Ultimate aerobic biodegradabilities of an array of sugar ester surfactants were determined by International Standards Organisation method 7827, "Water Quality-Evaluation in an Aqueous Medium of the Aerobic Biodegradability of Organic Compounds, Method by Dissolved Organic Carbon" (1984). The surfactants were nonionic sugar esters with different-sized sugar head groups (formed from glucose, sucrose, or raffinose) and different lengths and numbers of alkyl chains [formed from lauric (C 12 ) or palmitic (C 16 ) acid]. Analogous anionic sugar ester surfactants, formed by attaching an α-sulfonyl group adjacent to the ester bond, and sugar esters with α-alkyl substituents were also studied. It was found that variations in sugar head group size or in alkyl chain length and number do not significantly affect biodegradability. In contrast, the biodegradation rate of sugar esters with α-sulfonyl or α-alkyl groups, although sufficient for them to be classified as readily biodegradable, was dramatically reduced compared to that of the unsubstituted sugar esters. An understanding of the relationship between structure and biodegradability provided by the results of this study will aid the targeted design of readily biodegradable sugar ester surfactants for use in consumer products.Surfactant biodegradability is a crucial factor in determining whether their concentrations in the environment remain below detrimental levels. Surfactants derived from sugar fatty acid esters are attractive because of their ready biodegradability, low toxicity, low irritation to eyes and skin, and the renewable nature of the sugar and fatty acid starting materials. They are widely used in food, cosmetic, and pharmaceutical formulations (1-3). Physicochemical properties of these surfactants can be tailored to suit potential applications by varying the sugar head group size and the length and number of alkyl chains. As well as nonionic surfactants, analogous anionic sugar ester surfactants can be produced by incorporation of a sulfonate group. These anionic sugar esters are more water soluble than their nonionic counterparts and may more easily replace conventional anionic surfactants in product formulations. Many effects of structural variations on the physicochemical properties of sugar ester surfactants have been reported (4-6).Sucrose fatty acid esters are rapidly biodegradable (7-13). However, the relationship between biodegradability and chemical structure of sugar ester surfactants has not been comprehensively studied. The aim of the current research was to investigate the ultimate aerobic biodegradation of surfactants derived from sugar fatty acid esters so as to develop an understanding of the relationships between surfactant structure and biodegradability. The biodegradabilities of an array of sugar ester surfactants in which the structure was systematically varied were determined. Structures of the surfactants studied are indicated in Scheme 1. Sugar head group size was varied from a monosaccharide (glucose) to a trisaccharide (raffinose). ...

The triterpenes of Lantana camara vary widely between taxa. In taxa toxic to livestock 22β-angeloyloxy-3-oxoolean-12-en-28-oic acid (lantadene A) and 22β-dimethylacryloyloxy-3-oxoolean-12-en-28- oic acid (lantadene B) are present, usually as major constituents, although 3-oxolup-20(29)-en-28-oic acid (betulonic acid) predominates in the taxon Helidon White. 22β-Angeloyloxy-3β-hydroxyolean- 12-en-28-oic acid, 22β -dimethylacryloyloxy-3β -hydroxyolean-12-en-28-oic acid and 22β-hydroxy-3-oxoolean-12-en-28-oic acid, not previously known to occur in L. camara, have been isolated as well as a number of other well-known triterpenes. The non-toxic Townsville Prickly Orange contains small amounts of lantadenes A and B, and is the only taxon found to contain 228-angeloyloxy-23- hydroxy-3-oxoo1ean-12-en-28-oic acid (icterogenin). Another constituent is the new triterpene 24-hydroxy-3-oxoolean-12-en-28-oic acid. Common Pink, which is non-toxic and does not contain lantadenes A and B, is characterized by triterpene acids which have a C3, C25 oxide-bridge. It contains lantanolic acid, lantic acid, and a new acid, lantabetulic acid, considered to be 3,25-epoxy- 3a-hydroxylup-20(29)-en-28-oic acid. A mixture of the 22β-angeloyloxy and 22β-dimethylacryloyloxy derivatives of lantanolic acid from Common Pink has been converted into 22P-hydroxylantanolic acid. Wolff-Kishner reduction of 22~-hydroxy-3-oxoolean-12-en-28-oic acid gives a low yield of 22β-hydroxyolean-12-en-28-oic acid, and the major product is the C22-epimer, 22a-hydroxyolean- 12-en-28-oic acid. Corresponding products are obtained from Wolff-Kishner reduction of 22β- hydroxylantanolic acid.

From the leaves of Elaeocarpus sphaericus (Gaertn.) K . Schum., seven isomeric alkaloids of molecular formula, C16H21NOZ, have been isolated. Two of the alkaloids are identical with (-)-isoelaeocarpiline and (+)-elaeocarpiline previously isolated from E. dolichostylis. Complete structures and absolute configurations have now been determined for the two previously known alkaloids (1) and (6), and for the five new-alkaloids (4), (8), (lo), ( l l ) , and (12), and a study has been made of the products obtained by sodium borohydride reduction of some of the isomeric alkaloids. The previously known Elaeocarpus alkaloids, elaeocarpidine, (&)-elaeocarpine, and (&)-isoelaeocarpine have also been isolated from E. sphaericus.Earlier studies on Elaeocarpus polydactylus Schltr., E . dolichostylis Schltr., and E . densiflorus Knuth, all of which are rain-forest species from New Guinea, have shown that the Elaeocarpus alkaloids comprise a new and major class of alkaloids.2-4 These studies have now been exterded to Elaeocarpus sphaericus (Gaertn.) K . Schum., a large tree, widely distributed in New Guinea. The alkaloids of E. sphaericus are an extremely complex mixture and ten alkaloids have been isolated, although not all from the same collection of plant material. The differences in composition observed between the samples of crude alkaloids examined, however, have been relatively slight, and the same major constituents have been common to all samples. E. sphaericus and E . dolichostylis are much more alike in their alkaloid composition than the other species examined, and it seems probable that some of the constituents now reported for E. sphaericus also occur in E . dolichostylis. Another species, E . altisectus Schltr., has not been examined in detail but preliminary results indicate that the alkaloids are similar to those of E. sphaericus and E. dolichostylis, a t least in major constituents.* Part 111, Aust. J. Chem., 1969, 22, 801. .t The alkaloids of E. sphaericus have been the subject of a preliminary communication.1

The known triterpenes ursonic acid, oleanonic acid, ursolic acid, oleanolic acid and 24-hydroxy-3-oxoolean-12-en-28-oic acid occur in Lantana tiliaefolia Cham., together with a new triterpene,24-hydroxy-3-oxours-12-en-28-oic acid. A detailed 13C n.m.r. study has been made of a number of olean-12-enes and urs-12-enes, and the 1H n.m.r. signals from the secondary methyl groups in urs-12-enes have been investigated. N.m.r. evidence shows significant conformational differences in ring A between a number of 3-oxo derivatives that differ in their ring A substituents. Methyl ursonate and methyl oleanonate have been separated on columns of Spherosorb A5Y alumina.

The taxa of Lantana camara toxic to animals contain lantadene A lantadene B, whereas in two non-toxic taxa other triterpenes predominate. Several new triterpenes have been characterized. Contrary to earlier claims, lantadene A and to a lesser extent lantadene B are toxic when administered intraruminally to sheep.