The structure of the alkaloid protostemonine

Irie, Hiroshi; Harada, Hiroshi; Ohno, Kimio; Mizutani, Tamio; Uyeo, Shojiro

doi:10.1039/c29700000268

Cited by 24 publications

(28 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The chemical shifts of the secondary methyls were quite similar to those of sternonine. 5 ) Strong carbonyl absorption was observed at 1755 em-I. These suggest the presence of two a-methyl-r-lactone functionarities in 1 14.8 (q)] attributable to a ,-substituted amethyl-r-lactone moiety are identical with those of the corresponding signals in the spectrum of III (see EXPERIMENTAL).…”

supporting

confidence: 58%

“…(Stemonaceae) have hitherto been isolated several alkaloids: stemonine (111),3) stemonamine/) isostemonamine 4 ) and protostemonine. 5 ) Irie et al recently isolated a new alkaloid named stemofoline (II) from leavcs and stems of this plant and established the structure as II by X-ray crystallographic analysis. 6 ) However, the insecticidal activity of the individual alkaloid has never been examined up to now.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Stemospironine, a New Insecticidal Alkaloid ofStemona japonicaMiq. Isolation, Structural Determination and Activity

Sakata

Aoki

Chang

et al. 1978

Agricultural and Biological Chemistry

View full text Add to dashboard Cite

supporting

confidence: 58%

mentioning

confidence: 99%

Stemospironine, a New Insecticidal Alkaloid ofStemona japonicaMiq. Isolation, Structural Determination and Activity

Sakata

Aoki

Chang

et al. 1978

Agricultural and Biological Chemistry

View full text Add to dashboard Cite

“…The well-known tuberostemonine (1) and its closely related derivatives tuberostemoenone (18), tuberostemoninol (19), oxotuberostemonine (24), and stenine (26) can be derived by linking C-12 of the lactone ring with C-1 of the pyrroloazepine core, whereas in parvineostemonine (38) an unusual linkage between C-11 and C-3 can be observed. The formation of an ether bridge between C-11 and C-8 leads to the spiro system of stemoninine (21), and another between C-12 and C-16 to the structure of parvistemonine (35). The unusual six-membered piperidone ring of tuberostemoninol (19) can be explained by opening the bond between C-1 and C-9a of tuberostemonine (1) and linking C-1 with C-9.…”

Section: Stichoneurine (Tuberostemonine-)-type Alkaloidsmentioning

confidence: 99%

Structural Relationships, Distribution and Biological Activities ofStemonaAlkaloids

2006

View full text Add to dashboard Cite

Stemona alkaloids represent a unique class of natural products exclusively isolated from the monocotyledonous family Stemonaceae comprising three genera mainly distributed in southeast Asia. Structurally the alkaloids are characterised by a pyrrolo[1,2-a]azepine nucleus usually linked with two carbon chains mostly forming terminal lactone rings. Based on biosynthetic considerations and their various distribution the present review describes 82 Stemona alkaloids grouped into three skeletal types. Due to different carbon chains attached to C-9 of the pyrroloazepine nucleus they were classified into stichoneurine-, protostemonine-and croomine-type alkaloids. The genera Croomia and Stichoneuron only accumulate croomine or stichoneurine derivatives, respectively, whereas the genus Stemona produces all three types of alkaloids. However, species-specific accumulation trends towards certain structural types represent valuable chemosystematic criteria. Bioassays with larvae of Spodoptera littoralis exhibited very high insect toxicity for the roots of Stemona species containing certain protostemonine derivatives, especially didehydrostemofoline, whereas those with dominating stichoneurine or croomine derivatives showed low toxicity but sometimes remarkable repellence due to an accumulation of tuberostemonine. Tuberostemonine also showed effects on the motility of helminth worms and reduced the excitatory transmission at the crayfish neuromuscular junction. Significant antitussive activity was shown for the stereoisomeric neotuberostemonine in guinea-pig after cough induction by citric acid aerosol stimulation. Studies on structure-activity relationship with seven related compounds revealed that the saturated tricyclic pyrrolobenzazepine nucleus of tuberostemonines is the prerequisite for antitussive activity.

show abstract

“…2 A few of these alkaloids do not fit these five structural groups and have a more complex bridged structure or ring structures that most likely arises from initial oxidative cleavage of the pyrrolo [1,2-a] presence of the C-and D-ring system that is typically found in the stemoamide group of alkaloids, including stemofoline (1). 1,6,[9][10][11][12][13][14][15][16][17] The 13 C/DEPT NMR spectra of 2 indicated four methine carbons, and six methylene carbons and, unlike the other Stemona alkaloids, except 1 and its didehydro and 2'-hydroxy derivatives, 2 a quaternary carbon at  120.4 was apparent, indicative of a acetal-like structure (C-9).…”

mentioning

confidence: 99%