Structures of albanols a and b, two novel phenols from Morus alba bark

Rao, A. V. Rama; Deshpande, V. H.; Shastri, Rajesh; Tavale, Sudam S.; Dhaneshwar, N. N.

doi:10.1016/s0040-4039(00)88083-1

Cited by 27 publications

(8 citation statements)

References 11 publications

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“…F062 (eluted with 60% MeOH in H 2 O; 75% inhibition at 4 μg/mL) was purified using HPLC (YMC ODS-AQ Pack, 250 × 20 mm i.d., 50% MeCN in H 2 O, flow rate 5 mL/min) to afford pure 3‘-[γ-hydroxymethyl-( E )-γ-methylallyl]-2,4,2‘,4‘-tetrahydroxychalcone 11‘- O -coumarate ( 9 , t R 27 min, 2 mg, 0.000042%), isogemichalcone C ( 8 , t R 31 min, 1.5 mg, 0.000031%), and isolicoflavonol ( 12 , t R 38 min, 0.8 mg, 0.000017%) . F063 (eluted with 80% MeOH in H 2 O; 76% inhibition at 4 μg/mL) was purified using HPLC (YMC ODS-AQ Pack, 250 × 20 mm i.d., 30% MeCN in H 2 O, flow rate 5 mL/min), resulting in the purification of (2 R ,3 R )-5,7,2‘,4‘-tetrahydroxyflavanonol ( t R 11 min, 3.5 mg, 0.000073%) 47 and albanol A ( 21 , t R 21 min, 3.7 mg, 0.000077%) …”

Section: Methodsmentioning

confidence: 99%

Aromatase Inhibitors from Broussonetia papyrifera

et al. 2001

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Bioassay-guided fractionation of an ethyl acetate-soluble extract from the whole plants of Broussonetia papyrifera, using an in vitro aromatase inhibition assay, led to the isolation of five new active compounds, 5,7,2',4'-tetrahydroxy-3-geranylflavone (1), isogemichalcone C (8), 3'-[gamma-hydroxymethyl-(E)-gamma-methylallyl]-2,4,2',4'-tetrahydroxychalcone 11'-O-coumarate (9), demethylmoracin I (10), and (2S)-2',4'-dihydroxy-2' '-(1-hydroxy-1-methylethyl)dihydrofuro[2,3-h]flavanone (11), and 10 known (12-21) compounds which were also found to be active. Of these compounds, the most potent were 9 (IC(50) 0.5 microM), 11 (IC(50) 0.1 microM), isolicoflavonol (12, IC(50) 0.1 microM), and (2S)-abyssinone II (13, IC(50) 0.4 microM). Additionally, six new compounds, 5,7,3',4'-tetrahydroxy-6-geranylflavonol (2), 5,7,3',4'-tetrahydroxy-3-methoxy-6-geranylflavone (3), (2S)-7,4'-dihydroxy-3'-prenylflavan (4), 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)propane (5), 1-(2,4-dihydroxy-3-prenylphenyl)-3-(4-hydroxyphenyl)propane (6), and 1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxy-3-prenylphenyl)propane (7), were isolated and characterized, but proved to be inactive as aromatase inhibitors, as were an additional 21 known compounds. The structures of the new compounds (1-11) were elucidated by spectroscopic methods. Structure-activity relationships in the aromatase assay were determined for the benzofurans, biphenylpropanoids, coumarins, and various types of flavonoids (chalcones, flavans, flavanones, and flavones) obtained among a total of 42 constituents of B. papyrifera.

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Section: Methodsmentioning

confidence: 99%

Aromatase Inhibitors from Broussonetia papyrifera

et al. 2001

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“…Absolute Configuration of the Ketal Compounds, Mulberrofurans F, G, and K Structures of mulberrofurans F (131), G (27), and K (179) have been established by correlation with chalcomoracin (103) and with mulberrofuran C (130) using a ketalization reaction (91,112). Therefore, the configuration of the three chiral centers in the methylcyc10hexene ring of the ketal compounds is the same as those of 103 and 130. The relative configuration of the four chiral centers in 27 was determined by considering the Dreiding model (112) and by X-ray analysis of albanol A pentamethyl ether (115) (Fig. 31).…”

Section: +85°mentioning

confidence: 99%

“…reported isolation of two compound from M orus alba which they called albanol A and B and assigned formulae 27 and 136 to them, on the basis of an X-ray analysis of albanol A pentamethyl ether (27a) (115). Mulberrofuran G proved to be identical with albanol A by direct comparison.…”

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confidence: 99%

Phenolic Compounds of the Mulberry Tree and Related Plants

Nomura

1988

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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“…Interestingly, all these adducts are optically active with the absolute configuration of mulberrofuran C (3) determined as 3′′ S, 4′′R, 5′′S by a combination of CD spectroscopy and X-ray crystallography. 10,11 Furthermore, all adducts with a positive optical rotation value are cis, trans (endo)-adducts whilst the adducts with negative values are the trans, trans (exo) adducts. 10 This infers that the [4 + 2]-cycloaddition is under some type of enzymatic control [12][13][14] but the question of whether this process in Nature is concerted or stepwise is a subject of debate.…”

Section: Introductionmentioning

confidence: 99%

Synthetic studies towards the mulberry Diels–Alder adducts: H-bond accelerated cycloadditions of chalcones

et al. 2012

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The methyl ether derivatives 2, 4 and 6 of the mulberry Diels-Alder adducts chalcomoracin (1) and mulberrofuran C (3) and kuwanon J (5) respectively have been synthesized by a thermal [4 + 2]-cycloaddition reaction between a chalcone and dehydroprenyl diene. A H-bonded ortho OH substituent on the chalcone was found to be essential for Diels-Alder reactivity. Density functional theory calculations show that the OH group lowers the barrier for the Diels-Alder reaction by 2-3 kcal mol(-1) compared with OMe. The acceleration by the OH group is traced to two transition-state effects: a stronger diene-chalcone interaction and better planarity of the aryl-diene unit.

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Structures of albanols a and b, two novel phenols from Morus alba bark

Cited by 27 publications

References 11 publications

Aromatase Inhibitors from Broussonetia papyrifera

Aromatase Inhibitors from Broussonetia papyrifera

Phenolic Compounds of the Mulberry Tree and Related Plants

Synthetic studies towards the mulberry Diels–Alder adducts: H-bond accelerated cycloadditions of chalcones

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