• 한국약용작물학회지
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• 제16권1호
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• pp.51-56
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• 2008

The content of two steroids-campesterol (1) and ${\beta}$-sitosterol (2), and four triterpenes-taraxetrone (5), ${\beta}$-amyrin (6), (-)-friedelin (7), glutinol (8) in the Orostachys japonicus A. Berger cultivated under various conditions was estimated and compared with those in wild one. The present investigation disclosed that there are no significant difference in their contents between cultivated Orostachys japonicus A. Berger and wild one. from viewpoint of the content of the steroids 1 and 2, and the triterpenes 5-8, the quality of cultivated Orostachys japonicus A. Berger is not inferior to the wild one.

• Natural Product Sciences
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• 제22권4호
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• pp.263-269
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• 2016

Rhynchophylline (RP) is a major tetracyclic oxindole alkaloid of Uncariae Ramulus et Uncus which has been used to treat hypertension, seizures, pain and anxiety in the oriental countries. A recent report revealed that RP attenuated ischemia-induced neuronal damage and kainite-induced convulsions in animals. This study was performed to investigate whether RP enhances pentobarbital-induced sleep behaviors and modulates sleep architecture in mice. Locomotor activity was significantly inhibited by RP at 0.25 and 0.5 mg/kg, similar to 2 mg/kg diazepam (a benzodiazepine agonist) in mice. RP shortened sleep latency and increased total sleep time in a dose-dependent manner when administrated with pentobarbital (42 mg/kg, i.p.). RP also increased the number of sleeping mice and total sleep time by concomitant administration with the sub-hypnotic dosage of pentobarbital (28 mg/kg, i.p.). On the other hand, RP (0.25 mg/kg, p.o.) itself significantly inhibited sleep-wake cycles, prolonged total sleep time, and rapid eye movement in rats. In addition, RP also increased chloride influx in the primary cultured hypothalamic neuronal cells. In addition, we found that glutamic acid decarboxylase ($GAD_{65/67}$) was activated by RP. In conclusion, RP augments pentobarbital-induced sleeping behaviors, and can be a candidate for treating insomnia.

• Applied Biological Chemistry
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• 제38권6호
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• pp.577-580
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• 1995

다제내성 Staphylococcus aureus균주에 강력한 항균활성을 나타내는 CNU30122 균주를 선발하였다. 선발된 CNU30122균주의 배양액 추출물로부터 Diaion HP-20 column chromatograpy, ethylacetate 추출, silica gel 및 Sephadex LH-20 column chromatography, HPLC 등에 의해 백색분말의 순수한 화합물을 분리정제 하였다. 본 물질의 구조분석을 위하여 $^1H$ 및 $^{13}C\;NMR,\;DEPT,\;^1H-^1H\;COSY,\;^1H-^{13}C\;COSY$ 및 HMBC spectrum을 분석한 결과 본 물질은 분자량 516, 분자식 $C_{31}H_{48}O_6$의 tetracyclic triterpenoic acid 계열인 fusidic acid로 동정 되었다. 본화합물은 streptomycin, pecicillin, kanamycin, tetracycline 등의 약제에 내성균주인 Staphylococcus aureus R209 균주에 선택적으로 강한 항균활성을 나타내었다.

• Molecules and Cells
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• 제37권10호
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• pp.727-733
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• 2014

Spinosyns A and D are potent ingredient for insect control with exceptional safety to non-target organisms. It consists of a 21-carbon tetracyclic lactone with forosamine and tri-Omethylated rhamnose which are derived from S-adenosyl-methionine. Although previous studies have revealed the involvement of metK1 (S-adenosylmethionine synthetase), rmbA (glucose-1-phosphate thymidylyltransferase), and rmbB (TDP-D-glucose-4, 6-dehydratase) in the biosynthesis of spinosad, expression of these genes into rational screened Saccharopolyspora spinosa (S. spinosa MUV) has not been elucidated till date. In the present study, S. spinosa MUV was developed to utilize for metabolic engineering. The yield of spinosyns A and D in S. spinosa MUV was $244mgL^{-1}$ and $129mgL^{-1}$, which was 4.88-fold and 4.77-fold higher than that in the wild-type ($50mgL^{-1}$ and $27mgL^{-1}$), respectively. To achieve the better production; positive regulator metK1-sp, rmbA and rmbB genes from Streptomyces peucetius, were expressed and co-expressed in S. spinosa MUV under the control of strong $ermE^*$ promoter, using an integration vector pSET152 and expression vector pIBR25, respectively. Here-with, the genetically engineered strain of S. spinosa MUV, produce spinosyns A and D up to $372/217mgL^{-1}$ that is 7.44/8.03-fold greater than that of wild type. This result demonstrates the use of metabolic engineering on rationally developed high producing natural variants for the production.

• Bulletin of the Korean Chemical Society
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• 제35권5호
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• pp.1485-1490
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• 2014

We have designed and developed a new ladder type tetrafused ${\pi}$-conjugated building block such as dihydroindolo[3,2-b]indole (DINI) and investigated its role as an electron rich unit. The photovoltaic properties of a new semiconducting ${\pi}$-conjugated polymer, poly[[5,10-bisoctyl-5,10-dihydroindolo[3,2-b]indole-[5,6- bis(octyloxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole]], represented by PDINI-OBTC8 are described. The new polymer PDINI-OBTC8 was synthesized in donor-acceptor (D-A) fashion, where fused ${\pi}$-conjugated tetracyclic DINI, and 5,6-bis(octyloxy)-4,7-di(thiophen-2-yl) benzo[c][1,2,5]thiadiazole (OBTC8) were employed as electron rich (donor) and electron deficient (acceptor) moieties, respectively. The conventional bulk heterojunction (BHJ) device structure ITO/PEDOT:PSS/PDINI-OBTC8:PCB71M/LiF/Al was utilized to fabricate polymer solar cells (PSCs), which comprises the blend of PDINI-OBTC8 and [6,6]-phenyl-$C_{71}$-butyric acid methyl ester ($PC_{71}BM$) in BHJ network. A BHJ PSC that contain PDINI-OBTC8 delivered power conversion efficiency (PCE) value of 1.68% with 1 vol% of 1,8-diidooctane (DIO) under the illumination of A.M 1.5G 100 $mW/cm^2$.

• Journal of Ginseng Research
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• 제40권1호
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• pp.47-54
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• 2016

Background: The roots of Panax ginseng contain noble tetracyclic triterpenoid saponins derived from dammarenediol-II. Dammarene-type ginsenosides are classified into the protopanaxadiol (PPD) and protopanaxatriol (PPT) groups based on their triterpene aglycone structures. Two cytochrome P450 (CYP) genes (CYP716A47 and CYP716A53v2) are critical for the production of PPD and PPT aglycones, respectively. CYP716A53v2 is a protopanaxadiol 6-hydroxylase that catalyzes PPT production from PPD in P. ginseng. Methods: We constructed transgenic P. ginseng lines overexpressing or silencing (via RNA interference) the CYP716A53v2 gene and analyzed changes in their ginsenoside profiles. Result: Overexpression of CYP716A53v2 led to increased accumulation of CYP716A53v2 mRNA in all transgenic roots compared to nontransgenic roots. Conversely, silencing of CYP716A53v2 mRNA in RNAi transgenic roots resulted in reduced CYP716A53v2 transcription. HPLC analysis revealed that transgenic roots overexpressing CYP716A53v2 contained higher levels of PPT-group ginsenosides ($Rg_1$, Re, and Rf) but lower levels of PPD-group ginsenosides (Rb1, Rc, $Rb_2$, and Rd). By contrast, RNAi transgenic roots contained lower levels of PPT-group compounds and higher levels of PPD-group compounds. Conclusion: The production of PPD- and PPT-group ginsenosides can be altered by changing the expression of CYP716A53v2 in transgenic P. ginseng. The biological activities of PPD-group ginsenosides are known to differ from those of the PPT group. Thus, increasing or decreasing the levels of PPT-group ginsenosides in transgenic P. ginseng may yield new medicinal uses for transgenic P. ginseng.

• 대한화학회지
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• 제34권1호
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• pp.1-9
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• 1990

콜레스테릴 펜타노에이트의 결정은 사방정계에 속하며 a = 21.930(3), b = 21.404(3), c = 6.419(5) $\AA$이며 단위세포안에 4개의 분자가 있다. 1.0 $\sigma$ (I)보다 큰 강도를 가진 1,520개의 회절 반점에 대한 최종 R값은 0.086이다. 직접법에 의하여 구조를 풀었으며 C-H 결합길이와 메틸기는 길이를 고정시켜 이상적인 기하학적 구조에 맞춰 cascade diagonal least-squares refinement에 의하여 정밀화하였다. 테트라시클로 고리는 정상적인 구조를 하고 있으나 에스텔과 곁사슬 부분은 열적효과에 의하여 정상적인 길이와 각도의 값에서 변화를 보이고 있으며 에스텔의 끝부분이 굽어져 치켜들고 있다. 분자는 비결합성 van der waals힘에 의하여 서로 쌓여져 있고 가장 짧은 분자간 거리는 3.529 $\AA$이다.

• Journal of Ginseng Research
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• 제41권3호
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• pp.373-378
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• 2017

Ocotillol-type saponins are one kind of tetracyclic triterpenoids, sharing a tetrahydrofuran ring. Natural ocotillol-type saponins have been discovered in Panax quinquefolius L., Panax japonicus, Hana mina, and Vietnamese ginseng. In recent years, the semisynthesis of 20(S/R)-ocotillol-type saponins has been reported. The biological activities of ocotillol-type saponins include neuroprotective effect, antimyocardial ischemia, antiinflammatory, antibacterial, and antitumor activities. Owing to their chemical structure, pharmacological actions, and the stereoselective activity on antimyocardial ischemia, ocotillol-type saponins are subjected to extensive consideration. In this review, we sum up the discovery, semisynthesis, biological activities, and metabolism of ocotillol-type saponins.

• Journal of Ginseng Research
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• 제46권4호
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• pp.505-514
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• 2022

Background: The roots of Panax ginseng contain two types of tetracyclic triterpenoid saponins, namely, protopanaxadiol (PPD)-type saponins and protopanaxatiol (PPT)-type saponins. In P. ginseng, the protopanaxadiol 6-hydroxylase (PPT synthase) enzyme catalyses protopanaxatriol (PPT) production from protopanaxadiol (PPD). In this study, we constructed homozygous mutant lines of ginseng by CRISPR/Cas9-mediated mutagenesis of the PPT synthase gene and obtained the mutant ginseng root lines having complete depletion of the PPT-type ginsenosides. Methods: Two sgRNAs (single guide RNAs) were designed for target mutations in the exon sequences of the two PPT synthase genes (both PPTa and PPTg sequences) with the CRISPR/Cas9 system. Transgenic ginseng roots were generated through Agrobacterium-mediated transformation. The mutant lines were screened by ginsenoside analysis and DNA sequencing. Result: Ginsenoside analysis revealed the complete depletion of PPT-type ginsenosides in three putative mutant lines (Cr4, Cr7, and Cr14). The reduction of PPT-type ginsenosides in mutant lines led to increased accumulation of PPD-type ginsenosides. The gene editing in the selected mutant lines was confirmed by targeted deep sequencing. Conclusion: We have established the genome editing protocol by CRISPR/Cas9 system in P. ginseng and demonstrated the mutated roots producing only PPD-type ginsenosides by depleting PPT-type ginsenosides. Because the pharmacological activity of PPD-group ginsenosides is significantly different from that of PPT-group ginsenosides, the new type of ginseng mutant producing only PPD-group ginsenosides may have new pharmacological characteristics compared to wild-type ginseng. This is the first report to generate target-induced mutations for the modification of saponin biosynthesis in Panax species using CRISPR-Cas9 system.

• 생명과학회지
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• 제28권6호
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• pp.733-737
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• 2018

박과 작물에 함유되어 있는 tetracyclic triterpene 성분 중 하나인 쿠쿠르비타신(cucurbitacin)-I는 대장암, 유방암, 간암세포에서의 항종양 활성이 밝혀져 있으나 난소암에서의 쿠쿠르비타신-I의 역할은 보고된 바 없다. CD44는 세포막에 존재하는 당단백질로 생체 내 리간드인 glycosaminoglycan hyaluronic acid를 통해 세포 외부 매트릭스와 다른 세포와의 접촉을 매개한다. 최근 연구에 의해 CD44의 발현이 난소암세포의 증식 및 세포 부착과 침윤을 증가시키는 주요 원인이라는 것이 보고되었다. 이러한 결과는 CD44의 발현을 억제함으로써 난소암의 진행을 조절할 수 있음을 시사하고 있다. 본 연구에서는 쿠쿠르비타신-I가 난소암세포의 CD44의 발현을 억제할 수 있는 지의 여부를 조사하였다. 인간의 난소암 세포인 SKOV-3를 이용한 MTS assay를 수행한 결과, 쿠쿠르비타신-I는 100 nM이상의 농도에서 세포독성을 나타내었다. 세포독성을 나타내지 않는 농도의 쿠쿠르비타신-I를 SKOV-3 세포에 처리하여 Western blot 분석과 qRT-PCR을 수행한 결과, 쿠쿠르비타신-I에 의해 CD44의 단백질과 mRNA의 발현이 유의적으로 감소되는 것을 확인하였다. 또한 쿠쿠르비타신-I에 의한 CD44의 발현 억제가 $NF-{\kappa}B$와 AP-1의 인산화 감소에 기인하고 있음을 밝혔다. 이러한 결과는 쿠쿠르비타신-I가 CD44 발현을 억제하는 기능을 가지며, 이는 난소암 치료에 도움을 줄 수 있는 제재로서 쿠쿠르비타신-I의 가능성을 제시하는 것이다.