Kalanchosides A−C, New Cytotoxic Bufadienolides from the Aerial Parts of Kalanchoe gracilis

Wu, Pei‐Lin; Hsu, Yu-Lin; Wu, Tong; Bastow, Kenneth F.; Lee, Kuo‐Hsiung

doi:10.1021/ol061873m

Cited by 50 publications

(27 citation statements)

References 18 publications

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“…The relative amounts of ferulic acid (~7.59% w/w), quercetin (~0.33% w/w), and kaempferol (~0.16% w/w) were also identified in K. gracilis leaf extract of ethyl acetate layer and were found to be in agreement with identified flavonoids of K. gracilis in previous reports [3–5]. Flavonoids exhibit multiple functions, of which inhibition on viral replication [11–14] is among.…”

Section: Discussionsupporting

confidence: 89%

“…K. gracilis leaf extract is suggested to contain other potent anti-enteroviral components besides quercetin. Phytochemically, Kalanchoe species are known to contain flavonoids (e.g., teolin, quercetin, quercitrin, kaempferol, eupafolin), glycosidic derivatives of eupafolin, bufadienolides, and coumarins [4, 5, 16], of which bis- and tetra-coumarins have been shown with inhibitory effects on the activity of HIV-1 integrase [7], while bufadienolides can reduce the activation of Epstein-Barr virus early antigen [16]. In addition, many active compounds of natural products have been identified as potential anti-EV71 agents, including gallic acid (IC 50 = 0.8 μ g/mL) [34], allophycocyanin (IC 50 = 0.056 μ M) [35], chrysosplenetin (IC 50 = 0.2 μ M), penduletin (IC 50 = 0.2 μ M) [36], and aloe-emodin (IC 50 = 0.14 μ M) [37].…”

Section: Discussionmentioning

confidence: 99%

“…Extracts of K. gracilis have high amounts of polyphenol and flavonoid contents that may generate potential antioxidant, anti-inflammatory, and antiproliferative activities [2, 3]. Identified constituents include coumarin, bufadienolides, flavonoids (e.g., teolin, quercetin, quercitrin, kaempferol and eupafolin), and glycosidic derivatives of eupafolin [4, 5]. The latter is a vital bioactive compound shown to possess antioxidant and anti-inflammatory effects in lipopolysaccahride-treated RAW264.7 cells as well as antiproliferating effect against HepG2 cells [3].…”

Section: Introductionmentioning

confidence: 99%

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Antiviral Ability ofKalanchoe gracilisLeaf Extract against Enterovirus 71 and Coxsackievirus A16

Huang

Zhang²,

Lai

et al. 2012

Evidence-Based Complementary and Alternative Medicine

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Pandemic infection or reemergence of Enterovirus 71 (EV71) and coxsackievirus A16 (CVA16) occurs in tropical and subtropical regions, being associated with hand-foot-and-mouth disease, herpangina, aseptic meningitis, brain stem encephalitis, pulmonary edema, and paralysis. However, effective therapeutic drugs against EV71 and CVA16 are rare. Kalanchoe gracilis (L.) DC is used for the treatment of injuries, pain, and inflammation. This study investigated antiviral effects of K. gracilis leaf extract on EV71 and CVA16 replications. HPLC analysis with a C-18 reverse phase column showed fingerprint profiles of K. gracilis leaf extract had 15 chromatographic peaks. UV/vis absorption spectra revealed peaks 5, 12, and 15 as ferulic acid, quercetin, and kaempferol, respectively. K. gracilis leaf extract showed little cytotoxicity, but exhibited concentration-dependent antiviral activities including cytopathic effect, plaque, and virus yield reductions. K. gracilis leaf extract was shown to be more potent in antiviral activity than ferulic acid, quercetin, and kaempferol, significantly inhibiting in vitro replication of EV71 (IC50 = 35.88 μg/mL) and CVA16 (IC50 = 42.91 μg/mL). Moreover, K. gracilis leaf extract is a safe antienteroviral agent with the inactivation of viral 2A protease and reduction of IL-6 and RANTES expressions.

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Section: Discussionsupporting

confidence: 89%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Antiviral Ability ofKalanchoe gracilisLeaf Extract against Enterovirus 71 and Coxsackievirus A16

Huang

Zhang²,

Lai

et al. 2012

Evidence-Based Complementary and Alternative Medicine

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“…In another study, three new compounds, kalanchosides A-C, as well as five known compounds, were isolated from the aerial parts of Kalanchoe gracilis , where all eight isolated compounds showed significant cytotoxic activity against a panel of human tumor cell lines. However, only one of the known compound bryophyllin B inhibited HIV replication in H9 lymphocyte cells [44]. …”

Section: Discussionmentioning

confidence: 99%

Anticancer property of Bryophyllum pinnata (Lam.) Oken. leaf on human cervical cancer cells

Mahata

Maru

Shukla

et al. 2012

BMC Complement Altern Med

100

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Background Bryophyllum pinnata ( B. pinnata ) is a common medicinal plant used in traditional medicine of India and of other countries for curing various infections, bowel diseases, healing wounds and other ailments. However, its anticancer properties are poorly defined. In view of broad spectrum therapeutic potential of B. pinnata we designed a study to examine anti-cancer and anti-Human Papillomavirus (HPV) activities in its leaf extracts and tried to isolate its active principle. Methods A chloroform extract derived from a bulk of botanically well-characterized pulverized B . pinnata leaves was separated using column chromatography with step- gradient of petroleum ether and ethyl acetate. Fractions were characterized for phyto-chemical compounds by TLC, HPTLC and NMR and Biological activity of the fractions were examined by MTT-based cell viability assay, Electrophoretic Mobility Shift Assay, Northern blotting and assay of apoptosis related proteins by immunoblotting in human cervical cancer cells. Results Results showed presence of growth inhibitory activity in the crude leaf extracts with IC 50 at 552 μg/ml which resolved to fraction F4 (Petroleum Ether: Ethyl Acetate:: 50:50) and showed IC 50 at 91 μg/ml. Investigations of anti-viral activity of the extract and its fraction revealed a specific anti-HPV activity on cervical cancer cells as evidenced by downregulation of constitutively active AP1 specific DNA binding activity and suppression of oncogenic c-Fos and c-Jun expression which was accompanied by inhibition of HPV18 transcription. In addition to inhibiting growth, fraction F4 strongly induced apoptosis as evidenced by an increased expression of the pro-apoptotic protein Bax, suppression of the anti-apoptotic molecules Bcl-2, and activation of caspase-3 and cleavage of PARP-1. Phytochemical analysis of fraction F4 by HPTLC and NMR indicated presence of activity that resembled Bryophyllin A. Conclusions Our study therefore demonstrates presence of anticancer and anti-HPV an activity in B . pinnata leaves that can be further exploited as a potential anticancer, anti-HPV therapeutic for treatment of HPV infection and cervical cancer.

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“…These compounds showed remarkably potent cytotoxicity against a HTCL panel, particularly against the A549 lung cancer cell line, where the EC 50 value of 103 was 0.5 ng/mL (Table 5). 61…”

Section: Antitumor Agentsmentioning

confidence: 99%

Discovery and Development of Natural Product-Derived Chemotherapeutic Agents Based on a Medicinal Chemistry Approach

2010

Self Cite

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Medicinal plants have long been an excellent source of pharmaceutical agents. Accordingly, the long term objectives of the author's research program are to discover and design new chemotherapeutic agents based on plant-derived compound leads by using a medicinal chemistry approach, which is a combination of chemistry and biology. Different examples of promising bioactive natural products and their synthetic analogs, including sesquiterpene lactones, quassinoids, naphthoquinones, phenylquinolones, dithiophenediones, neo-tanshinlactone, tylophorine, suksdorfin, DCK, and DCP, will be presented with respect to their discovery and preclinical development as potential clinical trial candidates. Research approaches include bioactivity- or mechanism of action-directed isolation and characterization of active compounds, rational drug design-based modification and analog synthesis, as well as structure-activity relationship and mechanism of action studies. Current clinical trials agents discovered by the Natural Products Research Laboratories, University of North Carolina, include bevirimat (dimethyl succinyl betulinic acid), which is now in Phase IIb trials for treating AIDS. Bevirimat is also the first in a new class of HIV drug candidates called “maturation inhibitors”. In addition, an etoposide analog, GL-331, progressed to anticancer Phase II clinical trials, and the curcumin analog JC-9 is in Phase II clinical trials for treating acne and in development for trials against prostate cancer. The discovery and development of these clinical trials candidates will also be discussed.

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Kalanchosides A−C, New Cytotoxic Bufadienolides from the Aerial Parts of Kalanchoe gracilis

Cited by 50 publications

References 18 publications

Antiviral Ability ofKalanchoe gracilisLeaf Extract against Enterovirus 71 and Coxsackievirus A16

Antiviral Ability ofKalanchoe gracilisLeaf Extract against Enterovirus 71 and Coxsackievirus A16

Anticancer property of Bryophyllum pinnata (Lam.) Oken. leaf on human cervical cancer cells

Discovery and Development of Natural Product-Derived Chemotherapeutic Agents Based on a Medicinal Chemistry Approach

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