A New Trinor-guaiane Sesquiterpene from an Indonesian Soft Coral <i>Anthelia</i> sp

Hanif, Novriyandi; Murni, Anggia; Yamauchi, Marie; Higashi, Masahiro; Tanaka, Junichi

doi:10.1177/1934578x1501001124

Cited by 4 publications

(6 citation statements)

References 24 publications

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“…Therefore, the current primary issues in marine conservation, such as the loss of biodiversity through over-exploitation and habitat degradation, can be overcome. Additional information can be found in the Supplementary Materials [95,96,97,98,99,100,101,102,103,104,105,106,107,108,109,110,111,112,113,114,115,116,117,118,119,120,121,122,123,124,125,126,127,128,129,130,131,132,133,134,135,136,137,138,139,140,141,142,143,144,145,146,147,148,149,150,151,152,153,154,…”

Section: Discussionmentioning

confidence: 99%

Marine Natural Products from Indonesian Waters

et al. 2019

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Natural products are primal and have been a driver in the evolution of organic chemistry and ultimately in science. The chemical structures obtained from marine organisms are diverse, reflecting biodiversity of genes, species and ecosystems. Biodiversity is an extraordinary feature of life and provides benefits to humanity while promoting the importance of environment conservation. This review covers the literature on marine natural products (MNPs) discovered in Indonesian waters published from January 1970 to December 2017, and includes 732 original MNPs, 4 structures isolated for the first time but known to be synthetic entities, 34 structural revisions, 9 artifacts, and 4 proposed MNPs. Indonesian MNPs were found in 270 papers from 94 species, 106 genera, 64 families, 32 orders, 14 classes, 10 phyla, and 5 kingdoms. The emphasis is placed on the structures of organic molecules (original and revised), relevant biological activities, structure elucidation, chemical ecology aspects, biosynthesis, and bioorganic studies. Through the synthesis of past and future data, huge and partly undescribed biodiversity of marine tropical invertebrates and their importance for crucial societal benefits should greatly be appreciated.

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Section: Discussionmentioning

confidence: 99%

Marine Natural Products from Indonesian Waters

et al. 2019

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“…In 2015, Hanif et al reported on a “new” compound with the same structure as claruviridin B ( 92 ) [ 268 ]. However, an overall comparison of the NMR data of the two compounds unexpectedly showed that the structures were different, indicating that the metabolite isolated by Hanif was a stereoisomer of compound 92 [ 267 ].…”

Section: Tri- Nor -Guaianes: 111213-tri- ...mentioning

confidence: 99%

“…However, an overall comparison of the NMR data of the two compounds unexpectedly showed that the structures were different, indicating that the metabolite isolated by Hanif was a stereoisomer of compound 92 [ 267 ]. This metabolite, whose stereochemistry has yet to be elucidated, was mildly cytotoxic against NBT-T2 rat bladder epithelial cells [ 268 ].…”

Section: Tri- Nor -Guaianes: 111213-tri- ...mentioning

confidence: 99%

Structures, Occurrences and Biosynthesis of 11,12,13-Tri-nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites

Coca-Ruíz

Suárez

Aleu

et al. 2022

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The compounds 11,12,13-tri-nor-sesquiterpenes are degraded sesquiterpenoids which have lost the C3 unit of isopropyl or isopropenyl at C-7 of the sesquiterpene skeleton. The irregular C-backbone originates from the oxidative removal of a C3 side chain from the C15 sesquiterpene, which arises from farnesyl diphosphate (FDP). The C12-framework is generated, generally, in all families of sesquiterpenes by oxidative cleavage of the C3 substituent, with the simultaneous introduction of a double bond. This article reviews the isolation, biosynthesis and biological activity of this special class of sesquiterpenes, the 11,12,13-tri-nor-sesquiterpenes.

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“…Among them, cembrane and briarane skeletons comprise a majority of the known diterpenoids in soft corals globally [ 2 , 3 ]. To date, soft corals of the genus Anthelia , family Xeniidae, have been shown to contain one type of sesquiterpenoid [ 4 ], three types of diterpenoids (xenicane [ 5 ], dolabellane [ 6 ], a C 24 -acetoacetylated diterpenoid [ 7 , 8 ]), and one type of steroid [ 9 ] with cytotoxic activity against various cell lines [ 4 , 5 , 6 , 7 , 8 , 9 ]. Moreover, the dolabellane stolonidiol ( 4 ), was identified as a promising candidate against Alzheimer’s disease after its mode of action in HEK293 cells was determined [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, the dolabellane stolonidiol ( 4 ), was identified as a promising candidate against Alzheimer’s disease after its mode of action in HEK293 cells was determined [ 10 ]. In our continuing study of metabolites of Indonesian Anthelia [ 4 , 6 ], we isolated known diterpenoids 3 – 8 and new dolabellanes, named sangiangols A ( 1 ) and B ( 2 ), the structures of which are the subject of this article.…”

Section: Introductionmentioning

confidence: 99%

Sangiangols A and B, Two New Dolabellanes from an Indonesian Marine Soft Coral, Anthelia sp.

2020

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A new, rare trinor-dolabellane diterpenoid, sangiangol A (1), and one new dolabellane diterpenoid, sangiangol B (2), together with known cembranes and dolabellanes (3–8), were isolated from the ethyl acetate layer of an extract of an Indonesian marine soft coral, Anthelia sp. Compounds 1–8 exhibited moderate cytotoxicity against an NBT-T2 cell line (0.5–10 µg/mL). The structures of the new compounds were determined by analyzing their spectra and a molecular modelling study. A possible biosynthetic pathway for sangiangols A (1) and B (2) is presented. Cytotoxicity requires two epoxide rings or a chlorine atom, as in 4 (stolonidiol) and 5 (clavinflol B).

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A New Trinor-guaiane Sesquiterpene from an Indonesian Soft Coral Anthelia sp

Cited by 4 publications

References 24 publications

Marine Natural Products from Indonesian Waters

Marine Natural Products from Indonesian Waters

Structures, Occurrences and Biosynthesis of 11,12,13-Tri-nor-Sesquiterpenes, an Intriguing Class of Bioactive Metabolites

Sangiangols A and B, Two New Dolabellanes from an Indonesian Marine Soft Coral, Anthelia sp.

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