On the chemistry of indian orchidaceae plants—II: Dengibsin and dengibsinin, the first natural fluorenone derivatives from dendrobium gibsonii lindl

doi:10.1016/S0040-4020(01)96378-1

Tetrahedron

Volume 41, Issue 13, 1985, Pages 2765-2769

https://doi.org/10.1016/S0040-4020(01)96378-1 Get rights and content

Abstract

Dendrobium gibsonii, an Orchidaceae plant yielded the first natural fluorenone derivatives designated dengibsin and dengibsinin to which 1,5-dihydroxy-7-methoxy-9-fluorenone (1) and 1,6-dihydroxy-5, 7-dimethoxy-9-fluorenonc (2) structures have been assigned respectively. The structures are fully supported by the ¹H-NMR, IR, UV and MS spectral data of dengibsin and dengibsnin and a number of their pertinent derivatives. Aurantiamide acetate, dimethyl terephthalate and β-sitosterol have been isolated as the other constituents.

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Fluorenones are an inevitable and important class of organic compounds that are found in rock extracts and other crude oils [7] as well as in diesel fuels [8]. Widespread interest has been developed on these molecules due to their interesting bioactive properties [9–11]. Fluorenone derivatives have been known to be used for the treatment of ophthalmic conditions [12].
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TLC (CH2Cl2–MeOH, 9:1) of subfraction 6/2 (1.6 g) afforded kaempferol (7, 12 mg) (Ulubelen et al., 1980) and naringenin (8, 15 mg) (Shen et al., 1993). Subfractions 6/4 (1.2 g) was chromatographed on Sephadex LH-20 column with MeOH–CH2Cl2 (7:3) to provide dengibsin (9, 30 mg) (Talapatra et al., 1985) and dendroflorin (10, 11 mg) (Zhang et al., 2004). The compounds were identified conclusively by UV, IR, MS, 1HNMR and 13C NMR analysis.

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¹: For Part I see Ref. 1.

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On the chemistry of indian orchidaceae plants—II1: Dengibsin and dengibsinin, the first natural fluorenone derivatives from dendrobium gibsonii lindl

Abstract

Tetrahedron

Phytochem.

Indian J. Chem.

On the chemistry of indian orchidaceae plants—II¹: Dengibsin and dengibsinin, the first natural fluorenone derivatives from dendrobium gibsonii lindl