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NMR Assignments of Rotameric Aporphine Alkaloids from Liriodendron tulipifera

  • Park, InWha;Na, MinKyun
    • Natural Product Sciences
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    • v.26 no.2
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    • pp.171-175
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    • 2020
  • Liriodendron tulipifera, belonging to the family Magnoliaceae, is commonly called tulip tree. Four N-acetylated aporphine alkaloids, N-acetylnornuciferine (1), N-acetylanonaine (2), N-acetyl-3-methoxynornuciferine (3), and N-acetyl-3-methoxynornantenine (4) were isolated from the roots of L. tulipifera. Although the purity of each compound (1 - 4) was determined to be 97, 96, 99, and 98%, respectively, the 1H and 13C NMR spectroscopic data of the aporphine alkaloids 1 - 4 displayed all signals in duplicate, indicating the presence of two rotamers due to restricted rotation of N-COCH3 functionality in solution status. The absolute configurations of 1 - 4 w ere established by measuring specific rotation and comparison with the reported data. This is the first report on the 1H and 13C NMR assignments of N-acetyl-3-methoxynornuciferine (3) and N-acetyl-3-methoxynornantenine (4). This study provides advanced NMR spectroscopic data for the structure determination of rotameric aporphine alkaloids.

A New Sphingosine from a Marine Sponge Haliclona (Reniera) sp.

  • Mansoor, Tayyab A.;Park, Tae-Seong;Luo, Xuan;Hong, Jong-Ki;Lee, Chong-O.;Jung, Jee-H.
    • Natural Product Sciences
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    • v.13 no.3
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    • pp.247-250
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    • 2007
  • A new sphingosine (1) was isolated from the MeOH extract of a marine sponge Haliclona (Reniera) sp. by bioactivity-guided fractionation. The 1D and 2D NMR, and MS spectroscopic analyses were used to establish the planar structure of 1. The stereochemistry of the compound was defined on the basis of modified Mosher's method, comparison of optical rotation and NMR data with those of the reported. Compound 1 was mildly cytotoxic to a panel of five human solid tumor cell lines.

The Study of Correlationship of the Fukuda Stepping Test to Determine Type of Idiopathic Scoliosis Curve (척주측만증 환자의 만곡과 후쿠다 검사의 상관성에 관한 연구)

  • Lee, Sang-Yeol;Jo, Marg-Eun;Ko, Min-Ji;Kim, Young-Ju;Lee, Seung-Min
    • Journal of the Korean Society of Physical Medicine
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    • v.11 no.2
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    • pp.13-16
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    • 2016
  • PURPOSE: The Fukuda test can be used at home and in school to diagnose scoliosis at an early stage and prevent serious curvature of the spine. This study aimed to use the Fukuda test to detect scoliosis. An additional aim was to invoke the national interest in imbalanced postures and habits, which result in scoliosis, by providing data obtained in periodic assessments. METHODS: The study consisted of 35 idiopathic scoliosis patients (22 in right lumbar spinal region and 13 in the left lumbar spinal region). The distance of displacement and angle of displacement were measured following the Fukuda test. A correlation analysis was then used to examine the distance of displacement and angles of displacement and rotation with regard to the direction of the curve in scoliosis. RESULTS: There was a significant negative correlation (p<0.00) between the direction of the curve in scoliosis and the angle of displacement, but there was no correlation between the cobb's angle and distance of displacement or between the cobb's angle and angle of rotation. CONCLUSION: The Fukuda test did not capture changes in spinal curvature such as the cobb's angle, or subsequent changes in the muscles. Thus, the Fukuda test is not suited to examining the direction or status of the thoracic curve in scoliosis patients. Simple methods to objectively measure scoliosis need to be developed.

Comparison of Pharmacy Practice Experience in Pharmacy School between Korea and Canada (우리나라와 캐나다 약학대학 실무실습 교과과정 비교)

  • Kang, Minku
    • Korean Journal of Clinical Pharmacy
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    • v.25 no.2
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    • pp.68-73
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    • 2015
  • With the changes in the pharmacy curriculum from a 4 year program to a 6 year program in 2009, a new subject called Pharmacy Practice Experience (PPE) has been launched into the curriculum. The purpose of introducing this subject is to increase the competency of new pharmacy graduates in providing quality healthcare to the community. This study has been done, via comparison among different pharmacy schools in Canada and Korea, to ensure that the competency of future Korean pharmacists can be increased with the introduction of this subject. In general, the Introductory Pharmacy Practice Experience (IPPE) in Korea consists of 60 hours while Canada consists of 320 hours (minimum). Furthermore, the Advanced Pharmacy Practice Experience (APPE) required in Korea is 1340 hours while Canada requires minimum of 960 hours. Specifically, comparing the Korean PPE curriculum to the PPE curriculums of University of Toronto (UT) and University of Waterloo (UW), UT and UW required a minimum of 75% and 89% direct clinical patient care experience respectively, either in hospital or community setting, compared to 45% in Korea; the remaining percentage in any of the universities can be fulfilled by taking other electives that may not require direct patient care experience. Observing these differences, it seems clear that the current PPE experience in Canada takes more of a patient focused approach than in Korea. Thus, with the recent movement in the Korean pharmacy community towards a more patient focused approach rather than a product focused approach, it would be beneficial to learn the differences between the PPE curriculums in Korea and Canada and apply any new understandings to the relatively newly introduced PPE program in Korea to further enhance the value of the new curriculum in helping to deliver quality patient care.

A Novel Bromoindole Alkaloid from a Korean Colonial Tunicate Didemnum sp.

  • Hahn, Dongyup;Kim, Geum Jin;Choi, Hyukjae;Kang, Heonjoong
    • Natural Product Sciences
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    • v.21 no.4
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    • pp.278-281
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    • 2015
  • Chemical investigation on a colonial marine tunicate, Didemnum sp. led to the isolation of a series of indole alkaloids including a new (1) and two known metabolites (2-3). Based on the spectroscopic analysis including 1D and 2D NMR along with MS spectra, the structure of 1 (16-epi-18-acetyl herdmanine D) was elucidated as a new amino acid derivative. The absolute configuration of 1 was determined by comparison of specific rotation with the known compound. The structures of compounds 2 and 3 were also identified as bromoindole containing compounds N-(6-bromo-1H-indole-3-carbonyl)-L-arginine and (6-bromo-^1H-indol-3-yl) oxoacetamide, respectively, based on $^1H$ and $^{13}C$ NMR data, MS data and specific rotation value. Their pharmacological potentials as antibacterial agents and FXR antagonists were investigated, but no significant activity was found. However, the structural similarity of compound 1 to compound 4 suggested the anti-inflammatory potential of compound 1.

Synthesis and Binding Affinity of Homologated Adenosine Analogues as A3 Adenosine Receptor Ligands

  • Lee, Hyuk-Woo;Choi, Won-Jun;Jacobson, Kenneth A.;Jeong, Lak-Shin
    • Bulletin of the Korean Chemical Society
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    • v.32 no.5
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    • pp.1620-1624
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    • 2011
  • Homologated analogues 3a and 3b of potent and selective A3 adenosine receptor ligands, IB-MECA and dimethyl-IB-MECA were synthesized from commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-${\beta}$-D-ribofuranose (4) via $Co_2(CO)_8$-catalyzed siloxymethylation as a key step. Unfortunately, homologated analogues 3a and 3b did not show significant binding affinities at three subtypes of adenosine receptors, indicating that free rotation, resulting from homologation, induced unfavorable interactions in the binding site of the receptor maybe due to the presence of many conformations.

Chemical Constituents from Aegle marmelos Fruits

  • Kim, Hye Jin;Seo, Young Ju;Htwe, Khin Myo;Yoon, Kee Dong
    • Natural Product Sciences
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    • v.27 no.4
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    • pp.240-244
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    • 2021
  • Aegle marmelos (Rutaceae) is a deciduous shrub or tree and typically known as bael throughout Southeast Asia and has been used as a medicinal plant and a food ingredient. In this study eight compounds were determined to be O-(3,3-dimethylallyl) halfordinol (1), (R)-aegeline (2), (R)-marmeline (3), imperatorin (4), xanthotoxol (5), valencic acid (6), vanillic acid (7) and rutin (8). The chemical structures of the isolates were elucidated through spectroscopic evidence including 1D, 2D NMR, ESI-Q-TOF-MS and optical rotation.

Chemical Constituents from the Aerial Parts of Artemisia capillaris Thunb. and Their Anti-allergic and Anti-inflammatory Effects

  • Nguyen, Thi Thu;Vu, Thi Oanh;Cao, Thao Quyen;Min, Byung Sun;Kim, Jeong Ah
    • Natural Product Sciences
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    • v.26 no.1
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    • pp.90-96
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    • 2020
  • Artemisia capillaris Thunb. (Compositae) is a traditional medicinal plant with various pharmacological activities. To elucidate new anti-allergic and anti-inflammatory constituents, the aerial parts of A. capillaries were investigated to afford a new compound, (6E,8E)-6-methylundeca-6,8-diene-2,5,10-trione (17) together with 19 known compounds (1 - 16, 18 - 20). The structures of these compounds were determined by extensive spectroscopic analyses including 1D, 2D NMR, HREIMS, and optical rotation [α]D. The absolute configuration of compound 2 was determined to be S form for the first time. All isolates (1 - 20) were tested their inhibitory effects on interleukin 2 (IL-2) expression in T cells and NO production in lipopolysaccharide (LPS)-stimulated RAW246.7. Among them, compounds 10, 11, 19, and 20 reduced IL-2 expression in a dose-dependent manner. In addition, compound 10 also inhibited NO production with an IC50 value of 37.3 ± 0.4 μM.

Isolation and Synthesis of an Antifungal Metabolite Derived from the Commensal Vaginal Bacterium Dermabacter vaginalis (질 내 공생세균 Dermabacter vaginalis 유래 항진균 대사체의 분리 및 합성)

  • So, Jae Seong;Kwon, Kang Mu;Lee, Munseon;Kim, Dae Keun;Hwang, In Hyun
    • Korean Journal of Pharmacognosy
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    • v.53 no.3
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    • pp.119-124
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    • 2022
  • Vaginal microbiome deeply influences vaginal health via production of messenger molecules. The healthy vaginal pH ranges between 3.5 and 4.5. However, dysbiosis of vaginal microbiome increases the pH level, leading to the incidence of vaginitis. The commensal vaginal bacterium Dermabacter vaginalis-which was isolated from the vaginal fluid of a Korean female-was incubated in acidic and neutral pH to simulate healthy and vaginitis conditions, respectively. The chemical profiles of the two different cultures were compared using HPLC. The compound showing distinctive difference between the two sets of data was presumed to be a chemical messenger, which was identified as cyclo(L-pro-L-met) by analysis of NMR, MS, and specific rotation data. Synthesis was achieved in three steps (overall yield 15%), enabling structure confirmation and antimicrobial evaluation against vaginal pathogens. Cyclo(L-pro-L-met) showed antifungal activity against Candida albicans, a major cause of vulvovaginal candidiasis.

Middle East Respiratory Syndrome Outbreak and Responsiveness of the Pharmacy Programs on the Pharmacy Practice Education (중동호흡기증후군(MERS) 발생관련 전국 약학대학의 실무실습교육 대응현황)

  • Choi, Kyung Hee;Choi, Kyung Suk;Lee, Young Sook;Kim, Jaeyoun;Jeong, Kyeong Hye;Oh, Jung Mi;Choi, Kyung Eob;Ra, Hyeon Oh;Lee, Euni
    • Korean Journal of Clinical Pharmacy
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    • v.27 no.1
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    • pp.9-14
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    • 2017
  • Background: Pharmacy curriculum change was made from a 4-year program to a 2+4 year program in year 2009 in Korea. The change has resulted in more educational exposures on patient-centered practice environments for about 1,400 hours in the last year of the professional pharmacy program. When the Middle East Respiratory Syndrome (MERS) outbreak hit Seoul and suburban areas and propagated to other provinces in Korea, emergency response to avoid student infection in the pharmacy practice sites became an urgent issue. While other health professional programs such as medicine and nursing had activated emergency preparedness manuals, timely and clear guidelines were not disseminated to all pharmacy programs and protective measures largely relied on individual pharmacy program. Methods: A survey was developed by the Committee on Pharmacy Practice Experience Programs in the Korean College of Clinical Pharmacy to document the status of pharmacy programs during the Korea MERS outbreak in 2015. The 10-question survey was distributed to the pharmacy practice experience coordinators to 34 out of 35 pharmacy schools in Korea by emails. Results: Our findings showed that 82.4% of the program coordinators (28/34) responded to the survey, 96.4% of the programs did not have emergency preparedness manuals, administrative meetings were held in 89.3% of the pharmacy programs, the rotation schedules were modified or withheld in 53.6% of schools, and the changes were mostly observed from the programs classified as MERS outbreak regions. Conclusion: Further needs in establishing the emergency preparedness manual should be explored for pharmacy education stakeholders.