Chemistry of buprestins A and B. Bitter principles of jewel beetles (Coleoptera: Buprestidae)

Brown, W.; Jones, AJ; Lacey, MJ; Moore, B.

doi:10.1071/ch9850197

Cited by 13 publications

(5 citation statements)

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“…Mass spectra were determined on a VG 70-70 mass spectrometer interfaced to a VG 11-250 data system. Compounds were analyzed by flash volatilization from an extended gold support (22) with rapid data acquisition. Ei mass spectra were determined with an ionization energy of 70 eV and trap current of 100 µ .…”

Section: Resultsmentioning

confidence: 99%

Biologically Active Metabolites from Xenorhabdus Spp., Part 2. Benzopyran-1-one Derivatives with Gastroprotective Activity

McInerney¹,

Taylor²,

Lacey³

et al. 1991

J. Nat. Prod.

169

138

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Two novel antibiotic compounds, named xenocoumacins 1 [2] and 2 [3], with potent antiulcer activity were isolated from cultures of Xenorhabdus spp. Both compounds exhibit antibacterial activity and potent antiulcer activity against stress-induced ulcers when dosed orally. In addition, 2 has antifungal activity. Their chemical structures were determined by extensive 1H-nmr, 13C-nmr, and mass spectral studies to be 3,4-dihydro-8-hydroxy-1H-2-benzopyran-1-one derivatives.

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Section: Resultsmentioning

confidence: 99%

Biologically Active Metabolites from Xenorhabdus Spp., Part 2. Benzopyran-1-one Derivatives with Gastroprotective Activity

McInerney¹,

Taylor²,

Lacey³

et al. 1991

J. Nat. Prod.

169

138

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“…Xenorhabdin 1 [1],-Mp 192-193°; uv X max (MeOH) 387 nm, 300, 242 (s); ir (Nujol) 3250 (br), 1670, 1640, 1600, 1555 cm™1; 13C nmr (Me2SO-df6) 171.9 (s), 168.0(s), 134. l(s), 133.6(s), 115.4(s), 110.7 (d), 34.7 (t), 30.9 (t), 24.9 (t), 21.9 (t), 14.0 (q); *H nmr [(CD3)2CO] 9.64 (1H, s br, CO-NH), 8.64 (1H, s br, CO-NH), 6.93 (1H, s, H-3), 2.45 (2H, t, CO-CH2J = 7.2 Hz), 1.64 (2H, m, CH), 1.32 (4H, m, CH2-CH2), 0.88 (3H, t, Me); eims miz (%) 272 (2), 271 (3), [M]+ 270 (20), (caled for CuH14N202S2, 270.0498, found 270.0496), 174 (10), 173 (10), 172 (100) (caled for C,H4N2OS2, 171.9766, found 171.9759), 171(4), 144(2), 143(2), 117(2), 99(2), 72(2), 71(5), 55(3), 45 (4), 43 (24). Analytical hplc Rt 4.6 min.…”

Section: Experimental General Experimentalmentioning

confidence: 96%

“…Mass spectra were determined on a VG 70-70 mass spectrometer interfaced to a VG 11-250 data system. Samples were analyzed by flash volatilization from an extended gold support (24) and rapid data acquisition. This method minimized any competing thermolysis and accentuated the molecular parent ions compared with conventional probe techniques.…”

Section: Experimental General Experimentalmentioning

confidence: 99%

Biologically Active Metabolites from Xenorhabdus Spp., Part 1. Dithiolopyrrolone Derivatives with Antibiotic Activity

McInerney¹,

Gregson²,

Lacey³

et al. 1991

J. Nat. Prod.

138

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Five related antibiotic compounds, named xenorhabdins, were isolated from cultures of Xenorhabdus spp., bacteria symbiotically associated with insect-pathogenic nematodes. Their chemical structures were elucidated by X-ray crystallography, nmr, and mass spectral analyses to be N-acyl derivatives of either 6-amino-4,5-dihydro-5-oxo-1,2-dithiolo [4,3-b] pyrrole (compounds 1-3) or 6-amino-4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b] pyrrole (compounds 4 and 5). They are previously unreported members of the pyrrothine family of antibiotics. Antimicrobial and insectidical activities were found. These metabolites are specific to phase one Xenorhabdus.

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“…Although we did not find any evidence of chemical studies on Chalcophora japonica in our search, other Buprestids have been investigated. Excellent work by Brown, Moore, and colleagues ( Brown et al ., 1985 ; Moore and Brown, 1985 ) not only isolated and described the main defensive chemicals of Buprestids, but did so by surveying a wide variety of jewel beetles from Australia along with a few from Europe and Asia. They elucidated that these “bitter principles” were based upon β-D-glucose with three aromatic acyl groups attached, and called them buprestins A and B (6-7 in Fig.…”

Section: Beetles Used In Tcm By Familymentioning

confidence: 99%

Drug Discovery Insights from Medicinal Beetles in Traditional Chinese Medicine

Deyrup

Stagnitti

Perpetua

et al. 2021

Biomolecules & Therapeutics

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Traditional Chinese medicine (TCM) was the primary source of medical treatment for the people inhabiting East Asia for thousands of years. These ancient practices have incorporated a wide variety of materia medica including plants, animals and minerals. As modern sciences, including natural products chemistry, emerged, there became increasing efforts to explore the chemistry of this materia medica to find molecules responsible for their traditional use. Insects, including beetles have played an important role in TCM. In our survey of texts and review articles on TCM materia medica, we found 48 species of beetles from 34 genera in 14 different families that are used in TCM. This review covers the chemistry known from the beetles used in TCM, or in cases where a species used in these practices has not been chemically studied, we discuss the chemistry of closely related beetles. We also found several documented uses of beetles in Traditional Korean Medicine (TKM), and included them where appropriate. There are 129 chemical constituents of beetles discussed.

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Chemistry of buprestins A and B. Bitter principles of jewel beetles (Coleoptera: Buprestidae)

Abstract: The isolation an structural elucidation of β-D- glucopyranose 1,2,6- tris (pyrrole-2-carboxylate) ( buprestin A) (1) and β-D- glucopyranose 6- (4-hydroxybenzoate) 1,2-bis(pyrrole-2-carboxylate) ( buprestin B) (3), bitter principles of beetles of the family Buprestidae , are reported.

Cited by 13 publications

References 0 publications

Biologically Active Metabolites from Xenorhabdus Spp., Part 2. Benzopyran-1-one Derivatives with Gastroprotective Activity

Biologically Active Metabolites from Xenorhabdus Spp., Part 2. Benzopyran-1-one Derivatives with Gastroprotective Activity

Biologically Active Metabolites from Xenorhabdus Spp., Part 1. Dithiolopyrrolone Derivatives with Antibiotic Activity

Drug Discovery Insights from Medicinal Beetles in Traditional Chinese Medicine

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