Nauclea

Takayama H et al. (2003) Gluco-indole alkaloids from Nauclea cadamba in Thailand and transformation of 3alpha-dihydrocadambine into the indolopyridine alkaloid, 16-carbomethoxynaufoline. Chem Pharm Bull (Tokyo) 51(2) 232-233... 

Three new alkaloids have been isolated from Nauclea officinalis Pierre ex Pitaxd naucleficine (630), nauclefoline (631), and nauclefidine (632) (391). 

Nauclea rhynchophylla Miq. N. sinensis Oliv. Gou Teng (stem, spine) Rhynchophylline, isorhynchophylline.49-72 Lower blood pressure, paralyze sympathetic nerve ending, sedative, antispasmodic in infantile nervous disorders. 

Uncaria hirsuta Havil U. rhynchophylla Miq. (Syn. Nauclea sinensis Oliv.) Gou Teng (Gambir) (stem) Rhynchophylline, corynoxeine, iso-rhynchophylline, isocorynoxeine, corynantheine, hirsutine, hirsuteine.33 A sedative, anticonvulsive, lower blood pressure, it has a triphasic effect. Treat childhood epilepsy. 

Nauclea rhynchophylla Miq., N. sinensis Oliv., Uncaria hirsuta Havil, U. rhynchophylla Miq. 

Hippophae rhamnoides Nauclea rhynchophylla, N. sinensis Ricinus communis Eupatorium odoratum... 

M. pubescens, M. (aihokuensis, Mynneconauclea strigosa, Nauclea chalmersii, N. cordata, N. diderichii, N. esculenta, N. junghuhnii,... 

Four major classes of alkaloids have been found in the Pauridiantha species studied. The first class consists of harman and harman-type alkaloids, which appear to be ubiquitous in this genus. As far as chemotaxonomic considerations are concerned, it can be noted that these alkaloids have also been found in at least four tribes of the subfamily Cinchonoideae, namely, Naucleae (12), Cinchoneae (13), Gardenieae (14), and Rondeletieae (12), and in two tribes of the subfamily of Rubioideae as defined by Verdcourt, namely, in the Urophylleae (75) and in the Ophiorrhizeae (72). Formerly, the Ophiorrhizeae were a part of the Hedyoti-deae, a tribe classified near the tribe Mussaendeae in the subfamily Cinchonoideae (2). 

It is interesting to note that the presence of a dihydropyridine unit, analogous to the one observed in lyaline (10) and lyadine (11), has also been identified in nauclefoline (14), an alkaloid isolated from the leaves of Nauclea latifolia (21). On the other hand, the structural analogy between the angustine bases (15) and... 

Among, the reported cadambine-type alkaloids should be included several natural non-glucosidic derivatives, such as 32 (40), nauclefoline (14), and the numerous compounds of basic skeleton 33 [e.g., naufoline, R = R = H (21,26) nauclechine, R = C02Me, R = OH (21,45,46)] found in various species of Nauclea. Again, chemotaxonomic correlations seem to favor a reassembling of the genus Pauridiantha and the tribe Naucleae into a unique subfamily. 

A limited number of alkoyl-glucoalkaloids have been reported in the literature so far. The first specimen of this class of compounds to be isolated was rubescine (43), which was found in Adina rubescens (64). More recently another esterified vincoside lactam, rhynchophine (44), was extracted from the leaves of Uncaria rhynchophylla, a member of the tribe Cinchoneae (65). Thus, chemotaxonomic correlations again tend to raise the question whether Pauridiantha should not join, along with Adina and Uncaria, the tribe Naucleae. 

Pathway D implies rotation around the C-14-C-15 bond, followed by lac-tamization. Vincoside lactam is the precursor of esterified derivatives, e.g., rubescine found in Adina (Naucleae) and rhynchophine found in Uncaria (Cinchoneae). These compounds are alkoyl-glucoakaloids, as are lyalosidoferine and lyalosidosinapine found in Pauridiantha (Urophylleae). 

STRICTOSIDINE Lactam Type Naucleae and Logan iaceae... 

Angus t ine bases (Mitragyna, Nauclea, Uncaria Strychnos)... 

Urophylleae, Psychotrieae, Naucleae, and Cinchoneae. Only some genera of each of these tribes are concerned and constitute thus a rather homogeneous group Adina, Anthocephalus, Nauclea, Uncaria, Pauridiantha, and Palicourea. 

Pauridiantha appears, therefore, to be a genus in which the biosynthetic pathways are limited in number and are stopped at primitive alkaloids. It follows a lack of structural specificity, permitting chemotaxonomic correlations with other plants characterized by the same features. From this point of view, the genus Pauridiantha resembles not only many Nauclea, but also a number of Strychnos. 

The leaves of Nauclea latifolia contain naufoline, angustine, cadambine, 3a-dihydrocadambine, and a new alkaloid, naulafine, which has been formulated,57 on spectroscopic evidence, as (81). Another new alkaloid is strychno-rubigine (10-methoxyisositsirikine), which occurs in the root bark of Strychnos rubiginosa DC.58 Antirhine and pleiocarpamine have been found in the leaves and stem bark of Alstonia odontophora Boiteau [A. roeperi van Heurck et Mull.-Arg.],59 and pleiocarpamine, pleiocarpamine N-oxide, geissoschizine,... 

Nauclea coadunata Roxb. ex S. E. Smith (valid name N. orientalis Linn.) Rubiaceae Angustine (65)... 

The indole alkaloids of Mitragyna hirsuta Havil, M.javanica Koord. et Val. var. microphylla Craib, M. speciosa, and Nauclea coadunata are mostly in the corynantheine-heteroyohimbine-yohimbine group. The alkaloids isolated from the leaves of Mitragyna hirsuta have been identified as hirsutine, rhynchophylline, isorhynchophylline, mitraphylline, isomi-... 

Finally, in this group, McLean s work on the alkaloids of Nauclea diderrichii has been published in full.90 The structure earlier given to nauclederine (154) receives support from its synthesis (Scheme 15), although it is admitted that this does not amount to an unequivocal proof of structure, owing to uncertainty concerning the... 

Nauclea latifolia. la Isodolichantoside and 16-ep/-diploceline are new epimers of known bases which have been reported416 to occur in the root bark of Strychnos gossweileri. 

Azayohimbine-Type Alkaloids. Recently, some new types of alkaloids nauclefine (29), naucletine (210), angustidine (213), and angustoline (215), were isolated (71,120-122) from the Nauclea and Strychnos plants, which... 

Nauclea latifolia Rubiaceae Antihypertensive, antimicrobial Fever, stomachache, diarihea Alkaloids. 10, 17, 19... 

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