# US 5,276,177 A · Physiologically active substance

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,276,177 A
- Document ID: US5276177A
- Status: Granted
- Kind: A
- Application number: 07/899,730
- Filed: 1992-06-17
- Granted: 1994-01-04
- Earliest claimed: 1991-08-29
- Assignees: Tetsuya Matsuno; Mpi Corporation
- Inventors: Mayumi Yoshida; Yutaka Saito; Tetsuya Matsuno
- Web page: https://patentgrep.com/patent/US5276177A

## CPC

- C07C 59/46: containing rings other than six-membered aromatic rings
- A61P 35/00: Antineoplastic agents
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A novel physiologically active substance is represented by the formula. ##STR1## The substance is preferably derived from propolis, has excellent antitumor activity and is useful as an antitumor drug.

## Claims

### Claim 1

A compound represented by the formula (I): ##STR8## and characterized by the following physical and chemical properties: (a) Specific rotatory power: .sub.D.sup.25 =-83.degree. (c=0.44, methanol)
(b) Ultraviolet absorption spectrum: (in methanol) .lambda.max: 212 nm (.epsilon.=4,600, 288 nm) (.epsilon.=2,600)
(c) Infrared absorption spectrum: (KBr tablet method) .nu.(cm.sup.-1): 3,600-2,400, 3,450, 2,941, 1,695, 1,641, 1,439, 1,385, 1,259
(d) Solubility: Soluble in methanol, ethyl acetate, chloroform and DMSO. Sparingly soluble in acidic water
(e) Color reaction: Positive to an iodine reagent, a BCG reagent and a cerium sulfate reagent
(f) High performance liquid chromatography: Reversed phase silica gel filler column: (ODS, spherical, 5 .mu.m, pore diameter 60 angstrom, 6.0 mm.phi..times.150 mm); eluent: 0.02M acetic acid-ammonium acetate (pH 5.0)-methanol; flow rate 1 ml/min; detection: detected by means of 240 nm ultraviolet absorption; retention time; 16.7 minutes.