• Title/Summary/Keyword: Triterpenes

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Cloning and Molecular Analysis of cDNA Encoding Cycloartenol Synthase from Centella asiatica (L.) Urban

  • Kim Ok-Tae;Kim Min-Young;Hwang Sung-Jin;Ahn Jun-Cheul;Hwang Baik
    • Biotechnology and Bioprocess Engineering:BBE
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    • v.10 no.1
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    • pp.16-22
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    • 2005
  • cDNA for oxidosqualene cyclase was cloned by a homology-based PCR method and sequenced from Centella asiatica. In a sequences analysis, the putative polypeptide of C. asiatica cycloartenol synthase (CaCYS) deduced from the 2,274 bp nucleotide sequence, consisted of 758 amino acids and had a molecular mass of 86.3 kD. The predicted amino acid sequence exhibited high homology to that of PNX (cycloartenol synthase) from Panax ginseng ($89\%$). Southern blot analysis suggests that CaCYS may be present in one copy of the C. asiatica genome. If methyl jasmonate (MJ) is applied exogenously to plants, not only triterpene saponins are accumulated in tissues, but also it produces effects such as growth inhibition and the promotion of ethylene production. In order to investigate the effect of MJ and thidiazuron (TDZ), a cytokinin that plays a role as an antisenescence agent in several plants, on the level of CaCYS mRNA, we performed northern blot analysis. When MJ is alone treated by adding to culture medium, CaCYS transcripts were inhibited. However, sustained levels of the expression of CaCYS, by adding TDZ to the medium despite MJ treatments, were demonstrated in C. asiatica leaves.

Biological Characterization of the Chemical Structures of Naturally Occurring Substances with Cytotoxicity

  • Park, Hee-Juhn;Jung, Hyun-Ju;Lee, Kyung-Tae;Choi, Jong-Won
    • Natural Product Sciences
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    • v.12 no.4
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    • pp.175-192
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    • 2006
  • Screening for the cytotoxicity from plant origin is the first stage for anti-cancer drug development. A variety of terpenoids with exomethylene, epoxide, allyl, $\alpha,\beta-unsaturated$ carbonyl, acetylenes, and $\alpha-methylene-\gamma-lactone$ induces apoptosis and/or differentiation as well as cytotoxicity through the ROS signal transduction pathways. These are found among monoterpenes, sesquiterpenes, triterpenes, flavonoids, coumarins, diarylheptanoids, and even organosulfuric compounds. The most essential characteristics of natural cytotoxic substances is to possess the strong electrophilicity that is susceptible to nucleophilic biomolecules in the cell. Thiol-reductants and superoxide dismutase can block or delay apoptosis. Thus, ROS and the resulting cellular redox-potential changes can be parts of the signal transduction pathway during apoptosis. Disturbance of the balance of oxireduction by the pigment of natural quinones also caused the induction of the differentiation and apoptosis. Saponins with the cytotoxicity are restricted to their monodesmosides, rather than to bisdesmosides. Those saponins exhibited calcium ion-mediated apoptosis in addition to cytotoxicity whereas they showed also differentiation without extracellular calcium ion. The properties on cytotoxicity, apoptosis, and differentiation were assumed to depend on resultant oxidative stress to the cells. In this review, we describe a spectrum of cytotoxic compounds with various action mechanisms.

Ginsenoside Rg12, a new dammarane-type triterpene saponin from Panax ginseng root

  • Lee, Dong Gu;Lee, Jaemin;Cho, Ik-Hyun;Kim, Hak-Jae;Lee, Sang-Won;Kim, Young-Ock;Park, Chun-Gun;Lee, Sanghyun
    • Journal of Ginseng Research
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    • v.41 no.4
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    • pp.531-533
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    • 2017
  • Background: Panax ginseng has been used as Korean medicine for various diseases. It has antioxidant, hypotensive, sedative, analgesic, and endocrine activities. Dammarane-type triterpenes from the plant have various beneficial effects. Methods: A dammarane-type triterpene saponin was isolated from P. ginseng root through chromatography such as repeated column chromatography and medium pressure liquid chromatography. Results and conclusion: New dammarane-type triterpene saponin was isolated for the first time from nature. The structure was elucidated as ginsenoside Rg12 (1) based on spectral data. There may be good materials from P. ginseng for the development of industrial applications such as nutraceutical, pharmaceutical, and cosmeceutical purposes.

Secondary metabolites (Triterpenes) from Couroupita guianensis

  • Begum, Rokeya;Rahman, Mohammad S;Chowdhury, A M Sarwaruddin;Hasan, Choudhury M;Rashid, Mohammad A
    • Advances in Traditional Medicine
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    • v.9 no.2
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    • pp.200-205
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    • 2009
  • The n-hexane and carbon tetrachloride soluble fractions of a methanolic extract of the stem bark of the Couroupita guianensis furnished three compounds, identified as $\beta$-amyrin (1), betulin-$3{\beta}$-caffeate (2) and lupeol-$3{\beta}$-caffeate (3). The structures of the isolated compounds were deduced by extensive spectroscopic analysis as well as by comparison with published values. Compounds 1-3 were subjected to antioxidant screening through free radical scavenging activity by DPPH (1,1-diphenyl-2-picrylhydrazyl), where compound 2 showed moderate antioxidant activity with $IC_{50}$ value $108.0{\mu}g/ml$.

Antimicrobial Potential of Moringa oleifera Seed Coat and Its Bioactive Phytoconstituents

  • Arora, Daljit Singh;Onsare, Jemimah Gesare
    • Microbiology and Biotechnology Letters
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    • v.42 no.2
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    • pp.152-161
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    • 2014
  • The in vitro antimicrobial potential of the unexplored Moringa oleifera seed coat (SC) was evaluated against some Gram-positive and Gram-negative bacteria and yeast pathogens. Antimicrobial studies with various solvent extracts indicated ethyl acetate to be the best extractant, which was used for the rest of the antimicrobial studies as it tested neither toxic nor mutagenic. Gram-positive bacteria including a methicillin resistant Staphylococcus aureus (MRSA) strain were more susceptible with a minimum inhibitory concentration (MIC) range of 0.03-0.04 mg/ml. The antimicrobial pharmacodynamics of the extract exhibited both concentration-dependent and time-dependent killing. Most of the test organisms exhibited a short post antibiotic effect (PAE) except Enterococcus faecalis, Staphylococcus aureus, and Klebsiella pneumoniae 1, which exhibited longer PAEs. Amongst the major phytoconstituents established, flavonoids, diterpenes, triterpenes and cardiac glycosides exhibited inhibitory properties against most of the test organisms. The identified active phytochemicals of the M. oleifera seed coat exhibited antimicrobial potential against a wide range of medically important pathogens including the multidrug-resistant bugs. Hence, the M. oleifera seed coat, which is usually regarded as an agri-residue, could be a source of potential candidates for the development of drugs or drug leads of broad spectrum that includes multidrug-resistant bugs, which are one of the greatest concerns of the $21^{st}$ century.

In Vitro Effect of Methanolic Extract of Argemone mexicana against Trichomonas vaginalis

  • Elizondo-Luevano, Joel Horacio;Verde-Star, Julia;Gonzalez-Horta, Azucena;Castro-Rios, Rocio;Hernandez-Garcia, Magda Elizabeth;Chavez-Montes, Abelardo
    • Parasites, Hosts and Diseases
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    • v.58 no.2
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    • pp.135-145
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    • 2020
  • Infections caused by Trichomonas vaginalis in humans are one of the main public health problems caused by sexually transmitted diseases. Objective of this study was to evaluate potential biological activity of the medicinal plant Argemone mexicana (Mexican poppy) on T. vaginalis. Methanolic extracts of the stems and leaves of A. mexicana, and different fractions were prepared with solvents of different polarities. The extracts and functional groups were detected containing sterols, triterpenes, quinones, flavonoids and, alkaloids. Extracts from both the stems and leaves of A. mexicana inhibited the growth of T. vaginalis with half-maximal inhibitory concentration value of 70.6 and 67.2 ㎍/ml, respectively. In the active fractions, the most abundant compounds were berberine and jatrorrhizine, with presumed antiparasitic activity.

Four Dammarane Triterpenes and Their Inhibitory Properties Against Eight Receptor Tyrosine Kinases

  • Heliawati, Leny;Khatimah, Husnul;Hermawati, Elvira;Syah, Yana Maolana
    • Natural Product Sciences
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    • v.26 no.4
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    • pp.345-350
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    • 2020
  • In recent years, tyrosine kinases (TKs) have been the target to combat cancers, and most of the developed inhibitors are of synthetic origin. Natural compounds that have the properties as the TK's inhibitors are very limited. This paper described the isolation of a new dammarane triterpene from the tree bark of Sandoricum koetjape, along with three known related dammaranes from the damar resin of Shorea javanica, as well as their inhibitory properties against eight receptor TKs (RTKs: EGFR, HER2, HER4, IGF1R, InsR, KDR, PDGFRα, and PDGFRβ). Based on the NMR and mass spectral data the new compound was identified as (12β,20S)-12,20-dihydroxy-3,4-seco-dammaran-4,24-dien-3-oic acid (12β-hydroxydammarenolic acid) (1), while the three known compounds were identified as (20S)-20-hydroxy-3,4-seco-dammaran-4,24-dien-3-oic acid (dammarenolic acid) (2), (3β,20S)-3,20-dihydroxydammaran-24-ene (3), and (20S)-3-oxo-20-hydroxydammaran-24-ene (4). The tyrosine kinase assay of the four compounds resulted only 1 and 2 at concentration of 10 μM that had weak activity against EGFR and InsR, with their % inhibitory were 30%, 27% (1), 45%, and 32% (2), respectively. The results suggested that the presence of a linear carboxylic acid group in both compounds could be of significance to the inhibitory properties against the two RTKs.

Chemical Constituents from Agrimonia pilosa with Inhibitory Activity against Interleukin 1β Production via NLRP3 and NLRC4 Inflammasomes

  • Nhoek, Piseth;Chae, Hee-Sung;An, Chae-Yeong;Pel, Pisey;Kim, Young-Mi;Chin, Young-Won
    • Natural Product Sciences
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    • v.27 no.4
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    • pp.228-233
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    • 2021
  • Bioactivity-guided fractionation by preliminary screening using interleukin-1β production in lipopolysaccharides (LPS)-induced J774A.1 cell line led to the isolation of fourteen structures including chromone, isocoumarins, flavanoids, and triterpenes from the aerial part of Agrimonia pilosa Ledeb. All structures were determined by measuring their spectroscopic data and comparing their spectroscopic data with the literatures. All the isolates were tested for their inhibitory activities against interleukin-1β production in LPS-induced J774A.1 cell. Of the tested compounds, (S)-(+)-5,7-dihydroxy-2-(1-methylpropyl)chromone (1), agrimonolide-6-O-β-D-glucopyranoside (5), agrimonolide-6-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (6), and catechin (10) were found to be active. Furthermore, compound 1 suppressed the protein expressions of NLRP3 and NLRC4 in murine macrophage.

Functional Ingredient and Their Some Variance in Amaranth and Quinoa (비름(Amaranth)과 명아주(Quinoa) 재배종의 기능성 물질과 변이)

  • Lee, Jae-Hak;Kim, Ki-Jun;Lee, Jung-Il;Lee, Seung-Tack;Ryu, Su-Noh
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.41 no.spc1
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    • pp.145-165
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    • 1996
  • Amaranth(Amaranthus spp. L.) and quinoa (Chenpodium quinoa Willd.) are old crops from South, Central America and Central Asia and their grains have been identified as very promising food crops because of their exceptional nutritive value. Squalene is an important ingredient in skin cosmetics and computer disc lubricants as well as bioactive materials such as inhibition of fungal and mammalian sterol biosynthesis, antitumor, anticancer, and immunomodulation. Amaranth has a component called squalene (2,6,10,15,19,23-hexamethyl-2,6,10,14,22-tetraco-sahexaene) about 1/300 of the seed and $5\~8\%$ of its seed oil. Oil and squalene content in amaranth seed were different for the species investigated. Squalene content in seed oil also increased by $15.5\%$ due to puffing and from 6.96 to $8.01\%$ by refining and bleaching. Saponin concentrations in quinoa seed ranged 0.01 to $5.6\%$. Saponins are located in the outer layers of quinoa grain. These layers include the perianth, pericarp, a seed coat layer, and a cuticle like structure. Oleanane-type triterpenes saponins are of great interest because of their diverse pharmacological properties, for instance, anti-inflammatory, antibiotic, contraceptive, and cholesterol-lowering effects. It is known that quinoa contains a number of structurally diverse saponins including the aglycones, oleanolic acid, hederagenin, and phytolaccagenic acid, which are new potential in gredient for pharmacological properties. It is likely that these saponin levels will be considerably affected by genetic, agronomic and environmental factors as well as by processing. With the current enhanced public interest in health and nutrition amaranth and quinoa will most likely remain in the immediate future within the realm of exotic health foods until such time as agricultural production meets the quantities and qualify required by industrial food manufacturers.

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Tertiary Structure of Ginsenoside Re Studied by NMR Spectroscopy

  • Kang, Dong-Il;Jung, Ki-Woong;Kim, Seoung-Keum;Lee, Sung-Ah;Jhon, Gil-Ja;Kim, Yang-Mee
    • Bulletin of the Korean Chemical Society
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    • v.28 no.12
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    • pp.2209-2213
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    • 2007
  • Ginseng has long been used as a traditional medicine in Asian countries including Korea and China. In recent years, it has been reported that the biological activities of ginseng are due to its active components, ginsenosides. Ginsenosides are represented by triterpenes of the dammarane type. Ginsenoside Re consists of two glucose rings, one rhamnose ring, and the triterpene ring. In the present study ginsenoside Re has been isolated from the Korean ginseng (Panax ginseng) and the tertiary structure has been determined using NMR spectroscopy. Flexibilities around each linkages described by seven torsion angles were considered. The structures of ginsenoside Re obtained by NMR spectroscopy show the rigidity around the glucopyranosyl ring II and alkene side chain. The dihedral angles of φ5, φ6, φ7 are about 150o, 50o and 45o, respectively. In addition, flexibility exists around rhamnopyranosyl and glucopyronosyl moiety. The linkage around the rhamnopyranosyl and glucopyranosyl ring I, are divided into three groups. This flexibility seems to play important role in regulation of the hydrophobic surface exposed to the solvent. Because of the growing need for the structural determination of ginsenoside, this result can help to understand their well-accepted pharmacological effects of ginsenoside Re.