New 2,5-bis-aryl-3,4-dimethyltetrahydrofuran lignans from the aril of Myristica fragrans.

Abstract

Several new tetrahydrofuran lignans, named fragransins A2 (II), B, (IV), B2 (V), 133 (VI), C1 (VII), C2 (VIII), C3a. (IX) and C3b (X) were isolated from the methanolic extract of the aril of Myristica fragrans HOUTT. (Myristicaceae), along with nectandrin B (I) and verrucosin (III). The structures of these compounds were elucidated by spectroscopic methods.

Biological activities of lignoids from Amazon Myristicaceae species: Virola michelii, V. mollissima, V. pavonis and Iryanthera juruensis

“…The subfraction coded IJ-A2 (422.0 mg) gave a white precipitate which was identified as guaiacin (1,136.0 mg), 5 while IJ-A3 (52.0 mg) was fractioned by preparative TLC (silica gel and hexane:EtOAc 7:3) providing verrucosin (2, 18.0 mg). 6 The hydroalcoholic residue of the hexane extract of V. mollissima pericarps (2.5 g) was fractionated by silica gel column chromatography and eluted with hexane:EtOAc of increasing polarity, resulting in the isolation of grandisin (3, 13.8 mg). 7,8 The hexane residue of the EtOH extract from the arils (3.84 g) showed formation of crystals, which recrystallized in CH 2 Cl 2 afforded hydroxy-oxo-otobain (4, 11.0 mg).…”

Stereoselective Synthesis of Highly Substituted Tetrahydrofurans through Diverted Carbene OH Insertion Reaction

“…[4] Examples include (+)-fragransin A2 [5] and amphidinolide F [6] (Figure 1). As a consequence, a number of strategies have been employed for the stereoselective synthesis of tetrahydrofurans.…”

Three New Compounds from Kadsura longipedunculata

“…Its molecular formula, C 15 (Table 2) and DEPT experiments clearly indicated the basic C 15 -sesquiterpene skeleton of the cadinane skeleton. 24,25) The structure of 3 was elucidated from HSQC, 1 H-1 H COSY, and HMBC studies (Fig.…”

“…[11][12][13] To search more novel and biologically potent active compounds, and to compare the chemical constituents' differences of the same Kadsura species belonging to different geographical distribution and climatic conditions, we investigated the leaves and stems of K. longipedunculata collected in the Yibin region of Sichuang Province, China. This paper deals with the isolation and structure elucidation of three new compounds, named as kadlongirins A and B (1, 2) and 2,7-dihydroxy-11,12-dehydrocalamenene (3), together with seven known compounds, grandisin (4), 14) fragransin B 1 (5), 15) vladirol F (6), 16) kadsuralignan C (7), 17) otobaphenol (8), 18) isoanwulignan (9), 19) and 4-[4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-2-methoxy-phenol (10). 20) The anti-HIV-1 activities of the three new compounds were evaluated.…”