Chakyunglupulins A and B, two novel 4,8,8-trimethylcyclooct-2-enone derivatives from Barleria lupulina

Kim, Ki‐Hyun; Clardy, Jon; Senger, Donald R.; Cao, Shugeng

doi:10.1016/j.tetlet.2015.04.023

Cited by 14 publications

(8 citation statements)

References 22 publications

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“…For 21,D U8 + predicted a 1 H-1 Hc oupling for the 7a-hydroxy group that was not present in the experimental spectrum. However, closer agreement was observed if C7 was inverted to 7b (36). Thep redicted 13 Cc hemical shifts were also in much better agreement with the experimental data, rmsd(d C ) = 1.37 ppm.…”

Section: Angewandte Chemiesupporting

confidence: 73%

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Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

2019

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Structural misassignments of natural products are prevalent in the literature.Developing methods and theoretical concepts to assist those undertaking structural elucidation is therefore of paramount importance,s uch that biologists and synthetic chemists avoid pursuing phantom chemical entities. Herein described is astrategy for predicting the isolabilities of oxygen-substituted bridgehead natural products based on calculations of olefin strain energies,N MR chemical shifts and coupling constants (DU8 +). This approachp rovides corroborating evidence for the structures of certain bridgehead alkene natural products while leading to the reassignment of several other structures.

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Section: Angewandte Chemiesupporting

confidence: 73%

“…Forthe Cytisus monoterpene 28,abiosynthetic analysis [35] suggested ap ossible origin in chakyunglupulin A( 37)o rB (38), [36] via ac yclodehydration step ( Figure 6). Therefore oxetane 39 was postulated as an alternative structure, however, the predicted NMR did not match with experiment.…”

Section: Angewandte Chemiementioning

confidence: 99%

Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

2019

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“…Spectral analysis conducted on the aerial extracts from B. lupulina showed the presence of chakyunglupulins A and B, which are the 4,8,8-trimethylcyclooct-2-enone derivatives. The molecular formula of chakyuglupulin A and B was found to be C11H18O4 (16). In the aqueous extract of B. lupulina, 4-ethylcatechol, 4-vinylcatechol and 4methylcatechol were isolated (17).…”

Section: Phytochemistry Of Barleria Speciesmentioning

confidence: 99%

Phytochemical, pharmacological and tissue culture studies of some important species of the genus Barleria L. (Acanthaceae) - a review

Sudheer

Nagella

2021

Plant Sci. Today

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Ayurvedic sciences helped the early humans to overcome chronic dangerous diseases. There are thousands of varieties of herbs and medicinal plants used to overcome such dreadful diseases. The genus Barleria L. belongs to family Acanthaceae, a medicinally significant group of plants having diversified phytochemicals used for different pharmacological properties. It has been utilized since ancient times for medicinal purposes. It has many plant secondary metabolites such as terpenes, flavonoids, lignins, alkaloids, particularly the iridoid glycosides. The secondary metabolites extracted from Barleria spp. show potential pharmacological activities viz., anti-microbial, anti-inflammatory, anti-oxidant, anti-fertility, anti-arthritic and anti-ulcer activity. In view of these, present review is focused on the phytochemistry, pharmacology and tissue culture studies of some of the important species of the genus Barleria L.

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“…For the Cytisus monoterpene 28 , a biosynthetic analysis suggested a possible origin in chakyunglupulin A ( 37 ) or B ( 38 ), via a cyclodehydration step (Figure ). Therefore oxetane 39 was postulated as an alternative structure, however, the predicted NMR did not match with experiment.…”

Section: Figurementioning

confidence: 99%

Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

2019

View full text Add to dashboard Cite

Structural misassignments of natural products are prevalent in the literature. Developing methods and theoretical concepts to assist those undertaking structural elucidation is therefore of paramount importance, such that biologists and synthetic chemists avoid pursuing phantom chemical entities. Herein described is a strategy for predicting the isolabilities of oxygen‐substituted bridgehead natural products based on calculations of olefin strain energies, NMR chemical shifts and coupling constants (DU8+). This approach provides corroborating evidence for the structures of certain bridgehead alkene natural products while leading to the reassignment of several other structures.

show abstract

Chakyunglupulins A and B, two novel 4,8,8-trimethylcyclooct-2-enone derivatives from Barleria lupulina

Cited by 14 publications

References 22 publications

Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

Phytochemical, pharmacological and tissue culture studies of some important species of the genus Barleria L. (Acanthaceae) - a review

Reassignments and Corroborations of Oxo‐Bridged Natural Products Directed by OSE and DU8+ NMR Computation

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