Two New Natural Diels-Alder-Type Adducts from the Root Bark of Artocarpus heterophyllus

Hano, Yoshio; Aida, Miwa; Nomura, Taro

doi:10.1021/np50068a018

Cited by 30 publications

(25 citation statements)

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“…1) and CD spectrum (with three negative Cotton effects at 269, 288 and 303 nm, and a positive Cotton effect at 333 nm), the relative configurations of H-3Љ, H-4Љ and H-5Љ were assigned as all-trans, and the absolute configurations of C-3Љ, C-4Љ, C-5Љ and C-2 were assigned as R, R, S and S, respectively. [10][11][12] In the case of the bioactivities of compounds 1, 2, 5, 6 and Vit E, the inhibitory rates of MDA were 91.8%, 97.6%, 98.3%, 100.0% and 18.2% at concentrations of 10 Ϫ5 mol/l, respectively. Thus, it could be concluded that these compounds had good anti-oxidant activities.…”

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confidence: 99%

“…1) Previously, many novel compounds, which were regarded biogenetically as Diels-Alder adducts of dehydroprenylphenols and chalcone derivatives, were isolated from M. alba, M. lhou, M. bombycis, and so on. [2][3][4][5][6][7][8] In the course of our seeking novel bioactive compound, we started phytochemical research on the stem bark of M. macroura. The EtOH extract of M. macroura was partitioned with CHCl 3 and EtOAc, and the EtOAc fraction was sequentially subjected to column chromatography over silica gel, silica gel RP-18 and Sephadex LH-20 to give six compounds.…”

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New Diels-Alder Type Adducts from Morus macroura and Their Anti-oxidant Activities

Dai

Wang

et al. 2004

Chem. Pharm. Bull.

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Fractionation of the ethanolic extract of the stem bark of Morus macroura resulted in the isolation of four new Diels-Alder type adducts, named guangsangons K-N (1, 2, 5, 6), together with two known compounds, mulberrofuran G (3) and K (4). Their structures were determined on the basis of spectroscopic analyses and chemical methods. Furthermore, by means of 1 H-NMR variable temperature experiments and the Cotton curves in the circular dichroism (CD) spectra, the stereochemistry of four new compounds was elucidated. The isolated new compounds showed good activity on anti-oxidant in vitro, with the inhibitory rates of MDA being from 91.8 to 100.0% at concentrations of 10 ؊5 mol/l.

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New Diels-Alder Type Adducts from Morus macroura and Their Anti-oxidant Activities

Dai

Wang

et al. 2004

Chem. Pharm. Bull.

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“…Artocarpus species have been used in folk medicine for their anti-inflammatory, antioxidant, antibacterial, and antiplatelet activities [3][4][5][6]. Plants of the genus Artocarpus are rich in prenylflavonoids [3,[7][8][9][10][11][12][13][14][15][16].To further understand the chemotaxonomy of the genus Artocarpus and to continue searching for novel bioactive metabolites from Moraceae plants, A. heterophyllus was chosen for a phytochemical investigation.Carefull examination of this plant has resulted in the isolation of nine constituents, 1-9. Compounds 3-9 were isolated from this species for the first time.…”

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Secondary metabolites from the stems of Artocarpus heterophyllus

et al. 2010

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Artocarpus species (Moraceae) are evergreen trees with a milky juice and large edible fruits. There are about 50 species in tropical Asia, Polynesia, and the Pacific islands [1,2]. Artocarpus species have been used in folk medicine for their anti-inflammatory, antioxidant, antibacterial, and antiplatelet activities [3][4][5][6]. Plants of the genus Artocarpus are rich in prenylflavonoids [3,[7][8][9][10][11][12][13][14][15][16].To further understand the chemotaxonomy of the genus Artocarpus and to continue searching for novel bioactive metabolites from Moraceae plants, A. heterophyllus was chosen for a phytochemical investigation.Carefull examination of this plant has resulted in the isolation of nine constituents, 1-9. Compounds 3-9 were isolated from this species for the first time. The structures of these compounds were established by means of spectral experiments.Cyclomorusin (1) [3] and cycloartocarpin A (2) [17] were obtained as colorless needles, whereas brosimone I (3) [18] was isolated as a yellow powder with mp 150-152qC. The IR and NMR data of these compounds were consistent with corresponding authentic samples. It is noteworthy that brosimone I (3) was isolated for the first time from this plant.Stearic acid (4) [19], palmitic acid (5) [19], and linoleic acid (6) [19] were isolated as colorless needles. They were identified by comparison of their physical and spectral data with reported values [19]. Squalene (7) was obtained as a colorless oil. The IR and 1 H NMR data corresponded with literature values [20]. Two steroids, E-sitosterol (8) [21] and stigmasterol (9) [21]), gave a positive Liebermann-Burchard test. The molecular formula of compounds 8 and 9 was determined to be C 29 H 50 O (414) and C 29 H 48 O (412), respectively, from EI-MS and 13 C NMR spectra. These two compounds were further identified by comparison of the IR and 1 H NMR spectra with the corresponding literature data. Brosimone I (3). Yellowish powder; mp 150-152qC; [ ] 25 D D +100q (c 0.12, acetone). UV (MeOH, O max , nm) (log H): 260 (4.91), 290 (4.21), 370 (4.25). IR (KBr, Q max , cm -1 ): 3400 (OH), 1652 (C=O). 1 H NMR (500 MHz, acetone-d 6 , G, ppm, J/Hz): 1.08 (6H, t, J = 6.8, CH 3 -19, 20), 1.68, 1.93 (each 3H, d, J = 1.5, CH 3 -14, 15), 2.43 (1H, m, H-18), 5.45 (1H, m, H-12), 6.20 (1H, d, J = 9.0, H-11), 6.40 (1H, d, J = 2.0, H-3c), 6.58 (1H, s, H-8), 6.51-6.60 (2H, m, H-5c, 16), 6.74 (1H, dd, J = 16.0, 7.0, H-17), 7.65 (1H, d, J = 8.0, H-6c), 13.70 (1H, s, OH-5, D 2 O exchangeable). EI-MS m/z (rel. int): 420 [M] + (52), 403 (11), 377 (13), 321 (100).

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The minor flavonoids

Bohm¹

1993

The Flavonoids

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Two New Natural Diels-Alder-Type Adducts from the Root Bark of Artocarpus heterophyllus

Cited by 30 publications

References 5 publications

New Diels-Alder Type Adducts from Morus macroura and Their Anti-oxidant Activities

New Diels-Alder Type Adducts from Morus macroura and Their Anti-oxidant Activities

Secondary metabolites from the stems of Artocarpus heterophyllus

The minor flavonoids

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