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Record W2317369246 · doi:10.1055/s-2009-1216410

Relative and Absolute Structures of Diospongin A, B and C

2009· article· en· W2317369246 on OpenAlexfundno aff
Jun Yin, Na Han

Bibliographic record

VenuePlanta Medica · 2009
Typearticle
Languageen
FieldBiochemistry, Genetics and Molecular Biology
TopicNatural product bioactivities and synthesis
Canadian institutionsnot available
FundersNational Institute on Drug AbuseAgricultural Research ServiceUniversity of British ColumbiaUniversity of Illinois at Urbana-ChampaignChinese Academy of SciencesKurukshetra UniversityUniversity of Illinois at ChicagoNational Oceanic and Atmospheric AdministrationU.S. Food and Drug AdministrationNational Science Foundation of Sri LankaUniversity of ColomboU.S. Department of AgricultureWestern Carolina UniversityInternational Science CouncilNational Center for Complementary and Alternative MedicineChina Academy of Traditional Chinese MedicineNational Institutes of HealthNational Center for Research ResourcesNational Institute of Allergy and Infectious DiseasesTürkiye Bilimsel ve Teknolojik Araştırma KurumuHong Kong Polytechnic UniversityNational Science FoundationDeutsche KrebshilfeNational Natural Science Foundation of ChinaTata TrustsUniversity Grants CommissionWake Forest University
KeywordsChemistryAbsolute configurationStereochemistryDiarylheptanoidsOsteoclastNMR spectra databaseSpectral lineIn vitroBiochemistry

Abstract

fetched live from OpenAlex

While screening 60 extracts for their stimulatory activity on proliferation of osteoblast-like cell line and on inhibition of osteoclastic formation, the water extract of Dioscorea spongiosa displayed the strongest stimulation on osteoblastic proliferation and strong inhibition on osteoclastic formation. This water extract was separated using bioassay-guiding fractionation and three new diarylheptanoids were isolated and purified. The structures of three new diarylheptanoids were elucidated by analysis of NMR, IR spectra and high resolution FAB-MS. The relative stereochemistry of diospongin A and B was determined by ROESY spectra and coupling constants in 1 H-NMR spectra and their absolute structures were identified by advanced Mosher method. By analyzing the NMR data, diospongin C was found to be an acyclic diarylheptanoid with four hydroxyl groups at C-1, C-3, C-5 and C-7; i.e., 1,7-diphenylheptan-1,3,5,7-tetraol. So there was some difficulty in the decision of its relative and absolute configuration. The relative configuration of diospongin C also can be determined by analysis coupling constants of two protons of C-2, C-4 and C-6 in Newman projections of one corresponding acetonide derivative and optimizing dihedral angles [1]. Its absolute stereochemistry was identified by the CD spectrum of its dibenzoat product [2]. All the three compounds were examined the inhibitory activity on osteoclast formation and bone resorption induced by PTH in bone organ culture system. Except for diospongin A, diospongin B and C showed potent inhibition even at a concentration of 20 µM, which demonstrates that the stereochemistry was important to structure-activity relationship of these diarylheptanoids. Structures of diospongin A, B and C. Acknowledgement: Thanks to Professor Qishi Sun and Yingjie Chen of Shenyang Pharmaceutical University in China for purchasing and identifying the crude drug. Toyama Medical and Pharmaceutical University is also appreciated for the structural measurement of compounds. References: [1] Rychnovsky SD, Richardson TI et al (1997). J Org Chem, 62: 2925–2934. [2] Wiesler WT, Nakanishi K. (1989). J Am Chem Soc, 111: 9205–9213.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.008
Threshold uncertainty score0.025

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0080.001

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.005
GPT teacher head0.217
Teacher spread0.212 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations1
Published2009
Admission routes1
Has abstractyes

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