PHLOROGLUCINOL DERIVATIVES OF ELEVENDRYOPTERISSPECIES FROM JAPAN

Abstract

Phloroglucinol derivatives o f eleven Dryopteris species from Japan hai~e been investigated. Aspidin AB, trisdesaspidin BBB, trisflavaspidic acid, rnethylene-bisaspidinol, and trisaspidinol have been found for' the first time in Japanese Dryopteris. D. erythrosora is unique among the Dryopteris species examined so far in containirzg isobutyryl (iB) side chain homologues. The phlorogl~~cinol derivatives of the eleven Dryopteris taxa investigated have been compared with those of related taxa on a worldwide basis. Les de'rivks phloroglucinoliques de onze espkces de Dryopteris d'origine japonaise orzt e'tk examinb. L'aspidine AB, le trisdesaspidine BBB, l'acide trisflavaspidique, le mkthylkne-bis-aspidinol et le trisaspidinol ont e'te' trouve's pour la premikre fois duns les Dryopteris japonais. D. erythrosora est unique parmi les espkces de Dryopteris examinkes jusqu'ici contenant des homologues isobutyryles (iB) des chaines late'rales. Les dkrivks phloroglucinoliques des onze taxons exa m i n b de Dryopteris ont e'te' compares avec ceux des taxons apparentb stir la base globule. Dryopteris is largely a north-temperate genus with many abundant species in Eurasia, especially in China. However, there are scattered species in all parts of the world, including the southern hemisphere. In the tropics these ferns are confined to the mountains and higher altitudes. HOLTTUM [I] notes that some 90 species have been recorded from China, but only three from the Malay Peninsula. HIRABAYASHI [2] lists 59 species from Japan of which 56 have been cytologically investigated. The phloroglucinol derivatives of thirty five Japanese Dryopteris species have been studied by HISADA and coworkers [3-171 in a series. of works from 1961. However, in continuation of our investigations on anthelmintically active phloroglucinol derivatives in European [18-231, North American 10 rhizomes sent by K. IWATSUKI); According to ITO [31], the Dryopteris genus of Japan can be divided into four sections: Eudryopteris, Polysticho-drys, Lophodium, and Nephrocystis, which are still divided into several subsections [cf. also ref. 21. The divisions of ITO were later changed so that two Japanese ferns, which previously were considered to belong in the genus Ctenitis, at present are included in the Dryopteris genus as an separate group, Dryopteris snbg. Nothoperanema TACAWA. This group is sometimes also separated as an own genus Nothoperanema (TACAWA) CHING. Excellent photographs of most Japanese Dryopteris species are published by TACAWA [32].

Phloroglucinol compounds of natural origin

“…These differ in the nature of the side chain, the number of methyl groups and level of oxygenation. Tasmanone (319) is the first member of this class of compounds, first isolated (from oils of Eucalyptus risdoni and E. linearis) in 1914 by Robinson and Smith, who called it tasmanol, as they thought it to be a phenol. 242 Later on, Trikojus and White assigned its probable molecular formula and considered it to be an acid, as it was soluble in sodium carbonate solution, and it gave other positive tests for acid.…”

“…A structurally similar group of compounds, aspidins AA (445), AP (446), PP (447), AB (448), PB (449) and BB (450), have been reported from various species of Dryopteris and Aspidium. 319,320 Aspidins are reported to possess various biological activities, including anthelmintic, ichthyotoxic and antitumourpromoting activities. 56 Similarly, desaspidins AA (451), AB (452), AP (453), PB (454), BB (455), PA (456) and PP (457) have been reported from Dryopteris species ferns.…”

Kaempferol Acetylrhamnosides from the Rhizome of Dryopteris crassirhizoma and Their Inhibitory Effects on Three Different Activities of Human Immunodeficiency Virus-1 Reverse Transcriptase.

“…12) Species of the genus Dryopteris are generally characterized by the presence of phloroglucinol derivatives, such as flavaspidic acids, triflavaspidic acids, dryocrassins, albaspidins and filixic acids. [13][14][15][16][17][18] Some of them showed anti-tumor promoting activity 19) and anti-bacterial activity. 20) Recently, kaempferol glycosides have been isolated from the Dryopteris species.…”

Potent and Non-Cytotoxic Antibacterial Compounds Against Methicillin-Resistant Staphylococcus aureus Isolated from Psiloxylon mauritianum, A Medicinal Plant from Reunion Island

“…Crystallographic data were recorded at 150 K to reduce agitation induced by the length of the valeryl side chain. Compound 2 was named Aspidin VB, and although its presence has already been mentioned in the literature [ 14 , 15 ], this is the first time that it has been isolated and characterized.…”