Mucronine J, a 14-Membered Cyclopeptide Alkaloid from <i>Zizyphus mucronata</i>

Auvin, Catherine; Lezenven, Françoise; Blond, Alain; Augeven-Bour, Isabelle; Pousset, Jean-Louis; Bodo, Bernard; Cámara, José Ignacio Mayordomo

doi:10.1021/np9601972

Cited by 27 publications

(11 citation statements)

References 14 publications

(34 reference statements)

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“…In addition, triterpenes, compounds such as phenols, saponins, peptide alkaloids, and others have been identified in Rhamnaceae species (5,(25)(26)(27)(28).…”

Section: Resultsmentioning

confidence: 99%

In vitro evaluation of the cytotoxic and trypanocidal activities of Ampelozizyphus amazonicus (Rhamnaceae)

Rosas

Cordeiro

Campos

et al. 2007

Braz J Med Biol Res

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Ampelozizyphus amazonicus Ducke is a tree commonly found in the Amazon region and an extract of its stem bark is popularly used as an antimalarial and anti-inflammatory agent and as an antidote to snake venom. Ursolic acid; five lupane type triterpenes: betulin, betulinic acid, lupenone, 3ß-hydroxylup-20(29)-ene-27,28-dioic acid, and 2α,3ß-dihydroxylup-20(29)-ene-27,28-dioic acid, and three phytosteroids: stigmasterol, sitosterol and campesterol, have been isolated from stem extracts of A. amazonicus Ducke. Their structures were characterized by spectral data including COSY and HMQC. In an in vitro biological screening of the isolated compounds, 3ß-hydroxylup-20(29)-ene-27,28-dioic acid was cytotoxic against the SKBR-3 human adenocarcinoma cell line (1 to 10 mg/mL), while 2α,3ß-dihydroxylup-20(29)-ene-27,28-dioic acid exhibited cytotoxicity against both SKBR-3 human adenocarcinoma and C-8161 human melanoma tumor cell lines (>0.1 mg/mL). In the present study, different extracts and some fractions of this plant were also investigated for trypanocidal activity due to the presence of pentacyclic triterpenes. The triterpene classes are potent against Trypanosoma cruzi. The bioassays were carried out using blood collected from Swiss albino mice by cardiac puncture during the parasitemic peak (7th day) after infection with the Y strain of T. cruzi. The results obtained showed that A. amazonicus is a potential source of bioactive compounds since its extracts and fractions isolated from it exhibited in vitro parasite lysis against trypomastigote forms of T. cruzi at concentrations >100 µg/mL. Fractions containing mainly betulin, lupenone, 3ß-hydroxylup-20(29)-ene-27,28-dioic acid, and 2α,3ß-dihydroxylup-20(29)-ene-27,28-dioic acid showed more activity than crude extracts.

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“…In addition, triterpenes, compounds such as phenols, saponins, peptide alkaloids, and others have been identified in Rhamnaceae species (5,(25)(26)(27)(28).…”

Section: Resultsmentioning

confidence: 99%

In vitro evaluation of the cytotoxic and trypanocidal activities of Ampelozizyphus amazonicus (Rhamnaceae)

Rosas

Cordeiro

Campos

et al. 2007

Braz J Med Biol Res

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“…Alkaloids found in Ziziphus mucronata (Auvin et al, 1996) may also be responsible for the activity seen in this plant.…”

Section: Species With Strong Evidence Of Activitymentioning

confidence: 94%

Anthelmintic screening of Sub-Saharan African plants used in traditional medicine

Waterman

Smith

Pontiggia

et al. 2010

Journal of Ethnopharmacology

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“…In particular, the traditional medicinal use of Z. mucronata can be attributed to the various cyclopeptide alkaloids it contains (Table 3) (Auvin et al, 1996;Pareek, 2001). These include mucronines A -H (Moloto, 2004), the recently discovered mucronine J (Auvin et al, 1996), abyssenine A and frangufoline (sanjoinine A) which are isolated from the bark of its stem, root bark, roots and leaves (Auvin et al, 1996;Tan and Zhou, 2006). The frangufoline (sanjoinine A), possessing a strong sedative property, has attracted increasing attention in chemical investigations of natural products since the mid 1960's (Tan and Zhou, 2006).…”

Section: Active Medicinal Componentsmentioning

confidence: 99%

“…spinachristi (Dafni et al, 2005), are in certain African countries cured using Z. mucronata ( Table 2). The active components of Z. spina-christi include zizyphine F, Auvin et al, 1996;Tan and Zhou, 2006. jubanine A, amphibine H and spinanine A (Shappira et al, 1990). Therefore, in view of these similarities, Z. mucronata is an equally potential source of medicine.…”

Section: Other Related Ziziphus Species 41 Medicinal Valuementioning

confidence: 99%

Ziziphus mucronata: an underutilized traditional medicinal plant in Africa

2011

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In Africa, rural people depend heavily, if not exclusively, on medicinal plants and indigenous healthcare knowledge to meet their medical needs. Over 80000 fl owering plant species are used medicinally worldwide. Amongst them are the underutilized Ziziphus species in the Rhamnaceae family. In terms of abundance and economic value, Z. jujuba and Z. mauritiana are currently the most important, especially in China and India where they are cultivated and exploited for medicinal use and their edible fruits. We examined a related common species widely distributed in Africa, Z. mucronata, whose economic value has not, as yet, been explored. Local people in various African countries use its different parts to cure a large number of diseases, many of which are similar to those treated with Z. jujuba and Z. mauritiana. Several studies have shown that Z. mucronata has cyclopeptide alkaloids, i.e., mucronines F, G and H, with antibacterial properties. Conservation strategies to sustain and maximize the benefi ts of Z. mucronata to people are proposed.

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Mucronine J, a 14-Membered Cyclopeptide Alkaloid from Zizyphus mucronata

Cited by 27 publications

References 14 publications

In vitro evaluation of the cytotoxic and trypanocidal activities of Ampelozizyphus amazonicus (Rhamnaceae)

In vitro evaluation of the cytotoxic and trypanocidal activities of Ampelozizyphus amazonicus (Rhamnaceae)

Anthelmintic screening of Sub-Saharan African plants used in traditional medicine

Ziziphus mucronata: an underutilized traditional medicinal plant in Africa

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