2. Academic Validation
  3. Kleinhospitine E and Cycloartane Triterpenoids from Kleinhovia hospita

Kleinhospitine E and Cycloartane Triterpenoids from Kleinhovia hospita

  • J Nat Prod. 2018 Jul 27;81(7):1619-1627. doi: 10.1021/acs.jnatprod.8b00211.
Abdul Rahim 1 2,  Yohei Saito 1,  Katsunori Miyake 3,  Masuo Goto 4,  Chin-Ho Chen 5,  Gemini Alam 2,  Susan Morris-Natschke 4,  Kuo-Hsiung Lee 4 6,  Kyoko Nakagawa-Goto 1 4
Affiliations

Affiliations

  • 1 School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences , Kanazawa University , Kanazawa , 920-1192 , Japan.
  • 2 Department of Pharmacognosy-Phytochemistry, Faculty of Pharmacy , Hasanuddin University , Makassar , Indonesia.
  • 3 Tokyo University of Pharmacy and Life Sciences , Hachioji , Tokyo 192-0392 , Japan.
  • 4 Division of Chemical Biology and Medicinal Chemistry, UNC Eshelman School of Pharmacy , University of North Carolina , Chapel Hill , North Carolina 27599-7568 , United States.
  • 5 Duke University Medical Center , Durham , North Carolina 27710 , United States.
  • 6 Chinese Medicine Research and Development Center , China Medical University and Hospital , Taichung 401 , Taiwan.
PMID: 30010341 DOI: 10.1021/acs.jnatprod.8b00211
Abstract

A novel cycloartane triterpenoid alkaloid, kleinhospitine E (1), six new cycloartane triterpenoids (2-7), three known cycloartane triterpenoids (8-10), and taraxerone (11) were isolated from a methanol extract of Kleinhovia hospita. Their structures were elucidated by 1D- and 2D-NMR spectroscopy as well as HRMS analysis. The absolute configurations of all isolated compounds were determined from their ECD spectra by comparison with theoretical values. Kleinhospitine E (1) is the first cycloartane alkaloid possessing an unusual γ-lactam with an oxopropylidene side chain. Compounds 2, 3, and 6 were assigned as cycloartane triterpenoids with a 9α,10α-cyclopropyl ring, which is found rarely among naturally occurring compounds, while 4 and 5 were established as isomers of compound 3 containing a 21,23-diacetal side chain. Biological evaluation revealed that compounds 4 and 9 exhibited more potent antiproliferative activities against a multidrug-resistant tumor cell line compared with its parent chemosensitive cell line. Furthermore, compound 6 exhibited submicromolar anti-HIV activity.

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