Hyperbeanone A, a 5,6-seco-spirocyclic polycyclic polyprenylated acylphloroglucinol derivative with an unprecedented skeleton from Hypericum beanii

Organic Chemistry Frontiers ◽

10.1039/d1qo01302e ◽

2021 ◽

Author(s):

Beiye Yang ◽

Jianzheng Huang ◽

Shuang Lin ◽

Qingyi Tong ◽

Zeyu Yao ◽

...

Keyword(s):

Ring System ◽

Aerial Parts ◽

Ketone Carbonyl

Hyperbeanone A (1), a novel 5,6-seco-polycyclic PPAP derivative characterized by an undescribed benz[f]indene-1,9(4H)-dione ring system fused to a tricyclic γ-lactone unit via a ketone carbonyl, was isolated from the aerial parts of Hypericum beanii.

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Crystal structure of (1S,2R,4R,9S,11S,12R)-9α-hydroxy-4,8-dimethyl-12-[(thiomorpholin-4-yl)methyl]-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one

Acta Crystallographica Section E Crystallographic Communications ◽

10.1107/s205698901500170x ◽

2015 ◽

Vol 71 (2) ◽

pp. o140-o141

Author(s):

Ahmed Benharref ◽

Mohamed Akssira ◽

Lahcen El Ammari ◽

Mohamed Saadi ◽

Moha Berraho

Keyword(s):

Crystal Structure ◽

Hydrogen Bond ◽

Chair Conformation ◽

Chloroform Extract ◽

Ring System ◽

Membered Ring ◽

Epoxy Ring ◽

Aerial Parts ◽

Compound C ◽

Hydrogen Bonding Interactions

The title compound, C19H29NO4S, was synthesised from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of the plantAnvillea radiata. The molecule is built up from two fused five- and ten-membered rings, with an additional epoxy ring system and a thiomorpholine group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the thiomorpholine ring displays a chair conformation and the five-membered ring has an envelope conformation, with the C atom closest to the hydroxy group forming the flap. An intramolecular O—H...N hydrogen bond closes anS(8) ring. The crystal structure features weak C—H...O hydrogen-bonding interactions, which link the molecules into [010] chains.

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A New Antifeedant Withanolide from Jaborosa lanigera

Zeitschrift für Naturforschung B ◽

10.1515/znb-2007-0415 ◽

2007 ◽

Vol 62 (4) ◽

pp. 573-576 ◽

Cited By ~ 6

Author(s):

M. Cristina Tettamanzi ◽

Fernando N. Biurrun ◽

Adriana M. Cirigliano

Keyword(s):

Ceratitis Capitata ◽

Fruit Fly ◽

2D Nmr ◽

Ring System ◽

Mediterranean Fruit Fly ◽

Feeding Deterrent ◽

Aerial Parts ◽

The Mediterranean ◽

Deterrent Activity

A new trechonolide-type withanolide, jaborosolactol, possessing a hemiketal ring system and a 5-membered lactol, has been isolated from the aerial parts of Jaborosa lanigera. The structure was elucidated based on spectroscopic and spectrometric methods (1D and 2D NMR, MS). The feeding deterrent activity of the compound against the Mediterranean fruit fly Ceratitis capitata was examined.

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12-{[4-(4-Bromophenyl)piperazin-1-yl]methyl}-9α-hydroxy-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one

Acta Crystallographica Section E Structure Reports Online ◽

10.1107/s1600536814006473 ◽

2014 ◽

Vol 70 (4) ◽

pp. o497-o498 ◽

Cited By ~ 1

Author(s):

Mohamed Loubidi ◽

Ahmed Benharref ◽

Lahcen El Ammari ◽

Mohamed Saadi ◽

Moha Berraho

Keyword(s):

Molecular Conformation ◽

Crystal Packing ◽

Chair Conformation ◽

Chloroform Extract ◽

Ring System ◽

Membered Ring ◽

Epoxy Ring ◽

Piperazine Ring ◽

Aerial Parts ◽

Compound C

The title compound, C25H33BrN2O4, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts ofAnvillea radiata. The molecule is built up from two fused five- and ten-membered rings with an additional epoxy ring system and a bromophenylpiperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hydroxy group forming the flap. An intramolecular O—H...N hydrogen bond stabilizes the molecular conformation. The crystal packing features C—H...O hydrogen bonds, which link the molecules into zigzag chains running along theb-axis direction.

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9α-Hydroxy-12-{[4-(4-hydroxyphenyl)piperazin-1-yl]methyl}-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one

Acta Crystallographica Section E Structure Reports Online ◽

10.1107/s1600536814007430 ◽

2014 ◽

Vol 70 (5) ◽

pp. o530-o531

Author(s):

Mohamed Loubidi ◽

Ahmed Benharref ◽

Lahcen El Ammari ◽

Mohamed Saadi ◽

Moha Berraho

Keyword(s):

Phenyl Ring ◽

Molecular Conformation ◽

Chair Conformation ◽

Chloroform Extract ◽

Ring System ◽

Membered Ring ◽

Hydroxyl Group ◽

Epoxy Ring ◽

Aerial Parts ◽

Compound C

The title compound, C25H34N2O5, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3, 14-dioxa-tricyclo[9.3.0.02,4]tetradec-7-en-13-one), which in turn was isolated from the chloroform extract of the aerial parts ofAnvillea radiata. The molecule comprises a ten-membered ring fused to a five-membered ring with an additional epoxy ring system fused to the ten-membered ring. The five-membered ring also carries a 4-hydroxyphenyl-piperazin-1-ylmethyl substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hydroxy group forming the flap. Two C atoms in the phenyl ring and the O atom of the hydroxyl group are disordered over two sites, with an occupancy ratio of 0.53 (5):0.47 (5). An intramolecular O—H...N hydrogen-bond stabilizes the molecular conformation. In the crystal, C—H...O hydrogen bonds link the molecules into zigzag chains running along thea-axis direction.

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Stochasting modeling of planetary ring systems

International Astronomical Union Colloquium ◽

10.1017/s025292110010154x ◽

1984 ◽

Vol 75 ◽

pp. 461-469 ◽

Cited By ~ 1

Author(s):

Robert W. Hart

Keyword(s):

Maximum Entropy ◽

Ring System ◽

The Sun ◽

Ultimate State ◽

Interparticle Interactions ◽

Ring Systems ◽

First Order ◽

Planetary Ring ◽

Insight Into

ABSTRACTThis paper models maximum entropy configurations of idealized gravitational ring systems. Such configurations are of interest because systems generally evolve toward an ultimate state of maximum randomness. For simplicity, attention is confined to ultimate states for which interparticle interactions are no longer of first order importance. The planets, in their orbits about the sun, are one example of such a ring system. The extent to which the present approximation yields insight into ring systems such as Saturn's is explored briefly.

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