Literature DB >> 33525521

New Isomalabaricane-Derived Metabolites from a Stelletta sp. Marine Sponge.

Sophia A Kolesnikova1, Ekaterina G Lyakhova1, Anastasia B Kozhushnaya2, Anatoly I Kalinovsky1, Dmitrii V Berdyshev1, Roman S Popov1, Valentin A Stonik1,2.   

Abstract

In continuation of our studies on a Vietnamese collection of a Stelletta sp., sponge we have isolated two new isomalabaricane triterpenoids, stellettins Q and R (1 and 2), and four new isomalabaricane-derived nor-terpenoids, stellettins S-V 3-6, along with previously known globostelletin N. Among them, compound 3 contains an acetylenic fragment, unprecedented in the isomalabaricane family and extremely rare in other marine sponge terpenoids. The structures and absolute configurations of all new compounds were established by extensive NMR, MS, and ECD analyses together with quantum-chemical modeling. Additionally, according to obtained new data we report the correction in stereochemistry of two asymmetric centers in the structures of two known isomalabaricanes, 15R,23S for globostelletin M and 15S,23R for globostelletin N.

Entities:  

Keywords:  Stelletta sp.; isomalabaricanes; marine sponge; structure elucidation; terpenoid

Mesh:

Substances:

Year:  2021        PMID: 33525521      PMCID: PMC7866221          DOI: 10.3390/molecules26030678

Source DB:  PubMed          Journal:  Molecules        ISSN: 1420-3049            Impact factor:   4.411


  18 in total

1.  Jaspolides A-F, six new isomalabricane-type terpenoids from the sponge Jaspis sp.

Authors:  Shengan Tang; Yuehu Pei; Hongzheng Fu; Zhiwei Deng; Jun Li; Peter Proksch; Wenhan Lin
Journal:  Chem Pharm Bull (Tokyo)       Date:  2006-01       Impact factor: 1.645

2.  Globostelletins A-I, cytotoxic isomalabaricane derivatives from the marine sponge Rhabdastrella globostellata.

Authors:  Jin Li; Bo Xu; Jinrong Cui; Zhiwei Deng; Nicole J de Voogd; Peter Proksch; Wenhan Lin
Journal:  Bioorg Med Chem       Date:  2010-05-15       Impact factor: 3.641

3.  Globostellatic acids A-D, new cytotoxic isomalabaricane triterpenes from the marine sponge Stelletta globostellata.

Authors:  G Ryu; S Matsunaga; N Fusetani
Journal:  J Nat Prod       Date:  1996-05       Impact factor: 4.050

4.  Identification of non-heme diiron proteins that catalyze triple bond and epoxy group formation.

Authors:  M Lee; M Lenman; A Banaś; M Bafor; S Singh; M Schweizer; R Nilsson; C Liljenberg; A Dahlqvist; P O Gummeson; S Sjödahl; A Green; S Stymne
Journal:  Science       Date:  1998-05-08       Impact factor: 47.728

5.  Cyclobutastellettolides A and B, C19 Norterpenoids from a Stelletta sp. Marine Sponge.

Authors:  Sophia A Kolesnikova; Ekaterina G Lyakhova; Anatoly I Kalinovsky; Dmitrii V Berdyshev; Evgeny A Pislyagin; Roman S Popov; Boris B Grebnev; Tatyana N Makarieva; Chau Van Minh; Valentin A Stonik
Journal:  J Nat Prod       Date:  2019-10-24       Impact factor: 4.050

6.  Discovery of a Dual Function Cytochrome P450 that Catalyzes Enyne Formation in Cyclohexanoid Terpenoid Biosynthesis.

Authors:  Yu-Rong Chen; Annavareddi Naresh; Suh-Yuen Liang; Chun-Hung Lin; Rong-Jie Chein; Hsiao-Ching Lin
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-02       Impact factor: 15.336

7.  New isomalabaricane derivatives from a new species of Jaspis sponge collected at the Vanuatu islands.

Authors:  A Zampella; M V D'Auria; C Debitus; J L Menou
Journal:  J Nat Prod       Date:  2000-07       Impact factor: 4.050

8.  Cytotoxic triterpenes from a marine sponge, Stelletta sp.

Authors:  J L McCormick; T C McKee; J H Cardellina; M Leid; M R Boyd
Journal:  J Nat Prod       Date:  1996-11       Impact factor: 4.050

9.  Three new cytotoxic isomalabaricane triterpenes from the marine sponge Stelletta tenuis.

Authors:  Yuan Li; Haifeng Tang; Xiangrong Tian; Houwen Lin; Minchang Wang; Minna Yao
Journal:  Fitoterapia       Date:  2015-09-15       Impact factor: 2.882

10.  De novo biosynthesis of terminal alkyne-labeled natural products.

Authors:  Xuejun Zhu; Joyce Liu; Wenjun Zhang
Journal:  Nat Chem Biol       Date:  2014-12-22       Impact factor: 15.040

View more
  2 in total

Review 1.  Malabaricane and Isomalabaricane Triterpenoids, Including Their Glycoconjugated Forms.

Authors:  Valentin A Stonik; Sophia A Kolesnikova
Journal:  Mar Drugs       Date:  2021-06-05       Impact factor: 5.118

2.  Good Practices in Sponge Natural Product Studies: Revising Vouchers with Isomalabaricane Triterpenes.

Authors:  Paco Cárdenas; Jayani Gamage; Chamari M Hettiarachchi; Sunithi Gunasekera
Journal:  Mar Drugs       Date:  2022-03-04       Impact factor: 5.118

  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.