Triterpene Glycosides from the Far Eastern Sea Cucumber Thyonidium (=Duasmodactyla) kurilensis (Levin): The Structures,Cytotoxicities, and Biogenesis of Kurilosides A3, D1, G,H, I,I1, J,K, and K1

Nine new mono-, di-, and trisulfated triterpene penta- and hexaosides, kurilosides A₃ (1), D₁ (2), G (3), H (4), I (5), I₁ (6), J (7), K (8), and K₁ (9) and two desulfated derivatives, DS-kuriloside L (10), having a trisaccharide branched chain, and DS-kuriloside M (11), having hexa-nor-lanostane aglycone with a 7(8)-double bond, have been isolated from the Far-Eastern deep-water sea cucumber Thyonidium (=Duasmodactyla) kurilensis (Levin) and their structures were elucidated based on 2D NMR spectroscopy and HR-ESI mass-spectrometry. Five earlier unknown carbohydrate chains and two aglycones (having a 16β,(20S)-dihydroxy-fragment and a 16β-acetoxy,(20S)-hydroxy fragment) were found in these glycosides. All the glycosides 1–9 have a sulfate group at C-6 Glc, attached to C-4 Xyl1, while the positions of the other sulfate groups vary in different groups of kurilosides. The analysis of the structural features of the aglycones and the carbohydrate chains of all the glycosides of T. kurilensis showed their biogenetic relationships. Cytotoxic activities of the compounds 1–9 against mouse neuroblastoma Neuro 2a, normal epithelial JB-6 cells, and erythrocytes were studied. The highest cytotoxicity in the series was demonstrated by trisulfated hexaoside kuriloside H (4), having acetoxy-groups at C(16) and C(20), the latter one obviously compensated the absence of a side chain, essential for the membranolytic action of the glycosides. Kuriloside I₁ (6), differing from 4 in the lacking of a terminal glucose residue in the bottom semi-chain, was slightly less active. The compounds 1–3, 5, and 8 did not demonstrate cytotoxic activity due to the presence of hydroxyl groups in their aglycones.     

A review of the biology and control of selected weed species in the genus Oxalis: O. stricta L., O. latifolia H.B.K. and O. pes-caprae L.

This review considers the distribution, weed problems, biology and control of Oxalis stricta, O. latifolia and O. pes-caprae. The rhizomatous O. stricta is a persistent seed-producing weed which invades horticultural crops in North America. Chemical control is generally most effective in situations where soil-applied residual herbicides can be used; in turfgrass however, foliage-applied herbicides provide suppression only. O. latifolia is widely distributed in a range of annual and perennial crops growing in temperate and tropical locations. This pernicious perennial weed reproduces exclusively by asexual structures, underground bulbs, stolons and tubers. The complexities of the perennating system have rendered ineffective a wide range of herbicide families as a means of restricting the spread of O. latifolia. Similarly, cultural methods of control have not been successful. O. pes-caprae also grows and perennates from bulbs. This weed is essentially a problem in cereal crops in Southern Australia and Mediterranean fruit orchards. Cultural and chemical control difficulties and inadequacies are similar to those in O. latifolia. Future research strategies involving weed physiology, herbicide action and cultural control including biological control are discussed in relation to obtaining improved control methods for the selected Oxalis species.