Novel acyclic diterpene glycosides, capsianosides A-F and I-V from Capsicum plants. Solanaceous studies. XVI.

Izumitani, Yukio; Yahara, Shoji; Nohara, Toshihiro

doi:10.1248/cpb.38.1299

Cited by 34 publications

(54 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…fasciculatum (Yatsubusa) [1][2][3] ; capsianosides II, III, C, D from C. annuum L. var. fasciculatum (Shishitougarashi) 1-3) ; capsianosides II, III, VIII-X, XIII, from C. annuum L. var.…”

mentioning

confidence: 99%

“…C-NMR signals due to the aglycone moiety, it was suggested that the aglycone part was composed of 6E,10E,14Z-(3S)-17-hydroxy geranyllinalool 2) and 6ЈE,10ЈE,14ЈE-(3ЈS)-13ЈR,19Ј-dihydroxy-geranyllinalool-16Ј-oic acid.…”

mentioning

confidence: 99%

“…[1][2][3][4][5][6] Further, by analyzing their chemical shifts including glycosylation shifts, the signals were shown to be attributable to the occurrence of two sets of 4ϫ2, 76.9ϫ2, 79.1ϫ2, 72.1ϫ2, 78.6ϫ2, 62.8ϫ2, 100.2ϫ2, 75.7ϫ2, 77.3ϫ2, 81.5, 81.6, 78.9ϫ2, 63.2ϫ2 and a-L-rhamnopyranosyl- 4, 73.1, 73.2, 74.9, 71.4, 18.9, 99.6, 75.7, 71.4, 73.9, 71.0 18.9, 101.7, 72.9, 73.1, 74.5, 70.4, 19.0, 102.9, 76.3, 77.3, 80.1, 76.1, 66.6. With regard to the respective connectivities of the aglycone part and each sugar moiety, the following heteronuclear multiple bond correlation (HMBC)s were observed: from glc II H-1 and glc V H-1 at …”

mentioning

confidence: 99%

See 2 more Smart Citations

Two New Acyclic Diterpene Glycosides from Fruits of Habanero, Capsicum chinense

Lee

El‐Aasr

Ikeda

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

Previously, we had found the occurrence of novel characteristic acyclic diterpene glycosides, which are rarely present in the natural plant kingdom, from a series of Capsicum genera as follows: capsianosides I-III, A-D from C. annuum L. var. fasciculatum (Yatsubusa) [1][2][3] ; capsianosides II, III, C, D from C. annuum L. var. fasciculatum (Shishitougarashi) 1-3) ; capsianosides II, III, VIII-X, XIII, from C. annuum L. var. annuum (jalapeño) 4) ; capsianosides IЈ, II, III, C-F from C. annuum (red hot pepper used in Kimchi, a fermented Chinese cabbage product) 5) ; capsianosides II, III, IX, X, XIII, XV, XVI from C. annuum L. var. grossum (paprika) 4) ; and capsianosides IЈ, II-IV, C-F from C. annuum L. grossum (pimento).6) These acyclic diterpene glycosides are major, typical components of Capsicum plants. We are now investigating their pharmacological activities in reducing blood pressure and facilitating the combustion of fatty acids. As part of a continuing study, we have examined the acyclic diterpene glycosides in Habanero, the fruits of Capsicum chinense JACQ., which is known as one of the hottest peppers in existence.The fruits of Capsicum chinense (768.3 g) were refluxed with MeOH to obtain a residue (42.4 g) after evaporation. The residue was then partitioned between n-hexane and water. The aqueous layer (35.1 g) was passed through Diaion HP-20 with 50-100% MeOH to afford the following three fractions: fr. 1 (0.66 g), fr. 2 (1.57 g), and fr. 3 (0.95 g). Fr. 2 was further chromatographed on octadecyl silica (ODS) with 60-90% MeOH to provide 5 fractions, fr. 2-1-fr. 2-5. Fr. 2-2 (205.0 mg) was chromatographed on silica gel with CHCl 3 , MeOH and water in the ratio 7 : 3 : 0.5 and further subjected to HPLC with 75% MeOH to yield HAB-2 (17.4 mg) and HAB-1 (1, 17.8 mg). Fr. 2-4 (262.0 mg) was chromatographed on silica gel with CHCl 3 , MeOH and water in the ratio 7 : 3 : 0.5→6 : 4 : 0.5 and separated with HPLC by using 70% MeOH to yield HAB-3 (11.1 mg) and HAB-4 (2, 18.0 mg).HAB-2 and HAB-3 were identified in capsianoside XV, which was obtained from C. annuum L. var. grossum (paprika), 4) and capsianoside XIII, which was isolated from C. annuum L. var. annuum (jalapeño) and C. annuum L. var. grossum (paprika), 4) respectively, as shown in Fig. 1 Medical and Pharmaceutical Sciences, Kumamoto University; 5-1 Oe-honmachi, Kumamoto 862-0973, Japan: and c Faculty of Pharmaceutical Sciences, Fukuoka University; 8-19-1 Jyounan-ku, Nanakuma, Fukuoka 814-0180, Japan. Received March 18, 2009; accepted April 22, 2009; published online May 11, 2009 Four acyclic diterpene glycosides were extracted from Habanero, the fruits of Capsicum chinense JACQ., which is known as one of the hottest peppers in existence. Two of these glycosides were identified as capsianoside XIII and capsianoside XV.

show abstract

“…fasciculatum (Yatsubusa) [1][2][3] ; capsianosides II, III, C, D from C. annuum L. var. fasciculatum (Shishitougarashi) 1-3) ; capsianosides II, III, VIII-X, XIII, from C. annuum L. var.…”

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Two New Acyclic Diterpene Glycosides from Fruits of Habanero, Capsicum chinense

Lee

El‐Aasr

Ikeda

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

show abstract

“…Previous studies in this laboratory led to the isolation of novel acyclic diterpene glycosides, capsianoside A-H and I-VI from Capsicum plants. 5) In this study, we isolated six new acyclic diterpene glycosides termed capsianosides XIII (2), XV (3), IX (4), XVI (5), X (6) and VIII (7) along with one known compound. 5) Since the known compound, capsianoside II 5) had an error in sugar sequence, we revised it.…”

mentioning

confidence: 99%

“…5) In this study, we isolated six new acyclic diterpene glycosides termed capsianosides XIII (2), XV (3), IX (4), XVI (5), X (6) and VIII (7) along with one known compound. 5) Since the known compound, capsianoside II 5) had an error in sugar sequence, we revised it. Distribution of these new compounds is summarized in Table 1 Fig.…”

mentioning

confidence: 99%

Acyclic Diterpene Glycosides, Capsianosides VIII, IX, X, XIII, XV and XVI from the Fruits of Paprika Capsicum annuum L. var. grossum BAILEY and Jalapeno Capsicum annuum L. var. annuum

Lee

Kiyota

Ikeda

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

Evaluation of Food Intake Biomarkers for Red Bell Peppers in Human Urine Based on HPLC‐MS/MS Analysis

Schulz,

Hübner,

Humpf

2023

Molecular Nutrition Food Res

View full text Add to dashboard Cite

ScopeThe validation of dietary biomarkers is essential for the use in objective and quantitative assessment of the human dietary intake. In this study, the urinary excretion of previously identified potential biomarkers after intake of red bell peppers is analyzed.Methods and resultsThe urine samples obtained after a two‐phase dietary intervention study in which 14 volunteers participated are quantitatively analyzed by high‐performance liquid chromatography with tandem mass spectrometry (HPLC‐MS/MS) after an extensive validation. In the first phase, the volunteers abstain completely from bell peppers and paprika products (control group) and in the second phase, the volunteers consume a defined amount of fresh red bell peppers (case group). After analysis, all potential biomarkers show high dispersions of their concentration, indicating interindividual differences. The glucuronidated apocarotenoid (compound 1), which probably resulted from the main carotenoids of red Capsicum fruits, shows a rapid urinary excretion. The other glucuronidated metabolites (compounds 2–8), described as potential derivatives of capsianosides from Capsicum, show a slightly delayed but longer urinary excretion.ConclusionsA correlation between an intake of red bell pepper and the urinary excretion of recently described potential biomarkers is observed. Due to large interindividual differences, it is reasonable to assume that at least the qualitative detection of the consumption of bell peppers and possibly all Capsicum fruits is feasible.

show abstract

Novel acyclic diterpene glycosides, capsianosides A-F and I-V from Capsicum plants. Solanaceous studies. XVI.

Cited by 34 publications

References 0 publications

Two New Acyclic Diterpene Glycosides from Fruits of Habanero, Capsicum chinense

Two New Acyclic Diterpene Glycosides from Fruits of Habanero, Capsicum chinense

Acyclic Diterpene Glycosides, Capsianosides VIII, IX, X, XIII, XV and XVI from the Fruits of Paprika Capsicum annuum L. var. grossum BAILEY and Jalapeno Capsicum annuum L. var. annuum

Evaluation of Food Intake Biomarkers for Red Bell Peppers in Human Urine Based on HPLC‐MS/MS Analysis

Contact Info

Product

Resources

About