• Title/Summary/Keyword: Triterpenoids

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Cytotoxic Triterpenoids from the Fruits of Ligustrum japonicum

  • Thi Ngo, Quynh-Mai;Cao, Thao Quyen;Woo, Mi Hee;Min, Byung Sun;Weon, Kwon-Yeon
    • Natural Product Sciences
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    • v.24 no.2
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    • pp.93-98
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    • 2018
  • Medicinal plants are potential sources of anticancer agents screening. A large number of phytochemicals, including triterpenoids, have been reported to have significant cytotoxic effects on cancer cells. From the fruits of Ligustrum japonicum Thunb., thirteen triterpenoids (1 - 13) were isolated and evaluated for their cytotoxic activity against Hela and HL-60 cells. As results, 8 (oleanolic acid) showed significant effects on Hela with $IC_{50}$ values of $5.5{\mu}M$, and moderate effects on HL-60 cells with $IC_{50}$ values of $55.9{\mu}M$. Meanwhile, 10 (oleanderic acid) and 11 ($3{\beta}$-acetoxy-urs-12-en-28-oic acid) exhibited moderate inhibitory effects on Hela with $IC_{50}$ value of 55.0 and $68.8{\mu}M$, respectively. Moreover, 10 showed cytotoxic effect on HL-60 cell line with $IC_{50}$ value of $63.9{\mu}M$. To our knowledge, this is the first report that oleanderic acid was isolated from L. japonicum and investigated in cytotoxic effects on Hela and HL-60 cells.

Inhibitory Effects of Triterpenoids on Interleukin-8/CINC-1 Induction in LPS-Stimulated Rat Peritoneal Macrophages

  • Min, Bok-Gi;Lee, Gyeong-Im;Ha, Joo-Young;Min, Kyung-Rak;Kim, Ju-Sun;Kang, Sam-Sik;Kim, Young-Soo
    • Natural Product Sciences
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    • v.2 no.1
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    • pp.48-55
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    • 1996
  • The CINC-1 is a member of rat interleukin-8 with chemotactic and activating properties to neutrophils. The CINC-1 induction in LPS-stimulated rat peritoneal macrophages was analyzed using a sensitive enzyme-linked immunosorbent assay. The peritoneal macrophages contained about 3 ng/ml as a basal level, and induced to maximal 18 ng/ml of CINC-1 by stimulation with 5 ${\mu}g/ml$ of LPS. Antiinflammatory steroids of dexamethasone and triamcinolon significantly suppressed the CINC-1 induction, where as aspirin and idomethacin did not show suppression. Inhibitory effects on the CINC-1 induction by natural triterpenoids having steroidal structures were analyzed. Among the 39 kinds of triterpenoids isolated from herbal medicines, acacigenin B and nigaichigoside F1 exhibited the highest suppression on the CINC-1 induction.

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Triterpenoid-Containing Liposome by Micelle-to-Vesicle Transition and Their Biological Activities

  • Kang, Hyung-Seok;Park, Ji-Eun;Nam, Gae-Won;Han, Sang-Hoon;Chang, Ih-Seop
    • Proceedings of the SCSK Conference
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    • 2003.09b
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    • pp.319-329
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    • 2003
  • Ursolic acid (UA) and oleanolic acid (OA) are pentacyclic triterpenoids which are widely distributed in plants, and their derivatives are aglycones of many naturally occurring saponins. It is known that pentacyclic acids may possibly enhance the mechanical barrier functions of cell membranes in plants. Recently, it has been reported that OA and UA have interesting biological activities on skin, such as anti-inflammatory and anti-wrinkle activities. Since triterpenoids are extremely insoluble and their solubility problem limits skin-care application, OA and UA were encapsulated in liposomes via micelle-to-vesicle transition to overcome poorly soluble property and enhance biological efficacy. Optimal molar ratio of OA to lecithin was found to exist for producing liposomes of small hydrodynamic size and liposomal suspensions without recrystallized precipitation of OA. From electron micrograph and dynamic light scattering studies, reconstituted OA-containing liposomes without severe mechanical treatment showed small hydrodynamic size about 150 nm. Wide-angle X-ray diffraction coupled with dynamic light scattering revealed that optimal amount of OA in liposome was 25.4 mole %. In biological evaluation, OA-containing liposome significantly increased filaggrin and transglutaminase as markers of keratinocyte differentiation in epidermal layer of hairless mouse, whereas ursolic acid-containing liposome did not show noticeable increase of filaggrin and transglutaminase compared to empty liposome. It is concluded that nano-scaled liposomes containing triterpenoids were spontaneously prepared by vesicular transition from mixed micelle and liposomal triterpenoids can enhance skin absorption of triterpenoid and biological efficacy.

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Development of a Transformation System for the Medicinal Fungus Sanghuangporus baumii and Acquisition of High-Value Strain

  • Zengcai Liu;Ruipeng Liu;Li Zou
    • Mycobiology
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    • v.51 no.3
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    • pp.169-177
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    • 2023
  • To further explore the molecular mechanism of triterpenoid biosynthesis and acquire high-value strain of Sanghuangporus baumii, the Agrobacterium tumefaciens-mediated transformation (ATMT) system was studied. The key triterpenoid biosynthesis-associated gene isopentenyl diphosphate isomerase (IDI) was transformed into S. baumii by ATMT system. Then, the qRT-PCR technique was used to analyze gene transcript level, and the widely targeted metabolomics was used to investigate individual triterpenoid content. Total triterpenoid content and anti-oxidant activity were determined by spectrophotometer. In this study, we for the first time established an efficient ATMT system and transferred the IDI gene into S. baumii. Relative to the wild-type (WT) strain, the IDI-transformant (IT) strain showed significantly higher transcript levels of IDI and total triterpenoid content. We then investigated individual triterpenoids in S. baumii, which led to the identification of 10 distinct triterpenoids. The contents of individual triterpenoids produced by the IT2 strain were 1.76-10.03 times higher than those produced by the WT strain. The triterpenoid production showed a significant positive correlation with the IDI gene expression. Besides, IT2 strain showed better anti-oxidant activity. The findings provide valuable information about the biosynthetic pathway of triterpenoids and provide a strategy for cultivating high-value S. baumii strains.

Evaluation of processing methods and harvest timings for the efficient extraction of Syzygium formosum

  • Jaeyoon Lim;Jaehan Kim;In-Seok Yeo;Jong-Tae Park
    • Korean Journal of Agricultural Science
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    • v.51 no.3
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    • pp.361-373
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    • 2024
  • Syzygium formosum has been traditionally used in Vietnam as a folk medicine for treating skin and respiratory diseases. With the recent recognition of its beneficial effects such as anticancer, antioxidant, and anti-inflammatory properties, there is an increasing interest in industrial extraction of its bioactive compounds, such as triterpenoids and flavonoids. In this study, the extraction efficiencies of S. formosum were analyzed by extraction methods and harvest timings. Firstly, it was found that distilled water treatment substantially eliminated almost all flavonoids, suggesting that minimal pretreatment is important to preserve both triterpenoids and flavonoids. Secondly, extractions with 70% ethanol at both lab and pilot scales effectively yielded more than 70% of triterpenoids and flavonoids from S. formosum. Lastly, to investigate the seasonal variation in phytochemicals, extracts from the leaves of S. formosum harvested in April, August, October, and December in Vietnam were analyzed. It was revealed that seasons with lower temperatures led to higher concentrations of triterpenoids and flavonoids. Specifically, December was found to be optimal for obtaining high concentrations of triterpenoid and October for flavonoid. Consequently, this research provides a foundation for the industrial application of S. formosum, providing critical insights into maximizing the extraction efficiency and phytochemical contents through optimized processing methods and strategic harvesting.

Analysis of Chemical Constituents of Saccharides and Triterpenoids in the Korean Native Mistletoes - I. Triterpenoids - (한국산(韓國産) 겨울살이류(類)의 당류(糖類)와 triterpenoids의 화학적(化學的) 조성(組成) 분석(分析))

  • Ahn, Won-Yung
    • Journal of the Korean Wood Science and Technology
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    • v.24 no.1
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    • pp.27-33
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    • 1996
  • The aim of this research was to investigate the chemical components of C30 compounds, especially triterpenoids in Korean native mistletoes of Korthalsella japonicus Engler parasiting to Camellia japonica L., Viscum album var. coloratum (Kom.) Ohmi, to Quercus acutissima Carruth. and Loran-thus yadoriko Sieb. to Neolitsea sericea (BI.) Koidz. For the identification of triterpenoidal components, alkaline hydrolyzates of mistletoes meals were analyzed by TLC, GC, and GC/MS. The content of oleanolic acid and ursolic acid derivatives were highest in K. japonica. In V. album, there was no big difference between leaves and twigs in content. but oleanolic acid in leaves. and olean-12-en-$3{\beta}$-ol and lup-20(29)-en-3-one in twigs were prominent. Similiar to V. album in L. yadoriki there was no difference between leaves and twigs in content, and both olean-12-en-$3{\beta}$-ol, lup-20(29)-en-3-one and urs-12-en-$3{\beta}$-ol in leaves, lup-20(29)-en-3-one in twigs were abundant. Triterpenoids as olea-12-en-$3{\beta}$-ol, lupe-20(29)-en-3-one, 3-oxo-urs-12-en-24-oic acid, and $21{\beta}$-A'-neogam-macer-22(29)-en-3-ol acetate were common in all samples tested. whereas ursolic acid only in P. japonicus and ursenol in L. yadoriki were detected. And P. japonicus had the largest number of triterpenoids and showed the highest in biological activity. So it is noted that Korean mistletoes tested in the study had three types of triterpenoid, oleanane, lupane, and ursane, irrespective of hosts, sampling positions and species.

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Anti-Platelet Pentacyclic Triterpenoids from Leaves of Campsis grandiflora

  • Jin Jing Ling;Lee Yong Yook;Heo Jung Eun;Lee Sanghyun;Kim Jeong Mi;Yun-Choi Hye Sook
    • Archives of Pharmacal Research
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    • v.27 no.4
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    • pp.376-380
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    • 2004
  • Five pentacyclic triterpenoids, oleanolic acid (1), hederagenin (2), ursolic acid (3), tormentic acid (4) and myrianthic acid (5), were isolated from the methanol extract of the leaves of Campsis grandiflora, and structures of the compounds were established by the spectroscopic methods. Compounds 2, 3, 4, and 5 were isolated for the first time from the genus Campsis. All of the compounds ($IC_{50}$: 45.3, 32.8, 82.6, 42.9 and $46.2{\mu}M$ respectively) were as equivalently inhibitive as acetylsalicylic acid ($IC_{50}:57.0{\mu}M$) on epinephrine induced platelet aggregation.

Effects of Lupane-Triterpenoids on Mitogen-induced Proliferation of Lymphocytes (Lupane계 Triterpenoid류가 임파구 분열에 미치는 효과)

  • 김영옥;조대현;정혜주;김진호;장승엽;육창수;양기숙;오오진
    • YAKHAK HOEJI
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    • v.43 no.2
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    • pp.208-213
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    • 1999
  • The effects of five lupane-triterpenoids from leaves of two Acanthopanax spp., chiisanogenin, chisanoside and $22{\alpha}-hydroxychiisanogenin$, acakoreoside A and acantrifoside A on the mitogen-induced proliferation were investigated in vitro. T cell proliferation (TCP) to concanavalin A (Con A) and the B cell proliferation (BCP) to lipopolysaccharide (LPS) were increased by chiisanogenin. TCP to Con A was significantly increased by chiisanoside and acankoreoside A, but not affected by chiisanogenin, $22{\alpha}-hydroxychiisanogenin$ and acantrifoside A, BCP to LPS was significantly increased by acankoreoside A and acantrifoside A, and slightly increased by chiisanoside, chiisanogenin and $22{\alpha}-hydroxychiisanogenin$.

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Cytotoxic Constituents from the Aerial Part of Clematis apiifolia L.

  • Youn, Ui-Jung;Jin, Wen-Yi;Song, Kyung-Sik;Seong, Yeon-Hee;Bae, Ki-Hwan
    • Korean Journal of Medicinal Crop Science
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    • v.14 no.5
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    • pp.299-302
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    • 2006
  • Three known triterpenoids were isolated from MeOH extract of C. apiifolia (Ranunculaceae). Their structures were identified as oleanolic acid (1), ursolic acid (2), hederagenic acid (3) by comparison of their physicochemical and spectral data with the literature values. Among them, 2 was isolated for the first time from this plant. The isolated compounds were evaluated for their cytotoxicity against L1210, HL-60, SK-OV-3 tumor cell lines. All compounds 1-3 were shown good activities with $IC_{50}$ values ranging from 7.7 to $25.6\;{\mu}g/ml. This result suggests that triterpenoids 1-3 are main cytotoxic principles of this plant.

Isolation of Pentacyclic Triterpenoids from Semi-fermented Tea and Its Effects on Oxidative Stress

  • Chung, Ha-Sook
    • Preventive Nutrition and Food Science
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    • v.14 no.1
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    • pp.49-53
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    • 2009
  • Antioxidative activities of major pentacyclic terpenoids from the semi-fermented tea of Camellia sinensis L. were investigated. The free radical scavenging activities of triterpenoids $1{\sim}3$ were examined with of DPPH and superoxide anion radical scavenging activity. The $IC_{50}$ of compounds 1 and 2 for DPPH radical scavenging activities were 23.1 and $37.2{\mu}g/mL$ respectively, and for superoxide anion radical scavenging activities were 37.2 and $35.2{\mu}g/mL$, respectively. According to this result, compounds 1 or 2 in semi-fermented tea could be the candidates for bioactive material having antioxidant activity.