Sesterterpenes from Salvia hypoleuca

Rustaiyan, Abdolhossein; Niknejad, Akram; Nazarians, Lilly; Jakupovic, Jasmin; Bohlmann, Ferdinand

doi:10.1016/s0031-9422(82)85076-0

Cited by 37 publications

(21 citation statements)

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“…The known compounds were identified as the methyl ester of salvileucolide ( 10 ), 52 salvileucolide-6,23-lactone ( 11 ), 52 , 59 (15 S ,16 S, 13 E )-8α,15-dihydroxylabd-13(14),17(18)-dien-23,6α-16,19-diolide ( 12 ), 47 (16 R, 13 E )-6α,8α,23-trihydroxylabd-13(14),17(18)-dien-16,19-olide ( 13 ), 47 (15 S ,16 S, 13 E )-6α,8α,15-trihydroxy-23-carboxymethyllabd-13(14),17(18)-dien-16,19-olide ( 14 ), 47 sclareol ( 15 ), 60 14α-epoxysclareol ( 16 ), 61 manool ( 17 ), 62 6β-hydroxysclareol ( 18 ), 61 (12 Z )-8α-12,14-labdadien-8-ol ( 19 ), 63 hinokiol ( 20 ), 64 β-eudesmol ( 21 ), 65 3′,4′,5,6,7-pentamethoxyflavone ( 22 ), 66 salvigenin ( 23 ), 67 eupatorin ( 24 ), 68 and cirsimaritin ( 25 ). 69 …”

Section: Resultsmentioning

confidence: 99%

Antibacterial and ATP Synthesis Modulating Compounds from Salvia tingitana

et al. 2020

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A surface extract of the aerial parts of Salvia tingitana afforded a nor-sesterterpenoid ( 1 ) and eight new sesterterpenoids ( 2 –- 9 ), along with five known sesterterpenoids, five labdane and one abietane diterpenoid, one sesquiterpenoid, and four flavonoids. The structures of the new compounds were established by 1D and 2D NMR spectroscopy, HRESIMS, and VCD data and Mosher’s esters analysis. The antimicrobial activity of compounds was evaluated against 30 human pathogens including 27 clinical strains and three isolates of marine origin for their possible implications on human health. The methyl ester of salvileucolide ( 10 ), salvileucolide-6,23-lactone ( 11 ), sclareol ( 15 ), and manool ( 17 ) were the most active against Gram-positive bacteria. The compounds were also tested for the inhibition of ATP production in purified mammalian rod outer segments. Terpenoids 10 , 11 , 15 , and 17 inhibited ATP production, while only 17 inhibited also ATP hydrolysis. Molecular modeling studies confirmed the capacity of 17 to interact with mammalian ATP synthase. A significant reduction of ATP production in the presence of 17 was observed in Enterococcus faecalis and E. faecium isolates.

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Section: Resultsmentioning

confidence: 99%

Antibacterial and ATP Synthesis Modulating Compounds from Salvia tingitana

et al. 2020

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“…The nature of the second lactone ring, present in both compounds, was evident from the downfield signals at δ 4.90 (dd) and 5.89 (dq). The remaining signals in the spectra of both compounds were similar to those of labdanes with a carboxyl group at C-4 [60]. The absolute configuration of the sesterterpenoid salvileucolide methyl ester, which has also been isolated from the aerial parts of S. sahendica Boiss.…”

Section: Diterpenesmentioning

confidence: 64%

“…and its structure established by high field NMR spectroscopy and X-ray diffraction analysis Rustaiyan et al [64]. Comparison of the 1 H NMR spectrum of 12 with the revised data of 1, isolated from S. sahendica [65], 13 years after its first report from S. hypoleuca [60] indicated a great similarity between these two compounds. Two sesterterpene lactones with a partial structure of manoyl oxide (13) and 13-epi-manoyl oxide ( 14), both as epimeric pairs at the anomeric carbon atom C-16 of a γ-methoxybutenolide were isolated from the aerial parts of S. aethiopis [66].…”

Section: Diterpenesmentioning

confidence: 99%

Terpenoids from Iranian Salvia Species

Rustaiyan

Masoudi

Tabatabaei-Anaraki

2007

Natural Product Communications

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Apart from their common constituents (terpenoids and flavonoids) and their interesting biological activities, the genus Salvia is unusual as it is the only genus in the Labiatae that contains sesterterpenes (C25). Since these rare and interesting compounds were, for the first time, isolated and identified from Iranian Salvia species by the senior author, their NMR spectroscopic data are briefly reviewed. The terpenoid constituents of the Iranian Salvia species are also summarized.

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“…In 1982, Rustaiyan et al first described the isolation of a bicyclic sesterterpene lactone with a methyl ester of carboxylic acid at C-23 and named it salvileucolide methyl ester ( 33 ) ( Figure 9 ) from a diethyl ether extract of the aerial parts of S. hypoleuca Benth, collected from the north of Teheran, Iran [ 58 ]. Later, Rustaiyan and Sadjadi also reported the isolation of 33 ( Figure 6 ) from a MeOH-soluble fraction of S. syriaca L., collected from north of Taleghan, Iran [ 55 ].…”

Section: Sesterterpenoidsmentioning

confidence: 99%

“…Like 33 , the structure of 41 and the stereochemistry at C-5 and C-6 were established based on the observation of the 1 H NMR spectrum through spin decoupling and the addition of the chemical shift reagent, Eu(fod) 3 , and the 13 C NMR spectrum. However, the relative and absolute configurations of C-16 were not determined [ 58 ].…”

Section: Sesterterpenoidsmentioning

confidence: 99%

Uncommon Terpenoids from Salvia Species: Chemistry, Biosynthesis and Biological Activities

et al. 2022

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The search for new bioactive compounds from plant sources has been and continues to be one of the most important fields of research in drug discovery. However, Natural Products research has continuously evolved, and more and more has gained a multidisciplinary character. Despite new developments of methodologies and concepts, one intriguing aspect still persists, i.e., different species belonging to the same genus can produce different secondary metabolites, whereas taxonomically different genera can produce the same compounds. The genus Salvia L. (Family Lamiaceae) comprises myriad distinct medicinal herbs used in traditional medicine worldwide that show different pharmacological activities due to the presence of a variety of interesting specialized metabolites, including mono-, sesqui-, di-, sester-, tri-, tetra-, and higher terpenoids as well as phenylpropanoids, phenolic acid derivatives, lignans, flavonoids, and alkaloids. We herein summarize the research progress on some uncommon terpenoids, isolated from members of the genus Salvia, which are well recognized for their potential pharmacological activities. This review also provides a current knowledge on the biosynthesis and occurrence of some interesting phytochemicals from Salvia species, viz. C23-terpenoids, sesterterpenoids (C25), dammarane triterpenoids (C30), and uncommon triterpenoids (C20+C10). The study was carried out by searching various scientific databases, including Elsevier, ACS publications, Taylor and Francis, Wiley Online Library, MDPI, Springer, Thieme, and ProQuest. Therefore, 106 uncommon terpenoids were identified and summarized. Some of these compounds possessed a variety of pharmacological properties, such as antibacterial, antiviral, antiparasitic, cytotoxic and tubulin tyrosine ligase inhibitory activities. Due to the lack of pharmacological information for the presented compounds gathered from previous studies, biological investigation of these compounds should be reinvestigated.

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Sesterterpenes from Salvia hypoleuca

Cited by 37 publications

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Antibacterial and ATP Synthesis Modulating Compounds from Salvia tingitana

Antibacterial and ATP Synthesis Modulating Compounds from Salvia tingitana

Terpenoids from Iranian Salvia Species

Uncommon Terpenoids from Salvia Species: Chemistry, Biosynthesis and Biological Activities

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