Modified ent-Abietane Diterpenoids from the Leaves of Suregada zanzibariensis

Thobias M Kalenga; Jackson T Mollel; Joanna Said; Andreas Orthaber; Jas S Ward; Yoseph Atilaw; Daniel Umereweneza; Monica M Ndoile; Joan J E Munissi; Kari Rissanen; Edward Trybala; Tomas Bergström; Stephen S Nyandoro; Mate Erdelyi

doi:10.1021/acs.jnatprod.2c00147

Modified ent-Abietane Diterpenoids from the Leaves of Suregada zanzibariensis

J Nat Prod. 2022 Sep 23;85(9):2135-2141. doi: 10.1021/acs.jnatprod.2c00147. Epub 2022 Sep 8.

Authors

Thobias M Kalenga^{1

2}, Jackson T Mollel^{3

4}, Joanna Said⁴, Andreas Orthaber⁵, Jas S Ward⁶, Yoseph Atilaw⁷, Daniel Umereweneza^{7

8}, Monica M Ndoile¹, Joan J E Munissi¹, Kari Rissanen⁶, Edward Trybala⁴, Tomas Bergström⁴, Stephen S Nyandoro¹, Mate Erdelyi⁷

Affiliations

¹ Chemistry Department, College of Natural and Applied Sciences, University of Dar es Salaam, P.O. Box 35061, Dar es Salaam, Tanzania.
² Department of Chemistry, College of Education, Mwalimu Julius K. Nyerere University of Agriculture and Technology, P.O. Box 976, Butiama, Tanzania.
³ Institute of Traditional Medicine, Muhimbili University of Health and Allied Sciences, P.O. Box 65001, Dar es Salaam, Tanzania.
⁴ Department of Infectious Diseases/Virology, Institute of Biomedicine, Sahlgrenska Academy, University of Gothenburg, S-413 46 Gothenburg, Sweden.
⁵ Department of Chemistry - Ångström, Uppsala University, SE-751 20 Uppsala, Sweden.
⁶ University of Jyvaskyla, Department of Chemistry, 40014 Jyväskylä, Finland.
⁷ Department of Chemistry - BMC, Uppsala University, SE-751 23 Uppsala, Sweden.
⁸ Department of Chemistry, College of Science and Technology, University of Rwanda, P.O Box 3900, Kigali, Rwanda.

Abstract

The leaf extract of Suregada zanzibariensis gave two new modified ent-abietane diterpenoids, zanzibariolides A (1) and B (2), and two known triterpenoids, simiarenol (3) and β-amyrin (4). The structures of the isolated compounds were elucidated based on NMR and MS data analysis. Single-crystal X-ray diffraction was used to establish the absolute configurations of compounds 1 and 2. The crude leaf extract inhibited the infectivity of herpes simplex virus 2 (HSV-2, IC₅₀ 11.5 μg/mL) and showed toxicity on African green monkey kidney (GMK AH1) cells at CC₅₀ 52 μg/mL. The isolated compounds 1-3 showed no anti-HSV-2 activity and exhibited insignificant toxicity against GMK AH1 cells at ≥100 μM.

MeSH terms

Abietanes* / chemistry
Abietanes* / isolation & purification
Abietanes* / pharmacology
Animals
Antiviral Agents* / chemistry
Antiviral Agents* / isolation & purification
Antiviral Agents* / pharmacology
Chlorocebus aethiops
Herpesvirus 2, Human / drug effects
Molecular Structure
Plant Extracts / chemistry
Suregada* / chemistry
Triterpenes* / chemistry
Triterpenes* / isolation & purification
Triterpenes* / pharmacology

Substances

Abietanes
Antiviral Agents
Plant Extracts
Triterpenes