Preparation of Ambrox from Labdanes of Dysoxylum hongkongense, and the Preparation of New Diterpenoids from Dysoxylum hongkongense

Active Publication Date: 2016-02-18
NAT TAIWAN UNIV
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Problems solved by technology

However, because it is difficult to obtain ambergris from endangered sperm whales at present the availability, ambergris and natural AMBROX® are largely

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  • Preparation of Ambrox from Labdanes of Dysoxylum hongkongense, and the Preparation of New Diterpenoids from Dysoxylum hongkongense
  • Preparation of Ambrox from Labdanes of Dysoxylum hongkongense, and the Preparation of New Diterpenoids from Dysoxylum hongkongense
  • Preparation of Ambrox from Labdanes of Dysoxylum hongkongense, and the Preparation of New Diterpenoids from Dysoxylum hongkongense

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[0020]The present invention will now be described more specifically with reference to the following embodiments. It is to be noted that the following descriptions of preferred embodiments of this invention are presented herein for purpose of illustration and description only; they are not intended to be exhaustive or to be limited to the precise form disclosed.

[0021]The structures of the new compounds in the present invention were established by interpretation of spectroscopic data, especially two-dimensional nuclear magnetic resonance (2D NMR). The stereochemistry of the compounds was established by chemical correlation, and the configurations thereof were definitively confirmed by X-ray crystallographic analysis.

[0022]Melting points of the compounds were recorded on a Büchi® B540 melting point apparatus. Optical rotations were recorded on a JASCO DIP-1000 polarimeter. Infrared (IR) spectra were taken on a HORIBA® FT-720 spectrophotometer. The 1H and 13C NMR spectra as well as 2D N...

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Abstract

The present invention discloses eight new diterpenoids, i.e. Dysongensins A to H, extracted from the leaves and twigs of Dysoxylum hongkongense, wherein AMBROX® which is applicable in the perfume industry is prepared from Dysongensin A via a series of chemical reactions, and the cytotoxicity of Dysongensins A to H against human cancer cell lines and their antiviral and anti-inflammatory activities are determined. Therefore, in the present invention, AMBROX® prepared from Dysongensin A is a new idea for application as an odorous compound in the perfume industry, and the novel diterpenoids can be prepared as a pharmaceutical compositions and / or a drug having antiviral, anti-inflammatory and / or anti-cancer activities.

Description

CROSS-REFERENCE TO RELATED APPLICATION AND CLAIM OF PRIORITY[0001]This application claims the benefit of Taiwan Patent Application No. 103127686, filed on Aug. 12, 2014, at the Taiwan Intellectual Property Office, the disclosures of which are incorporated herein in their entirety by reference.FIELD OF THE INVENTION[0002]The present invention relates to a preparation method for AMBROX® ((−)-3a,6,6,9a-tetramethyl-dodecahydronaphtho[2,1-b]furan), and new compounds which are extracted from Dysoxylum hongkongense and used for anti-virus, anti-inflammation or anti-cancer treatments, as well as pharmaceutical compositions and drugs thereof.BACKGROUND OF THE INVENTION[0003]Ambergris is a solid wax, which is formed from excretions of the sperm whale, Physeter macrocephalus L. (Physeteridae), via a bacterial and enzymatic process. It has been known that the odorous compound AMBROX® (a registered trademark name of Firmemich SA, Geneva, Switzerland), a naturally occurring triterpenoid with wide...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D307/92C07C45/78C07C49/743
CPCC07D307/92C07C2102/28C07C49/743C07C45/78C07C45/79C07C2602/28A61P29/00A61P31/22A61P35/00
Inventor SHEN, YA-CHING
Owner NAT TAIWAN UNIV
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