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Linear Triquinane Sesquiterpenoids: Their Isolation, Structures

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Linear Triquinane Sesquiterpenoids: Their Isolation, Structures molecules Review Review Linear Triquinane Sesquiterpenoids:Sesquiterpenoids: TheirTheir Isolation,Isolation, Structures, Biological Activities, and Chemical andSynthesis Chemical Synthesis 1 2 1, ID 1, Yi QiuQiu 1, Wen-Jian LanLan 2, Hou-Jin Li 1,** andand Liu-Ping Liu-Ping Chen Chen 1,* * 1 1 SchoolSchool of of Chemistry, Chemistry, Sun Sun Yat-sen Yat-sen Univer University,sity, Guangzhou Guangzhou 510275, 510275, China; China; [email protected] [email protected] 2 2 SchoolSchool of of Pharmaceutical Pharmaceutical Sciences, Sciences, Sun Sun Yat-sen Yat-sen Universi University,ty, Guangzhou Guangzhou 510006, 510006, China; China; [email protected]@mail.sysu.edu.cn ** Correspondence:Correspondence: [email protected] [email protected] (H.-J.L.); (H.-J.L.); [email protected] [email protected] (L.-P.C.); (L.-P.C.); Tel.:Tel.: +86-20-8411-3698 +86-20-8411-3698 (H.-J.L.); (H.-J.L.); +86-20-8411-5559 +86-20-8411-5559 (L.-P.C.) (L.-P.C.) Received: 22 July 2018; Accepted: 19 Augu Augustst 2018; Published: 21 August 2018 Abstract: LinearLinear triquinane triquinane sesquiterpenoids sesquiterpenoids represent represent an important an important class class of natural of natural products. products. Most Mostof these of compounds these compounds were isolated were isolated from fungi, from sponge fungi,s, sponges, and soft andcorals, soft and corals, many and of them many displayed of them displayeda wide range a wide of biological range of biological activities. activities. On account On of account their structural of their structural diversity diversity and complexity, and complexity, linear lineartriquinane triquinane sesquiterpenoids sesquiterpenoids present present new challenges new challenges for chemical for chemical structure structure identification identification and total and totalsynthesis. synthesis. 118 linear 118 lineartriquinane triquinane sesquiterpenoids sesquiterpenoids were classified were classified into 8 types, into 8 types,named namedtypes I–VIII, types I–VIII,based basedon the on carbon the carbon skeleton skeleton and andthe theposition position of ofcarbon carbon substituents. substituents. Their Their isolation, isolation, structure structure elucidations, biologicalbiological activities, activities, and and chemical chemical synthesis synthesis were were reviewed. reviewed. This paperThis citedpaper 102 cited articles 102 fromarticles 1947 from to 2018.1947 to 2018. Keywords: linear triquinane sesquiterpenoid; hirsutane; capnellene; isolation; structure; biologicalbiological activity; synthesis 1. Introduction Sesquiterpenoids represent anan importantimportant classclass ofof naturalnatural products.products. Among them,them, linearlinear triquinane sesquiterpenoidssesquiterpenoids have have a a basic basic skeleton skeleton 1H 1-cyclopenta[H-cyclopenta[a]pentalenea]pentalene (Figure (Figure1a) [1a)1]. [1]. Since Since the firstthe first linear linear triquinane triquinane sesquiterpenoid, sesquiterpenoid, named named hirsutic hirsutic acid acid C C obtained obtained in in 1947 1947 [[2,3],2,3], moremore thanthan 100 linearlinear triquinanetriquinane sesquiterpenoids sesquiterpenoids have have been been isolated, isolated mainly, mainly from from fungi, fungi, sponges, sponges, and soft and corals. soft Manycorals. compoundsMany compounds displayed displayed a wide range a wide of biological range of activities, biological such activities, as cytotoxic, such antimicrobial,as cytotoxic, andantimicrobial, anti-inflammatory and anti-inflammatory activities [4–7]. Hirsutanesactivities [4 and–7]. capnellenes Hirsutanes are and the capnellenes most common are scaffolds the most of thecommon linear triquinanescaffolds of sesquiterpenoids the linear triquinane (Figure 1sesquiterpenoidsb,c) [ 8]. However, (Figure many compounds 1b,c) [8]. cannotHowever, be simplymany classifiedcompounds into cannot these be two simply types. classified Here, we into categorize these two the types. linear Here, triquinane we categorize sesquiterpenoids the linear triquinane into eight types,sesquiterpenoids types I–VIII, into according eight types, to the types carbon I–VIII, skeleton according and the to position the carbon of carbon skeleton substituents and the position (Figure 2of). Thiscarbon review substituents gives an(Figure overview 2). This about review the gives isolation, an overview structure, about biological the isolation, activities, structure, and biological chemical synthesisactivities, ofand linear chemical triquinane synthesis sesquiterpenoids. of linear triquinane sesquiterpenoids. 13 5 6 8 68 3 14 7 2 10 4 3 9 2 1 1 15 11 1 11 11 12 14 13 12 15 (a) basic scaffold (b) hirsutane scaffold (c) capnellene scaffold Figure 1. Skeleton of linear triquinanetriquinane sesquiterpenoids. Molecules 2018, 23, x; doi: www.mdpi.com/journal/molecules Molecules 2018, 23, 2095; doi:10.3390/molecules23092095 www.mdpi.com/journal/molecules Molecules 2018, 23, 2095 2 of 33 Molecules 2018, 23, x 2 of 31 FigureFigure 2. StructureStructure types types of of linear linear triquinane sesquiterpenoids. 2. Isolation Isolation and and Structure Structure Elucidation 2.1. Type Type I There are are four four carbon carbon substituents substituents at at C-2, C-2, 3, 3, 10 10,, 10 10 in in type type I compounds I compounds (Figure (Figure 3).3 ).A Atotal total of of76 compounds,76 compounds, constitute constitute the the largest largest classification classification of of linear linear triquinane triquinane sesquiterpenoids. sesquiterpenoids. Hirsutic Hirsutic acid acid CC( (1), was the first first linear triquinane sesquite sesquiterpenoidsrpenoids isolated fr fromom the cultures of Stereum hirsutum inin 1947 1947 [2,3]. [2,3]. The The antibiotic antibiotic coriolin coriolin (2 (),2 ),coriolin coriolin B ( B3), (3 C), ( C4), ( 4and), and hirsutene hirsutene (7) were (7) were purified purified from from the myceliathe mycelia of basidiomycetes of basidiomycetes CoriolusCoriolus consors consors [9–11].[9 –However,11]. However, the initial the initial structures structures of coriolins of coriolins were notwere exactly not exactly right, afterwards right, afterwards their structures their structures and stereochemistry and stereochemistry were revised were by revised the same by theresearch same groupresearch based group on based spectroscopic on spectroscopic analysis, analysis, biogenetic biogenetic consideration consideration and andchemical chemical transformations, transformations, in 1971in 1971 [12]. [12 The]. The revised revised structures structures of ofcoriolins coriolins show showeded that that they they were were hirsutane-type hirsutane-type sesquiterpenes. sesquiterpenes. (−)-Complicatic)-Complicatic acid acid (5 ()5 )was was first first isolated isolated from from the the fungus fungus Stereum Stereum complicatum complicatum in 1973 in 1973 [13]. [13 5-]. Dihydrocoriolin5-Dihydrocoriolin C C(6) ( 6was) was obtained obtained from from CoriolusCoriolus consors consors (ATCC(ATCC 11574) 11574) [14]. [14 ]. Hypnophilin ( (88)) was isolated from mycelial cultures of Pleurotellus hypnophilus (Berk.) Sacc. in 1981 [15[15,16].,16]. Six Six new new hirsutane hirsutane metabolites, metabolites, arthrosporone arthrosporone (9), anhydroarthrosporone (9), anhydroarthrosporone (10), arthrosporol (10), arthrosporol(11), 4-O-acetylarthrosporo (11), 4-O-acetylarthrosporo (12), arthrosporodione (12), arthrosporodione (13), and compound (1314), wereand obtainedcompound from 14 fungus were obtainedUAMH 4262 from by fungus Amouzou UAMH in 1989 4262 [4]. by Incarnal Amouzou (15) wasin 1989 purified [4]. Incarnal from the ( culture15) was fluid purified of Gloeostereum from the cultureincarnatum fluidin 1991of Gloeostereum [17]. In 1992, incarnatum gloeosteretriol in 1991 (16 ),[17]. also namedIn 1992, hirsutanol gloeosteretriol F was obtained(16), also from named the hirsutanolfluid fermentation F was obtained products from of thGloeostereume fluid fermentation incarnatum products[18]. From of Gloeostereum the culture incarnatum extract of the[18]. fungus From theLentinus culture crinitus extract, 1-desoxy-hypnophilin of the fungus Lentinus (17 crinitus), and, hypnophilin1-desoxy-hypnophilin (8) were isolated (17), and as hypnophilin the most active (8) werecompounds. isolated In as addition the most to theseactive ketones, compounds. their corresponding In addition to alcohols these ketones, 6,7-epoxy-4(15)-hirsutene-5-ol their corresponding alcohols(18) and 6,7-epoxy-4(15)-hirsutene-5-ol diol 4 (19) were obtained in 1994 (18 [)19 and]. diol 4 (19) were obtained in 1994 [19]. Chloriolin B B ( 20)) and C ( 21) were purifiedpurified from an unidentifiedunidentified fungus, which was separated fromfrom a marine sponge Jaspis aff. johnstoni [20].[20]. Hirsutanols A–C A–C ( (2222––2424)) and and ent-gloeosteretriol entgloeosteretriol (25) were obtained from from an an unidentified unidentified fungus, fungus, separated from an Indo-Pacific Indo-Pacific sponge Haliclona sp. in 1998, and study study showed that hirsutanol B was an epimer of hirsutanol A [5]. [5]. In In 1998, 1998, from from mycelial mycelial cultures cultures of of the the agaric MacrocystidiaMacrocystidia cucumis cucumis,, cucumis A–D ( 26–29) were were found found together together with with arthrosporone arthrosporone ( 9)[) [21].21]. Hirsutenols Hirsutenols A–C A–C ( (30–32)) were were isolatedisolated in in 2002, 2002, from from the the culture culture broth broth of the mushroom Stereum hirsutum [22].[22]. Connatusins Connatusins A A ( (3333)) and B ( 34)
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