208), (−)-19(R)-hydroxy-O-ethylisoeburnamine (209), and larutienine B (210) were isolated from Kopsia pauciflora [91]. Moreover, twelve compounds, paucidactine A (211), paucidactine B (212) [105], paucidactine C (213) [88], 5, 22dioxokopsane (214) [98], (+)-eburnamonine (215) [94], (+)-eburnamenine (216) [106], (−)eburnamine (217), (+)-isoeburnamine (218) [94], (+)-19-oxoeburnamine (219) [105], (−)-19(R)hydroxyisoeburnamine (220), (+)-19(R)-hydroxyeburnamine (221)[87], and larutienine A (222)[90] were published. Furthermore, three bisindole compounds have been identified, (−)norpleiomutine (223), (+)-kopsoffinol(224) [107], and (−)-demethylnorpleiomutine (225)[87]…”

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confidence: 99%

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Chemical Diversity and Bioactivities of Monoterpene Indole Alkaloids (MIAs) from Six Apocynaceae Genera

et al. 2021

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By the end of the twentieth century, the interest in natural compounds as probable sources of drugs has declined and was replaced by other strategies such as molecular target-based drug discovery. However, in the recent times, natural compounds regained their position as extremely important source drug leads. Indole-containing compounds are under clinical use which includes vinblastine and vincristine (anticancer), atevirdine (anti-HIV), yohimbine (erectile dysfunction), reserpine (antihypertension), ajmalicine (vascular disorders), ajmaline (anti-arrhythmic), vincamine (vasodilator), etc. Monoterpene Indole Alkaloids (MIAs) deserve the curiosity and attention of researchers due to their chemical diversity and biological activities. These compounds were considered as an impending source of drug-lead. In this review 444 compounds, were identified from six genera belonging to the family Apocynaceae, will be discussed. These genera (Alstonia, Rauvolfia, Kopsia, Ervatamia, and Tabernaemontana, and Rhazya) consist of 400 members and represent 20% of Apocynaceae species. Only 30 (7.5%) species were investigated, whereas the rest are promising to be investigated. Eleven bioactivities, including antibacterial, antifungal, anti-inflammatory and immunosuppressant activities, were reported. Whereas cytotoxic effect represents 47% of the reported activities. Convincingly, the genera selected in this review are a wealthy source for future anticancer drug lead.

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The Diaza[5.5.6.6]fenestrane Skeleton—Synthesis of Leuconoxine Alkaloids

Pfaffenbach

Gaich

2015

Chemistry A European J

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Among the Aspidosperma-derived monoterpene indole alkaloids, the leuconoxine subgroup has drawn significant attention from the synthetic community during the past few years. This Minireview summarizes the hitherto six completed total syntheses of leuconoxines emphasizing the different strategies for assembling the key structural motif, an unprecedented diaza[5.5.6.6]fenestrane skeleton. In addition, the proposed biogenetic relationships within the group of these alkaloids are described.

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Corynanthean, eburnan, secoleuconoxine, and pauciflorine alkaloids from Kopsia pauciflora

Cited by 20 publications

References 36 publications

Aspidofractinine and Eburnane Alkaloids from a North Borneo Kopsia. Ring-Contracted, Additional Ring-Fused, and Paucidactine-Type Aspidofractinine Alkaloids from K. pauciflora

Aspidofractinine and Eburnane Alkaloids from a North Borneo Kopsia. Ring-Contracted, Additional Ring-Fused, and Paucidactine-Type Aspidofractinine Alkaloids from K. pauciflora

Chemical Diversity and Bioactivities of Monoterpene Indole Alkaloids (MIAs) from Six Apocynaceae Genera

The Diaza[5.5.6.6]fenestrane Skeleton—Synthesis of Leuconoxine Alkaloids

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