Goniotriol from Goniathalamus giganteus

Abstract

The known styrylpyrone, goniotriol, has been isolated from Goniothalamus giganteus. Its bioactivities are reported, and its structure and relative stereochemistry have been determined by X-ray crystallography as 6R-(7R,8R-dihydro-7,8-dihydroxystyryl)-5S,6R-dihydro-5-hydroxy-2-p yrone.

A 2:1 Solid Solution of 6-Chloro-2,3,6-trideoxy-D-erythro-hex-2-enono-1,5-lactone and its 6-Bromo Analogue

“…1. The bond lengths and angles observed in the title structure are comparable with those observed in its precursor (1) and other related naturally occurring 6-1actones, such as asperlin, asperlinol (Fukuyama, Katsube, Noda, Hamasaki & Hatsuda, 1978) and goniotriol (Alkofahi, Ma, McKenzie, Byrn & McLaughlin, 1989). In general, the observed bond lengths are shorter than normal values; for example, the C1--C2 single-bond distance of 1.452 (5),~ is much less than the usual value and may be attributed to the effect of the neighbouring C==O and C==C bonds.…”

Bioactive styryllactones and alkaloid from flowers of Goniothalamus laoticus

“…The structures of the isolated compounds were identified by spectroscopic methods and comparison with the literature data as cinnamic acid (1) (Lan et al, 2003), dihydrochrysine (2) (Hsieh et al, 1998), ␤-sitosterol (3) (Pouchert and Behnke, 1993), (+)-3-acetylaltholactone (4) (Peris et al, 2000), goniotriol (5) (Alkofahi et al, 1989), (+)-altholactone (6) (Loder and Nearn, 1977), (+)-goniofufurone (7) (Bermejo et al, 1998), 9-deoxygoniopypyrone (8) (Fang et al, 1991), howiinin A (9) (Chen et al, 1998) and (−)-nordicentrine (10) (Likhitwitayawuid et al, 1993). Seven compounds were evaluated for their antiplasmodial activity against Plasmodium falciparum, antimycobacterial activity against Mycobacterium tuberculosis, and cytotoxicity against four cancer cell lines.…”

Synthesis of Polyhydroxylated Pyrano‐Pyrrole Derivatives from Carbohydrate Precursors

“…α-Pyrones with a polyol system form the basic skeleton of several natural products. For example, α-pyrones bearing free or acetylated polyhydroxylated side-chains, such as passifloricin A (1), [4] (+)-goniotriol (2a), [5] (+)-boronolide (3a), [6] and analogues 2b [7] and 3b, express antiprotozoal, antimalarial, and antitumoral activities ( α-Pyrones fused to hydroxylated aromatic or nonaromatic rings ( Figure 2) are also found in antimalarial dihydroisocoumarin derivatives 5, [9] antitumoral psymberin (6), [10] and cytotoxic hippeastrine (7), [11] whereas dehydroaltenusin (8) has been observed to inhibit mammalian DNA polymerase α. [12] A large number of active sesquiterpene lactones, like vernolepin (9), [13] have been isolated from plant extracts and show tumor-inhibiting activity.…”