Diterpenoid alkaloids Aconitum

Amiya T and Bando H (1988) Aconitum alkaloids. The Alkaloids, Chemistry and Pharmacology (ed Brossi A) Vol 34. Academic, San Diego, pp 95-179. Atta-ur-Rahman and Choudhary MI (1998) Chemistry and biology of steroidal alkaloids. The Alkaloids, Chemistry and Pharmacology (ed Cordell GA) Vol 50. Academic, San Diego, pp 61-108. Atta-ur-Rahman and Choudhary MI (1999) Diterpenoid and steroidal alkaloids. Nat Prod Rep 16, 619-635. Earlier reviews 1997, 14, 191-203 1995, 12, 361-379. 

Bao Y, Yang F, Yang X (2011) CE-electrochemiluminescence with ionic liquid forthe facile separation and determination of diester-diterpenoid aconitum alkaloids in traditional Chinese herbal medicine. Electrophoresis 32 1515-1521. doi 10.1002/elps.201100040... 

In spite of various and detailed studies of Aconitum alkaloids, very little information is available on their antitumor activity. De Ines et al. [46] have screened 43 Ci9-diterpenoid alkaloids on CT26 (murine colon adenocarcinoma), SW480 (human colon adenocarcinoma), HeLa (human cervical adenocarcinoma), SK-MEL-25 and SK-MEL-28 (human melanomas), and on the non-tumor cell line CHO (Chinese hamster ovary cells). Several compotmds (neoline, 8-0-methylco-lumbianine, 18-0-demethylpubescenine, lycoctonine, acetylajadine, etc.) exhibit... 

The third group of Cig-diterpenoid alkaloids comprises lycoctonine, neoline, and heteratisine. They are devoid of any ester group on C-8 or C-14 positions consequently, they have been reported to be among the least toxic of all Aconitum alkaloids. 

Diterpenoid alkaloids Aconitum leucostomum SiOj CHCI3 - MeOH - MCjCO DragendorlTs reagent IR, NMR, EI-MS 12... 

Zhao XY, Wang Y, Li Y, et al. Songorine, a diterpenoid alkaloid of the genus Aconitum, is a novel GABAa receptor antagonist in rat brain. Neurosci Lett 2003 337 33-36. 

The genera of Aconitum (commonly known as Monkshood) and Delphinium, and to a lesser extent Rumex, Consolida, and Spiraea, have long been recognized as a rich source of alkaloid natural products [1], The diterpenoid alkaloids are generally classified into two major groups the Ci9-diterpenoid alkaloids (sometimes referred to as the Cig-norditerpenoid alkaloids) and the C2o-diterpenoid alkaloids. Within the C2o-diterpenoid alkaloids, at least 11 separate classes have been isolated, including the hetisine alkaloids (Chart 1.1). 

There is a long history of the use of Aconitum, Delphinium and Consolida species as the source of poisons and medicinals [1]. These three genera in Ranunculaceae family yield diterpenoid and norditerpenoid alkaloids. The name Delphinium derived from dolphine-delphine due to the shape of their flower buds [2]. Aconitum has an evil reputation from the antiquity [3]. The plant was used as poison in old Greece, also in north-west Pacific the natives used it to poison the whales and also as arrow poison. In England in the ancient times the plant was used against wolves, boars, tigers as well as against rodents, and it was also a homicide material [4]. 

Distribution of alkaloids in traditional Chinese medicinal plants, 32, 241 (1988) Diterpenoid alkaloids Aconitum, 7, 473 (1960), 12, 2 (1970)... 

Peng, C. S., Chen, D. L., Chen Q. H. and Wang, F. P. 2005. New diterpenoid alkaloids from roots of Aconitum sinomontanum. Chinese Journal of Organic Chemistry, 25 1235-1239. 

Diterpenoid alkaloids have been isolated from the genera of the families Ranunculaceae (Aconitum, Consolida, Delphinium, Thalictrum), Garryaceae (Garraya), Rosaceae (Spiraea), and Compositae (Inula). These alkaloids can be divided into two broad categories norditerpenoid alkaloids (based on a C -skeleton) and the diterpenoid alkaloids (based on a Cft-skeleton).1 The chemistry of the diterpenoid alkaloids has been reviewed in earlier literature. ... 

Comparison of the I3C NMR spectrum of pyrodelphinine [552] and delphinine [553] shows the large high frequency shift of C(17) in [552] (S 78-6 in [552], d 63-3 in [553]) resulting from interaction between the nitrogen lone pair and the C(8)-C(15) double bond. (326) The 13C NMR spectra of a variety of other diterpenoid alkaloids (from aconitum... 

The diterpenoid alkaloids, isolated mainly from Aconitum and Delphinium species (Ranunculaceae), have been of great interest since the early 1800s because of their pharmacological properties. Extracts of Aconitum species were used in ancient times for treatment of gout, hypertension, neuralgia, rheumatism, and even toothache. Extracts have also been used as arrow poisons. Some Delphinium species are extremely toxic and constitute a serious threat to livestock in the western United States and Canada. Delphinium extracts also manifest insecticidal properties. In the last 30 to 40 years, interest in the diterpenoid alkaloids has increased because of the complex structures and interesting chemistry involved. 

The genus Consolida, Aconitum, and Delphinium (Ranunculaceae) are well-known to be rich in diterpene alkaloids, which possess a diverse range of biological activities. These plants have also been the cause of poisonings, which primarily occur in cattle as well as human beings, due to toxicity of their alkaloids. In one of our recent studies, five diterpenoid-derivative alkaloids, lycoctonine (9), 18-O-methyllycoctonine (10), delcosine (11), 14-acetyldelcosine (12), and 14-acetylbrowniine (13) (as shown in Fig. 3) were screened for their antibacterial, antifungal, and antiviral activities [39]. 

Five new diterpenoid alkaloids have been isolated from Aconitum species (Ranunculaceae) and five from Delphinium species (Ranunculaceae). Four new Anopterus (Escalloniaceae) bases have been identified. The most significant synthetic achievement has been the total synthesis of racemic chasmanine. A detailed review of the alkaloids of Delphinium staphisagria has appeared.1... 

Alkaloids of Aconitum falconeri Falaconitine and Mithaconitine. In addition to the previously known veratroylpseudaconine (5), pseudaconitine (6) and indaconi-tine (7), two new C19 diterpenoid alkaloids, falaconitine and mithaconitine, have been isolated from the roots of Aconitum falconeri Stapf.13,14 Singh and coworkers15 had reported a preliminary study of the two alkaloids, bishatisine and bishaconitine , isolated from this species. However, in the recent work,13,14 no bishatisine or any atisine-type alkaloid was identified, and the data reported for bishaconitine were consistent with a mixture of falaconitine and several closely related bases. The identities of (5), (6), and (7) were determined primarily by H and 13C n.m.r. techniques and confirmed by comparison with authentic samples.14... 

Revisions Based on 13C N.M.R. Analysis.—The revision of the structures of five C19 diterpenoid alkaloids on the basis of the 13C n.m.r. spectral data has been reported.8,9 Yunusov and co-workers,10 relying predominantly on mass-spectral data, had proposed structure (43) for acomonine (C2jH41N07), isolated from the roots of Aconitum monticola. Based partially on chemical correlations with acomonine, they later assigned structures to iliensine (44) (Cj NO,)11 and 14-dehydroiliensine (45),12 isolated from Delphinium biternatum. These were the first reported C19 diterpenoid alkaloids lacking an oxygen function at C-l. 

Alkaloids of Aconitum yesoense Nakai.—Sakai and co-workers42 have reported the isolation and elucidation of the structure of three new C19 diterpenoid alkaloids from Aconitum yesoense Nakai. These minor bases, ezochasmanine, ezo-chasmaconitine, and anisoezochasmaconitine, were isolated together with pseudo-kobusine (92), chasmanine (59), and jesaconitine (93). Ezochasmanine (94) (C25H41N07 m.pt 115—118 °C) formed a mixture of the monoacetate (95) and the diacetate (96) when treated with acetic anhydride in pyridine. The reaction of... 

Diterpenoid alkaloids Aconitum sinomontanum CHCI3 MeOH-0.3/0.2 M HCl (4 1.5 2) HSCCC... 

Research on diterpenoid alkaloids published during the past year has continued to expand the body of structural and synthetic information available on these complex plant bases. The structures of ten new alkaloids from Aconitum and Delphinium species, including seven new bisditerpenoid alkaloids, have been reported. Tlie most significant progress in methods of structure elucidation has been the very successful applications of n.m.r. to the study of complex diterpenoid alkaloids. The New Bruns wick group under Professor Karel Wiesner has continued its progress toward the syntheses of the Ci9-aconitine-type alkaloids. An historical account of the synthesis of talatisamine (1), the first synthesis of a hexacyclic aconite alkaloid, has been published. This work was reviewed in a previous Report. ... 

DalTAcqua, S., Shrestha, B.B., Gewali, M.B., Jha, P.K., Carrara, M. and Innocenti, G. (2008). Diterpenoid alkaloids and phenolic glycosides from Aconitum naviculare (Briihl) Stapf. Natural Product Communication, 3 1985-1989. 

Gao, L., Wei, X. and Yang, L. (2004). A New diterpenoid alkaloid from a Tibetan medicinal herb Aconitum naviculare Stapf. Journal of Chemical Research, 4 307-308. 

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