Sesquiterpenoids of Riccardia and Pallavicinia species

Riccardia species (Metzgeriales) contain various types of sesquiterpenes. R. jackii produces ent-selinane-, ent-aromadendrane-and ent-bicyclogermacrane-type sesquiterpenes together with (R)-cuparene and α-barbatene. Aneura pinguis (= Riccardia pinguis) is chemically quite different from R. multifida and R. jackii. The former produces a large amount of pinguisone. R. multifida contains 6-(3-methyl-2-butenyl)-indole and (+)-β-elemene as the major components. Pallavicinia longispina (Dilaenaceae; Metzgeriales) produces mainly spathulenol. The chiral properties of the sesquiterpenes isolated from R. jackii are quite similar to those of red algae, Laurencia species.     

Contributo preliminare alla sistematica di Chamaecytisus hirsutus e Chamaecytisus supinus

Abstract

Chamaecytisus hirsutus and C. supinus: a preliminary report. – Chamaecytisus hirsutus (L.) Link and C. supinus (L.) Link have been described as twostrictly related species, which differ mainly in the form of inflorescence: C. hirsutus has lateral flowers, C. supinus has terminal flowers. Besides, most Floras provide a set of additional differential characters that should permit to di-C. hirsutus and C. supinus.

The author analyses such differential characters and demonstrates that all of them are inconsistent: therefore the inflorescence seems to be the only difference between C. hirsutus and C. supinus.

The inflorescence itself, however, is not a constant character: indeed, it is known that C. supinus may develop vernal latera flowers besides the normal aestival terminal ones.

The geographic distributions of the two inflorescence types are accurately examined (a report of the distributions is given, a list of herbarium specimens is presented in appendix, a point distribution map of the two types is given in figs. 1 and 2); the only differences are the following ones: plants with flowers in leafy racemes (usually identified as C. hirsutus) seem to be absent from Spain and from Southern Poland, and to be unfrequent in Central and Western France; instead, plants with flowers in heads (usually identified as C. supinus) are very unfrequent in the Southern Balcan Peninsula, and are absent from Southern Greece and the Italian Peninsula.

After a discussion of the biological significance of the capitate and lateral inflorescence, and on the basis of in vivo observations, the author argues that probably the same taxonomic unit is present in the whole area, showing some differences in its flowering behaviour; in the largest part of the areal – including the center of distribution of the species – most individuals flower twice, and therefore have been recorded as two different species; a trend toward the capitate inflorescence is remarkable in the North and in the West; instead, in the South and the East the trend is toward lateral flowers (fig. 3).

Further biometrical and biochemical studies on the species are now in progress; more observations in field in different parts of Europe are necessary in order to get conclusive evidence of the identity of these two so-called «species».     

The structures of new flavone di-C-glycosides from Apometzgeria pubescens

The structures of seven flavone C-glycosides from Apometzgeria pubescens were determined with the aid of ¹³CNMR spectroscopy. They were all     

Aromatic esters and terpenoids of the liverworts in the genera Trichocolea, Neotrichocolea and Trichocoleopsis

Three liverworts, Trichocolea tomentella, Neotrichocolea bissethii and Trichocoleopsis sacculata belonging to Jungermanniales were chemically investigated. Isoprenyl benzoates are the important chemical markers of Trichocolea tomentella. Neotrichocolea bissethii elaborates sesquiterpenes as the major components. The sacculatane-type diterpenes and pinguisane-type sesquiterpenes are the significant chemosystematic markers of Trichocoleopsis sacculata. These three species are chemically quite different. Trichocoleopsis sacculata is chemically rather close to Porella species. The present chemical results support the recent morphological classification of the above three species proposed by Schuster. Some species of Jungermanniales are chemically identical to those of Metzgeriales and these results also support the phylogenetic classification in which the two orders have been united within the subclass Jungermanniae.     

Flavone C-glycosides of two Metzgeria species

Six known tricin and apigenin di-C-glycosides, including 2″-O-ferulylisoschaftoside, have been identified in gametophytic material of Metzgeria conjugata. M. leptoneura contains a new di-C-glycoside, tricin 6-C-xyloside-8-C-hexoside. The chemotaxonomic relevance of the flavonoid patterns is briefly discussed.     

Occurrence of a potent piscicidal diterpenedial in the liverwort Riccardia lobata var. Yakushimensis

Sacculatal and isosacculatal, two diterpene dialdehydes, have been isolated from the liverwort Riccardia lobata var. yakushimensis as the major components. Orizia latipes ( killie fish) is killed within 2 hr by a 0.4 ppm solution of sacculatal. It is suggested that R. lobata var. yakushimensis and Pellia endiviifolia might have originated from a common ancestor since the latter produces the same sacculatals as the former species.     

Phytochemical support for the existence of two species in the genus Hymenophyton

Evidence based on flavonoid constituents is cited in support of the existence of two species in the genus Hymenophyton, H. flabellatum and H. leptopodum. A number of apigenin 6,8-di-C-pentosides and pentoside-hexosides are common to both species but the proposed additional species, H. leptopodum, is distinguished from H. flabellatum by the presence of kaempferol di- and triglycosides. This is the first detailed study of the flavonoid chemistry of any member of the order Metzgeriales and the significance of the findings is discussed.     

Flavone C-glycosides of Apometzgeria pubescens

Eleven flavone di-C-glycosides, including nine which are new, have been identified in gametophytic material of Apometzgeria pubescens. Tricetin 6,8-di-C-glucoside and tricin 6-C-arabinoside-8-C-pentoside are the major compounds. Another identified was ferulylisoschaftoside. The chemotaxonomic relevance of the flavonoid pattern of Apometzgeria pubescens is briefly discussed.