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
Three aporphine alkaloids isolated from Cassytha pubescens R.Br. have been identified as nantenine, domesticine, and isoboldine, all of which were previously known to occur in Nandino domestics, and a fourth as laurelliptine, an alkaloid of Beilschnziedia elliptica. One other aporphine alkaloid from C. pubescens is new, namely (+)-l-hydroxy-2-methoxy-9,1O.methylenedioxynoraporphine (nordomesticine).A sixth and minor alkaloid from C. pubescens, identified as sinoacutine, the (-)-enantiomer of salutaridine, appears to be the first example of a morphine group alkaloid to be found in the family Lauraceae.Cassytha pubescens R.Br., known as "downy dodder laurel", is a trailing parmitic vine belonging to the family Lauraceae. It occurs widely in southeastern Australia, and an examination has been made of samples collected in South Australia and near Melbourne in Victoria. Earlier investigations of the related species Cassytha jiliformmi L. led to the characterization of two new aporphine alkaloids, ($)-9-hydroxy-3,10-dimethoxy-1,2-methylenedio~poraporphine~~ and (+)-3-methoxy-1,2,9,10-bismethylenedio~ynoraporphine,~ which belong to a small group of aporphines having a C3 oxygen substituent. The name cassythinel suggested for the former base in our earlier paper should be dropped in favour of ~assyfiline,~ since Professor Tomita's publication on this Cassytha Jiliformis base was received for publication before ours. Although several aporphine alkaloids have been isolated from C. pubescens none has a C3 substituent. Sinoacutine ( I )Particular interest is attached to a minor base, C,,H21N0,, which is not an aporphine and has been identified as the (-)-enantiomer (I) of salutaridine, a dienone alkaloid of the morphine group found naturally in Croton salutaris3 and also obtained by synthesis.3 Direct comparison of the infrared spectra of the Cassytha base and its 0-acetate with spectra of an authentic sample of salutaridine and its 0-acetate * P a r t I, Aust. J . Chem., 1966, 19, 297.
Two new alkaloids from the leaves of Beilschmiedia podagrica Kostermans (family Lauraceae) have been identified as (+)-2-hydroxy-1,9,10- trimethoxy-aporphine (Va), which has previously been prepared by O- methylation of the alkaloid boldine, and (+)-2-hydroxy-1,9,10- trimethoxynoraporphine. The leaves also contain three known aporphine alkaloids, glaucine, isocorydine, and (+)-2,11-dihydroxy-1,10- dimethoxyaporphine, and the bark contains the known alkaloid laurelliptine and probably also isoboldine.
Two new alkaloids, cryptopleuridine and cryptopleurospermine, have been isolated from the bark of Cryptocarya pleurosperma White & Francis. From analysis of the 100-MHz n.m.r, spectra of cryptopleuridine and O-acetylcryptopleuridine, and the relationship of cryptopleuridine to cryptopleurine established from other spectroscopic data, cryptopleuridine is considered to be (5a). Spectroscopic and degradative evidence has shown that cryptopleurospermine is 2-dimethylaminoethyl-3'-hydroxy-4'-methoxy-4,5-methylenedioxybenzil (8).
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