Mulinic and isomulinic acids. Rearranged diterpenes with a new carbon skeleton from mulinum crassifolium

Loyola, Luis A.; Morales, Glauco; Rodrı́guez, Benjamı́n; Jiménez‐Barbero, Jesús; Torre, Marı́a C. de la; Perales, Aurea; Torres, M. Rosario

doi:10.1016/s0040-4020(01)87848-0

Cited by 46 publications

(48 citation statements)

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“…The similarities observed in the 13 C NMR and 1 H NMR spectra of 1 and mulin-11,12-dien-20-oic acid (Loyola et al, 1997b), were indicative of the presence of a mulinane diterpenoid moiety in 1. We assumed, by analogy with other mulinane diterpenoids (Loyola et al, 1990(Loyola et al, , 1997a(Loyola et al, ,b, 1998a) that the substituents at C-3, C-5 and C-8 were b orientated as well as the proton at C-9. Additional proof of the relative stereochemistry of 1 was obtained from ROESY NMR spectroscopy experiments.…”

Section: Resultsmentioning

confidence: 99%

Mulinane-type diterpenoids from Azorella compacta display antiplasmodial activity

et al. 2004

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Section: Resultsmentioning

confidence: 99%

Mulinane-type diterpenoids from Azorella compacta display antiplasmodial activity

et al. 2004

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“…We have undertaken the X-ray crystal-structure determination of (I) in order to establish its molecular conformation and relative stereochemistry. We are not able to determine the absolute stereochemistry by X-ray methods and the configuration shown here was chosen to be in accord with that reported in previous chemical studies (Loyola et al, 1990). The structure consists of a mulinane skeleton, and the isopropyl, acetyloxymethyl and carboxylic groups at C3, C5A and C3A are β-oriented, respectively, whereas the endo-peroxide group is α-oriented.…”

Section: Commentmentioning

confidence: 99%

“…For related literature on Mulinane diterpenes, see: Munizaga & Gunkel (1958); Araya et al (2003); Loyola et al (1990Loyola et al ( , 2004. For a related structure, see: Brito et al (2008).…”

Section: Related Literaturementioning

confidence: 99%

17-Acetoxymulinic acid

et al. 2010

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The title compound, [systematic name: 5a-acetoxymethyl-3-isopropyl-8-methyl-1,2,3,3a,4,5,5a,6,7,10,10a,10b-dodecahydro-7,10-endo-epidioxycyclohepta[e]indene-3a-carboxylic acid], C22H32O6 (I), is closely related to methyl 5a-acetoxymethyl-3-isopropyl-8-methyl-1,2,3,3a,4,5,5a,6,7,10,10a,10b-dodecahydro-7,10-endo-epidioxycyclohepta[e]indene-3a-carboxylate, (II) [Brito et al., (2008 ▶). Acta Cryst. E64, o1209]. There are two molecules in the asymmetric unit, which are linked by two strong intramolecular O—H⋯O hydrogen bonds with graph-set motif R 2 2(8). In both (I) and (II), the conformation of the three fused rings are almost identical. The five-membered ring has an envelope conformation, the six-membered ring has a chair conformation and the seven-membered ring has a boat conformation. The most obvious differences between the two compounds is the observed disorder of the acetoxymethyl fragments in both molecules of the asymmetric unit of (I). This disorder is not observed in (II). The crystal structure and the molecular conformation is stabilized by intermolecular C—H⋯O hydrogen bonds. The ability to form hydrogen bonds is different in the two compounds. The crystal studied was a non-merohedral twin, the ratio of the twin components being 0.28 (1):0.72 (1)

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“…Mulinanes [15][16][17][18][19][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] Structurally, these compounds (or nearly of all them) are characterized by having an acid group in C-20, and a seven-member ring C functionalized. They show a wide variety of biological activities, such as antituberculosis, antimalaric, antibacterial, spermatostatic, and antihyperglycemic effects ( Table 5.3).…”

Section: Mulinanes and Azorellanesmentioning

confidence: 99%