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Natural disesquiterpenoids: an overview of their chemical structures, pharmacological activities, and biosynthetic pathways

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Abstract

Disesquiterpenoids are constructed by two sesquiterpenoid molecules, containing at least 30 carbons with various connection patterns, and numerous new skeletons have been constructed. The aim of this review is to comprehensively summarise the isolation, structural elucidation, chemical synthesis, possible biogenetic pathways, and important pharmacological activities of the natural disesquiterpenoids discovered between 2010 and 2020. Modern analytical tools and synthetic means that have led to structural revisions as well as name corrections have also been included. Here, 227 references and 470 compounds are summarized.

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Abbreviations

Bacillus cereus :

B. cereus

6BIO:

Wnt signaling activator (GSK3β inhibitor)

CD:

Circular dichroism

CI:

Combined index

DOX:

Doxorubicin

DEX:

Dexamethason

EC50 :

The concentration for 50% of maximal effect

Edwardsiella tarda :

E. tarda

Eupatorium perfoliatum :

E. perfoliatum

Fusarium graminearum :

F. graminearum

Human leukemia cells:

CCRF-CEM, 6T-CEM, Jurkat, K562, THP-1, Pfeiffer, HL-60, MOLT-4

Human breast cancer cells:

MCF-7, MDA-MB-231, MDA-MB-468, T47D

Human naso-pharyngeal cancer cells:

CNE1, CNE2, SUNE-1, HONE-1

Human colon cancer cells:

HCT116, HCT15, SW480, HT-29

Human liver cancer cells:

HepG2, SMMC-7721

Human lung cancer cells:

NCI-H460, NCI-H187, H1975, A549

Human gastric cancer cells:

SGC-7901, BGC-823

Human prostate cancer cells:

DU145, PC-3

Human normal breast cells:

MCF-10A

Human osteosarcoma cells:

U2OS

Human cervical cancer cells:

HeLa

Human lymphoma cells:

U937

Human renal epithelial cells:

293T

Human embryonic kidney cells:

HEK293

Human acute monocytic leukemia cells:

THP-1

Human embryonic lung cells:

WI-38

Human immunodeficiency virus type 1:

HIV-1

Hepatitis B virus:

HBV

Hepatitis C virus:

HCV

Helicobacter pylori :

H. pylori

IC50 :

The concentration that cause 50% reduction in cells growth

LC50 :

The concentration that cause 50% death

LDH:

Intracellular lactate dehydrogenases

l-NMMA:

N-monomethyl-l-arginine

Lamivudine:

3TC

MS:

Mass spectrum

Mp.:

Melting point

Mouse melanoma cells:

B16

Mouse monocyte macrophages:

Raw264.7

Mouse microglia cells:

BV-2

Micrococcus luteus :

M. luteus

α-MSH:

α-Melanocyte stimulating hormone

NNR:

Nuclear magnetic resonance

OR:

Optical rotation

Oral epidermoid cancer cells:

KB

Plasmodium falciparum :

P. falciparum

Plasmodium yoelii :

P. yoelii

Phytophthora infestans :

P. infestans

PTP1B:

Protein-tyrosine phosphatase 1B

RFI:

Relative fluorescent intensity

Rat skeletal myoblasts :

L6

Skin melanoma cell lines:

B16-F10

SI:

Selectivity Index

Staphylococcus aureus :

S. aureus

Trichophyton mentagrophytes :

T. mentagrophytes

UV:

Ultraviolet spectrum

References

  • Aboushoer MI, Fathy HM, Abdel-Kader MS, Goetz G, Omar AA (2010) Terpenes and flavonoids from an Egyptian collection of Cleome droserifolia. Nat Prod Rep 24:687–696

    CAS  Google Scholar 

  • Bai B, Ye SX, Yang DP, Zhu LP, Tang GH, Chen YY, Li GQ, Zhao ZM (2019) Chloraserrtone A, a sesquiterpenoid dimer from Chloranthus serratus. J Nat Prod 82:407–411

    PubMed  CAS  Google Scholar 

  • Baunach M, Ding L, Bruhn T, Bringmann G, Hertweck C (2013) Regiodivergent N-C and N-N aryl coupling reactions of indoloterpenes and cycloether formation mediated by a single bacterial flavoenzyme. Angew Chem Int Ed 52:9040–9043

    CAS  Google Scholar 

  • Bohlmann F, Ahmed M, Jakupovic J, King RM, Robinson H (1983) Dimeric sesquiterpene lactones and kolavane derivatives from Gochnatia paniculata. Phytochemistry 22:191–195

    CAS  Google Scholar 

  • Bohlmann F, Zdero C, Schmeda-Hirschmann G, Jakupovic J, Dominguez XA, King RM, Robinson H (1986) Dimeric guaianolides and other constituents from Gochnatia species. Phytochemistry 25:1175–1178

    CAS  Google Scholar 

  • Chen DW, Liu D, Shen S, Cheng W, Lin WH (2012a) Terpenoids from a Chinese Gorgonian Anthogorgia sp. and their antifouling activities. Chin J Chem 30:1459–1463

    CAS  Google Scholar 

  • Chen DW, Yu SJ, Ofwegen L, Proksch P, Lin WH (2012b) Anthogorgienes A – O, New guaiazulene-derived terpenoids from a Chinese Gorgonian Anthogorgia Species, and their antifouling and antibiotic activities. J Agric Food Chem 60:112–123

    PubMed  CAS  Google Scholar 

  • Chen J, Liu B (2018) Total synthesis of natural terpenoids: inspired but not limited by biohypothesis. Syn Lett 29:863–873

    CAS  Google Scholar 

  • Chen LP, Wu GZ, Dong HY, Yang N, Zhang WD, Li HL (2016) Lineariifolianoids I–L, four rare sesquiterpene lactone dimers inhibiting NO production from Inula lineariifolia. RSC Adv 6:103296–103298

    CAS  Google Scholar 

  • Chen LP, Wu GZ, Zhang JP, Ye J, Liu QX, Shen YH, Li HL, Zhang WD (2017) Vlasouliolides A–D, four rare C17/C15 sesquiterpene lactone dimers with potential anti-inflammatory activity from Vladimiria souliei. Sci Rep-UK 7:43837

    Google Scholar 

  • Chen YW, Li WH, Zeng ZQ, Tang YX (2018) (–)-Gochnatiolide B, synthesized from dehydrocostuslactone, exhibits potent anti-bladder cancer activity in vitro and in vivo. Sci Rep-UK 8:8807

    Google Scholar 

  • Chi J, Wei SS, Gao HL, Xu DQ, Zhang LN, Yang L, Xu WJ, Luo J, Kong LY (2019a) Diverse chemosensitizing 8,9-secolindenane-type sesquiterpenoid oligomers and monomers from Sarcandra glabra. J Org Chem 84:9117–9126

    PubMed  CAS  Google Scholar 

  • Chi J, Xu WJ, Wei SS, Wang XB, Li JX, Gao HL, Kong LY, Luo J (2019b) Chlotrichenes A and B, two lindenane sesquiterpene dimers with highly fused carbon skeletons from Chloranthus holostegius. Org Lett 21:789–792

    PubMed  CAS  Google Scholar 

  • Cichewicz RH, Clifford LJ, Lassen PR, Cao XL, Freedman TB, Nafie LA, Deschamps JD, Kenyon VA, Flanary JR, Holman TR, Crews P (2005) Stereochemical determination and bioactivity assessment of (S)-(+)-curcuphenol dimers isolated from the marine sponge Didiscus aceratus and synthesized through laccase biocatalysis. Bioorg Med Chem 13:5600–5612

    PubMed  CAS  Google Scholar 

  • Jiangsu New Medical College (1977) Dictionary of Traditional Chinese Materia Medica. Shanghai Scientific and Technological, Shanghai

    Google Scholar 

  • Dastan D, Salehi P, Aliahmadi A, Gohari AR, Maroofi H, Ardalan A (2016) New coumarin derivatives from Ferula pseudalliacea with antibacterial activity. Nat Prod Res 30:2747–2753

    PubMed  CAS  Google Scholar 

  • Dastan D, Salehi P, Ghanati F, Gohari AR, Maroofi H, Alnajar N (2014) Phytotoxicity and cytotoxicity of disesquiterpene and sesquiterpene coumarins from Ferula pseudalliacea. Ind Crop Prod 55:43–48

    CAS  Google Scholar 

  • Dastan D, Salehi P, Gohari AR, Zimmermann S, Kaiser M, Hamburger M, Khavasi HR, Ebrahimi SN (2012) Disesquiterpene and sesquiterpene coumarins from Ferula pseudalliacea, and determination of their absolute configurations. Phytochemistry 78:170–178

    PubMed  CAS  Google Scholar 

  • Deng X, Wang Y, Wu HH, Zhang WZ, Dong XQ, Wang ZM, Zhu Y, Gao XM, Li L, Wang YN, Xu YT (2018) Six kanshone C-derived sesquiterpenoid hybrids nardochalaristolones A–D, nardoflavaristolone A and dinardokanshone F from Nardostachys jatamansi DC. Bioorg Chem 81:35–43

    PubMed  CAS  Google Scholar 

  • Do TL (1991) Glossary of Vietnamese Medicinal Plants. Science and Technics Publication, Hanoi, Vietnam

    Google Scholar 

  • Dong L, Qin DP, Di QQ, Liu Y, Chen WL, Wang SM, Cheng YX (2019) Commiphorines A and B, unprecedented sesquiterpenoid dimers from Resina Commiphora with striking activities on anti-inflammation and lipogenesis inhibition. Org Chem Front 6:3825–3833

    CAS  Google Scholar 

  • Du B, Huang ZS, Wang X, Chen T, Shen G, Fu SM, Liu B (2019) A unified strategy toward total syntheses of lindenane sesquiterpenoid [4 + 2] dimers. Nat Commun 10:1892

    PubMed  PubMed Central  Google Scholar 

  • Editorial Commission of Traditional Chinese Medicine, State Administration of Traditional Chinese Medicine (Ed.) (1999) Traditional Chinese Medicine, vol 7. Shanghai Science & Technology Press, Shanghai

  • Fan YY, Sun YL, Zhou B, Zhao JX, Sheng L, Li JY, Yue JM (2018) Hedyorienoids A and B, two sesquiterpenoid dimers featuring different polycyclic skeletons from Hedyosmum orientale. Org Lett 20:5435–5438

    PubMed  CAS  Google Scholar 

  • Fang PL, Cao YL, Yan H, Pan LL, Liu SC, Gong NB, Lu Y, Chen CX, Zhong HM, Guo Y, Liu HY (2011) Lindenane disesquiterpenoids with anti-HIV-1 activity from Chloranthus japonicus. J Nat Prod 74:1408–1413

    PubMed  CAS  Google Scholar 

  • Feng J, Lei XQ, Bao RY, Li YH, Xiao CQ, Hu LH, Tang YF (2017) Enantioselective and collective total syntheses of xanthanolides. Angew Chem Int Ed 56:16323–16327

    CAS  Google Scholar 

  • Fraga BM (2013) Natural sesquiterpenoids. Nat Prod Rep 30:1226–1264

    PubMed  CAS  Google Scholar 

  • Furr SR, Marriott I (2012) Viral CNS infections: role of glial pattern recognition receptors in neuroinflammation. Front Microbiol 3:201

    PubMed  PubMed Central  CAS  Google Scholar 

  • Georgantea P, Ioannou E, Vagias C, Roussis V (2013) Perezoperezone and curcuperezone: bisabolane dimers from the soft coral Pseudopterogorgia rigida. Tetrahedron Lett 54:6920–6922

    CAS  Google Scholar 

  • Gu Q, Chen Y, Cui H, Huang D, Zhou J, Wu T, Chen Y, Shi L, Xu J (2013) Chrysanolide A, an unprecedented sesquiterpenoid trimer from the flowers of Chrysanthemum indicum L. RSC Adv 3:10168–10172

    CAS  Google Scholar 

  • Guo YG, Xie YG, Wu GJ, Cheng TF, Zhu SL, Yan SK, Jin HZ, Zhang WD (2019) Xylopidimers A – E, five new guaiane dimers with various carbon skeletons from the roots of Xylopia vielana. ACS Omega 4:2047–2052

    PubMed  PubMed Central  CAS  Google Scholar 

  • Guo YQ, Tang GH, Li ZZ, Lin SL, Yin S (2015) Chlojapolactone A, an unprecedented 1,3-dioxolane linked-lindenane sesquiterpenoid dimer from Chloranthus japonicus. RSC Adv 5:103047–103051

    CAS  Google Scholar 

  • Guo YQ, Zhao JJ, Li ZZ, Tang GH, Zhao ZM, Yin S (2016) Natural nitric oxide (NO) inhibitors from Chloranthus japonicus. Bioorg Med Chem Lett 26:3163–3166

    PubMed  CAS  Google Scholar 

  • Hadden M, Blagg B (2008) Dimeric approaches to anti-cancer chemotherapeutics. Anticancer Agents Med Chem 8:807–816

    PubMed  PubMed Central  CAS  Google Scholar 

  • Haffor AS (2010) Effect of myrrh (Commiphora molmol) on leukocyte levels before and during healing from gastric ulcer or skin injury. J Immunotoxicol 7:68–75

    PubMed  CAS  Google Scholar 

  • Hall TB (1974) Eupatorium perfoliatum. A plant with a history. Mo Med 71:527–528

    PubMed  Google Scholar 

  • Han ZZ, Ye J, Liu QX, Shen YH, Yue RC, Li HL, Zhang WD (2015) Valeriadimers A–C, three sesquiterpenoid dimers from Valeriana officinalis var. latifolia. RSC Adv 5:5913–5916

    CAS  Google Scholar 

  • He XF, Zhang S, Zhu RX, Yang SP, Yuan T, Yue JM (2011) Sarcanolides A and B: two sesquiterpenoid dimers with a nonacyclic scaffold from Sarcandra hainanensis. Tetrahedron 67:3170–3174

    CAS  Google Scholar 

  • Hirsch EC, Vyas S, Hunot S (2012) Neuroinflammation in Parkinson’s disease. Parkinsonism Relat D 18:210–212

    Google Scholar 

  • Hu BY, Qin DP, Wang SX, Qi JJ, Cheng YX (2018) Novel terpenoids with potent cytotoxic activities from Resina Commiphora. Molecules 23:3239

    PubMed Central  Google Scholar 

  • Huang HL, Xu YJ, Liu HL, Liu XQ, Shang JN, Han GT, Yao MJ, Yuan CS (2011) Eremophilane-type sesquiterpene lactones from Ligularia hodgsonii Hook. Phytochemistry 72:514–517

    PubMed  CAS  Google Scholar 

  • Huang J, Ni JD, Liu K, Yu Y, Xie M, Kang R, Vernon P, Cao LZ, Tang DL (2012) HMGB1 promotes drug resistance in osteosarcoma. Cancer Res 72:230–238

    PubMed  CAS  Google Scholar 

  • Intaraudom C, Boonyuen N, Supothina S, Tobwor P, Prabpai S, Kongsaeree P, Pittayakhajonwut P (2013) Novel spiro-sesquiterpene from the mushroom Anthracophyllum sp. BCC18695. Phytochemistry Lett 6:345–349

    CAS  Google Scholar 

  • Isaka M, Chinthanom P, Danwisetkanjana K, Choeyklin R (2014) A new cryptoporic acid derivative from cultures of the basidiomycete Poria albocincta BCC 26244. Phytochemistry Lett 7:97–100

    CAS  Google Scholar 

  • Isaka M, Srisanoh U, Choowong W, Boonpratuang T (2011) Sterostreins A–E, new terpenoids from cultures of the basidiomycete Stereum ostrea BCC 22955. Org Lett 13:4886–4889

    PubMed  CAS  Google Scholar 

  • Janecka A, Wyrębska A, Gach K, Fichna J, Janecki T (2012) Natural and synthetic α-methylenelactones and α-methylenelactams with anticancer potential. Drug Discov Today 17:561–572

    PubMed  CAS  Google Scholar 

  • Jiang HL, Chen J, Jin XJ, Yang JL, Li Y, Yao XJ, Wu QX (2011) Sesquiterpenoids, alantolactone analogues, and seco-guaiene from the roots of Inula helenium. Tetrahedron 67:9193–9198

    CAS  Google Scholar 

  • Jiao WH, Dewapriya P, Mohamed O, Khalil ZG, Salim AA, Lin HW, Capon RJ (2019) Divirensols: sesquiterpene dimers from the Australian termite nest-derived fungus Trichoderma virens CMB-TN16. J Nat Prod 82:87–95

    PubMed  CAS  Google Scholar 

  • Jin QH, Lee JW, Jang H, Choi JE, Kim HS, Lee D, Hong JT, Lee MK, Hwang BY (2016) Dimeric sesquiterpene and thiophenes from the roots of Echinops latifolius. Bioorg Med Chem Lett 26:5995–5998

    PubMed  CAS  Google Scholar 

  • Jin QH, Lee JW, Jang H, Choi JE, Kim HS, Lee D, Hong JT, Lee MK, Hwang BY (2017) Corrigendum to ‘‘Dimeric sesquiterpene and thiophenes from the roots of Echinops latifolius” [Bioorg. Med. Chem. Lett. 26 (2016) 5995–5998]. Bioorg Med Chem Lett 27:1490

  • Jin QH, Lee JW, Jang H, Lee HL, Kim JG, Wu WY, Lee DH, Kim EH, Kim YS, Hong JT, Lee MK, Hwang BY (2018) Dimeric- and trimeric sesquiterpenes from the flower of Inula japonica. Phytochemistry 155:107–113

    PubMed  CAS  Google Scholar 

  • Kamperdick C, Phuong NM, Sung TV, Adam G (2001) Guaiane dimers from Xylopia vielana. Phytochemistry 56:335–340

    PubMed  CAS  Google Scholar 

  • Kamperdick C, Phuong NM, Adam G, Sung TV (2003) Guaiane dimers from Xylopia vielana. Phytochemistry 64:811–816

    PubMed  CAS  Google Scholar 

  • Kanokmedhakul S, Lekphrom R, Kanokmedhakul K, Hahnvajanawong C, Bua-art S, Saksirirat W, Prabpai S, Kongsaeree P (2012) Cytotoxic sesquiterpenes from luminescent mushroom Neonothopanus nambi. Tetrahedron 68:8261–8266

    CAS  Google Scholar 

  • Kawabata J, Fukushi Y, Tahara S, Mizutani J (1990) Shizukaol A, a sesquiterpene dimer from Chloranthus japonicus. Phytochemistry 29:2332–2334

    CAS  Google Scholar 

  • Kawabata J, Mizutani J (1992) Dimeric sesquiterpenoid esters from Chloranthus serratus. Phytochemistry 31:1293–1296

    CAS  Google Scholar 

  • Kim SY, Kashiwada Y, Kawazoe K, Murakami K, Sun HD, Li SL, Takaishi Y (2011) Spicachlorantins G–J, new lindenane sesquiterpenoid dimers from the roots of Chloranthus spicatus. Chem Pharm Bull 59:1281–1284

    PubMed  CAS  Google Scholar 

  • Kitai Y, Hayashi K, Otsuka M, Nishiwaki H, Senoo T, Ishii T, Sakane G, Sugiura M, Tamura H (2015) New sesquiterpene lactone dimer, uvedafolin, extracted from eight yacon leaf varieties (Smallanthus sonchifolius): cytotoxicity in HeLa, HL-60, and murine B16-F10 melanoma cell lines. J Agric Food Chem 63:10856–10861

    PubMed  CAS  Google Scholar 

  • Kitai Y, Zhang X, Hayashida Y, Kakehi Y, Tamura H (2017) Induction of G2/M arrest and apoptosis through mitochondria pathway by a dimer sesquiterpene lactone from Smallanthus sonchifolius in HeLa cells. J Food Drug Anal 25:619–627

    PubMed  CAS  Google Scholar 

  • Lee JW, Yun CY, Roh E, Lee C, Jin QH, Bang KK, Jung SH, Lee D, Lee MK, Kim Y, Hwang BY (2012) Melanogenesis inhibitory bisabolane-type sesquiterpenoids from the roots of Angelica koreana. Bioorg Med Chem Lett 22:2927–2931

    PubMed  CAS  Google Scholar 

  • León A, Reyes BM, Chávez MI, Toscano RA, Delgado G (2009) Sesquiterpene lactones, acyl phenyl propanoids and other constituents from Schkuhria pinnata var. wisliɀeni. Antioxidant evaluation. J Mex Chem Soc 53:193–200

    Google Scholar 

  • Li PL, Wang CM, Zhang ZX, Jia ZJ (2007) Five new eremophilane derivatives from Ligularia sagitta. Tetrahedron 63:12665–12670

    CAS  Google Scholar 

  • Li C, Dian LY, Zhang WD, Lei XG (2012a) Biomimetic syntheses of (–)-Gochnatiolides A – C and (–)-Ainsliadimer B. J Am Chem Soc 134:12414–12417

    PubMed  CAS  Google Scholar 

  • Li Y, Ni ZY, Zhu MC, Zhang K, Wu YB, Dong M, Shi QW, Huo CH, Sauriol F, Kiyota H, Gu YC, Cong B (2012b) Millifolides A–C, new 1,10-seco-guaianolides from the flowers of Achillea millefolium. Zeitschrift fur Naturforschung B 67:438–446

    CAS  Google Scholar 

  • Li Y, Zhu MC, Zhang ML, Wang YF, Dong M, Wen SQ, Huo CH, Sauriol F, Kiyota H, Gu YC, Cong B (2012c) Achillinin B and C, new sesquiterpene dimers isolated from Achillea millefolium. Tetrahedron Lett 53:2601–2603

    CAS  Google Scholar 

  • Li Y, Yue GZ, Yuan CC, Du B, Deng HP, Liu B (2014) Synthetic studies toward lindenane-type sesquiterpenoid dimers. Synlett 25:2471–2474

    Google Scholar 

  • Li QM, Luo JG, Zhang YM, Li ZR, Wang XB, Yang MH, Luo J, Sun HB, Chen YJ, Kong LY (2015a) Involucratustones A–C: unprecedented sesquiterpene dimers containing multiple contiguous quaternary carbons from Stahlianthus involucratus. Chem Eur J 21:13206–13209

    PubMed  CAS  Google Scholar 

  • Li XD, Li XM, Xu GM, Zhang P, Wang BG (2015b) Antimicrobial phenolic bisabolanes and related derivatives from Penicillium aculeatum SD-321, a deep sea sediment-derived fungus. J Nat Prod 78:844–849

    PubMed  CAS  Google Scholar 

  • Li CJ, Ma J, Sun H, Zhang D, Zhang DM (2016) Guajavadimer A, a dimeric caryophyllene-derived meroterpenoid with a new carbon skeleton from the leaves of Psidium guajava. Org Lett 18:168–171

    PubMed  CAS  Google Scholar 

  • Li PL, Liu XL, Zhu HY, Tang XL, Shi XF, Liu YH, Li GQ (2017a) Unusual inner-salt guaiazulene alkaloids and bis-sesquiterpene from the south China sea Gorgonian Muriceides collaris. Sci Rep-UK 7:7697

    Google Scholar 

  • Li XL, Kurtán T, Hu JC, Mándi A, Li J, Li XW, Guo YW (2017b) Structural and Stereochemical Studies of Laurokamurols A – C, uncommon bis-sesquiterpenoids from the Chinese red alga Laurencia okamurai Yamada. J Agric Food Chem 65:1550–1555

    PubMed  CAS  Google Scholar 

  • Li HY, Zheng ZQ, Wei WJ, Chen JJ, Gao K (2018a) Ligusaginoids A–D, four eremophilane-type sesquiterpenoid dimers and trimers from Ligularia sagitta. Tetrahedron Lett 59:3461–3466

    Google Scholar 

  • Li J, Wu W, Yang F, Liu L, Wang SP, Jiao WH, Xu SH, Lin HW (2018b) Popolohuanones G – I, dimeric sesquiterpene quinones with IL-6 inhibitory activity from the marine sponge Dactylospongia elegans. Chem Biodivers 15:e1800078

    PubMed  Google Scholar 

  • Li QY, Wang Y, Wen SS, Wu Y, Xu LH, Sun ZL (2019a) A new dimeric sesquiterpenoid from Chloranthus japonicus Sieb. Rec Nat Prod 13:483–490

    CAS  Google Scholar 

  • Li YZ, Dai M, Peng DY (2019b) New bisesquiterpenoid lactone from the wild rhizome of Atractylodes macrocephala Koidz grown in Qimen. Nat Prod Res 31:2381–2386

    Google Scholar 

  • Lian GY, Yu B (2010) Naturally occurring dimers from chemical perspective. Chem Biodivers 7:2660–2691

    PubMed  CAS  Google Scholar 

  • Liao SG, Yue JM (2016) Dimeric sesquiterpenoids. Prog in Chem Org Nat Prod 101:1–112

    CAS  Google Scholar 

  • Liu HX, Chen K, Sun QY, Yang FM, Hu GW, Wang YH, Long CL (2013a) Nudibaccatumone, a trimer comprising a phenylpropanoid and two sesquiterpene moieties from Piper nudibaccatum. J Nat Prod 76:732–736

    PubMed  CAS  Google Scholar 

  • Liu HY, Ran XH, Gong NB, Ni W, Qin XJ, Hou YY, Lü Y, Chen CX (2013b) Sesquiterpenoids from Chloranthus multistachys. Phytochemistry 88:112–118

    PubMed  Google Scholar 

  • Liu JQ, Shu JC, Zhang R, Zhang W (2011) Two new pterosin dimers from Pteris mutifida Poir. Fitoterapia 82:1181–1184

    PubMed  CAS  Google Scholar 

  • Liu JW, Liu Y, Yan YM, Yang J, Lu XF, Cheng YX (2018a) Commiphoratones A and B, two sesquiterpene dimers from Resina Commiphora. Org Lett 20:2220–2223

    PubMed  CAS  Google Scholar 

  • Liu JW, Zhang MY, Yan YM, Wei XY, Dong L, Zhu YX, Cheng YX (2018b) Characterization of sesquiterpene dimers from Resina Commiphora that promote adipose-derived stem cell proliferation and differentiation. J Org Chem 83:2725–2733

    PubMed  CAS  Google Scholar 

  • Liu TT, Wu HB, Jiang HY, Zhang L, Zhang YN, Mao LG (2019a) Echingridimer A, an oxaspiro dimeric sesquiterpenoid with a 6/6/5/6/6 fused ring system from Echinops grijissi and aphicidal activity evaluation. J Org Chem 84:10757–10763

    PubMed  CAS  Google Scholar 

  • Liu X, Yang J, Fu J, Yao XJ, Wang JR, Liu L, Jiang ZH, Zhu GY (2019b) Aggreganoids A – F, carbon-bridged sesquiterpenoid dimers and trimers from Lindera aggregata. Org Lett 21:5753–5756

    PubMed  CAS  Google Scholar 

  • Liu X, Yang J, Yao XJ, Yang X, Fu J, Bai LP, Liu L, Jiang ZH, Zhu GY (2019c) Linderalides A – D, disesquiterpenoid-geranylbenzofuranone conjugates from Lindera aggregata. J Org Chem 84:8242–8247

    PubMed  CAS  Google Scholar 

  • Liu YQ, Nugroho AE, Hirasawa Y, Nakata A, Kaneda T, Uchiyama N, Goda Y, Shirota O, Morita H, Aisa HA (2010) Vernodalidimers A and B, novel orthoester elemanolide dimers from seeds of Vernonia anthelmintica. Tetrahedron Lett 51:6584–6587

    CAS  Google Scholar 

  • Lu YS, Peng XS (2011) A concise construction of the chlorahololide heptacyclic core. Org Lett 13:2940–2943

    PubMed  CAS  Google Scholar 

  • Lu YS, Peng XS (2016) Correction to “A concise construction of the chlorahololide heptacyclic core”. Org Lett 18:5447–5448

    PubMed  CAS  Google Scholar 

  • Luo P, Cheng YF, Yin ZY, Li CJ, Xu J, Gu Q (2019) Monomeric and dimeric cytotoxic guaianolide-type sesquiterpenoids from the aerial parts of Chrysanthemum indicum. J Nat Prod 82:349–357

    PubMed  CAS  Google Scholar 

  • Lv JJ, Wang YF, Zhang JM, Yu S, Wang D, Zhu HT, Cheng RR, Yang CR, Xu M, Zhang YJ (2014) Anti-hepatitis B virus activities and absolute configurations of sesquiterpenoid glycosides from Phyllanthus emblica. Org Biomol Chem 12:8764–8774

    PubMed  CAS  Google Scholar 

  • Ma LF, Xu H, Wang JD, Tong XM, Zhan ZJ, Ying YM, Wang JW, Zhang H, Shan WG (2018) Three new eudesmane sesquiterpenoids and a new dimer from the aerial part of Salvia plebeia R. Br Phytochemistry lett 25:122–125

    CAS  Google Scholar 

  • Maas M, Hensel A, da Costa FB, Brun R, Kaiser M, Schmidt TJ (2011) An unusual dimeric guaianolide with antiprotozoal activity and further sesquiterpene lactones from Eupatorium perfoliatum. Phytochemistry 72:635–644

    PubMed  CAS  Google Scholar 

  • Madaus G (1938) Lehrbuch der biologischen heilmittel, abteilung I: Heilpflanzen. Georg-Thieme-Verlag, Leipzig

    Google Scholar 

  • Malik A, Afza N, Yasmeen S, Anwer MA, Ali MI, Tareen RB (2011) Eremophilenolide-type sesquiterpenes from Hertia intermedia. Helv Chim Acta 94:163–168

    CAS  Google Scholar 

  • Mao SC, Guo YW, Soest RV, Cimino G (2011) Trans-dimer D, a novel dimeric sesquiterpene with a bis-bisabolene skeleton from a Hainan sponge Axinyssa variabilis. J Asian Nat Prod Res 13:770–775

    PubMed  CAS  Google Scholar 

  • Marco JA, Sanz JF, Yuste A, Jakupovic J (1991) A novel germacranolide-aminoacid adduct dimer from Centaurea aspera. Tetrahedron Lett 32:5193–5194

    CAS  Google Scholar 

  • Martins D, Hamerski L, Alvarenga SAV, Roque NF (1999) Labdane dimers from Xylopia aromatica. Phytochemistry 51:813–817

    CAS  Google Scholar 

  • Nanjing University of Chinese Medicine (2006) Dictionary of Chinese traditional medicine (Zhong Yao Da Ci Dian). Shanghai Science and Technology Press, Shanghai

    Google Scholar 

  • Meng J, Li YY, Ou YX, Song LF, Lu CH, Shen YM (2011) New sesquiterpenes from Marasmius cladophyllus. Mycology 2:30–36

    CAS  Google Scholar 

  • Mimura R, Kitamori A, Ikeda A, Masuda T, Nakano K, Kotsuki H, Ichikawa Y (2015) Biomimetic approaches employing the Ugi five-center four-component reaction for synthesis of the right-hand portion of Halichonadin Q and the central part of Halichonadin M. Synthesis 47:3043–3048

    CAS  Google Scholar 

  • Mimura R, Kitamori A, Nakano K, Kotsuki H, Matsumoto K, Kaneno D, Masuda T, Ichikawa Y (2016) Synthesis of trans-2,6-piperidinedicarboxamide using the Ugi reaction, a plausible model for the biosynthesis of halichonadin P. Heterocycles 92:857–865

    CAS  Google Scholar 

  • Ni G, Zhang H, Liu HC, Yang SP, Geng MY, Yue JM (2013) Cytotoxic sesquiterpenoids from Sarcandra glabra. Tetrahedron 69:564–569

    CAS  Google Scholar 

  • Pérez Gutiérrez RM, Ramirez AM (2016) Hypoglycemic effects of sesquiterpene lactones from Byrsonima crassifolia. Food Sci Biotechnol 25:1135–1145

    Google Scholar 

  • Prawat H, Mahidol C, Kaweetripob W, Wittayalai S, Ruchirawat S (2012) Iodoesesquiterpene hydroquinone and brominated indole alkaloids from the Thai sponge Smenospongia sp. Tetrahedron 68:6881–6886

    CAS  Google Scholar 

  • Qian S, Zhao G (2012) Total synthesis of (+)-chloranthalactone F. Chem Comm 48:3530–3532

    PubMed  CAS  Google Scholar 

  • Qin DP, Pan DB, Xiao W, Li HB, Yang B, Yao XJ, Dai Y, Yu Y, Yao XS (2018) Dimeric cadinane sesquiterpenoid derivatives from Artemisia annua. Org Lett 20:453–456

    PubMed  CAS  Google Scholar 

  • Qin JJ, Huang Y, Wang D, Cheng XR, Zeng Q, Zhang SD, Hu ZL, Jin HZ, Zhang WD (2012) Lineariifolianoids A–D, rare unsymmetrical sesquiterpenoid dimers comprised of xanthane and guaiane framework units from Inula lineariifolia. RSC Adv 2:1307–1309

    CAS  Google Scholar 

  • Qin JJ, Jin HZ, Fu JJ, Hu XJ, Wang Y, Yan SK, Zhang WD (2009) Japonicones A–D, bioactive dimeric sesquiterpenes from Inula japonica Thunb. Bioorg Med Chem Lett 19:710–713

    PubMed  CAS  Google Scholar 

  • Qin JJ, Jin HZ, Fu JJ, Hu XJ, Wang Y, Yan SK, Zhang WD (2010) Corrigendum to ‘‘Japonicones A–D, bioactive dimeric sesquiterpenes from Inula japonica Thunb.” [Bioorg. Med. Chem. Lett. 19 (2009) 710–713]. Bioorg Med Chem Lett 20:5584

  • Qin JJ, Jin HZ, Huang Y, Zhang SD, Shan L, Voruganti S, Nag S, Wang W, Zhang WD, Zhang RW (2013) Selective cytotoxicity, inhibition of cell cycle progression, and induction of apoptosis in human breast cancer cells by sesquiterpenoids from Inula lineariifolia Turcz. Eur J Med Chem 68:473–481

    PubMed  PubMed Central  CAS  Google Scholar 

  • Qin JJ, Wang LY, Zhu JX, Jin HZ, Fu JJ, Liu XF, Li HL, Zhang WD (2011) Neojaponicone A, a bioactive sesquiterpene lactone dimer with an unprecedented carbon skeleton from Inula japonica. Chem Comm 47:1222–1224

    PubMed  CAS  Google Scholar 

  • Qin JJ, Wang W, Zhang RW (2017) Novel natural product therapeutics targeting both inflammation and cancer. Chin J Nat Med 15:401–416

    PubMed  PubMed Central  Google Scholar 

  • Qu J, Deng SD, Li L, Liu YB, Li Y, Ma SG, Chen XG, Yu SS (2016) Cytotoxic dimeric xanthanolides from fruits of Xanthium chinense. Phytochemistry 132:115–122

    PubMed  CAS  Google Scholar 

  • Ran XH, Teng F, Chen CX, Wei G, Hao XJ, Liu HY (2010) Chloramultiols A–F, lindenane-type sesquiterpenoid dimers from Chloranthus multistachys. J Nat Prod 73:972–975

    PubMed  CAS  Google Scholar 

  • Ren YL, Jiménez F, García R, Mejía M, Chai H, Farnsworth NR, Soejarto DD, Kinghorn DA (2013) A cytotoxic dimeric furanoheliangolide from Piptocoma rufescens. Tetrahedron Lett 54:5457–5460

    PubMed  PubMed Central  CAS  Google Scholar 

  • Rosen BR, Werner EW, O’Brien AG, Baran PS (2014) Total synthesis of dixiamycin B by electrochemical oxidation. J Am Chem Soc 136:5571–5574

    PubMed  PubMed Central  CAS  Google Scholar 

  • Saito K, Nishimori A, Mimura R, Nakano K, Kotsuki H, Masuda T, Ichikawa Y (2013) A biomimetic approach to the synthesis of the core structure of the marine sponge terpene halichonadin G. Eur J Org Chem 31:7041–7043

    Google Scholar 

  • Saito Y, Takashima Y, Kamada A, Suzuki Y, Suenaga M, Okamoto Y, Matsunaga Y, Hanai R, Kawahara T, Gong X, Tori M, Kuroda C (2012) Chemical and genetic diversity of Ligularia virgaurea collected in northern Sichuan and adjacent areas of China. Isolation of 13 new compounds. Tetrahedron 68:10011–10029

    CAS  Google Scholar 

  • Schüffler A, Wollinsky B, Anke T, Liermann JC, Opatz T (2012) Isolactarane and sterpurane sesquiterpenoids from the basidiomycete Phlebia uda. J Nat Prod 75:1405–1408

    PubMed  Google Scholar 

  • Senejoux F, Evanno L, Poupon E (2013) Biomimetic three-component assembly of the central core of halichonadins K and L. Eur J Org Chem 2013:453–455

    CAS  Google Scholar 

  • Shang H, Liu JH, Bao RY, Cao Y, Zhao K, Xiao CQ, Zhou B, Hu LH, Tang YF (2014) Biomimetic synthesis: discovery of xanthanolide dimers. Angew Chem Int Ed 53:14494–14498

    CAS  Google Scholar 

  • Shen CP, Luo JG, Yang MH, Kong LY (2015) Cafestol-type diterpenoids from the twigs of Tricalysia fruticosa with potential anti-inflammatory activity. J Nat Prod 78:1322–1329

    PubMed  CAS  Google Scholar 

  • Shen CP, Luo JG, Yang MH, Kong LY (2017) Sesquiterpene dimers from the roots of Chloranthus holostegius with moderate anti-inflammatory activity. Phytochemistry 137:117–122

    PubMed  CAS  Google Scholar 

  • Shen XY, Qin DP, Zhou H, Luo JF, Yao YD, Lio CK, Li HB, Dai Y, Yu Y, Yao XS (2018) Nardochinoids A – C, three dimeric sesquiterpenoids with specific fused-ring skeletons from Nardostachys chinensis. Org Lett 20:5813–5816

    PubMed  CAS  Google Scholar 

  • Shen Y, Chen H, Shen L, Li HX, Dong X, Xiao CJ, Jiang B (2020) Dodelates A–E: five dimeric eudesmane sesquiterpenoids from Dobinea delavayi. Bioorg Chem 95:103488

    PubMed  CAS  Google Scholar 

  • Shi XW, Lu QQ, Gennaro P, Ivsic T, Zhou JH, Gao JM (2016) Three sesquiterpenoid dimers from Chloranthus japonicus: absolute configuration of chlorahololide A and related compounds. Chirality 28:158–163

    PubMed  Google Scholar 

  • Somwong P, Suttisri R, Buakeaw A (2013) New sesquiterpenes and phenolic compound from Ficus foveolata. Fitoterapia 85:1–7

    PubMed  CAS  Google Scholar 

  • Stipanovic R, Puckhaber L, Frelichowski J Jr, Esquivel J, Westbrook J, O′Neil M, Bell A, Dowd M, Hake K, Duke S (2016) Gossypolhemiquinone, a dimeric sesquiterpenoid identified in cotton (Gossypium). Phytochemistry 122:165–171

    PubMed  CAS  Google Scholar 

  • Sun LL, Shao CL, Chen JF, Guo ZY, Fu XM, Chen M, Chen YY, Li R, Voogd NJ, She ZG, Lin YC, Wang CY (2012) New bisabolane sesquiterpenoids from a marine-derived fungus Aspergillus sp. isolated from the sponge Xestospongia testudinaria. Bioorg Med Chem Lett 22:1326–1329

    PubMed  CAS  Google Scholar 

  • Suto S, Tanaka N, Fromont J, Kobayashi J (2011) Halichonadins G–J, new sesquiterpenoids from a sponge Halichondria sp. Tetrahedron Lett 52:3470–3473

    CAS  Google Scholar 

  • Tanaka N, Suto S, Asai M, Kusama T, Takahashi-Nakaguchi A, Gonoi T, Fromont J, Kobayashi J (2015) Halichonadins M–Q, sesquiterpenes from an Okinawan marine sponge Halichondria sp. Heterocycles 90:173–185

    CAS  Google Scholar 

  • Tanaka N, Suto S, Ishiyama H, Kubota T, Yamano A, Shiro M, Fromont J, Kobayashi J (2012) Halichonadins K and L, new dimeric sesquiterpenoids from a sponge Halichondria sp. Org Lett 14:3498–3501

    PubMed  CAS  Google Scholar 

  • Thongnest S, Chawengrum P, Keeratichamroen S, Lirdprapamongkol K, Eurtivong C, Boonsombat J, Kittakoop P, Svasti J, Ruchirawat S (2019) Vernodalidimer L, a sesquiterpene lactone dimer from Vernonia extensa and anti-tumor effects of vernodalin, vernolepin, and vernolide on HepG2 liver cancer cells. Bioorg Chem 92:103197

    PubMed  CAS  Google Scholar 

  • Tian MQ, Liu R, Li JF, Zhang KQ, Li GH (2016) Three new sesquiterpenes from the fungus Stereum sp. YMF1.1686. Phytochemistry Lett 15:186–189

    CAS  Google Scholar 

  • Tori M, Otose K, Fukuyama H, Murata J, Shiotani Y, Takaoka S, Nakashima K, Sono M, Tanaka M (2010) New eremophilanes from Farfugium japonicum. Tetrahedron 66:5235–5243

    CAS  Google Scholar 

  • Trifman YJ, Aknin M, Gauvin-Bialecki A, Benayahu Y, Carmeli S, Kashman Y (2016) Bisdioxycalamenene: A bis-sesquiterpene from the soft coral Rhytisma fulvum fulvum. Mar Drugs 14:41

    PubMed Central  Google Scholar 

  • Tsarkova AS, Dubinnyi MA, Baranov MS, Oguienko AD, Yampolsky IV (2016) Nambiscalarane, a novel sesterterpenoid comprising a furan ring, and other secondary metabolites from bioluminescent fungus Neonothopanus nambi. Mendeleev Commun 26:191–192

    CAS  Google Scholar 

  • Turak A, Liu YQ, Aisa HA (2015) Elemanolide dimers from seeds of Vernonia anthelmintica. Fitoterapia 104:23–30

    PubMed  CAS  Google Scholar 

  • Turak A, Maimaiti Z, Ma HR, Aisa HA (2017) Pseudo-disesquiterpenoids from seeds of Vernonia anthelmintica and their biological activities. Phytochemistry Lett 21:163–168

    CAS  Google Scholar 

  • Turak A, Shi SP, Jiang Y, Tu PF (2014) Dimeric guaianolides from Artemisia absinthium. Phytochemistry 105:109–114

    PubMed  CAS  Google Scholar 

  • Utkina NK, Denisenko VA, Krasokhin VB (2010) Sesquiterpenoid aminoquinones from the marine sponge Dysidea sp. J Nat Prod 73:788–791

    PubMed  CAS  Google Scholar 

  • Utkina NK, Denisenko VA, Krasokhin VB (2011) Diplopuupehenone, a new unsymmetrical puupehenone-related dimer from the marine sponge Dysidea sp. Tetrahedron Lett 52:3765–3768

    CAS  Google Scholar 

  • Wang JC, Li GZ, Lv N, Gao L, Cao L, Shen LG, Si JY (2016a) Chemical constituents from the fruiting bodies of Cryptoporus volvatus. Arch Pharm Res 39:747–754

    PubMed  CAS  Google Scholar 

  • Wang PC, Ran XH, Luo HR, Ma QY, Zhou J, Hu JM, Zhao YX (2016b) Volvalerine A, an unprecedented N-containing sesquiterpenoid dimer derivative from Valeriana officinalis var. latifolia. Fitoterapia 109:174–178

    PubMed  CAS  Google Scholar 

  • Wang L, Wang J, Li F, Liu X, Chen B, Tang YX, Wang MK (2013a) Cytotoxic sesquiterpene lactones from aerial parts of Xanthium sibiricum. Planta Med 79:661–665

    PubMed  CAS  Google Scholar 

  • Wang S, Li J, Sun J, Zeng KW, Cui JR, Jiang Y, Tu PF (2013b) NO inhibitory guaianolide-derived terpenoids from Artemisia argyi. Fitoterapia 85:169–175

    PubMed  CAS  Google Scholar 

  • Wang JC, Li GZ, Gao L, Cao L, Lv N, Shen LG, Si JY (2015a) Two new cryptoporic acid derivatives from the fruiting bodies of Cryptoporus volvatus. Phytochemistry Lett 14:63–66

    CAS  Google Scholar 

  • Wang JF, He WJ, Zhang XX, Zhao BQ, Liu YH, Zhou XJ (2015b) Dicarabrol, a new dimeric sesquiterpene from Carpesium abrotanoides L. Bioorg Med Chem Lett 25:4082–4084

    PubMed  CAS  Google Scholar 

  • Wang LJ, Xiong J, Liu ST, Liu XH, Hu JF (2014) Sesquiterpenoids from Chloranthus henryi and their antineuroinflammatory activities. Chem Biodivers 11:919–928

    PubMed  CAS  Google Scholar 

  • Wang PC, Ran XH, Luo HR, Hu JM, Chen R, Ma QY, Dai HF, Liu YQ, Xie MJ, Zhou J, Zhao YX (2011a) Volvalerelactones A and B, two new sesquiterpenoid lactones with an unprecedented skeleton from Valeriana officinalis var. latifolia. Org Lett 13:3036–3039

    PubMed  CAS  Google Scholar 

  • Wang QH, Kuang HX, Yang BY, Xia YG, Wang JS, Kong LY (2011b) Sesquiterpenes from Chloranthus japonicus. J Nat Prod 74:16–20

    PubMed  Google Scholar 

  • Wang PF, Deng SD, Qu J, Yu SS (2018) A new dimeric xanthanolide from fruits of Xanthium chinense. China J Chin Mater Med 43:532–536

    Google Scholar 

  • Wu HH, Chen YP, Ying SS, Zhang P, Xu YT, Gao XM, Zhu Y (2015a) Dinardokanshones A and B, two unique sesquiterpene dimers from the roots and rhizomes of Nardostachys chinensis. Tetrahedron Lett 56:5851–5854

    CAS  Google Scholar 

  • Wu JW, Tang CP, Chen L, Qiao Y, Geng MY, Ye Y (2015b) Dicarabrones A and B, a pair of new epimers dimerized from sesquiterpene lactones via a [3 + 2] cycloaddition from Carpesium abrotanoides. Org Lett 17:1656–1659

    PubMed  CAS  Google Scholar 

  • Wang LJ, Xiong J, Lau C, Pan LL, Hua JF (2015c) Sesquiterpenoids and further diterpenoids from the rare Chloranthaceae plant Chloranthus sessilifolius. J Asian Nat Prod Res 17:1220–1230

    PubMed  CAS  Google Scholar 

  • Wang P, Luo J, Zhang YM, Kong LY (2015d) Sesquiterpene dimers esterified with diverse small organic acids from the seeds of Sarcandra glabra. Tetrahedron 71:5362–5370

    CAS  Google Scholar 

  • Wu JW, Tang CP, Ke CQ, Yao S, Liu HC, Lin LG, Ye Y (2017) Dicarabrol A, dicarabrone C and dipulchellin A, unique sesquiterpene lactone dimers from Carpesium abrotanoides. RSC Adv 7:4639–4644

    CAS  Google Scholar 

  • Wu W, Zhao F, Bao L, Lu JC, Liu HW (2011a) Two new cryptoporic acid derivatives from the fruiting bodies of Cryptoporus sinensis. Helv Chim Acta 94:2020–2026

    CAS  Google Scholar 

  • Wu W, Zhao F, Ding R, Bao L, Gao H, Lu JC, Yao XS, Zhang XQ, Liu HW (2011b) Four new cryptoporic acid derivatives from the fruiting bodies of Cryptoporus sinensis, and their inhibitory effects on nitric oxide production. Chem Biodivers 8:1529–1538

    CAS  Google Scholar 

  • Wu ZJ, Xu XK, Zeng HW, Shen YH, Tian JM, Su J, Li HL, Shan L, Liu RH, Zhang WD (2011c) New sesquiterpenoids from Ainsliaea macrocephala and their nitric oxide inhibitory activity. Planta Med 77:1545–1550

    PubMed  CAS  Google Scholar 

  • Wu XL, Xiong XJ, Lu WQ, Huang H, Shen YH, Wu ZJ, Chen WS (2016) New sesquiterpenenoids from Ainsliaea yunnanensis. Molecules 21:1031

    PubMed Central  Google Scholar 

  • Wu ZJ, Xu XK, Zeng HW, Shen YH, Tian JM, Su J, Li HL, Shan L, Liu RH, Zhang WD (2012) New sesquiterpenoids from Ainsliaea macrocephala and their nitric oxide inhibitory activity. Planta Med 78:E23

    Google Scholar 

  • Wu HH, Deng X, Zhang H, Chen YP, Ying SS, Wu YJ, Liu YT, Zhu Y, Gao XM, Xu YT, Li L (2018a) Dinardokanshones C–E, isonardoeudesmols A–D and nardoeudesmol D from Nardostachys jatamansi DC.. Phytochemistry 150:50–59

  • Wu JL, Lu YS, Tang BC, Peng XS (2018b) Total syntheses of shizukaols A and E. Nature commun 9:4040–4046

    Google Scholar 

  • Wu JL, Lu YS, Wong HN, Peng XS (2018c) Synthetic studies toward lindenane-type dimers via Diels-Alder reaction. Tetrahedron 74:6749–6760

    CAS  Google Scholar 

  • Wu ZL, Wang JX, Chen LP, Dong HY, Li HL, Zhang WD (2018d) Five rare C32 sesquiterpene lactone dimers with anti-inflammation activity from Vladimiria souliei. Fitoterapia 125:117–122

    PubMed  CAS  Google Scholar 

  • Wu ZL, Wang Q, Dong HY, Li HL, Wang SM, Zhang WD (2018e) Five rare dimeric sesquiterpenes exhibiting potential neuroprotection activity from Vladimiria souliei. Fitoterapia 128:192–197

    PubMed  CAS  Google Scholar 

  • Wu ZL, Wang Q, Wang JX, Dong HY, Xu XK, Shen YH, Li HL, Zhang WD (2018f) Vlasoulamine A, a neuroprotective [3.2.2] cyclazine sesquiterpene lactone dimer from the roots of Vladimiria souliei. Org Lett 20:7567–7570

    PubMed  CAS  Google Scholar 

  • Xie CF, Wang H, Sun XC, Meng LH, Wang MC, Bartlam M, Guo YQ (2015) Isolation, characterization, and antiproliferative activities of eudesmanolide derivatives from the flowers of Inula japonica. J Agric Food Chem 63:9006–9011

    PubMed  CAS  Google Scholar 

  • Xie GB, Xie Y, Hu YZ, Zhu ZX (2016) Cytotoxic sesquiterpenoids from Ligularia pleurocaulis. Phytochemistry 125:99–105

    PubMed  CAS  Google Scholar 

  • Xie WD, Liu YH, Weng CW, Zhao H, Row KH (2011) Fischelactone B: a new eremophilane dimer from Ligularia fischeri. J Chin Chem Soc 58:412–414

    CAS  Google Scholar 

  • Xie WD, Weng CW, Li X, Row KH (2010) Eremophilane sesquiterpenoids from Ligularia fischeri. Helv Chim Acta 93:1983–1989

    CAS  Google Scholar 

  • Xie YG, Guo YG, Wu GJ, Zhu SL, Cheng TF, Zhang Y, Yan SK, Jin HZ, Zhang WD (2018a) Xylopsides A–D, four rare guaiane dimers with two unique bridged pentacyclic skeletons from Xylopia vielana. Org Biomol Chem 16:7030–7034

    CAS  Google Scholar 

  • Xie YG, Wu GJ, Cheng TF, Zhu SL, Yan SK, Jin HZ, Zhang WD (2018b) Vielopsides A–E, five new guaiane-type sesquiterpenoid dimers from Xylopia vielana. Fitoterapia 130:43–47

    PubMed  CAS  Google Scholar 

  • Xie YG, Zhang WY, Zhu SL, Cheng TF, Wu GJ, Muhammad I, Yan SK, Zhang Y, Jin HZ, Zhang WD (2018c) Xyloplains A–F, six new guaiane-type sesquiterpenoid dimers from Xylopia vielana. RSC Adv 8:25719–25724

    CAS  Google Scholar 

  • Xie YG, Yan R, Zhong XL, Huang P, Muhammad I, Ke XS, Yan SK, Guo YQ, Jin HZ, Zhang WD (2019a) Xylopins A–F, six rare guaiane dimers with three different connecting modes from Xylopia vielana. RSC Adv 9:9235–9242

    CAS  Google Scholar 

  • Xie YG, Zhong XL, Xiao YZ, Zhu SL, Muhammad I, Yan SK, Jin HZ, Zhang WD (2019b) Vieloplains A–G, seven new guaiane-type sesquiterpenoid dimers from Xylopia vielana. Bioorg Chem 88:102891

    PubMed  CAS  Google Scholar 

  • Xu FW, Xiao CQ, Lv X, Lei M, Hu LH (2017) Two new dimmeric xanthanolides isolated from Xanthium mogolium Kitag plant. Tetrahedron Lett 58:1312–1315

    CAS  Google Scholar 

  • Xu J, Jin DQ, Shi DD, Ma YG, Yang B, Zhao P, Guo YQ (2011) Sesquiterpenes from Vladimiria souliei and their inhibitory effects on NO production. Fitoterapia 82:508–511

    PubMed  CAS  Google Scholar 

  • Xu XK, Ye J, Chen LP, Zhang WD, Yang YX, Li HL (2015a) Four new isomeric sesquiterpene lactone dimers from Carpesium faberi. Tetrahedron Lett 56:6381–6384

    CAS  Google Scholar 

  • Xu XY, Sun P, Guo DA, Liu X, Liu JH, Hu LH (2015b) Cytotoxic sesquiterpene lactone dimers isolated from Inula japonica. Fitoterapia 101:218–223

    PubMed  CAS  Google Scholar 

  • Xu XK, Ye J, Chen LP, Zhang WD, Yang YX, Li HL (2016) Three new sesquiterpene lactone dimers from Carpesium faberi. Phytochemistry Lett 16:277–282

    CAS  Google Scholar 

  • Xue GM, Han C, Chen C, Li LN, Wang XB, Yang MH, Gu YC, Luo JG, Kong LY (2017) Artemisians A – D, diseco-guaianolide involved heterodimeric [4 + 2] adducts from Artemisia argyi. Org Lett 19:5410–5413

    PubMed  CAS  Google Scholar 

  • Xue GM, Li XQ, Chen C, Chen K, Wang XB, Gu YC, Luo JG, Kong LY (2018) Highly oxidized guaianolide sesquiterpenoids with potential antiinflammatory activity from Chrysanthemum indicum. J Nat Prod 81:378–386

    PubMed  CAS  Google Scholar 

  • Xue GM, Zhu DR, Han C, Wang XB, Luo JG, Kong LY (2019a) Artemisianins A–D, new stereoisomers of seco-guaianolide involved heterodimeric [4 + 2] adducts from Artemisia argyi induce apoptosis via enhancement of endoplasmic reticulum stress. Bioorg Chem 84:295–301

    PubMed  CAS  Google Scholar 

  • Xue GM, Zhu DR, Zhu TY, Wang XB, Luo JG, Kong LY (2019b) Lactone ring-opening seco-guaianolide involved heterodimers linked via an ester bond from Artemisia argyi with NO inhibitory activity. Fitoterapia 132:94–100

    PubMed  CAS  Google Scholar 

  • Yan H, Ba MY, Li XH, Guo JM, Qin XJ, He L, Zhang ZQ, Guo Y, Liu HY (2016) Lindenane sesquiterpenoid dimers from Chloranthus japonicus inhibit HIV-1 and HCV replication. Fitoterapia 115:64–68

    PubMed  CAS  Google Scholar 

  • Yan H, Qin XJ, Li XH, Yu Q, Ni W, He L, Liu HY (2019) Japonicones A–C: three lindenane sesquiterpenoid dimers with a 12-membered ring core from Chloranthus japonicus. Tetrahedron Lett 60:713–717

    CAS  Google Scholar 

  • Yan YM, Wu GS, Dong XP, Shen L, Li Y, Su J, Luo HR, Zhu HJ, Cheng YX (2012) Sesquiterpenoids from Incarvillea arguta: absolute configuration and biological evaluation. J Nat Prod 75:1025–1029

    PubMed  CAS  Google Scholar 

  • Yang JL, Wang R, Shi YP (2011) Phytochemicals and biological activities of Ligularia species. Nat Prod Bioprospect 1:1–24

    PubMed Central  CAS  Google Scholar 

  • Yang XX, Su YZ, Tan J, Cai CE, He PM, Jia R (2018) A new dimeric sesquiterpene and other related derivatives from the marine red alga Laurencia okamurai. Biochem Syst Ecol 79:57–59

    CAS  Google Scholar 

  • Yang YX, Gao S, Zhang SD, Zu XP, Shen YH, Shan L, Li HL, Zhang WD (2015) Cytotoxic 2,4-linked sesquiterpene lactone dimers from Carpesium faberi exhibiting NF-κB inhibitory activity. RSC Adv 5:55285–55289

    CAS  Google Scholar 

  • Yang YX, Shan L, Liu QX, Shen YH, Zhang JP, Ye J, Xu XK, Li HL, Zhang WD (2014) Carpedilactones A – D, four new isomeric sesquiterpene lactone dimers with potent cytotoxicity from Carpesium faberi. Org Lett 16:4216–4219

    PubMed  CAS  Google Scholar 

  • Yuan C, Du B, Deng H, Man Y, Liu B (2016) Total syntheses of sarcandrolide J and shizukaol D: lindenane sesquiterpenoid [4 + 2] dimers. Angew Chem 128:1–5

    Google Scholar 

  • Yuan CC, Du B, Deng HP, Man Y, Liu B (2017) Total syntheses of sarcandrolide J and shizukaol D: lindenane sesquiterpenoid [4 + 2] dimers. Angew Chem Int Ed 56:637–640

    CAS  Google Scholar 

  • Yuan T, Zhu RX, Yang SP, Zhang H, Zhang CR, Yue JM (2012) Serratustones A and B representing a new dimerization pattern of two types of sesquiterpenoids from Chloranthus serratus. Org Lett 14:3198–3201

    PubMed  CAS  Google Scholar 

  • Yue GZ, Yang L, Yuan CC, Du B, Liu B (2012) Total syntheses of lindenane-type sesquiterpenoids: (±)-chloranthalactones A, B, F, (±)-9-hydroxy heterogorgiolide, and (±)-shizukanolide E. Tetrahedron 68:9624–9637

    CAS  Google Scholar 

  • Zan K, Chai XY, Chen XQ, Wu Q, Fu Q, Zhou SX, Tu PF (2012) Artanomadimers A–F: six new dimeric guaianolides from Artemisia anomala. Tetrahedron 68:5060–5065

    CAS  Google Scholar 

  • Zeng KW, Wang S, Dong X, Jiang Y, Jin HW, Tu PF (2014) Sesquiterpene dimmer (DSF-27) inhibits the release of neuroinflammatory mediators from microglia by targeting spleen tyrosine kinase (Syk) and Janus kinase 2 (Jak2): two major non-receptor tyrosine signaling proteins involved in inflammatory events. Toxicol Appl Pharm 275:244–256

    CAS  Google Scholar 

  • Zhan ZJ, Ying YM, Ma LF, Shan WG (2011) Natural disesquiterpenoids. Nat Prod Rep 28:594–629

    PubMed  CAS  Google Scholar 

  • Zhang C, Wang S, Zeng KW, Li J, Ferreira D, Zjawiony JK, Liu BY, Guo XY, Jin HW, Jiang Y, Tu PF (2016a) Nitric oxide inhibitory dimeric sesquiterpenoids from Artemisia rupestris. J Nat Prod 79:213–223

    PubMed  CAS  Google Scholar 

  • Zhang JP, Xu XK, Ye J, Yang YX, Gao S, Li HL, Zhang WD (2016b) Three new sesquiterpene lactone dimers from Carpesium macrocephalum. Fitoterapia 110:72–76

    PubMed  CAS  Google Scholar 

  • Zhang C, Wen R, Ma XL, Zeng KW, Xue Y, Zhang PM, Zhao MB, Jiang Y, Liu GQ, Tu PF (2018) Nitric oxide inhibitory sesquiterpenoids and its dimers from Artemisia freyniana. J Nat Prod 81:866–878

    PubMed  CAS  Google Scholar 

  • Zhang M, Iinuma M, Wang JS, Oyama M, Ito T, Kong LY (2012a) Terpenoids from Chloranthus serratus and their anti-inflammatory activities. J Nat Prod 75:694–698

    PubMed  CAS  Google Scholar 

  • Zhang QB, Mándi A, Li S, Chen YC, Zhang WJ, Tian XP, Zhang HB, Li HX, Zhang WM, Zhang S, Ju JH, Kurtán T, Zhang CS (2012b) N–N-coupled indolo-sesquiterpene atropo-diastereomers from a marine-derived actinomycete. Eur J Org Chem 27:5256–5262

    Google Scholar 

  • Zhang S, Yang SP, Yuan T, Lin BD, Wu Y, Yue JM (2010) Multistalides A and B, two novel sesquiterpenoid dimers from Chloranthus multistachys. Tetrahedron Lett 51:764–766

    CAS  Google Scholar 

  • Zhang XF, Ren J, Cheng XR, Jin HZ, Zhang WD (2015) One new unusual sesterterpenoid and four new sesquiterpene dimers from Inula britannica. RSC Adv 5:1979–1982

    CAS  Google Scholar 

  • Zhang YL, Xu QQ, Zhou XW, Wu L, Wang XB, Yang MH, Luo J, Luo JG, Kong LY (2019) Rare dimeric guaianes from Xylopia vielana and their multidrug resistance reversal activity. Phytochemistry 158:26–34

    PubMed  CAS  Google Scholar 

  • Zhang YL, Zhou XW, Wang XB, Wu L, Yang MH, Luo J, Yin Y, Luo JG, Kong LY (2017) Xylopiana A, a dimeric guaiane with a case-shaped core from Xylopia vielana: structural elucidation and biomimetic conversion. Org Lett 19:3013–3016

    PubMed  CAS  Google Scholar 

  • Zhao H, Weng CW, Tian X, Lai PX, Huang JJ, Xie WD (2010) Fischelactone: A novel eremophilane dimer from Ligularia fischeri. Chin Chem Lett 21:613–615

    CAS  Google Scholar 

  • Zheng ZQ, Wei WJ, Zhang JM, Li HY, Xu K, Xu JY, Tang BC, Li Y, Gao K (2019) Heliaquanoids A–E, five sesquiterpenoid dimers from Inula helianthus-aquatica. J Org Chem 84:4473–4477

    PubMed  CAS  Google Scholar 

  • Zhou B, Liu QF, Dalal S, Cassera MB, Yue JM (2017a) Fortunoids A – C, Three sesquiterpenoid dimers with different carbon skeletons from Chloranthus fortunei. Org Lett 19:734–737

    PubMed  CAS  Google Scholar 

  • Zhou B, Wu Y, Dalal S, Merino EF, Liu QF, Xu CH, Yuan T, Ding J, Kingston DGI, Cassera MB, Yue JM (2017b) Nanomolar antimalarial agents against chloroquine-resistant Plasmodium falciparum from medicinal plants and their structure-activity relationships. J Nat Prod 80:96–107

    PubMed  CAS  Google Scholar 

  • Zhou J, Wang JS, Zhang Y, Wang PR, Guo C, Kong LY (2012a) Disesquiterpenoid and sesquiterpenes from the Flos of Chrysanthemum indicum. Chem Pharm Bull 60:1067–1071

    PubMed  CAS  Google Scholar 

  • Zhou LY, Yu XH, Lu B, Hua Y (2012b) Bioassay-guided isolation of cytotoxic isocryptoporic acids from Cryptoporus volvatus. Molecules 21:1692

    Google Scholar 

  • Zhou LZ, Jiang JH, Li YP, Chen YG (2010) Chemical and bioactive studies on Tibetan medicines plants of Vladimiria genus. Yunnan Chem Technol 37:58–62

    CAS  Google Scholar 

  • Zhou XD, Chai XY, Zeng KW, Zhao MB, Jiang Y, Tu PF (2015) Artesin A, a new cage-shaped dimeric guaianolide from Artemisia sieversiana. Tetrahedron Lett 56:1141–1143

    CAS  Google Scholar 

  • Zhu CZ, Hu BY, Liu JW, Cai Y, Chen XC, Qin DP, Cheng YX, Zhang ZD (2019) Anti-mycobacterium tuberculosis terpenoids from Resina Commiphora. Molecules 24:1475

  • Zhu JX, Qin JJ, Jin HZ, Zhang WD (2013) Japonicones Q–T, four new dimeric sesquiterpene lactones from Inula japonica Thunb. Fitoterapia 84:40–46

    PubMed  CAS  Google Scholar 

  • Zhu Y, Wu QX, Hu PZ, Wu WS (2009) Biguaiascorzolides A and B: Two novel dimeric guaianolides with a rare skeleton, from Scorzonera austriaca. Food Chem 114:1316–1320

    CAS  Google Scholar 

  • Zhu YC, Wang G, Yang XL, Luo DQ, Zhu QC, Peng T, Liu JK (2010) Agrocybone, a novel bis-sesquiterpene with a spirodienone structure from basidiomycete Agrocybe salicacola. Tetrahedron Lett 51:3443–3445

    CAS  Google Scholar 

  • Zhuo ZG, Cheng ZY, Ye J, Li HL, Xu XK, Xie N, Zhang WD, Shen YH (2017) Two new sesquiterpenoids and a new lindenane sesquiterpenoid dimer from Chloranthus japonicus. Phytochemistry Lett 20:133–138

    CAS  Google Scholar 

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  1. Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, People’s Republic of China

    Ying-Hong Ma, Xiu-Xiu Dou & Xin-Hui Tian

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  1. Ying-Hong Ma
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  2. Xiu-Xiu Dou
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  3. Xin-Hui Tian
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Correspondence to Xin-Hui Tian.

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Ma, YH., Dou, XX. & Tian, XH. Natural disesquiterpenoids: an overview of their chemical structures, pharmacological activities, and biosynthetic pathways. Phytochem Rev 19, 983–1043 (2020). https://doi.org/10.1007/s11101-020-09698-1

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