Styryl-pyrones from Goniothalamus arvensis

doi:10.1016/S0031-9422(97)00770-X

Phytochemistry

Volume 47, Issue 7, April 1998, Pages 1375-1380

https://doi.org/10.1016/S0031-9422(97)00770-X Get rights and content

Abstract

Two novel styrl-pyrones, (+)-garvensintriol and (+)-etharvendiol, together with a known cytotoxic furano-furone, (+)-goniofufurone, have been isolated from the stem bark of Goniothalamus arvensis. A different relative configuration, cis-erythro-erythro for garvensintriol and cis-threo-erythro for etharvendiol, is established, and their absolute stereochemistry is discussed.

Abstract

Two novel styryl-pyrones, (+)-garvensintriol (1) and (+)-etharvendiol (2), together with a known cytotoxic furanofurone, (+)-goniofufurone, have been isolated from the stem bark of G. arvensis (Annonaceae).

References (17)

X.P. Fang et al.
Tetrahedron
(1991)
F.B. Ahmad et al.
Phytochemistry
(1991)
Y.C. Wu et al.
Phytochemistry
(1992)
X.P. Fang et al.
Tetrahedron
(1993)
C.M. Hasan et al.
Phytochemistry
(1994)
X.P. Fang et al.
Journal of Natural Products
(1991)
Y.C. Wu et al.
Journal of Natural Products
(1991)
S.H. Goh et al.
Natural Product Letters
(1995)

There are more references available in the full text version of this article.

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Phytochemical constituents from the stem barks of Goniothalamus tapis Miq
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For MS experiment, 1 mg of sample was dissolved in 1 mL of MS grade MeOH. The structure of the compounds were identified as 3-acetylisoaltholactone (1), goniothalamin (2) (de Fatima et al., 2005), isoaltholactone (3) (Colegate et al., 1990), cheliensisin A (4) (Li et al., 1998), 7-epi-goniofufurone (5) (Fang et al., 1991a), goniopypyrone (6) (Mahiwan et al., 2013), garvensintriol (7) (Bermejo et al., 1998), stigmasterol (8) (Chaturvedula and Prakash, 2012), β-sitosterol (9) (Chaturvedula and Prakash, 2012) (Fig. 1) with thorough spectroscopic analysis and by comparison with reported data. Compound 1 was isolated as yellow amorphous and gave a positive molecular ion peak [M+H]+ at m/z 275.1004 (calc.
Phytochemical investigation on the stem bark of Goniothalamus tapis Miq. led to the isolation of seven known styryl-lactones, 3-acetyl-isoaltholactone (1), goniothalamin (2), isoaltholactone (3), cheliensisin A (4), 7-epi-goniofufurone (5), goniopypyrone (6), garvensintriol (7), and two steroids, stigmasterol (8) and β-sitosterol (9). The structures of all the compounds were elucidated based on the analysis of spectroscopic data and comparison with reported literature. The chemotaxonomic significance of all these compounds were summarized. Among all the styryl-lactones, compound 1 was isolated naturally from plant for the first time while compounds 4, 5 and 7 have not been previously reported in Goniothalamus tapis Miq. Compound 2 was the first styryl-lactone isolated from many species of Goniothalamus including other families such as Cucurbitaceae, Lauraceae, Stemonaceae and Apocynaceae). Compounds 3 and 6 were found in ten species of Goniothalamus where the latter were also found in other genus (Polyalthia Blume).
Organocatalyzed α-aminooxylation/amination of aldehydes and their sequential reactions: A versatile tool for the synthesis of bioactive molecules
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The furanofurone skeleton is characterized by the presence of a saturated γ-lactone moiety fused with a furano-group to form a bicyclic ring system. Only two styryllactone with this skeleton, goniofufurone and 8-epi-goniofufurone, have been isolated from Goniothalamus giganteus (Fang et al., 1990, 1991a), Goniothalamus borneensis (Cao et al., 1998), and Goniothalamus arvensis (Bermejo et al., 1998a), which differ only with respect to their stereochemistry at C-8. Examination of the coupling constant J4,5 (4.4 Hz) in goniofufurone and 8-epi-goniofufurone indicated that H-4 and H-5 must be in the cis-configuration.
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Stereoselective total syntheses of aggregation pheromones (+)-exo-brevicomin (9a), (−)-exo-brevicomin (9b), (+)-endo-brevicomin (9c), (−)-endo-brevicomin (9d) and styryllactones (+)-cardiobutanolide (14a), (−)-cardiobutanolide (14b), and (+)-goniofufurone (19a) were achieved in good yields from enantiomerically pure highly functionalized furanoid glycal building blocks (1a–d) involving similar synthetic strategies, thus making these furanoid glycals highly useful building blocks in diversity-oriented synthesis (DOS).
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Plant chemistryStyryl-pyrones from Goniothalamus arvensis

Abstract

Abstract

Tetrahedron

Phytochemistry

Phytochemistry

Tetrahedron

Phytochemistry

Journal of Natural Products

Journal of Natural Products

Natural Product Letters

Plant chemistry
Styryl-pyrones from Goniothalamus arvensis