Neo-Clerodane Diterpenoids from American Salvia Species

Rodríguez‐Hahn, Lydia; Esquivel, Baldomero; Cárdenas, Jorge

doi:10.1007/978-1-4899-1778-2_12

Cited by 13 publications

(21 citation statements)

References 45 publications

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“…The structure and relative stereochemistry of this compound was proposed based on spectroscopic data and chemical correlation with languiduline (15). Treatment of 16 with SOCl 2 in pyridine at low temperature afforded 7-epi-languiduline 17, confirming in this way the structure proposed for tonalenin (16) [30].…”

Section: Ssupporting

confidence: 60%

Rearranged Clerodane and Abietane Derived Diterpenoids from American Salvia Species

Esquivel

2008

Natural Product Communications

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The genus Salvia L. (Tribe Mentheae) is the largest of the Lamiaceae with 1000 species widespread throughout the world. Phytochemical studies of several Salvia species have established an interesting chemical profile for the genus including sterols, flavonoids and triterpenoids. However, the most characteristic secondary metabolites of the genus are diterpenoids. One of the most distinguishing features of Salvia genus is the number of rearranged diterpene skeletons isolated from these plants. Until now, over 30 rearranged diterpene skeletons have been described for both Old and New World representatives of the genus. In this review, a survey of recent literature data regarding rearranged clerodane and abietane diterpenoids from American Salvia species is presented.

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Section: Ssupporting

confidence: 60%

Rearranged Clerodane and Abietane Derived Diterpenoids from American Salvia Species

Esquivel

2008

Natural Product Communications

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“…Optical rotation was measured on a JASCO DIP-1000 polarimater. 1 H, 13 C NMR spectra were recorded on a JEOL A-500 FT-NMR spectrometer, and the chemical shifts were expressed on the d (ppm) scale with the TMS as an internal standard. FAB-MS and HRFAB-MS were recorded on a JEOL JMS-700 spectrometer.…”

Section: Generalmentioning

confidence: 99%

“…Most of the Salvia species, subgenus Calosphace, have neoclerodane, or it can be biogenetically derived from a clerodane precursor. In Mexico, some of these plants are used as folk medicine, hallucinogens or culinary herbs [1]. During our search for bioactive metabolites from the Labiatae family, we became interested in the Mexican Salvia species, and started a study of the chemical components of these species [2][3][4].…”

Section: Introductionmentioning

confidence: 99%

A novel diterpenoid with a rearranged neoclerodane skeleton from Salvia leucantha CAV.

2006

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A new diterpenoid with a rearranged neoclerodane skeleton, spiroleucantholide (compound "S1"), along with four known diterpenoids-salvifaricin (compound "S2"), isosalvipuberulin (compound "S3"), salvileucantholide (compound "S4"), and salviandulin E (compound "S5")-was isolated from the aerial parts of Salvia leucantha CAV.. The structures were established by spectroscopic methods, including the X-ray analysis of spiroleucantholide (S1).

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“…Several rearranged diterpenoids with unusual carbocyclic skeletons of probable clerodanic origin have been described for these plants [10]. Abietane and icetexane diterpenoids are also known in a lesser extent in the aerial parts of Jungian Salvia species [6].…”

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confidence: 99%

“…Until now, a great number of abietane and rearranged abietane diterpenoids in both aerial parts and roots of the European and Asiatic members of the genus have been described [6]. The diterpenoids from Turkish Salvia species, belonging to subgenera Salvia, Leonia, and Sclarea, are good examples of this diversity [7].…”

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Abietane Diterpenoids from the Roots of some MexicanSalvia Species (Labiatae): Chemical Diversity, Phytogeographical Significance, and Cytotoxic Activity

Esquivel

Sánchez

Vergara

et al. 2005

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From the roots of some Mexican Salvia species, classified in subgenus Jungia, several diterpenoids belonging to abietane (i.e., 3-7), salvifolane (9-->20,10-->6)-diabeoabietane) (i.e., 2), and totarane (i.e., 10) carbocyclic skeletons were isolated together with two 20-nor- and one 6,7-secoabietane derivatives, 1 and 9, and 8, respectively. While compounds 2-10 were previously known from different sources, compound 1 is a new 20-norabietane derivative, whose structure was deduced by spectroscopic means and confirmed by X-ray-diffraction analysis. The phytogeographical significance of the distribution of 20-norabietanic diterpenoids in the genus suggested an evolutionary link between the Chinese and New-World Salvias. Compounds 2 and 8 were tested for cell-growth inhibition activity against several human cancer cell lines and human normal lymphocytes, while 2 showed a moderate cytotoxic activity, 8 exhibited a moderate yet selective activity against leukemia cell line.

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Neo-Clerodane Diterpenoids from American Salvia Species

Cited by 13 publications

References 45 publications

Rearranged Clerodane and Abietane Derived Diterpenoids from American Salvia Species

Rearranged Clerodane and Abietane Derived Diterpenoids from American Salvia Species

A novel diterpenoid with a rearranged neoclerodane skeleton from Salvia leucantha CAV.

Abietane Diterpenoids from the Roots of some MexicanSalvia Species (Labiatae): Chemical Diversity, Phytogeographical Significance, and Cytotoxic Activity

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