• Title/Summary/Keyword: sapogenin

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Studies on the Ginseng Plants(I) -Saponins and Sapogenins from American Ginseng Plants- (인삼식물(人蔘植物)에 관(關)한 연구(硏究)(I) -미국인삼(美國人蔘) 사포닌 및 그 비당체(非糖體)-)

  • Kim, Jung-Yun;Staba, E. John
    • Korean Journal of Pharmacognosy
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    • v.4 no.4
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    • pp.193-203
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    • 1973
  • The saponins of two- and four-year-old American ginseng plants (Panax quinquefolium L.) (Araliaceae) collected in July and September were studied. American ginseng saponins (panaquilins) differ from Korean ginseng $(Panax ginseng\;C.A.\;M_{EYER})$ saponins (ginsenosides). The American ginseng saponins separated and named were panaquilins A, B, C, D, E-1, E-2, E-3, G-1, G-2, (c) and (d). One-dimensional thin-layer chromatography did not completely separate panaquilin mixture and was subject to misinterpretation. The panaquilins were more accurately separated and identified by the two-dimensional thin-layer method established. Some differences in American ginseng saponins were dependent upon the plant age, time of collection, and part extracted. The American ginseng sapogenin components are panaxadiol (panaquilins B and C), oleanolic acid (panaquilin D) and panaxatriol (panaquilin G-1). The panaquilins E-1, E-2 and E-3 mixture contained both panaxadiol and panaxatriol. The genins of panaquilins A, (c), (d) and G-2 were not identified. In addition, ${\beta}-sitosterol$ and stigmasterol were identified from the root ether extracts.

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Characterization of ginseng extracts

  • Woo, Lin-Keun;Han, Byung-Hoon;Baik, Duck-Woo;Park, Dae-Sic
    • YAKHAK HOEJI
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    • v.17 no.3
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    • pp.129-136
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    • 1973
  • In order to establish the chemical standards for the quality control of ginsentgextract, an approach for the assay of sapogenin contents in the part of main roots and fibrous side roots was performed by combination of preparative thin layer chromotographic procedure and vanillin-$H_{2}SO_{4}$ color reaction. The contents of dammarane aglycones as funcction of dammarane glycosides in 80%-EtOH extracts were analyzed by the method from the main roots and fibrous side roots of Korean ginseng grown for 4-6 years. The differences by their grown ages in the contents of dammarane glycosides, in the ratio of panaxadiol to panaxatriol contents, and in the mounts of 80% EtOH extract were not significant in the parts of main roots and fibrous side roots of Korean gingeng. Differences due to the part for medicinal uses were highly significant in all parameters mentioned, showing following results ; in the main roots ; 80% EtOH extract, 12.7-15.7 % : the ratio of aglycone composition, 0.955-1.012 : dammarane glycoside (as diglucoside bases), 1.537-1.863 ; in fibrous isde roots ; 80% EtOH extract, 26.0-26.02% : dammarane glycoside, 4.767-5.641 : the ratio, 1.456-1.50.

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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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Specific Conversion of Ginseng Saponin by the Enzyme of Rhizopus japonicus (Rhizopus japonicus의 효소(酵素)에 의한 인삼(人蔘) 사포닌의 선택적(選擇的) 전환(轉換))

  • Kim, Sang-Dal;Seu, Jung-Hwn
    • The Korean Journal of Mycology
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    • v.14 no.3
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    • pp.195-200
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    • 1986
  • The enzyme produced by a strain of Rhizopus japonicus was able to covert selectively ginsenoside $Rb_1$ which was the most abundant ginseng saponin, into ginsenoside Rd which was known to be superior to ginsenoside $Rb_1$ pharmaceutically. This specific conversion of ginsenoside $Rb_1$ without any change of other ginsenoside patterns was confirmed by thin layer chromatography and high performance liquid chromatograpy quantitatively. The amount of ginsenoside Rd was increased to 4.8 and 34.7 folds by enzymatic conversion of ginsenoside $Rb_1$ in total saponin and ginsenoside Rb group saponin, respectively. The increased amount of ginsenoside Rd corresponded to total amount of released glucose and decreased amount of ginsenoside $Rb_1$ accurately.

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Cytotoxic and Apoptotic Effects of Saponins from Akebia quinata on HepG2 Hepatocarcinoma Cells (으름유래 사포닌의 HepG2 간암세포에 대한 세포독성 및 세포자살유도 효과)

  • Kang, Hye-Sook;Kang, Jae-Seon;Jeong, Woo-Sik
    • Food Science and Preservation
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    • v.17 no.3
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    • pp.311-319
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    • 2010
  • Four saponins (1~4) were isolated from Akebia quinata pericarp through bioassay-guided fractionation. Pericarps of A. quinata were extracted with ethanol and sequentially fractionated with dichloromethane, ethyl acetate, butanol and water. Compounds 1~4 from the butanol fraction were identified as 3-O-${\alpha}$-L-arabinopyranosyl hederagenin (${\delta}$-hederin), 3-O-${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$2) ${\alpha}$-L-arabinopyranoly oleanolic acid (${\beta}$-hederin), 3-O-${\beta}$-D-xylopyranosyl (1${\rightarrow}$3) ${\alpha}$-L-arabinopyranosyl hederagenin (saponin C), and 3-O ${\alpha}$-L-rhamnopyranosyl (1${\rightarrow}$2) ${\alpha}$-L-arabinopyranosyl hederagenin (${\alpha}$-hederin) based on the spectroscopic evidences, respectively. Oleanolic acid and hederagenin were identified as the corresponding sapogenins by acid-hydrolysis. These compounds exhibited strong cytotoxic activity in MTS [3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxy-methoxyphenyl)-2-(4-sulfophenyl)-2H- tetrazolium, inner salt] assay on HepG2 cells. ${\beta}$-Hederin obviously attenuated the expression of bcl-2, an anti-apoptotic protein. All of the compounds also induced the activity of caspase-3, an apoptotic enzyme, while ${\alpha}$-hederin was the most potent activator of the enzyme. Our data demonstrate for the first time the apoptosis-inducing activity of A. quinata. These results suggest that A. quinata could be used as a potential source of natural cancer chemopreventive agents.

Ginsenoside Change and Antioxidation Activity of Fermented Ginseng (발효인삼의 Ginsenoside 변화와 항산화 활성)

  • Doh, Eun-Soo;Chang, Jun-Pok;Lee, Kun-Hee;Seong, Nak-Sul
    • Korean Journal of Medicinal Crop Science
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    • v.18 no.4
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    • pp.255-265
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    • 2010
  • The extent of growth L. plantarum (LP), L. delbrueckii subsp. bulgaricus (LD), L. fermentum (LF), S. thermophilus (ST), B. longum (BI) and S. cerevisiae (SA) was generally good with the lower concentration of the ginseng extract. Total sapogenin content was slightly different with kinds of a fermentation microorganism and the time of fermentation process, and generally reduced compare to before fermentation. The content of ginsenoside Rb1, Rb2, Rb3, Re and Rf were decreased with the fermentation but ginsenoside Rd was increased by the E, LF and SA fermented extract. The content of compound K increased in the order of not-fermented extrac < enzyme fermented extract < enzyme and microorganism fermented extract, and as the fermented time get longer, the content of compound K was sightly increased. Especially, the content of compound K of the SA fermented extract was the most increased, also it of the BI, LD and LF fermented extract was increased, so these extract were considered a high valuable. Polyphenol content of the BI, LD, LP and ST fermented extract indicated $9.18{\pm}0.39{\sim}15.68{\pm}0.54$ mg/10 g which was lower than it of a not-fermented extract ($11.92{\pm}0.26{\sim}28.41{\pm}0.39$ mg/10 g). Flavonoid content of a ginseng fermented extract indicated $26.93{\pm}0.17{\sim}156.45{\pm}1.29$ mg/10 g, it was higher than a not-fermented extract ($18.06{\pm}0.90$ mg/10 g). As the fermented time get longer, the flavonoid content tendency to increase. DPPH radical scavenging activity of a fermented ginseng extract was $24.11{\pm}1.41{\sim}55.62{\pm}0.33%$, it was slightly lower compared to a natural antioxidant, vitamin C. But it of the LF and ST fermented extract was similar to a natural antioxidant, vitamin C. It has not a concerned in a fermentation. Nitrite scavenging ability of a 24 hr fermented extract was above 80% at pH 2.5 and 4.2, it was similar to an artificial antioxidant, BHT ($84.76{\pm}0.13%$; pH2.5, $84.98{\pm}0.11%$; pH 4.2). It has not a concerned in a fermentation. SOD-like activity of a fermented extract was lower than that of a not-fermented extract ($19.22{\pm}0.51%$), but it of the E and LP-fermented extract was a very highly notable value. As the fermented time get longer, the SOD-like activity tendency to increase.

Cultivation Factors for Pot-plant Production of Arenaria juncea M.Bieb. (벼룩이울타리의 분화 생산을 위한 재배 요인)

  • Yeon, Soo Ho;Lee, Seung Yeon;Lee, Cheol Hee
    • Proceedings of the Plant Resources Society of Korea Conference
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    • 2019.04a
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    • pp.59-59
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    • 2019
  • 벼룩이울타리(Arenaria juncea M.Bieb.)는 7~8월에 백색의 꽃이 취산화서로 아름답게 피며, 산지, 산비탈 또는 메마른 초지에 자생한다. 청열 및 양혈의 효능이 있고, 은시호의 대용으로 쓰이며, 뿌리에는 triterpenoid saponins과 sapogenin이 함유되어 있다. 본 연구는 분화용 식물로 벼룩이울타리를 활용하기 위한 효율적인 포트 정식방법을 개발하기 위하여 수행되었다. 실험은 2018년 선행연구에서 생산된 유묘를 7월 2일에 정식하여 10월 15일까지 약 15주 동안 재배하였다. 대조구는 플라스틱 화분 10호($9{\times}9cm$)에 원예상토를 충진하고 200구 트레이에 셀 당 4립씩 파종하여 생산된 1셀을 정식하였다. 재배 실험은 용기종류[비닐포트(3, 4치), 플라스틱 포트(8, 10, 12호)], 토양 종류[원예상토, 중화 피트모스:펄라이트(3:1, 4:1), 마사토:중화 피트모스(2:1, 3:1)], 묘의 소질[파종 립수(1, 2, 4, 6립), 파종 용기(162, 200, 288구 트레이)] 등을 달리하여 진행하였다. 연구의 결과, 벼룩이울타리는 토양의 양이 많을수록 생육이 양호한 결과를 보여, 플라스틱 12호에 재배하는 것이 분화용으로 가장 효과적이었다. 한편, 비닐 4치와 플라스틱 10호의 경우, 플라스틱 12호와 생육에 큰 차이가 없어 경제적인 것으로 판단된다. 벼룩이울타리는 원예상토에서 재배하는 것이 전반적으로 생육이 우수하였으며, 다음으로 마사토와 피트모스 혼용토 순이었다. 그러나 피트모스와 펄라이트 혼용토는 비율과 관계없이 생육이 감소하며, 잎에 황백화 현상이 나타났다. 셀당 파종량을 달리하여 육묘한 후 정식한 결과, 전반적인 생육은 1립 파종묘에서 양호하였으나, 2, 4, 6립 파종묘가 1립 처리구에 비해 포트당 엽수가 약 1.35, 1.44, 2.01배 증가하는 경향을 보였다. 그러므로 유묘 생산시 셀당 파종량을 늘려 재배하는 것이 분화용으로 효과적일 것으로 판단된다. 파종용기별 유묘의 생육은 162, 200, 288구 트레이 순이었으나, 정식 후 약 15주 동안 재배한 결과, 162, 200구에서 생산된 유묘를 정식하는 것이 288구보다 양호하였다. 따라서, 육묘 단계에서 토양 및 공간을 절약할 수 있는 200구에 파종하여 재배하는 것이 효율적인 방법으로 생각된다. 결론적으로, 벼룩이울타리의 분화용 재배는 플라스틱포트 12호에 원예상토를 충진하고 200구 트레이에 4립 또는 6립을 파종하여 육묘한 묘를 정식하는 것이 가장 효과적이다. 한편, 경제적인 측면을 고려할 때, 재배면적을 적게 차지하는 비닐포트 4치 또는 플라스틱 포트 10호에 마사토와 중화 피트모스를 혼용하여 충진한 다음 유묘를 이식하는 것도 하나의 방법으로 판단된다.

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Ginsengenin derivatives synthesized from 20(R)-panaxotriol: Synthesis, characterization, and antitumor activity targeting HIF-1 pathway

  • Guo, Hong-Yan;Xing, Yue;Sun, Yu-Qiao;Liu, Can;Xu, Qian;Shang, Fan-Fan;Zhang, Run-Hui;Jin, Xue-Jun;Chen, Fener;Lee, Jung Joon;Kang, Dongzhou;Shen, Qing-Kun;Quan, Zhe-Shan
    • Journal of Ginseng Research
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    • v.46 no.6
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    • pp.738-749
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    • 2022
  • Background: Ginseng possesses antitumor effects, and ginsenosides are considered to be one of its main active chemical components. Ginsenosides can further be hydrolyzed to generate secondary saponins, and 20(R)-panaxotriol is an important sapogenin of ginsenosides. We aimed to synthesize a new ginsengenin derivative from 20(R)-panaxotriol and investigate its antitumor activity in vivo and in vitro. Methods: Here, 20(R)-panaxotriol was selected as a precursor and was modified into its derivatives. The new products were characterized by 1H-NMR, 13C-NMR and HR-MS and evaluated by molecular docking, MTT, luciferase reporter assay, western blotting, immunofluorescent staining, colony formation assay, EdU labeling and immunofluorescence, apoptosis assay, cells migration assay, transwell assay and in vivo antitumor activity assay. Results: The derivative with the best antitumor activity was identified as 6,12-dihydroxy-4,4,8,10,14-pentamethyl-17-(2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl(tert-butoxycarbonyl)glycinate (A11). The focus of this research was on the antitumor activity of the derivatives. The efficacy of the derivative A11 (IC50 < 0.3 µM) was more than 100 times higher than that of 20(R)- panaxotriol (IC50 > 30 µM). In addition, A11 inhibited the protein expression and nuclear accumulation of the hypoxia-inducible factor HIF-1α in HeLa cells under hypoxic conditions in a dose-dependent manner. Moreover, A11 dose-dependently inhibited the proliferation, migration, and invasion of HeLa cells, while promoting their apoptosis. Notably, the inhibition by A11 was more significant than that by 20(R)-panaxotriol (p < 0.01) in vivo. Conclusion: To our knowledge, this is the first study to report the production of derivative A11 from 20(R)-panaxotriol and its superior antitumor activity compared to its precursor. Moreover, derivative A11 can be used to further study and develop novel antitumor drugs.