Cyclopeptide alkaloids from stems of Paliurus ramossisimus

Six 14-membered cyclopeptide alkaloids, i.e., ramosines A ± C, mucronine J, and lotusines A and D, were isolated from the roots of Paliurus ramosissimus, and an additional four, hemsines A ± D, from the roots of P. hemsleyanus. Among these, ramosines A ± C (1, 5, and 6, resp.) and hemsines A and B (7 and 8, resp.) are new bases of the amphibine-B type, and hemsines C and D (9 and 10, resp.) are new integerrine-type alkaloids. Additionally, ramosine C (6) represents the first 14-membered cyclopeptide alkaloid possessing a substitution (ÀOH) at C(13'). Their structural elucidations were based on spectral analysis and molecular-modeling studies. Pronounced solvent effects in the 1 H-and 13 C-NMR spectra of these two types of alkaloids were observed.

show abstract

“…For the recording of physical data, see [3] [4]. TLC: silica gel; Me 2 CO/toluene 3 : 7 (A), or 4 : 6 (B), both saturated with 25% NH 4 OH soln.…”

Section: Experimental Partmentioning

confidence: 99%

“…Poir. (Rhamnaceae) have resulted in the isolation from its root and stem of triterpenes of the ceanothane and lupane types [1] [2], and of 13-membered cyclopeptide alkaloids of the zizyphine type [3] [4]. Some of these alkaloids showed either shortening or prolonging of the methahexital-induced sleeping time in mouse experiments [4].…”

mentioning

confidence: 99%

14‐Membered Cyclopeptides from Paliurus ramosissimus and P. hemsleyanus

Lin¹,

Chen

Liu

et al. 2003

Helvetica Chimica Acta

Self Cite

View full text Add to dashboard Cite

show abstract

“…Nummularine-H (47) could shorten the mexthohexital-induced sleeping time, in mice, instead of prolonging as shown for the paliurines A (37) and F (43) (Lee et al 2001). …”

Section: Cns Activitiesmentioning

confidence: 84%

“…Stereochemistry of the epoxide was also supported by the NOESY correlations from H-8 to H-9b and H-11, Phytochem Rev (2007) 6:143-165 163 and the amide proton (NH) to H-9a and H-11¢ (Isaka et al 2005). The stereochemistry in the ring nucleus of Paliurines G (44), H (45) and I (46) were deduced by the CD spectrometry, which established both ring bond amino acids and proline to be in the L-form (Lee et al 2001).…”

Section: (62) Hirsutellone Amentioning

confidence: 99%

Cyclopeptide alkaloids

et al. 2006

View full text Add to dashboard Cite

show abstract

“…10 Knowing that some cyclopeptide alkaloids can induce a sedative effect, 12 we assessed the undesirable effects of discarine B (2), scutianines B (3), C (4), and D (5), franganine (1), and adouetine X (6) in mice. The openfield test is sensitive to compounds that cause sedation or motor impairment.…”

Section: Resultsmentioning

confidence: 99%

Antinociceptive Effects of 14-Membered Cyclopeptide Alkaloids

et al. 2009

View full text Add to dashboard Cite

The analgesic potential of six 14-membered-ring cyclopeptide alkaloids, namely, franganine (1), discarine B (2), scutianines B (3), C (4), and D (5), and adouetine X (6), have been investigated. Among the compounds tested, only franganine (1) and adouetine X (6) produced antinociceptive effects in a mouse model of acute pain, without inducing undesirable side effects. Furthermore, compound 6 also exhibited a pronounced analgesic effect in a chronic neuropathic pain model in mice. It has been found that adouetine X (6) can decrease the activities of Ca(2+)-ATPase and Na(+)/K(+)-ATPase in vitro. Thus, the present findings have demonstrated that adouetine X (6) is a promising analgesic agent.

show abstract

Cyclopeptide alkaloids from stems of Paliurus ramossisimus

Cited by 20 publications

References 5 publications

14‐Membered Cyclopeptides from Paliurus ramosissimus and P. hemsleyanus

14‐Membered Cyclopeptides from Paliurus ramosissimus and P. hemsleyanus

Cyclopeptide alkaloids

Antinociceptive Effects of 14-Membered Cyclopeptide Alkaloids

Contact Info

Product

Resources

About