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(9?H)-Pimaranes and Derivatives from the Tuber of Icacina trichantha.

ABSTRACT: New 17-nor-pimaranes (1, 2), (9?H)-pimaranes (3, 4), and 17-nor-(9?H)-pimarane (5) were isolated from the tuber of Icacina trichantha. The structures were elucidated based on spectroscopic and HRMS data. The absolute configurations of 3 and 5 were determined by single-crystal X-ray diffraction. Compound 5 possesses a unique 19,20-?-lactone moiety. Compound 3 showed cytotoxicity against MDA-MB-435 (human melanoma cancer) cells with an IC50 value of 7.04 ?M. A plausible biogenetic pathway for compounds 1-5 is proposed.

SUBMITTER: Zhao M

PROVIDER: S-EPMC4703074 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

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(9βH)-Pimaranes and Derivatives from the Tuber of Icacina trichantha.

Zhao Ming M Onakpa Monday M MM Santarsiero Bernard D BD Chen Wei-Lun WL Szymulanska-Ramamurthy Karina M KM Swanson Steven M SM Burdette Joanna E JE Che Chun-Tao CT

Journal of natural products 20151102 11

New 17-nor-pimaranes (1, 2), (9βH)-pimaranes (3, 4), and 17-nor-(9βH)-pimarane (5) were isolated from the tuber of Icacina trichantha. The structures were elucidated based on spectroscopic and HRMS data. The absolute configurations of 3 and 5 were determined by single-crystal X-ray diffraction. Compound 5 possesses a unique 19,20-δ-lactone moiety. Compound 3 showed cytotoxicity against MDA-MB-435 (human melanoma cancer) cells with an IC50 value of 7.04 μM. A plausible biogenetic pathway for comp ...[more]

PMID: 26523419

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Project description:Tubers are important crops as well as staple foods in human nutrition. Among tubers, the potato in particular has been investigated for its health effects. However, except for its contribution to energy and effects related to resistant starch, the role of potatoes and other tubers in human health is still debated. In order to establish firm evidence for the health effects of dietary tubers and processed tuber products, it is essential to assess total intake accurately. The dietary assessment in most studies relies mainly on self-reporting and may give imprecise quantitative information on dietary intakes. Biomarkers of food intake (BFIs) are useful objective means to assess intake of specific foods or may be used as an additional measure to calibrate the measurement error in dietary reports. Here, intake biomarkers for common tubers, including potatoes and heated potato products, sweet potato, cassava, yam, and Jerusalem artichoke, are reviewed according to the biomarker of food intake reviews (BFIRev) standardized protocols for review and validation. Candidate BFIs for heated potato product include α-chaconine, α-solanine, and solanidine; less evidence is available to indicate peonidin 3-caffeoylsophoroside-5-glucoside and cyanidin 3-caffeoylsophoroside-5-glucoside as putative biomarkers having high potential specificity for purple sweet potato intake; linamarin may in addition be considered as a putative BFI for cassava. Other tubers also contain toxic glycosides or common contaminants as characteristic components but their putative use as intake biomarkers is not well documented. Alkyl pyrazines, acrylamide, and acrolein are formed during cooking of heated potato products while these have not yet been investigated for other tubers; these markers may not be specific only to heated potato but measurements of these compounds in blood or urine may be combined with more specific markers of the heated products, e.g., with glycoalkaloids to assess heated potato products consumption. Further studies are needed to assess the specificity, robustness, reliability, and analytical performance for the candidate tuber intake biomarkers identified in this review.

Dataset Information

(9?H)-Pimaranes and Derivatives from the Tuber of Icacina trichantha.

Publications

(9βH)-Pimaranes and Derivatives from the Tuber of Icacina trichantha.

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