Macrocyclic spermidine alkaloids from Maytenus serrata and Tripterygium wilfordii

Kupchan, S. Morris; Hintz, H. P. J.; Smith, Roger M.; Karim, Aziz; Cass, Malcolm W.; Court, William A.; Yatagai, Mitsuyoshi

doi:10.1021/jo00443a005

Cited by 43 publications

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“…The 1 H-and 13 C-NMR spectra at 100°C of 1 and 2 showed one set of resonances (Table 1), which were similar to those of a cyclic spermidine alkaloid: (S)-dihydroperiphylline 22,23) Diosmetin-7-O-glucuronide bond. These spin system protons and corresponding carbons displayed the presence of a cyclic spermidine 13-membered ring moiety, which was either a periphylline-type 22) skeleton (1,4,9-triazacyclotridecan-4-one) or a celacinnine-type 24) skeleton (1,4,9-triazacyclotridecan-2-one). Both skeletons were possible via some biosynthetic pathway of naturally occurring macrocyclic spermidine alkaloids.…”

Section: -21)mentioning

confidence: 99%

“…These spectra and the UV spectra 29) of compounds 3-6 suggested that they were diosmetin-7-glycoside derivatives. For fargenin A (3), the molecular formula C 24 30) These data suggested that 5 had a b-D-glucuronic acid moiety instead of the acetyl group of 3. In the HMBC spectrum, the H-1ٞ signal was long-range coupled with the carbon of C-2Љ (d 82.3).…”

Section: -21)mentioning

confidence: 99%

“…Periphylline and celacinnine had been isolated from Celastraceae plants. 22,24) Meehania genus plants also have two types of skeletons. Compounds 3, 4, and 6 were esters of diosmetin-7-O-glucuronide which have hyaluronidase inhibitory activity, and 5 was diosmetin-diglucuronide.…”

Section: -21)mentioning

confidence: 99%

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Cyclic Spermidine Alkaloids and Flavone Glycosides from Meehania fargesii

Murata

Miyase

Yoshizaki

2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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The dried whole plant of Meehania fargesii (H. LÉV.) C. Y. WU is utilized as an antipyretic and antidote for poison in China. Water soluble fractions, obtained from an 80% acetone extract of the whole plant, showed hyaluronidase inhibitory activity. From these fractions, hyaluronidase inhibitors were isolated along with two new spermidine alkaloids (meefarnines A and B), four new flavone glycosides (fargenins A-D), and 10 known compounds. The structure of each was elucidated by spectroscopic methods.

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Section: -21)mentioning

confidence: 99%

Section: -21)mentioning

confidence: 99%

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Cyclic Spermidine Alkaloids and Flavone Glycosides from Meehania fargesii

Murata

Miyase

Yoshizaki

2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…-Pleurostylin schmilzt bei 246-247" und zeigt eine starke Linksdrehung ([a]:: c=0,896,CHCl,). Wie Celacinnin (4) und Celallocinnin (5) weist es im 1R.-Spektrum eine NH-Bande bei 2920 cm-' und CO-Amidbanden bei 1620 und 1640 cm-' auf [4]. Bei der Acetylierung rnit PyrididAcetanhydrid liefert Pleurostylin (1) eine Mono-Acetylverbindung (2, C2,H3,N,O3) und bei der katalytischen Hydrierung mit IOproz.…”

unclassified

“…Das UV.-Spektrum von 1 sieht ahnlich aus wie dasjenige von Celallocinnin (5): das Maximum bei 267 nm ist gegenuber dem von 5 nur um etwa 12 nm bathochrom verschoben, der 8-Wert (1 1700) in guter Ubereinstimmung mit einem cis-Zimtsaurechromophor [4] [5]. Fur einen cis-Cinnamoylchromophor sprechen auch eine 1R.-Bande bei 8 15 cm-' und zwei Dublettsignale eines A B-Systems bei 6 = 6,15 und 6=7,06 ppm rnit einer Kopplungskonstante J = 12,5 Hz im NMR.-Spektrum [6].…”

unclassified

Macrocyclische Spermidinalkaloide aus Pleurostylia africana LOES. 9. Mitteilung über Celastraceen‐Inhaltsstoffe

Wagner

Burghart

1981

Helvetica Chimica Acta

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Macrocyclic Spermidine Alcaloids from Pfeurostyfiu ufricana L o E s SummaryThe structure of pleurostyline, a new macrocyclic spermidine alkaloid from Pleurostylia africana (Celastraceae), has been elucidated mainly by 'H-and '3C-NMR.-spectroscopy. Pleurostyline represents a new structure type in which spermidine is incorporated in a 13-membered lactam ring to which an additional cinnamoyl residue is fused to yield a 7-membered ring. The same plant contains also the spermidine alkaloids celacinnine and celallocinnine of which 13C-and high field 'H-NMR.-measurements have been carried out for the first time. Both alkaloids are interconvertible by UV.-irradiation. In addition the existence of rotational isomerism of one amide group of these alkaloids has been demonstrated by NMR.-spectroscopy.

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Absolute configuration of macrocyclic spermidine alkaloids

et al. 1997

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In this short review of several macrocyclic spermidine alkaloids, special consideration has been given to the correct determination of the absolute configuration at their chiral centers. The bases of interest are characterized by possessing a 13‐membered macrocyclic lactam ring incorporating spermidine and either cinnammic or fatty acid precursorial units. In this context, the synthesis of some of these alkaloids is presented and the first total synthesis of optically pure (+)‐(S)‐viburnine, and (−)‐(S)‐celafurine is reported. Finally, a common initial step in biosynthesis starting with an enzyme‐catalyzed Michael addition of spermidine to an α,β‐unsaturated acid is proposed. Chirality 9:523–528, 1997. © 1997 Wiley‐Liss, Inc.

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Macrocyclic spermidine alkaloids from Maytenus serrata and Tripterygium wilfordii

Cited by 43 publications

References 1 publication

Cyclic Spermidine Alkaloids and Flavone Glycosides from Meehania fargesii

Cyclic Spermidine Alkaloids and Flavone Glycosides from Meehania fargesii

Macrocyclische Spermidinalkaloide aus Pleurostylia africana LOES. 9. Mitteilung über Celastraceen‐Inhaltsstoffe

Absolute configuration of macrocyclic spermidine alkaloids

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