Novel steroid and sesquiterpenes isolated from Saussurea involucrata

Ma, Qingdong; Zhang, Ke; Li, Guoyu; Chen, Xiaoxiang; Lü, Yang; Wang, Hangyu; Huang, Jian; Wang, Jinhui

doi:10.1016/j.phytol.2020.11.011

Cited by 4 publications

(2 citation statements)

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“…Sausinone (13), which was isolated from Saussurea involucrata, [53] proved considerably difficult. Utilizing ACD/SE clearly showed that the proposed structure was incorrect (see Figure S17), although the C and D rings and appendages were confirmed with a high degree of confidence (see blue highlights on 13 in Figure 4).…”

Section: Resultsmentioning

confidence: 99%

“…Taking into account that dexamethasone and betamethasone are common corticosteroid drugs, [55] the configuration at C16 for both acetates (i. e., 40 and 41) was compared, but the ~7 ppm discrepancy reinforced 40 as the reassigned structure for sausinone (13). Concerning the considerable difference in mass spectrometry results (TOF), unfortunately, the published mass range 439-468 [53] did not allow a comparison to the revised structure (i. e., exact mass of 434.2105) (Figure 4). However, that said, it is highly likely that 40 was the material isolated.…”

Section: Resultsmentioning

confidence: 99%

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Reassignment of Improbable Natural Products Identified through Chemical Principle Screening

Elyashberg¹,

Novitskiy

Bates

et al. 2022

Eur J Org Chem

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Natural products continue to be reported at an astonishing rate from a wide range of multidisciplinary research activities in the pursuit of understanding the chemistry of biodiversity. However, the elucidation of chemical structure in the modern era is heavily reliant on the analysis and interpretation of multiple spectroscopic outputs, and in most cases this activity is by no means trivial. Structural errors continue to be described given the inherent complexity of natural products. Computer‐Assisted Structure Elucidation (CASE) continues to provide improved resolving power in this regard, but for enhanced accuracy quantum chemical spectrum prediction methodology is paramount. Reported herein are a range of counterfactual natural products, identified through chemical principal screening, which have been reassigned using a combination of chemical intuition, chemical synthesis, CASE and DU8+ spectrum prediction.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%