Pyrrole alkaloids from the fruits of Morus alba

Kim, Seon Beom; Chang, Bo Yoon; Hwang, Bang Yeon; Kim, Sung Yeon; Lee, Mi Kyeong

doi:10.1016/j.bmcl.2014.10.073

Cited by 52 publications

(37 citation statements)

References 16 publications

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“…Pyrrole-containing molecules include commonly naturally produced compounds such as chlorophyll, chlorins, vitamin B12 and porphyrinogens [34][35][36]. A pyrrole ring is also a part of tryptamines including serotonin, melatonin and many other biologically important substances [37][38][39][40]. For that reason, apart from broadening our knowledge of the stacking interaction phenomenon itself, this extensive study of the intermolecular interaction in model pyrrole systems may be relevant in electronic properties of pyrrole-unit-based drugs.…”

Section: Introductionmentioning

confidence: 99%

The intricacies of the stacking interaction in a pyrrole–pyrrole system

Sierański

2016

Struct Chem

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Extensive calculations of potential energy surfaces for parallel-displaced configurations of pyrrole-pyrrole systems have been carried out by the use of a dispersion-corrected density functional. System geometries associated with the energy minima have been found. The minimum interaction energy has been calculated as -5.38 kcal/mol. However, bonding boundaries appeared to be relatively broad, and stacking interactions can be binding even for ring centroid distances larger than 6 Å . Though the contribution of the correlation energy to intermolecular interaction in pyrrole dimers appeared to be relatively small (around 1.6 smaller than it is in a benzenebenzene system), this system's minimum interaction energy is lower than those calculated for benzene-benzene, benzene-pyridine and even pyridine-pyridine configurations. The calculation of the charges and energy decomposition analysis revealed that the specific charge distribution in a pyrrole molecule and its relatively high polarization are the significant source of the intermolecular interaction in pyrrole dimer systems.

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Section: Introductionmentioning

confidence: 99%

The intricacies of the stacking interaction in a pyrrole–pyrrole system

Sierański

2016

Struct Chem

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“…Among the isolated compounds, 1 , 11 , and 17 were new compounds. The other fifty-four known compounds were identified, including eight lignans, (+)-pinoresinol ( 2 ) [14], syringaresinol ( 3 ) [15], medioresinol ( 4 ) [16], (+)- epi -syringaresinol ( 5 ) [15], (+)-pinoresinol monomethyl ether ( 6 ) [17], (+)-glaberide I ( 7 ) [18], sesamin ( 8 ) [19], and sesamolin ( 9 ) [20]; five pyrrole alkaloids, 5-(hydroxymethyl)-1 H -pyrrole-2-carbaldehyde ( 10 ) [21], methyl 4-[formyl-5-(hydroxymethyl)-1 H -pyrrol-1-yl] butanoate ( 12 ) [22,23], methyl 4-[formyl-5-(methoxymethyl)-1 H -pyrrol-1-yl] butanoate ( 13 ) [22,23], 4-[formyl-5-(methoxymethyl)-1 H -pyrrol-1-yl] butanoic acid ( 14 ) [22,23], and 4-[formyl-5-(hydroxymethyl)-1 H -pyrrol-1-yl] butanoic acid ( 15 ) [23]; seventeen benzenoids, rhodiolate ( 16 ) [24], methyl ferulate ( 18 ) [25], β-hydroxypropiovanillone ( 19 ) [26], 2-methyl-4,5-dimethoxybenzoic acid ( 20 ) [27], vanillic acid ( 21 ) [28], p -hydroxyl phenethanol ( 22 ) [29], tachioside ( 23 ) [30], icariside D 2 ( 24 ) [31], salidroside ( 25 ) [32], syringin ( 26 ) [33], cordifolioside A ( 27 ) [34], p -hydroxybenzoic acid ( 28 ) [35], 4-(2-hydroxyethyl)benzoic acid ( 29 ) [36], syringic acid-4- O -α- l -rhamnoside ( 30 ) [37], isovanillic acid ( 31 ) [38], syringic acid ( 32 ) [39]; ten terpenoids, loliolide ( 33 ) [40], abscisic acid ( 34 ) [41], 3(17)-phytene 1,2-diol ( 35 ) [42], malabarolide ( 36 ) [43], lupeol ( 37 ) [44], 3- O -acetyloleanolic acid ( 38 ) [45], cycloeucalenol ( 39 ) [46], cycloabyssinone ( 40 ) [47], cycloartane-3β,25-diol ( 41 ) [48], and cycloart-22-ene-3β,25-diol ( 42 ) [49]; eight steroids, β-sitosterol ( 43 ) [50], st...…”

Section: Resultsmentioning

confidence: 99%

“…The structure of compound 13 was elucidated as a methyl 4-[formyl-5-(methoxymethyl)-1 H -pyrrol-1-yl] butanoate. Furthermore, compounds 14 and 15 were determined as 4-[formyl-5-(methoxymethyl)-1 H -pyrrol-1-yl] butanoic acid and 4-[formyl-5-(hydroxymethyl)-1 H -pyrrol-1-yl] butanoic acid, respectively, by comparison of their spectral data with those reported [22,23]. According to the above results, pyrrole alkaloids 10–15 were reported from Tinospora genus for the first time.…”

Section: Resultsmentioning

confidence: 99%

Chemical Constituents from the Stems of Tinospora sinensis and Their Bioactivity

et al. 2018

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Fifty-seven compounds were purified from the stems of Tinospora sinensis, including three new compounds characterized as a lignan (1), a pyrrole alkaloid (11), and a benzenoid (17), respectively. Their structures were elucidated and established by various spectroscopic and spectrometric analytical methods. Among the isolates, fifteen compounds were examined for their anti-inflammatory potential in vitro. The results showed that several compounds displayed moderate inhibition of N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation and elastase release.

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“…Different authors' advocated mulberry fruit as a good source of alkaloids, which is a bioactive compound and acts as antifeedant (15,39,40). Alkaloid concentration increases with the ripening of the fruit as it belongs to secondary metabolites.…”

Section: Alkaloidsmentioning

confidence: 99%

Nutraceutical and Medicinal Property of Mulberry Fruits: A Review on Its Pharmacological Potential

Mandal¹

2020

Preprint

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Mulberry (Morus) cultivated worldwide in diverse agro-ecological conditions recognized as the fodder of silkworms (Bombyx mori). In India, ranging from high altitude Himalayan region to coastal region, the farmers generally cultivate these four species of mulberry (Morus alba, M. indica, M. serrata, and M. laevigata). Mulberry fruit is used in traditional medicine for several years in China and also consumed as food material in different countries of Asia and Africa.Mulberry fruit, along with high nutritious value, contains many bioactive phytochemicals that are of health benefits and can fight against many diseases. Many researchers attracted to this property of mulberry fruit, and they isolated bioactive polysaccharides, anthocyanins, flavonols, flavonols, phenolic acids, alkaloids, and melatonins. These compounds have antioxidant property and due to this, either in synergistically or in the pure form, these components have direct or indirect curative activity on diabetes, inflammation, tumor, hepatic diseases, immunomodulation, hyperlipidemia, neural damage, and chronic diseases. This tremendous bioactivity of mulberry fruit extract may open up a new dimension in the food and medicine industry. The present review provides recent findings of the phytochemical foundation and their bioactivities, which may encourage many researchers to explore the molecular mechanism of the biological activities which can be used for human welfare.

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Pyrrole alkaloids from the fruits of Morus alba

Cited by 52 publications

References 16 publications

The intricacies of the stacking interaction in a pyrrole–pyrrole system

The intricacies of the stacking interaction in a pyrrole–pyrrole system

Chemical Constituents from the Stems of Tinospora sinensis and Their Bioactivity

Nutraceutical and Medicinal Property of Mulberry Fruits: A Review on Its Pharmacological Potential

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