Melodinus henryi is a good source of terpenoid indole alkaloids, and traditionally used as a folk medicine in the treatment of meningitis and fracture. In order to further exploit their potential uses, its anti-inflammatory and immunosuppressive activities, safety evaluations and chemical profiles have been illustrated. Compared to the crude methanol extract from M. henryi and its non-alkaloidal fraction, the total alkaloidal fraction (MHTA) had the strongest anti-inflammatory and immunosuppressive activities. In the acute oral toxicity assay, the half lethal dose (LD 50) of MHTA was more than 2000 mg/kg. The sub-acute toxicity assay for consecutive 28 days exhibited MHTA at a lower concentrations of less than 500 mg/kg might be regarded as safe, and might damage spleen, liver, kidney, and heart when the dose is higher than 1000 mg/kg. In addition, a phytochemical investigation on MHTA led to the isolation of 15 monoterpenoid indole alkaloids. Thus, in regard with the potent side effects of MHTA, it should be used with caution in the development of phytomedicine. Meilian Yang and Yudan Wang have contributed equally to this work.
Melodinus henryi is a good source of terpenoid indole alkaloids, and traditionally used as a folk medicine in the treatment of meningitis and fracture. In order to further exploit their potential uses, its anti-inflammatory and immunosuppressive activities, safety evaluations and chemical profiles have been illustrated. Compared to the crude methanol extract from M. henryi and its non-alkaloidal fraction, the total alkaloidal fraction (MHTA) had the strongest anti-inflammatory and immunosuppressive activities. In the acute oral toxicity assay, the half lethal dose (LD 50) of MHTA was more than 2000 mg/kg. The sub-acute toxicity assay for consecutive 28 days exhibited MHTA at a lower concentrations of less than 500 mg/kg might be regarded as safe, and might damage spleen, liver, kidney, and heart when the dose is higher than 1000 mg/kg. In addition, a phytochemical investigation on MHTA led to the isolation of 15 monoterpenoid indole alkaloids. Thus, in regard with the potent side effects of MHTA, it should be used with caution in the development of phytomedicine. Meilian Yang and Yudan Wang have contributed equally to this work.
“…Three aspidofractinie-type compounds, 5,6-secokopsinine ( 175 ), 5β-hydroxykopsinine ( 176 ), 16- epi -kopsinilam ( 177 ) [ 97 ], two kopsine-type metabolites, 5-oxokopsinic acid ( 178 ), and N a -demethoxycarbonyl-12-methoxykopsine ( 179 ) [ 97 ], a strychnos-type, 14( S )-hydroxy-19(R)- methoxytubotaiwine ( 180 ), and vincamine-type, and strychnos type 19-oxo-(−)-eburnamonine ( 181 ), 19( S )-hydroxy-Δ 14 -vincamone ( 182 ) [ 97 ], along with ten known compounds, 163 [ 87 ], kopsinilam ( 183 ) [ 98 ], kopsinic acid ( 184 ), 12-methoxykopsine ( 185 ) [ 99 ], kopsanone 186 ), 19(R)- methoxytubotaiwine ( 187 ) [ 88 ], (−)-eburnamonine ( 188 ), 19-OH-(−)-eburnamonine ( 189 ), and Δ 14 -vincamone ( 190 ) [ 97 ] were yielded from the stem bark of the Thai Kopsia jasminiflora ( Figure 19 ). Compounds 163 , 183 , and 184 belong to aspidofractinie-type, 185 and 186 belong to Kopsine-type, 187 belongs to strycno-type, 188 – 190 belonging to the vincamine- type MIAs.…”
Section: Kopsiamentioning
confidence: 99%
“…Meanwhile, compounds 188 and 189 showed moderate activities with IC 50 values ranging from 2.00 to 2.61 μM (Docetaxel, IC 50 < 0.0005 μM). These results indicated the structural features that are necessary for the presence of a vincamine-type carbonyl group at the C-16 position, forming an amide function group, and a methylene group or hydroxyl methine at C-19 position in 182 , 188 , and 189 [ 97 ]. The presence of a double bond in the piperidine ring between C-15 and C-16 may be responsible for increasing the activity of compound 182 .…”
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.
“…[73] Among eburnane indole alkaloids, their C19 oxo-functionalized ones show promising antitumor activity. [74] For instance, 19-(S)-OH-Δ 14 accomplished the total synthesis of C19-oxo eburnane alkaloids 41-44 in 11 to 13 steps. [75] In this divergent asymmetric approach, the Pd-catalyzed AAS of an N-alkyl-α,β-unsaturated lactam played a key role.…”
Metal‐catalyzed asymmetric allylic substitution (AAS) reaction is one of the most synthetically useful reactions catalyzed by metal complexes for the formation of carbon‐carbon and carbon‐heteroatom bonds. It comprises the substitution of allylic substrates with a wide range of nucleophiles or SN2′‐type allylic substitution, which results in the formation of the above‐mentioned bonds with high levels of enantioselective induction. AAS reaction tolerates a broad range of functional groups, thus has been successfully applied in the asymmetric synthesis of a wide range of optically pure compounds. This reaction has been extensively used in the total synthesis of several complex molecules, especially natural products. In this review, we try to highlight the applications of metal (Pd, Ir, Mo, or Cu)‐catalyzed AAS reaction in the total synthesis of the biologically active natural products, as a key step, updating the subject from 2003 till date.
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