Ceanothane‐ and Lupane‐Type Triterpenes with Antiplasmodial and Antimycobacterial Activities from Ziziphus cambodiana.

Suksamrarn, Sunit; Panseeta, Panomwan; Kunchanawatta, Soykam; Distaporn, Thanomsin; Ruktasing, Saovaluk; Suksamrarn, Apichart

doi:10.1002/chin.200632212

Cited by 15 publications

(30 citation 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%

“…Earlier chemical investigations have reported the presence of saponins in A. amazonicus (1,3). Additionally, Rhamnaceae species have shown an inhibitory effect on alcohol-induced muscle relaxation and cytotoxic, genotoxic, neurotoxic, anti-inflammatory, antipyretic, and hepatoprotective activities have been associated with its extracts and pure compounds (4)(5)(6)(7)(8).…”

Section: Introductionmentioning

confidence: 99%

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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%

Section: Introductionmentioning

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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“…They can be extracted as a triterpene rich dry extract (TE) which is able to form a topically applicable oleogel [1,2]. The birch triterpenes have known antiviral, antimicrobial and hepatoprotective pharmacological activities [3][4][5]. BA, OA or BE also have antitumor effects [2,6,7].…”

Section: Introductionmentioning

confidence: 99%

A preliminary pharmacokinetic study of betulin, the main pentacyclic triterpene from extract of outer bark of birch (Betulae alba cortex)

Jäger

Laszczyk²,

Scheffler³

2009

Z Phytother

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During the last two decades triterpenes have attracted attention because of their pharmacological potential. Triterpene extract (TE) from outer bark of birch consisting mainly of betulin is able to form an oleogel which was successfully tested in the treatment of actinic keratosis. Some aspects of TE in vitro pharmacology are already known. Now we show preliminary pharmacokinetics of betulin and results of a subchronic toxicity study of TE in rats and dogs. Because of poor aqueous solubility of the TE-triterpenes (< 0.1 µg/mL respectively), for pharmacokinetic studies it was suspended in sesame oil (rats, i.p.) and PEG 400 / 0.9 % NaCl (dogs, s.c.). I.p. administered, betulin, the main component of TE, shows time dependency over a period of 4 h and reaches a dose-independent serum level of 0.13 µg/mL. Dose dependency was observed with s.c. administration. At 300 mg/kg a maximum plasma concentration of 0.33 µg/mL betulin was detected after 28 daily applications. The subchronic toxicity study showed no toxicity of TE in rats (i.p.) and dogs (s.c.). In conclusion, triterpene extract from birch bark is safe, its betulin is bioavailable and in addition to published triterpene biological activities TE provides high potential for further pharmaceutical and pharmacological research.

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“…5). The ceanothane type triterpenoids, with a contracted A-ring, have been isolated from species such as Ziziphus (Ganapaty et al 2006;Guo et al 2009;Jagadeesh et al 2000;Lee et al 2003;Suksamrarn et al 2006), Ceanothus (Li et al 1997), Paliurus (Lee et al 1991(Lee et al , 1997, Colubrina (Roitman and Jurd 1978), Hovenia Phytochem Rev (Yoshikawa et al 1998) and Alphitonia (Guise et al 1962). To the best of our knowledge, to date, only twenty of the ceanothane type triterpenes have been reported and noticeable all of them were obtained from members of this family.…”

Section: Terpenoidsmentioning

confidence: 96%

Chemical constituents and biological activities of South American Rhamnaceae

Alarcón

Cespedes‐Acuña

2015

Phytochem Rev

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Secondary metabolites have diverse functions into plants. These functions are products of the coevolution which result in synthesis of constitutive and/or induced chemical defense generated for protection against to different phytopathogenic attack. Many phytochemical studies are biodirected with the aim of finding biopesticides of botanical origins. Some taxa of Americas such as Rhamnaceae family are toxic to insects, fungi and several bacteria strains, and these effects has been associated with the presence of alkaloids, phenolics and terpenes. The natural compounds that have been isolated represent a valuable resource for future studies of plant chemical defense and the role of these substances in chemical ecology.Here are show recent advances in the phytochemistry and biological activities of selected members of Rhamnaceae from Latin-America.

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Ceanothane‐ and Lupane‐Type Triterpenes with Antiplasmodial and Antimycobacterial Activities from Ziziphus cambodiana.

Cited by 15 publications

References 1 publication

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)

A preliminary pharmacokinetic study of betulin, the main pentacyclic triterpene from extract of outer bark of birch (Betulae alba cortex)

Chemical constituents and biological activities of South American Rhamnaceae

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