• 제목/요약/키워드: Triterpene acid

검색결과 85건 처리시간 0.022초

Antioxidant Activity of γ-Oryzanol and Synthetic Phenolic Compounds in an Oil/Water (O/W) Emulsion System

  • Kim, Joo-Shin
    • Preventive Nutrition and Food Science
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    • 제12권3호
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    • pp.173-176
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    • 2007
  • ${\gamma}-Oryzanol$ is one of the chain breaking antioxidants. Both sterol (triterpene) and phenolic hydroxyl groups in the structure of ${\gamma}-oryzanol$ may be responsible for its antioxidative function. We hypothesize that ${\gamma}-oryzanol$ is more effective in preventing the autoxidation of polyunsaturated fatty acid (PUFA) than the synthetic phenolic compounds in an oil/water (O/W) emulsion system. The antioxidative effectiveness of different concentrations of ${\gamma}-oryzanol$ and synthetic antioxidants was evaluated at different incubation times (0, 4, 8, 16, and 32 h) by measuring both the formation of hydroperoxides and the decomposition product of hydroperoxides (hexanal) in each emulsion system. Overall, the order of effectiveness of various antioxidants for inhibiting the formation of hydroperoxide in the O/W emulsion was: ${\gamma}-oryzanol$> tert-butylhydroquinone (TBHQ)> butylated hydroxytoluene (BHT)> butylated hydroxyanisole (BHA). O/W emulsion with selective lower concentrations of ${\gamma}-oryzanol$ showed better effectiveness than that with higher concentration of synthetic antioxidants. However, the ability of both ${\gamma}-oryzanol$ and synthetic antioxidants to decompose hydroperoxide was similar. ${\gamma}-Oryzanol$ was more effective antioxidant than the synthetic phenolic compounds in preventing the formation of hydroperoxide in the O/W emulsion system.

Anthraquinones with Antibacterial Activities from Crucianella maritima L. Growing in Egypt

  • El-Lakany, Abdalla M.;Aboul-Ela, Maha A.;Abdel-Kader, Maged S.;Badr, Jihan M.;Sabri, Nawal N.;Goher, Yousry
    • Natural Product Sciences
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    • 제10권2호
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    • pp.63-68
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    • 2004
  • From the extracts of Crucianella maritima L. (Rubiaceae), five new anthraquinones namely; 1-hydroxy-2-methyl-6-methoxy anthraquinone, 6-methoxy-2-methyl quinizarin, 6-methyl-anthragallol-2,3-dimethyl ether, 6-methyl-anthragallol-2-methyl ether, and 1-hydroxy-2-carbomethoxyanthraquinone were isolated and identified. In addition, deacetyl asperulosidic acid 6'-glucoside sodium salt, a new iridoid diglucoside, along with twelve known anthraquinones, three flavonols, three sterols, and one triterpene were also isolated and identified for the first time from this plant. Their chemical structures were established by physical, chemical and spectroscopic data, including UV, MS, ID- and 2D-NMR analyses. The antimicrobial, cytotoxic activities and a preliminary clinical trial of the crude extracts and some isolates are also presented. Chemotaxonomical aspects are briefly discussed.

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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    • 제10권1호
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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.

Isolation and Characterization of Terpene Synthase Gene from Panax ginseng

  • Kim, Yu-Jin;Ham, Ah-Rom;Shim, Ju-Sun;Lee, Jung-Hye;Jung, Dae-Young;In, Jun-Gyo;Lee, Bum-Soo;Yang, Deok-Chun
    • Journal of Ginseng Research
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    • 제32권2호
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    • pp.114-119
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    • 2008
  • Terpene synthase plays a key role in biosynthesis of triterpene saponins (ginsenosides) and is intermediate in the biosynthesis of a number of secondary metabolites. A terpene synthase (PgTPS) cDNA was isolated and characterized from the root of Panax ginseng c.A. Meyer. The deduced amino acid sequence of PgTPS showed a similarity with A. deliciosa (AAX16121) 61%, V. vinifera (AAS66357) 61%, L. hirsutum (AAG41891) 55%, M. truncatula (AAV36464) 52%. And the segment of a terpene synthase gene was amplified by reverse transcriptase-polymerase chain reaction (RTPCR). We studied expression of terpene synthase under stressful conditions like chilling, salt, UV, and heavy metal stress treatment. Expression of PgTPS was increased gradually after exposure to stresses such as chilling, salt, and UV illumination. But its transcription seems to be reduced by cadmium and copper treatment.

DNA Topoisomerases I and II Inhibitory Activity of Constituents Isolated from Juglans mandshurica

  • Li, Gao;Lee, Sun-Young;Lee, Kyeung-Seon;Lee, Sung-Won;Kim, Sang-Hyun;Lee, Seung-Ho;Lee, Chong-Soon;Woo, Mi-Hee;Son, Jong-Keun
    • Archives of Pharmacal Research
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    • 제26권6호
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    • pp.466-470
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    • 2003
  • Nine diarylheptanoids (1-9), one triterpene (10), one sesquiterpenoid (11), one naphthoquinone (12), four tetralones (13-16), one naphthalene carboxylic acid glucoside (17) and six naphthalenyl glycosides (18-23) were isolated from the roots of Juglans mandshurica Maximowicz (Juglandaceae), and their structures determined from the chemical and spectral data. Here, we report the inhibitory effects, on the DNA topoisomerases I and II activities, of all these compounds. Compounds 10 and 23 showed more potent inhibitory effects, on the DNA topoisomerases I and II (94.0 and 86.0% inhibitions at the concentration of 5 $\mu$ g/mL, respectively), than the positive control compounds, camptothecin and etoposide.

Cloning and Characterization of Squalene Synthase (SQS) Gene from Ganoderma lucidum

  • Zhao, Ming-Wen;Liang, Wan-Qi;Zhang, Da-Bing;Wang, Nan;Wang, Chen-Guang;Pan, Ying-Jie
    • Journal of Microbiology and Biotechnology
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    • 제17권7호
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    • pp.1106-1112
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    • 2007
  • This report provides the complete nucleotide sequences of the full-length cDNA encoding squalene synthase (SQS) and its genomic DNA sequence from a triterpene-producing fungus, Ganoderma lucidum. The cDNA of the squalene synthase (SQS) (GenBank Accession Number: DQ494674) was found to contain an open reading frame (ORF) of 1,404 bp encoding a 468-amino-acid polypeptide, whereas the SQS genomic DNA sequence (GenBank Accession Number: DQ494675) consisted of 1,984 bp and contained four exons and three introns. Only one gene copy was present in the G. lucidum genome. The deduced amino acid sequence of Ganoderma lucidum squalene synthase (GI-SQS) exhibited a high homology with other fungal squalene synthase genes and contained six conserved domains. A phylogenetic analysis revealed that G. lucidum SQS belonged to the fungi SQS group, and was more closely related to the SQS of U. maydis than to those of other fungi. A gene expression analysis showed that the expression level was relatively low in mycelia incubated for 12 days, increased after 14 to 20 days of incubation, and reached a relatively high level in the mushroom primordia. Functional complementation of GI-SQS in a SQS-deficient strain of Saccharomyces cerevisiae confirmed that the cloned cDNA encoded a squalene synthase.

Complete $^1H$-NMR and $^{13}C$-NMR spectral analysis of the pairs of 20(S) and 20(R) ginsenosides

  • Yang, Heejung;Kim, Jeom Yong;Kim, Sun Ok;Yoo, Young Hyo;Sung, Sang Hyun
    • Journal of Ginseng Research
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    • 제38권3호
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    • pp.194-202
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    • 2014
  • Background: Ginsenosides, the major ingredients of Panax ginseng, have been studied for many decades in Asian countries as a result of their wide range of pharmacological properties. The less polar ginsenosides, with one or two sugar residues, are not present in nature and are produced during manufacturing processes by methods such as heating, steaming, acid hydrolysis, and enzyme reactions. $^1H$-NMR and $^{13}C$-NMR spectroscopic data for the identification of the less polar ginsenosides are often unavailable or incomplete. Methods: We isolated 21 compounds, including 10 pairs of 20(S) and 20(R) less polar ginsenosides (1-20), and an oleanane-type triterpene (21) from a processed ginseng preparation and obtained complete $^1H$-NMR and $^{13}C$-NMR spectroscopic data for the following compounds, referred to as compounds 1-21 for rapid identification: 20(S)-ginsenosides Rh2 (1), 20(R)-Rh2 (2), 20(S)-Rg3 (3), 20(R)-Rg3 (4), 6'-O-acetyl-20(S)-Rh2 [20(S)-AcetylRh2] (5), 20(R)-AcetylRh2 (6), 25-hydroxy-20(S)-Rh2 (7), 25-hydroxy-20(S)-Rh2 (8), 20(S)-Rh1 (9), 20(R)-Rh1 (10), 20(S)-Rg2 (11), 20(R)-Rg2 (12), 25-hydroxy-20(S)-Rh1 (13), 25-hydroxy-20(R)-Rh1 (14), 20(S)-AcetylRg2 (15), 20(R)-AcetylRg2 (16), Rh4 (17), Rg5 (18), Rk1 (19), 25-hydroxy-Rh4 (20), and oleanolic acid 28-O-b-D-glucopyranoside (21).

Inonotus obliquus균의 정치배양이 균사체의 화학적 조성분에 미치는 영향 (Chemical Constituents of Stationary Cultured Mycelia of Inonotus obliquus)

  • 신유수;寺澤實;조남석
    • Journal of the Korean Wood Science and Technology
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    • 제32권4호
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    • pp.52-57
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    • 2004
  • 본 연구는 액체 정치배양한 Inonotus obliquus의 균사체 조성분을 분석하였으며, I. obliquus의 균핵과 진탕배양한 균사체의 성분조성을 비교하였다. I. obliquus 균의 정치배양 균사체가 생산하는 화학성분을 분석한 결과, 단리된 화합물은 lanosterol(1), inotodiol(2), trametenolic acid(3), 3β,22,25-trihydroxy-lanosta-8-ene(6), 3β,22-dihydroxy-lanosta-8,24-diene(A), 3β-hydroxy-lanosta-8,24-dien-21-al(B) 및 methyl trametenolate(C)이 확인되었다. 액체진탕배양 균사체가 생산하는 화합물과의 비교에 의해, 공통화합물은 lanosterol(1)이었고, ergosterol(7)과 ergosterol peroxide(8)는 액체진탕배양, lanosterol(1)의 C-21치환화합물과 C-22치환화합물은 정치배양함으로써 얻어짐을 알 수 있었다.

Stichoposide D의 백혈병 세포주에서 세라마이드 생성을 통한 세포 사멸 유도 및 항암 작용 (Induction of Apoptosis and Antitumor Activity by Stichoposide D through the Generation of Ceramide in Human Leukemia Cells)

  • 박은선;윤성훈;신성원;곽종영;박주인
    • 생명과학회지
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    • 제22권6호
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    • pp.760-771
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    • 2012
  • 해양 트리테르펜 글리코시드(marine triterpene glycosides)는 해삼(Holothurians)으로부터 분리된 천연물질로서 항 진균작용, 항암작용 및 용혈 작용 등 여러 가지 생물학적 활성들을 가지고 있다고 보고되었다. 또한 이전의 연구 결과 Thelenota anax로부터 분리한 stichoposide C (STC)는 산성 스핑고마이엘리나제와 중성 스핑고마이엘리나제의 활성화에 의한 세라마이드의 생성을 통하여 백혈병 세포주에서 세포사멸을 유도한다는 것을 알 수 있었다. 본 연구에서는 STC와 구조 유사체인 STD가 백혈병 세포에서 세포사멸을 유도하는지와 이에 대한 분자적 기전을 살펴보았다. STC와 STD는 K562 세포와 HL-60 세포에서 농도와 시간 의존적으로 세포 사멸을 일으키고 이러한 세포 사멸은 caspase-8의 활성화, 미토콘드리아 손상, caspase-9의 활성화, 그리고 caspase-3의 활성화에 의해 유도된다. 이러한 결과는 STC와 STD가 외인성 경로와 내인성 경로의 활성화를 통해 세포 사멸을 유도함을 시사한다. 그리고 STC는 산성 SMase와 중성 SMase를 활성화시키고 이 결과로 세라마이드를 생성시킨다. 산성과 중성 SMase의 특이적인 저해제를 이용하여 STC에 의한 세포 사멸이 부분적으로 억제됨을 알 수 있었다. 반면에, STD는 세라마이드 합성 효소의 활성화에 의해서 세라마이드를 생성시킨다. 세라마이드 합성 효소 저해제를 이용하여 STD에 의한 세포 사멸이 부분적으로 억제되는 것을 확인하였다. 더욱이 STC와 STD는 HL-60 세포의 이종 이식 종양 모델에서 종양의 성장을 현저하게 억제하였고 세라마이드의 생성도 증가시켰다. 이러한 결과는 STC와 STD가 aglycone에 부착된 당이 다르므로 서로 다른 경로를 통해 세포 사멸과 항암 활성을 유도한다는 것을 암시하였다. 따라서 이러한 결과는 이들의 작용은 aglycone에 부착된 당에 의해 영향을 받을 수 있고 이들은 향후 백혈병의 치료제로 사용될 수 있다는 것을 제시하였다.

Chemical Variability of Leaf Cuticular Waxes According to Leaf Position in Tea Tree

  • Kim, Kwan-Su;Song, Yeon-Sang;Moon, Youn-Ho;Park, Si-Hyung
    • 한국작물학회지
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    • 제51권spc1호
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    • pp.297-303
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    • 2006
  • Cuticular waxes on tea (Camellia sinensis L.) loaves consisted mainly of alkanes, fatty acids, primary alcohols, triterpenes, and a group of unknown compounds, dominated by primary alcohols and triterpenes. Tea tree accessions used in this study were M-1, M-2, Sakimidori, and Yabukita. For all accessions, the alkane, fatty acid, and primary alcohol constituents consisted of a homologues series, and the major constituents of primary alcohol class were the C28 and C30 homologues. Triterpenes consisted of friedelin, $\beta-amyrin$, and three unidentified ones and friedelin was the most abundant. Leaf area and the total amounts of cuticular waxes per leaf increased with lower leaf position from the apical bud in Yabukita variety. With different leaf position, total wax amount per unit leaf area on the youngest leaves of P1 (the uppermost leaf position) showed the largest amount $(12.80{\mu}g/cm^2)$, and on mature loaves of P2 to P6 ranged from 7.08 to $7.77{\mu}g/cm^2$, and then on the oldest loaves of P7 (the lowest leaf position) remained at an increased level $(17.53{\mu}g/cm^2)$. During leaf development (lower leaf position), the amount of primary alcohols decreased from P1 to P6 and increased at P7, whereas that of triterpenes increased from P1 to P7. The percentage of each wax class in the total wax amount occurred a decrease in primary alcohol and an increase in triterpene, with leaf age.