Chemical Components and Tyrosinase Inhibitors from the Twigs of Artocarpus heterophyllus

Abstract

An HPLC method was developed and validated to compare the chemical profiles and tyrosinase inhibitors in the woods, twigs, roots, and leaves of Artocarpus heterophyllus . Five active tyrosinase inhibitors including dihydromorin, steppogenin, norartocarpetin, artocarpanone, and artocarpesin were used as marker compounds in this HPLC method. It was discovered that the chemical profiles of A. heterophyllus twigs and woods are quite different. Systematic chromatographic methods were further applied to purify the chemicals in the twigs of A. heterophyllus. Four new phenolic compounds, including one isoprenylated 2-arylbenzofuran derivative, artoheterophyllin A (1), and three isoprenylated flavonoids, artoheterophyllin B (2), artoheterophyllin C (3), and artoheterophyllin D (4), together with 16 known compounds, were isolated from the ethanol extract of the twigs of A. heterophyllus. The structures of compounds 1-4 were elucidated by spectroscopic analysis. However, the four new compounds did not show significant inhibitory activities against mushroom tyrosinase compared to kojic acid. It was found that similar compounds, such as norartocarpetin and artocarpesin in the twigs and woods of A. heterophyllus, contributed to their tyrosinase inhibitory activity.

Antimicrobial activities of the methanol extract and compounds from Artocarpus communis (Moraceae)

“…Numbers of terpenoids isolated from A. communis such as compounds 2 and 3 are ubiquitous in plant kingdom. The flavonoid, Artonin E was previously reported in other Artocapus species, A. kemando , A. nobilis and A. rigida [13,21,22] meanwhile the arylbenzofuran, 2-[(3,5-dihydroxy)-(Z)-4-(3-methylbut-1-enyl)phenyl]benzofuran-6-ol was reported in Artocarpus heterophyllus [23]. In the present work, the crude extract as well as most of the compounds isolated from the bark of A. communis were tested for their antibacterial activities and against C. albicans .…”

“…Sub-fraction E 1 (CHCl 3 to CHCl 3 -MeOH 97.5:2.5) and E 4 (CHCl 3 -MeOH 95:5 to 90:10) were repeatedly filtered through Sephadex LH-20 (CHCl 3 -MeOH 7:3) to yield artonin E C 25 H 24 O 7 ( 4 ; 10.0 mg, m/z 436.14; yellow crystals, m.p. : 255-257°C) [13] and 2-[(3,5-dihydroxy)-(Z)-4-(3-methylbut-1-enyl)phenyl]benzofuran-6-ol C 19 H 18 O 4 ( 5 ; 12.8 mg; m/z 310.0; yellow oil) [14]. The chemical structures of the isolated compounds are illustrated in Figure 1.…”

Bio-active Natural Products with TRAIL-Resistance Overcoming Activity

“…The isolation of a number of prenylated flavonoids was previously described from its heartwood. 39) Bioassay activity-guided separation of A. champeden roots resulted in the isolation of six com- pounds, pannokins A-C (29-31), 40) artonin B (32), 41,42) artoheterophyllin D (33), 43) and heterophyllin (34) 44) (Fig. 12).…”

KECENDERUNGAN POLA OKSIDASI FLAVONOID PADA KULIT BATANG DAN KAYU BATANG Artocarpus scortechinii KING. (Moraceae)

“…Dari kulit batang A. nobilis juga berhasil diisolasi artonin E (17) senyawa serupa hanya saja cincin piran terbentuk dari siklisasi prenil di posisi C-8 dengan gugus OH diposisi C-7 [16], sedangkan untuk artoheterophyllin B (18), artoheterophyllin C (19), dan artoheterophyllin D (20) berhasil diisolasi dari A. heterophyllus [17]. Secara biogenesis, senyawa oksepinoflavon dapat berasal dari senyawa 2',4'-dioksigenasi atau 2',4',5'-trioksigenasi 3-prenilflavon (sebagai prekursor), melalui reaksi siklisasi oksidatif yang melibatkan pembentukan ikatan -C-O-C-antara gugus OH pada C-2' dengan C-10 dari gugus isopren pada C-3.…”